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[ CAS No. 3012-80-4 ] {[proInfo.proName]}

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Chemical Structure| 3012-80-4
Chemical Structure| 3012-80-4
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Quality Control of [ 3012-80-4 ]

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Product Details of [ 3012-80-4 ]

CAS No. :3012-80-4 MDL No. :MFCD00142655
Formula : C9H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :SIRPHJCQZYVEES-UHFFFAOYSA-N
M.W : 160.17 Pubchem ID :762084
Synonyms :
Chemical Name :1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Calculated chemistry of [ 3012-80-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.38
TPSA : 34.89 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.04
Log Po/w (XLOGP3) : 1.09
Log Po/w (WLOGP) : 1.39
Log Po/w (MLOGP) : 0.67
Log Po/w (SILICOS-IT) : 1.56
Consensus Log Po/w : 1.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.01
Solubility : 1.57 mg/ml ; 0.0098 mol/l
Class : Soluble
Log S (Ali) : -1.41
Solubility : 6.16 mg/ml ; 0.0385 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.41
Solubility : 0.623 mg/ml ; 0.00389 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 3012-80-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3012-80-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3012-80-4 ]

[ 3012-80-4 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 3012-80-4 ]
  • [ 7467-35-8 ]
YieldReaction ConditionsOperation in experiment
50.4% 2- hydroxymethyl-l -methyl-1 H-benzimidazole (Compound 49a)A suspension of l -methyl-2-formyl-l H-benzimidazole (500 mg, 3.12 mmol) and NaBH4 (134 mg, 3.43 mmol) in anhydrous THF (25 ml) was stirred for 24 hours at r.t.. The reaction mixture was quenched with water, extracted with EtOAc, dried over Na2S04 and evaporated to dryness in vacuo. The crude was purified by automated flash chromatography (HorizonTM - Biotage) eluting with CHC13 - 1.7M NH3 sol. in MeOH 100:2 giving the title product as white solid. Yield: 50.4 %. MS: [ +H]+ = 163.5
Example 12; (1-Methyl-1H-benzoimidazol-2-yl)-methanol; Sodium borohydride (472 mg, 12.48 mmol) was added to the solution of 1-methyl-1H-benzoimidazole-2-carbaldehyde (1 g, 6.24 mmol) in ethanol (50 mL). The reaction mixture was stirred at room temperature for overnight. The reaction mixture was condensed, the residue was diluted with ethyl acetate; water was added. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered and condensed to give off-white solid as product (953 mg, 94%). This product was used in the later steps without further purification.1HNMR (300 MHz, CDCl3): (ppm) 7.63 (m, 1H), 7.21 (m, 3H), 4.84 (s, 2H), 3.75 (s, 3H)
With methanol; sodium tetrahydridoborate; at 0 - 20℃; for 5h; To a 0C solution of 1 -methyl- lH-benzimidazole-2-carbaldehyde (1.1 g, 6.8 mmol) in anhydrous methanol (50 mL) was added sodium borohydride (350 mg, 9.3 mmol). The reaction mixture was stirred at room temperature for 5 hours. Saturated ammonium chloride solution (20 mL) was added. Methanol was evaporated. The resultant mixture was extracted with EtOAc (3 x 50 mL) and CH2Cl2 (1 x 50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. (1 -methyl- lH-benzimidazol-2-yl)methanol was obtained (1.1 g, 99% yield). The product was used without further purification.
With sodium tetrahydridoborate; In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere; To a solution of 1-methyl- 1H-benzo[d]imidazole-2-carbaldehyde (5-5a, 150 mg, 936.49 umol, 1 eq) in THF (3 mL) was added NaBH4 (38.97 mg, 1.03 mmol, 1.1 eq) at 20C under N2. The mixture was stirred at 20C for 1 hour. LCMS showed 5-5a was comsumed completely and desired mass was detected. The reaction mixture was quenched by addition water (30 mL) at 20C. The aqueous phase was extracted with ethyl acetate (25 mL*2). The combined organic phase was washed with brine (20 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-TLC (ethyl acetate: methanol = 20:1) to give 5-5b as a white solid.1H NMR (400MHz, CDCl3-d) 7.77-7.67 (m, 1H), 7.34-7.28 (m, 2H), 7.27- 7.23 (m, 1H), 4.91 (s, 2H), 3.83 (s, 3H).

