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[ CAS No. 33024-60-1 ] {[proInfo.proName]}

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Chemical Structure| 33024-60-1
Chemical Structure| 33024-60-1
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Product Details of [ 33024-60-1 ]

CAS No. :33024-60-1 MDL No. :MFCD00100881
Formula : C5H12ClNO Boiling Point : No data available
Linear Structure Formula :- InChI Key :KWZSCXIYGVEHOB-UHFFFAOYSA-N
M.W : 137.61 Pubchem ID :44118693
Synonyms :

Calculated chemistry of [ 33024-60-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 34.79
TPSA : 35.25 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.49
Log Po/w (WLOGP) : 0.93
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 0.82
Consensus Log Po/w : 0.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.0
Solubility : 13.7 mg/ml ; 0.0996 mol/l
Class : Very soluble
Log S (Ali) : -0.8
Solubility : 21.8 mg/ml ; 0.159 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.34
Solubility : 62.6 mg/ml ; 0.455 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 33024-60-1 ]

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

Application In Synthesis of [ 33024-60-1 ]

* 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 [ 33024-60-1 ]

[ 33024-60-1 ] Synthesis Path-Downstream   1~11

  • 1
  • 4-methyl-1H-indazole-5-carboxylic acid [ No CAS ]
  • [ 33024-60-1 ]
  • 4-methyl-N-tetrahydro-2H-pyran-4-yl-1H-indazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
52.7% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 4h; Tetrahydro-2H-pyran-4-ylamine monohydrochloride (228 mg, 1.66 mmol), triethylamine (0.5 ml, 3.59 mmol), 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide monohydrochloride (367 mg, 1.91 mmol) and hydroxybenzotriazole (190 mg, 1.41 mmol) were added to a solution of 4-methyl-1H-indazole-5-carboxylic acid (225 mg, 1.28 mmol) in N,N-dimethylformamide (5.5 ml), and the resulting mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogencarbonate solution. A small amount of the insoluble material was collected by filtration and then dried to obtain 4-methyl-N-tetrahydro-2H-pyran-4-yl-1H-indazole-5-carboxamide (41 mg). The filtrate was extracted with ethyl acetate and chloroform, and the combined organic layer was dehydrated over magnesium sulfate and then filtered. The filtrate was concentrated and the resulting residue was suspended in chloroform. The resulting suspension was filtered and the precipitate was dried to obtain 4-methyl-N-tetrahydro-2H-pyran-4-yl-1H-indazole-5-carboxamide (134 mg, 52.7percent).1H-NMR (DMSO-d6) delta; 1.45-1.58 (m, 2H), 1.76-1.80 (m, 2H), 2.58 (s, 3H), 3.33-3.42 (m, 2H), 3.84-4.03 (m, 3H), 7.29 (d, J=8.6Hz, 1H), 7.35 (d, J=8.6Hz, 1H), 8.13 (d, J=7.9Hz, 1H), 8.19 (d, J=0.9Hz, 1H), 13.11 (br, 1H).
  • 2
  • 6-methyl-1H-indazole-5-carboxylic acid [ No CAS ]
  • [ 33024-60-1 ]
  • 6-methyl-N-tetrahydro-2H-pyran-4-yl-1H-indazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); Tetrahydro-2H-pyran-4-ylamine monohydrochloride (0.0402 g, 0.292 mmol), triethylamine (0.07 ml, 0.5 mmol), 1-hydroxybenztriazole (0.0460 g, 0.340 mmol) and 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide monohydrochloride (0.0606 g, 0.316 mmol) were added to a solution of 6-methyl-1H-indazole-5-carboxylic acid (0.0437 g, 0.248 mmol) in N,N-dimethylformamide (2 ml) and stirred overnight. A saturated aqueous sodium hydrogencarbonate solution was added thereto, followed by extraction with chloroform (x 3), and the extract solution was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, followed by replacement with toluene (three times), whereby a solid was precipitated. The solid obtained was suspended in ethyl acetate and stirred to be washed, and then it was collected by filtration and dried under reduced pressure to obtain 6-methyl-N-tetrahydro-2H-pyran-4-yl-1H-indazole-5-carboxamide (0.0587 g, 91percent).1H-NMR (DMSO-d6) delta; 1.46-1.58 (2H, m), 1.75-1.82 (2H, m), 2.44 (3H, s), 3.39 (2H, td, J=1.9, 11.6Hz), 3.83-3.90 (2H, m), 3.91-4.02 (1H, m), 7.35 (1H, m), 7.73 (1H, s), 8.06 (1H, s), 8.23 (1H, d, J=7.7Hz), 13.01 (1H, br).