  • 2
  • [ 3012-80-4 ]
  • [ 289037-48-5 ]
  • [3-(1-methyl-1H-benzoimidazol-2-ylmethyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In a flask under N2, added 2.15 g (13.4 mmol) of 1-methyl-1 H-benzo[d]imidazole-2- carbaldehyde, 15 mL (107 mmol) of Et3N and 200 mg MgSO4 to a solution of 2.0 g (13.4 mmol) of (3-aza-bicyclo[3.1.0]hex-6-yl)-methanol in 50 mL of anhydrous CH2CI2 at room temperature. After 30 minutes of stirring, 4.25 g (20.1 mmol, 1.5 eq) of sodium triacetoxyborohydride was added and the suspension was stirred at room temperature for 18 hours. The suspension was diluted with CH2CI2 and washed with saturated NaHCO3 aqueous solution and brine. The organic layer was dried with sodium sulfate, filtered and stripped in vacuo to give 3.55 g light yellow solid of [3-(1-methyl-1H-benzoimidazol-2-ylmethyl)-3-aza- bicyclo[3.1.0]hex-6-yl]-methanol, which was used without further purification. 400 MHz 1H NMR (CD3OD) δ 7.7 (d, 1 H), 7.5 (m, 1H), 7.2- 7.3 (m, 2H), 3.9 (s, 2H), 3.8 (s, 3H), 3.3 (d, 2H), 2.9 (d, 2H), 2.5 (broad d, 2H), 1.4 (m, 1 H), 1.3 (s, 2H); MS (M+1 ) 258.
  • 3
  • [ 3012-80-4 ]
  • [ 1378790-75-0 ]
  • 1-methyl-2-(6-phenethyl-3-aza-bicyclo[3.1.0]hex-3-ylmethyl)-1H-benzoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a stirred solution of 6-phenethyl-3-aza-bicyclo[3.1.0]hexane (25 mg, 0.13 mmol) in CH2CI2 (2 mL) under N2 at room temperature was added 1-Methyl-1 H-benzoimidazole-2- carbaldehyde (22 mg, 0.13 mmol), Et3N (150 uL, 1.1 mmol) and MgSO4 (5 mg). The mixture was stirred for 30 min and then Na(OAc)3BH (43 mg, 0.20 mmol) was added. After being stirred at room temperature for 12 h, the mixture was diluted with CH2CI2 (30 mL) and washed with water, brine and dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified with flash column (silica gel, 70% to 100% EtOAc in hexane) to give 26 mg thick oil, which was dissolved in 1 mL MeOH and treated with 50 uL 4N HCI in dioxane. The mixture was concentrated and triturated with ethyl ether to give 31 mg solid as the HCI salt of 1-methyl-2-(6-phenethyl-3-aza-bicyclo[3.1.0]hex-3-ylmethyl)-1 H-benzoimidazole. MS (ESI+) for C22H25N3 m/z 332 (M+H)+.
  • 4
  • [ 2249-28-7 ]
  • [ 3012-80-4 ]
  • 1-(1-methyl-1H-benzoimidazol-2-ylmethyl)-4-(3-trifluoromethyl-phenyl)-piperidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.25 M stock solutions of amines (II) and aldehydes (III) in DCE were prepared. When applicable, the aldehyde salt forms were neutralized by addition of 4 equivalents of DIPEA. A 0.25 M fine suspension of NaBH(OAc)3 in anhydrous DMF/ DCE mixture (20/80) was prepared. To each vial was added 0.2 mL of a solution of amine (II) follwed by 0.2 mL of a solution of aldehyde (III) and 0.5 mL of the NaBH(OAc)3 suspension to each vial. The vials were capped and shaken at room temperature for 16 h. Additional 0.5 mL of the NaBH(OAc)3 suspension was added to each vial, the vials were vortexed, capped, and shaken at room temperature for 16 h. The solvent was removed under reduced pressure. 1 mL of DMSO and 0.1 mL of water were added to each vial. The samples were vortexed for 1 h. 0.05 mL of concentrated NH4OH was added to each vial. The samples were filtered and directly submitted to HPLC purification.
  • 5
  • [ 3012-80-4 ]
  • [ 1004618-99-8 ]
  • 2-((4-(2-methoxy-4-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)-1-methyl-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a stirred solution of 4-(2-methoxy-4-(trifluoromethyl)phenyl)piperidine hydrochloride salt (444 mg, 1.5 mmol) in CH2CI2 under N2 at room temperature was added triethylamine (1.7 mL, 12.0 mmol), MgSO4 (20 mg) and 1-methyl-1H-benzo[d]imidazole-2- carbaldehyde (240 mg, 1.5 mmol). The reaction mixture was stirred for 30 min, then <n="79"/>NaBH(OAc)3 (477 mg, 2.25 mmol) was added. The mixture was stirred at room temperature overnight and was then diluted with methylene chloride (50 ml_) and washed with water, brine and dried with Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column with 1-5% MeOH in CH2CI2 to give 546 mg of 2-((4-(2-Methoxy-4- (trifluoromethyl)phenyl)piperidin-1-yl)methyl)-1-methyl-1H-benzo[d]imidazole as a white foam. The residue was dissolved in MeOH (3 ml_) and a 4N HCI solution in dioxane (0.4 mL) was added and the mixture was stirred for 10 min. The solvent was removed in vacuo to give 596 mg of 2-((4-(2-Methoxy-4-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)-1-methyl-1H- benzo[d]imidazole hydrochloride salt as a white solid. 400 MHz 1H NMR (CD3OD) δ (ppm) 7.75 (dd, 2H), 7.49 (m, 2H), 7.40 (d, 1 H), 7.26 (d, 1 H), 7.21 (s, 1 H), 4.73 (s, 2H), 4.03 (s, 3H), 3.91 (s, 3H), 3.76 (m, 2H), 3.20-3.30 (m, 3H), 2.05-2.20 (m, 4H); MS (m/z) 404.2.
  • 6
  • [ 3012-80-4 ]
  • cis-4-(3,4-difluorophenyl)-3-methylpiperidine hydrochloride [ No CAS ]
  • 2-[cis-4-(3,4-difluoro-phenyl)-3-methyl-piperidin-1-yl]methyl}-1-methyl-1H-benzoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a stirred solution of c/s-4-(3,4-Difluoro-phenyl)-3-methyl-piperidine hydrochloride salt (2.76 g, 11.1 mmol) in CH2CI2 (50 mL) under N2 at room temperature was added triethylamine (11.5 mL), MgSO4 (1.0 g) and 1 -methyl-1 H-benzo[d]imidazole-2-carbaldehyde (1.78 g, 11.1 mmol). The reaction mixture was stirred at rt for 30 min, then NaBH(OAc)3 (3.54g, 16.7 mmol) was added. The mixture was stirred at room temperature overnight and was then diluted with methylene chloride (100 mL) and washed with water, brine and dried with Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column with EtOAc to give 2.93 g of 2-[cis-4-(3,4-Difluoro-phenyl)-3-methyl-piperidin-1-yl]methyl}-1- methyl-1 H-benzoimidazole as a racemic mixture. 400 MHz 1H NMR (CD3OD) δ (ppm) 7.80 (d, H), 7.50 (d, 1 H), 7.28 (m, 2H), 7.10 (m 1H), 7.08 (m, 1H), 6.96 (m, br, 1 H), 3.92 (s, 3H), 3.80 (s, 2H), 3.00 (m, 1H), 2.85 (m, 1 H), 2.78 (d, 1H)1 2.48 (d, 1 H), 2.20 (m, 1 H), 2.10-2.17 (m, 2H), 1.60 (d, br, 1H), 0.76 (d, 3H); MS+ (m/z) 356.1.Two enantiomers were separated using a Chiralpak AD-H column (2.1 CM x 25 CM), with 80/20 CO2/MeOH as Mobile phase at flow rate of 65 g/min to obtain two enantiomers: Example 2a (corresponding to entry 472 in table 7): 2-[Cis-4-(3,4-Difluoro- phenyl)-3-methyl-piperidin-1-yl]methyl}-1 -methyl-1 H-benzoimidazole, Enantiomer No.1 : Retention time: 6.121 min, 100% eeExample 2b (corresponding to entry 473in table 7): 2-[Cis-4-(3,4-Difluoro- phenyl)-3-methyl-piperidin-1 -yl]methyl}-1 -methyl-1 H-benzoimidazole, Enantiomer No.2: Retention time: 9.82 min, 95% ee