  • 3
  • (2R,3R,4R,5R)-4-(acetoxy)-2-(6-chloro-9H-purin-9-yl)-5-(prop-2-ynyl)tetrahydrofuran-3-yl acetate [ No CAS ]
  • [ 33024-60-1 ]
  • C21H25N5O6 [ No CAS ]
  • [ 674367-58-9 ]
YieldReaction ConditionsOperation in experiment
12%; 36% With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; for 2.5h; Intermediate [II] (43mg, 0. [114MMOL)] was reacted with 4-amino-tetrahydropyran hydrochloride salt (31 mg, 0. [23MMOL)] according to general procedure C (0. [45MMOL] DIPEA in isopropanol, heated for 2.5hours). Purification by preparative HPLC gave the desired product (purine N-9 linked to the 1-position of ribose) as a yellow gum, [(18MG,] 0.041 mmol, 36percent). m/z 444 [(MH +),] LCMS retention time 2.64min. The isomeric product (purine [N-7-LINKED)] was also obtained as a gum, (6mg, 0. [014MMOL,] 12percent). m/z 444 (MH +), LCMS retention time 2.52min.
  • 4
  • [ 674367-27-2 ]
  • [ 33024-60-1 ]
  • [ 674367-41-0 ]
YieldReaction ConditionsOperation in experiment
79% With N-ethyl-N,N-diisopropylamine; In propanal, 2-; at 90℃; for 6h; Intermediate I (459mg, 1. [3MMOL),] [DIPEA] (1. [1 ML)] and 4-aminotetrahydropyran hydrochloride (219mg, 1. [6MMOL)] were heated in 2-propanal in a reacti-vial at [90°C] for 6 hours. The mixture was cooled to room temperature and evaporated. The residue was partitioned between ethyl acetate and saturated ammonium chloride. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organics were washed with saturated sodium bicarbonate, dried [(NA2SO4),] filtered and evaporated. The residue was purified by chromatography on silica using [BIOTAGENo., ]with cyclohexane containing ethyl acetate (60-80percent) as eluant, to give the desired intermediate (427mg, 79percent) as a white solid. LC/MS R5 2.70 min, mass spectrum [M/Z 430 [MH+].] An ice cold mixture of TFA-water (9: 1) (5mL) was added to the acetonide derivative (427mg, [1.] [OMMOL).] The mixture was left to stand at [0°C] overnight (17 hours) then added dropwise to a saturated solution of sodium bicarbonate, and extracted with ethyl acetate, dried [(NA2SO4),] filtered and evaporated. The residue was purified by chromatography on silica using [BIOTAGE,] with ethyl acetate containing ethanol (0-10percent) as eluant, to give the title compound (104mg, 27percent). 'H [NMR No. ] (DMSO) 1.56-1. 90 [(4H,] m), 3.36-3. 46 (2H, m), 3.49 [(1 H,] t), 3.63 [(1 H,] dd), 3.73 (1H, dd), 3.85-3. 94 (2H, m), 4.01-4. 07 (1H, m), 4.12-4. 17 (1H, m), 4.20 (2H, s), 4.26-4. 41 [(1 H,] m), 4.54-4. 62 (1H, m), 5.31 [(1 H,] d, OH), 5.52 (1H, d, OH), 5.91 (1H, d), 7.79 (1H, br. s, NH), 8.23 [(1 H,] s), 8.33 [(1 H,] s).
  • 5
  • [ 675111-72-5 ]
  • [ 33024-60-1 ]
  • N-benzyl-1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 85℃; for 16h; Intermediate 17 (0. 031g, 0.1 mmol) was dissolved in acetonitrile (lml). [4-AMINOTETRAHYDROPYRAN HYDROCHLORIDE] (Intermediate 8A, [0.] [015G,] 0.11 mmol) and N, N- diisopropylethylamine (0. [08ML,] 0.5 mmol) were added and the mixture stirred under nitrogen at [85°C] for 16h, then concentrated in vacuo. The residue was partitioned between dichloromethane (DCM) and water. The layers were separated and the organic layer was concentrated in vacuo to afford Example 21 (0.027g). LCMS showed [MH+ =] [380] ; [TRET = 2. 92 MIN.]
  • 6
  • [ 33024-60-1 ]
  • [ 30720-25-3 ]
  • [ 675112-01-3 ]
YieldReaction ConditionsOperation in experiment
Intermediate 1 (2. [5G)] was dissolved in acetonitrile [(15ML).] 4-Aminotetrahydropyran hydrochloride [(1.] [LG)] and N, N-diisopropylethylamine (9. [4ML)] were added and the mixture stirred under nitrogen at [85°C] for 16h. A trace of starting material remained, so an additional portion of 4-aminotetrahydropyran hydrochloride [(O.] [L] lg) was added and stirring continued at [85°C] for a further [16H.] The mixture was then concentrated in vacuo. The residue was partitioned between DCM and water. The layers were separated and the organic layer was washed with further water [(2X20ML)] then dried [(NA2S04)] and concentrated in vacuo. The residue was further purified by chromatography using Biotage (silica, 90g), eluting with cyclohexane: ethyl acetate to afford Example 3 (2.45g). LCMS showed MH+ [= 319] ; TRET = 2. [90MIN.]