  • 7
  • [ 3012-80-4 ]
  • [ 3013-07-8 ]
YieldReaction ConditionsOperation in experiment
94% With hydroxylamine hydrochloride; sodium acetate; In water; at 20℃; for 2h; To a stirred suspension of 1-METHYL-1H-BENZOIMIDAZOLE-2-CARBALDEHYDE (980mg, 6. 61mmol) in H2O (10ML) was added a solution of Sodium Acetate (3. 25g, 39. 68MMOL) and Hydroxylamine hydrochloride (1. 38g, 19. 84MMOL) in 10ml of H2O. The reaction was stirred at rt for 2hr and the thick precipitate was collected by filtration, washed with water and dried under vacuum to give 1. 02g (94%) of a white solid.'H NMR (DMSO-d6) 5 12.06 (1 H, s), 8.28 (1 H, s), 7.65 (1 H, d, J = 7.5 HZ), 7.60 (1 H, d, J = 6.8Hz), 7.32 (1 H, t, J = 7.2 Hz), 7.23 (1 H, t, J = 6.8 Hz), 4.00 (3H, s). Anal. Calcd for C9H9N30 : C, 61.70 ; H, 5.18 ; N, 23.99. Found: C, 61.80 ; H, 5.23 ; N, 23.98.
91% With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; at 20℃; for 8h; To a mixture of l-methyl-l H-benzo[d]imidazole-2-carbaldehyde (2.0 g, 13 mmol) and hydroxylamine hydrochloride (1.3 g, 19 mmol) in ethanol (20 mL) was added sodium hydroxide (0.8 g, 19 mmol. The mixture was stirred at room temperature for 8 hours. On completion, the reaction was filtered, and the filtrate was concentrated in vacuo to give compound B-150 (2.0 g, 91% yield) as a yellow solid. LCMS: (ES+) mix (M+H)+ = 176.1 , tR=0.946
With hydroxylamine hydrochloride; In neat (no solvent); for 0.0833333h;Milling; Green chemistry; General procedure: A Retsch MM200 grinder mill operating at 25 Hz frequency was used for the mechanochemical synthesis. Ball mill experiments were performed in stainless steel jar of 10 mL volume using one ball. Reactions were monitored by TLC (DC-Alufolien Aluminiumoxide 60 F254 plates (Merck) with 9:1 chloroform-methanol as the eluent) and no side products have been detected. FTIR spectra were recorded over the 4000-400 cm-1 range without baseline corrections up to 30 minutes except for compound 4a where the reaction was monitored during 90 minutes. In all reactions 100 mg of FTIR-grade KBr was added. Procedure A: in a jar, 100 mg of the carbonyl compound and equimolar amount of hydroxylamine hydrochloride were grounded together in a mill. Procedure B: (liquid assisted grinding, LAG): 100 mg of carbonyl compound, equimolar amount of hydroxylamine hydrochloride in the presence of 30 μL of methanol were grounded together in a mill. Procedure C: 100 mg of carbonyl compound, equimolar amount of hydroxylamine hydrochloride, equimolar amount of NaOH in the presence of 30 μL of methanol were grounded together in a mill.