  • 7
  • [ 33024-60-1 ]
  • [ 41095-07-2 ]
  • [ 675114-55-3 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 85℃; for 24h;Product distribution / selectivity; Alternative preparation of ethyl 1-ethyl-6-methyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H- pyrazolo[3,4-b]pyridine-5-carboxylate: 4-Aminotetrahydro-2/-/-pyran hydrochloride (e.g. see Intermediate 8A of WO 2004/024728 A2, 0.413g, 3.0mmol) is added to a mixture of ethyl 4-chloro-1-ethyl-6- methyl-1/-/-pyrazolo[3,4-]pyhdine-5-carboxylate (0.268g, LOmmol) and DIPEA (0.87ml, delta.Ommol) in MeCN (3ml). The resulting mixture is heated at 85 0C for 24 hours.Volatiles are removed in vacuo and the residue is dissolved in chloroform (1.5ml) and applied to a SPE cartridge (silica, 5g). The cartridge is eluted successively with Et2O, EtOAc and EtOAc-MeOH (9:1). Fractions containing the desired product (which might be contaminated with starting material) are combined and concentrated in vacuo. Further purification using a SPE cartridge (silica, 5g) eluting with EtOAc-cyclohexane (1 :3) affords ethyl 1-ethyl-6-methyl-4-(tetrahydro-2H-pyran-4-ylamino)-1/-/-pyrazolo[3,4- ]pyridine-5-carboxylate.
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 85℃; for 24h; 4-Aminotetrahydropyran hydrochloride (Intermediate 8A, 0. [413G,] 3. 0mmol) was added to a mixture of Intermediate 51 (0.268g, [L.] Ommol) and N, N-diisopropylethylamine (0. [87ML,] [5.] [0MMOL)] in acetonitrile (3ml). The resulting mixture was heated at [85 °C FOR] 24 hours. Volatiles were removed in vacuo and the residue was dissolved in chloroform (1. [5ML)] and applied to a SPE cartridge (silica, 5g). The cartridge was eluted successively with [ET20,] EtOAc and EtOAc-MeOH (9/1). Fractions containing the desired product were combined and concentrated in vacuo to give the desired product contaminated with starting material (Intermediate [51).] Further purification using a SPE cartridge (silica, 5g) eluting with ethyl acetate-cyclohexane (1/3) afforded Example 189 (0.248g). LCMS showed [MH+ =] 333; [TRET] = 2.75min.
  • 8
  • [ 675112-44-4 ]
  • [ 33024-60-1 ]
YieldReaction ConditionsOperation in experiment
N, N-dibenzyltetrahydro-2H-pyran-4-amine (20. [5G)] was dissolved in ethanol [(210ML)] and hydrogenated over 10percent palladium on carbon catalyst (4g) at 100 psi for 72h at room temperature. The reaction mixture was filtered and the filtrate was adjusted to pH 1 with 2M-hydrogen chloride in diethyl ether. Evaporation of solvents gave a solid which was triturated with diethyl ether to give the product as a white solid (9. [23G). 1H] NMR [(400MHZ] in d6-DMSO, [27°C,] [SPPRN)] 8.24 (br. s, 3H), 3.86 (dd, 12,4Hz, 2H), 3.31 (dt, 2, [12HZ,] 2H), 3.20 (m, 1H), 1.84 (m, 2H), 1.55 (dq, 4, [12HZ,] 2H).
N,N-dibenzyltetrahydro-2H-pyran-4-amine (20.5 g) is dissolved in ethanol (210 ml) and hydrogenated over 10percent palladium on carbon catalyst (4 g) at 100 psi for 72 h at room temperature. The reaction mixture is filtered and the filtrate is adjusted to pH 1 with 2M-hydrogen chloride in diethyl ether. Evaporation of solvents gives a residue (which may be a solid) which is triturated with diethyl ether to give the product (which may be a solid).
Step 2: Tetrahydro-2H-pyran-4-amine hydrochloridelambda/,lambda/-dibenzyltetrahydro-2H-pyran-4-amine (20.5g) is dissolved in ethanol (210ml) and hydrogenated over 10percent palladium on carbon catalyst (4g) at 100 psi for 72h at room temperature. The reaction mixture is filtered and the filtrate is adjusted to pH 1 with 2M- hydrogen chloride in diethyl ether. Evaporation of solvents gives a residue (which may be a solid) which is triturated with diethyl ether to give the product (which may be a solid).
  • 9
  • [ 299901-56-7 ]
  • [ 33024-60-1 ]
  • C22H30N4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