  • 8
  • [ 661458-46-4 ]
  • [ 3012-80-4 ]
  • 3-{5-[1-(1-methyl-1H-benzoimidazol-2-ylmethyl)-piperidin-2-yl]-[1,2,4]oxadiazol-3-yl}-benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.1% With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 0.0833333h; [3-] [{5- [1- ( 1-METHYL-LH-BENZOIMIDAZOL-2-YLMETHYL)-PIPERIDIN-2-YL]- [1,] 2,4] [OXADIAZOL-3-YL}-] benzonitrile (63 mg, 79.1%) was obtained from [3- (5-PIPERIDIN-2-YL- [1,] 2,4] oxadiazol-3-yl) - benzonitrile (50.8 mg, 0.2 mmol) with [1-METHYL-2-FORMYLBENZIMIDAZOLE] (32 mg, 0.2 mmol), sodium triacetoxyborohydride (59.3 mg, 0.28 mmol) and dichloroethane (1 mL) at room temperature for 5 [MIN. 1H] NMR [(CDC13),] 8 (ppm): 8. 30 (s, 1H), 8.27 (d, 1H), 7.76 (d, 1H), 7.62 (d, 1H), 7.59 (t, 1H), 7.30 (d, 1H), 7.20 (m, 2H), 4.02 (t, 1H), 3.90 (dd & s, [SH),] 3.00 (m, 1H), 2.43 (m, 1H), 2.01 (s, 2H), 1.48-1. [88] (m, 4H).
  • 9
  • [ 3012-80-4 ]
  • [ 370594-55-1 ]
  • [ 369654-59-1 ]
YieldReaction ConditionsOperation in experiment
Synthesis Example 6-1: Synthesis of 2-(4-(N-Boc-N-2-picolylamino methyl) benzoyl)-5-((1-methylbenzimidazol-2-ylmethyl) amino) valerate 1-naphthalenemethylamide (Compound XIII-6) 50.3 mg of the compound synthesised in Synthesis Example 1-4 was dissolved in 1 ml of anhydrous methanol, and then 16.1 mg of <strong>[3012-80-4]1-methyl-2-formylbenzimidazole</strong> was added to the solution and the resultant mixture was stirred for 1.5 hours at room temperature. After the solvent was distilled off, 1 ml of anhydrous methanol and a drop of acetic acid were added to the resultant and the resultant mixture was cooled to 0C. Subsequently, 14.2 mg of sodium borohydride was added thereto and the resultant mixture was stirred for 0.5 hour at room temperature. The residue obtained by concentrating the reaction solution was purified by means of silica gel column chromatography (2.5 g, chloroform/methanol = 15/1), and 31.3 mg of the above-mentioned compound was obtained as a white solid product. MS(FAB,Pos.):m/z=740[M+1]+ 1H-NMR(500MHz,CDCl3):δ=1.43 and 1.44(9H,2s),1.52-1.63(1H,m), 1.65-1.78(1H,m),1.89-2.01(2H,m),2.68-2.83(2H,m),3.58(3H,s),3. 75(1H,d,J=14.6Hz),3.81(1H,d,J=14.6Hz),4.41and4.44(2H,2s),4.52 and 4.55(2H,2s)4.69-4.75(1H,m),4.85(1H,dd,J=14.6,5.1Hz),4.98 (1H,dd,J=14.6,5.6Hz),7.10-7.35(7H),7.36(1H,d,J=6.6Hz),7.43-7. 51(2H,m),7.52-7.60(1H,m),7.69-7.78(7H,m),7.80-7.83(1H,m),7.99 -8.01 (1H,m), 8.53 (1H,ddd,J=4.9,2.0,1.0Hz).
  • 10
  • [ 3012-80-4 ]
  • [ 645-36-3 ]
  • [ 854745-40-7 ]
YieldReaction ConditionsOperation in experiment
64% A solution of <strong>[3012-80-4]1-methyl-2-formylbenzimidazole</strong> (1 g) in methanol (27 mL) and acetic acid (0.54 mL) was treated with aminoacetaldehyde diethylacetal (0.9 g, 1 eq.) and NaCNBH3 (0.85 g, 2 eq.) at 25 C., stirred for 1 hour. The mixture was partitioned between water and ethyl acetate. The organic phase layer was separated, washed sequentially with saturated NaHCO3 and brine, and concentrated. The residue was chromatographed on silica gel, eluting with 8% methanol/dichloromethane to give the title compound (1.2 g 64% yield).
64% With sodium cyanoborohydride; In methanol; acetic acid; at 25℃; for 1h; A solution of <strong>[3012-80-4]1-methyl-2-formylbenzimidazole</strong> (1 g) in methanol (27 mL) and acetic acid (0.54 mL) was treated with aminoacetaldehyde diethylacetal (0.9 g, 1 equivalent) and NaCNBH3 (0.85 g, 2 equivalents) at 25 C., stirred for 1 hour. The mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed sequentially with saturated NaHCO3 and brine, and concentrated. The residue was chromatographed on silica gel, eluting with 8% methanol/dichloromethane to give 1.2 g (64%) of the title compound.
64% With sodium cyanoborohydride; acetic acid; In methanol; at 25℃; for 1h; EXAMPLE 64A 2,2-dimethoxy-N-[(1-methyl-1H-benzimidazol-2-yl)methyl]ethanamine A solution of <strong>[3012-80-4]1-methyl-2-formylbenzimidazole</strong> (1 g) in methanol (27 mL) and acetic acid (0.54 mL) was treated with aminoacetaldehyde diethylacetal (0.9 g, 1 equivalent) and NaCNBH3 (0.85 g, 2 equivalents) at 25 C., stirred for 1 hour. The mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed sequentially with saturated NaHCO3 and brine, and concentrated. The residue was purified by eluding with 8% methanol/dichloromethane to give 1.2 g (64%) of the title compound.
  • 11
  • [ 3012-80-4 ]
  • [ 22483-09-6 ]
  • [ 854745-40-7 ]
YieldReaction ConditionsOperation in experiment
64% With sodium cyanoborohydride; acetic acid; In methanol; at 25℃; for 1h; Example 64A; 2, 2-dimethoxy-N-[(1-methyl-lH-benzimidazol-2-yl) methyl] ethanamine; A solution of <strong>[3012-80-4]1-methyl-2-formylbenzimidazole</strong> (lg) in methanol (27 mL) and acetic acid (0.54 mL) was treated with aminoacetaldehyde diethylacetal (0.9 g, 1 equivalent) and NaCNBH3 (0.85 g, 2 equivalents) at 25C, stirred for 1 hour. The mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed sequentially with saturated NaHC03 and brine, and concentrated. The residue was purified by eluting with 8% methanol/dichloromethane to give 1.2 g (64%) of the title compound.