A DMF (12 ml) solution of the compound of Reference Example 3 (340 mg) was mixed with tetrahydropyran-4-ylamine hydrochloride (367 mg) and potassium carbonate (672 mg), and the mixture was stirred in an oil bath of 50°C for 36 hours. After completion of the reaction, the reaction mixture was mixed with water and extracted with ethyl acetate. The insoluble matter was filtered, and the water layer was extracted with ethyl acetate. The organic layer was washed with water and then extracted with 1 M hydrochloric acid aqueous solution. The water layer was washed with chloroform, and then the water layer was adjusted to basic (pH 9 - 11) with saturated sodium bicarbonate aqueous solution and extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate and then concentrated under a reduced pressure. The resulting product was made into hydrochloride in the usual way and recrystallized from ethanol to obtain the title compound (77 mg).1H-NMR (DMSO-d6); 0.97 (s, 9 H), 1.71 (ddd, 2 H), 2.06 - 2.12 (m, 2 H), 3.27 - 3.38 (m, 3 H), 3.43 (br, 2 H), 3.47 (br, 3 H), 3.94 (dd, 2 H), 4.28 - 4.32 (m, 2 H), 7.66 (d, 1 H), 7.79 (d, 1 H), 8.24 (s, 1 H), 9.11 (s, 1 H), 9.32 - 9.54 (m, 2 H) MS (FAB +); 415 (M + 1).
  • 10
  • [ 33024-60-1 ]
  • (2E)-3-(1-benzhydryl-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-N-tetrahydro-2H-pyran-4-ylprop-2-enamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46.5% Example 71 (2E)-3-(1-benzhydryl-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-N-tetrahydro-2H-pyran-4-ylprop-2-enamide To a solution of (2E)-3-(1-benzhydryl-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl)propenoate (300 mg, 0.759 mmol) in THF (3 ml) were added DMF (0.03 ml) and oxalylchloride (0.0796 ml, 0.912 mmol), the mixture was stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure. The residue was added under ice-cooling to a solution of <strong>[33024-60-1]tetrahydro-2H-pyran-4-ylamine hydrochloride</strong> (184 mg, 1.51 mmol), triethylamine (0.560 ml, 4.01 mmol) and THF (3 ml), the mixture was stirred under ice-cooling for 1 hour and at room temperature for 12 hours. The reaction solution was poured into water, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from hexane and ethyl acetate. Yield (amount) 173 mg, yield (rate) 46.5percent 1H-NMR (CDCl3) delta: 1.26-1.62 (2H, m), 1.84-1.90 (2H, m), 2.57 (3H, s), 2.75 (3H, s), 3.38-3.49 (2H, m), 3.92-4.10 (3H, m), 5.54 (1H, d, J = 8.2 Hz), 6.78 (1H, d, J = 15.8 Hz), 6.92 (1H, s), 7.20-7.45 (11H, m), 8.05 (1H, s). IR (KBr) cm-1; 3300, 2215, 1657, 1618, 1591, 1547, 1426, 1335, 912, 735, 698.
  • 11
  • [ 33024-60-1 ]
  • (2E)-3-{1-[bis(4-fluorophenyl)methyl]-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-(tetrahydro-2H-pyran-4-yl)prop-2-enamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.7% Example 79 (2E)-3-{1-[bis(4-fluorophenyl)methyl]-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-(tetrahydro-2H-pyran-4-yl)prop-2-enamide To a solution of (2E)-3-{1-[bis(4-fluorophenyl)methyl]-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (250 mg, 0.570 mmol) in THF (2.5 ml) were added DMF (0.025ml) and oxalylchloride (0.060 ml, 0.680 mmol), the mixture was stirred at room temperature for 1 hour and the solvent distilled off under reduced pressure. The residue was added under ice-cooling to a solution of <strong>[33024-60-1]tetrahydro-2H-pyran-4-ylamine hydrochloride</strong> (136 mg, 1.13 mmol), triethylamine (0.472 ml, 3.39 mmol) and THF (3 ml), and the mixture was stirred under ice-cooling for 2 hours and at room temperature for 12 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to give the objective product as a solid material. The resultant material was recrystallized from hexane and ethyl acetate. Yield (amount) 200 mg, yield (rate) 66.7percent 1H-NMR (CDCl3) delta: 1.43-1.58 (2H, m), 1.87-1.92 (2H, m), 2.56 (3H, s), 2.75 (3H, s), 3.42-3.50 (2H, m), 3.94-4.05 (3H, m), 5.56 (1H, d, J = 7.8 Hz), 6.78 (1H, d, J = 15.3 Hz), 6.91-7.21 (9H, m), 7.43 (1H, d, J = 15.3 Hz), 7.92 (1H, s). IR (KBr) cm-1; 3277, 2924, 2216, 1661, 1607, 1549, 1510, 1231, 1161, 1013, 837, 801, 733.
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