  • 12
  • [ 3012-80-4 ]
  • [ 856900-35-1 ]
  • N'-cyclopentyl-N-[3-fluoro-4-(4-morpholinyl)phenyl]-N-({8-[(1-methyl-1H-benzimidazol-2-yl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}methyl) urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% Example 6: N'-Cyclopentyl-N-[3-fluoro-4-(4-morpholinyl)phenyl]-N-({8-[(1-methyl-1H- benzimidazol-2-yl) methyl]-8-azabicyclo [3. 2.1] oct-3-yl} methyl) urea MP-Triacetoxyborohydride resin (ex Argonaut, loading 2.1 mmol/g) (0.25 g, 0.5 mmol) was added to a solution of N- (8-azabicyclo [3.2. 1] oct-3-ylmethyl)-N-cyclopentyl-N- [3- fluoro-4- (4-morpholinyl) phenyl] ureaD12 (90 mg, 0.2 mmol) and 1-methyl-2- formylbenzimidazole (38 mg, 0.24 mmol) in dry THF (0.5 ml). The mixture was shaken at room temperature for 18 h. DCM (1 ml), PS-Isocyanate scavenger resin (ex Argonaut, loading 1.53 mmol/g) (90 mg, 0.14 mmol) and PS-p-toluensulfonyl hydrazide scavenger resin (ex Aldrich, loading 2.5 mmol/g) (128 mg, 0.32) were added. Shaking was continued for 18 h and the mixture filtered. The filtrate was loaded onto a 1g SCX cartridge and washed with methanol. After elution with 2. 0M NH3 in MeOH, the solution was concentrated in vacuo. The crude was purified by mass directed prep HPLC on a Terra MS Cis 5, um column (id 30 x 75 mm) eluting with 10-90% MeCN in water containing 0. 1 % TFA (flow rate 43 ml/min). The HPLC fractions were concentrated and loaded onto a 500 mg SCX cartridge. After elution with 2. 0M NH3 in MeOH, the solution was concentrated in vacuo to afford the title compound (41 mg, 36%). Mass spectrum (API+) : Found 575 (MH+). C33H43FN602 requires 574.
  • 13
  • [ 216686-77-0 ]
  • [ 3012-80-4 ]
  • [ 259861-26-2 ]
YieldReaction ConditionsOperation in experiment
With magnesium sulfate; lithium diisopropyl amide; In tetrahydrofuran; d (+-)-6-[1-Hydroxy-1-(1-methyl-1H-benzimidazol-2-yl)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione A solution of lithium diisopropylamide (3.15 mmol) in anhydrous tetrahydrofuran (5 ml) was added to a solution of 3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (500 mg) in anhydrous tetrahydrofuran (20 ml) at -78 C. After 10 minutes, 1-methylbenzimidazole-2-carboxaldehyde (600 mg) was added and the resultant solution kept at -78 C. for 1 hour. The reaction mixture was allowed to warm to ambient temperature and quenched with saturated sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate and washed with saturated sodium hydrogen carbonate and then brine, then dried over a mixture of magnesium sulfate and silica, filtered, and evaporated. Purification by HPLC over silica eluding with an isohexane:ethyl acetate gradient (4:1 to 0:1) gave the title compound (0.13 g). MS (APCI) ((M+H)+) 399; 1H NMR (CDCl3) δ 0.94 (6H, dd); 2.25-2.35 (1H, m); 3.39 (3H, s); 3.60-3.90 (2H, m); 370 (3H, s); 6.19 (1H, s); 7.18 (1H, s); 7.30-7.33 (3H, m); 7.77 (1H, dd).
  • 14
  • [ 3012-80-4 ]
  • 4-(1-methyl-3-{4-[(triphenyl-15-phosphanyl)-methyl]-phenyl}-1H-pyrazol-4-yl)-pyridine bromide [ No CAS ]
  • [ 943656-49-3 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 40℃; for 3h; Preparation 20 1-Methyl-2-{2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-vinyl}-1H-benzoimidazole To a solution of 4-(1-Methyl-3-(4-[(triphenyl-15-phosphanyl)-methyl]-phenyl}-1H-pyrazol-4-yl)-pyridine bromide (300 mg) in dimethyl formamide (3 mL) was added cesium carbonate (290 mg, 3 eq.) and <strong>[3012-80-4]1-Methyl-1H-benzoimidazole-2-carbaldehyde</strong> (52 mg) and the reaction mixture was heated at 40 C. for 3 h. The reaction mixture was poured into 1 N sodium hydroxide, extracted 3* chloroform, dried magnesium sulfate, filtered and concentrated. Purification via MPLC biotage chromatography eluding with 1-3% methanol/0.5% saturated ammonium hydroxide/80% ethyl acetate/hexanes provided the title compound. MS: (M+H m/z=392.0).
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