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[ CAS No. 133427-07-3 ] {[proInfo.proName]}

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Chemical Structure| 133427-07-3
Chemical Structure| 133427-07-3
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Quality Control of [ 133427-07-3 ]

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Product Details of [ 133427-07-3 ]

CAS No. :133427-07-3 MDL No. :MFCD09842621
Formula : C9H8N2O2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :UJLRMEAGEVCFNJ-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :15098894
Synonyms :

Calculated chemistry of [ 133427-07-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.47
TPSA : 43.6 ?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) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 1.61
Log Po/w (WLOGP) : 1.12
Log Po/w (MLOGP) : 0.63
Log Po/w (SILICOS-IT) : 0.76
Consensus Log Po/w : 1.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.33
Solubility : 0.83 mg/ml ; 0.00471 mol/l
Class : Soluble
Log S (Ali) : -2.14
Solubility : 1.28 mg/ml ; 0.00729 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.16
Solubility : 1.22 mg/ml ; 0.00693 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 133427-07-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 133427-07-3 ]

* 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 [ 133427-07-3 ]

[ 133427-07-3 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 67-56-1 ]
  • [ 136117-70-9 ]
  • [ 133427-07-3 ]
  • 2
  • [ 133427-07-3 ]
  • [ 136117-74-3 ]
YieldReaction ConditionsOperation in experiment
55% [0165] To a solution of methyl imidazo[l,2-a]pyridine-8-carboxylate (1.76 g, 10 mmol) in toluene was added DIBAL (IM/THF, 20 ml) at -78 C dropwise. The mixture was stirred at - 78 C for 1 h, quenched with MeOH (2 mL) and saturated NH4CI solution (50 mL) and warmed up to rt. The mixture was continued to stir at rt for 1 h and diluted with DCM (60 mL). The aqueous layer was extracted with DCM (60 mL) twice. The combined organic layer was dried over MgS04 and concentrate. The residue was purified on silica gel with 10 %MeOH/DCM to give imidazo[l,2-a] pyridine- 8-carbaldehyde (0.8g, 55%). LRMS (M+lf) m/z 147.1.
  • 3
  • [ 24517-64-4 ]
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  • 4
  • [ 133427-07-3 ]
  • [ 136117-78-7 ]
  • 5
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  • [ 136117-76-5 ]
  • 6
  • [ 133427-07-3 ]
  • [ 136117-87-8 ]
  • 7
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  • [ 136117-91-4 ]
  • 8
  • [ 107-20-0 ]
  • [ 14667-47-1 ]
  • [ 7440-44-0 ]
  • [ 133427-07-3 ]
YieldReaction ConditionsOperation in experiment
In ethanol; for 18h;Heating / reflux; A mixture of methyl 2-aminonicotinate (WO 89/01488 pg 33, prep 17) (1 g, 6.56 mmol), and chloroacetaldehyde (1.05 ml, 6.56 mmol) in ethanol (5 ml) was heated under reflux for 18 hours. The cooled mixture was diluted with water (10 ml), 0.88 ammonia (1 ml) added and the solution concentrated under reduced pressure. The residue was dissolved in methanol and the dark solution treated with charcoal, the mixture filtered and the filtrate evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (97:2.5:0.5) as eluant, and the product triturated with ether, to afford the title compound, 768 mg. 1H-NMR (CDCl3, 400 MHz) delta: 4.02 (s, 3H), 6.83 (s, 1H), 7.63 (s, 1H), 7.79 (s, 1H), 8.00 (d, 1H), 8.31 (d, 1H). LRMS: m/z TSP+ 177.2 [MH+]
  • 9
  • [ 17739-45-6 ]
  • [ 133427-07-3 ]
  • cis-5-fluoro-N-(4-{5-methyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoylamino}-cyclohexyl)-2-(tetrahydro-thiopyran-4-yloxy)-nicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 20 - 60℃; for 22h; A mixture of the phenol from example 22 (1.29 g, 2.65 mmol), potassium carbonate (690 mg, 5 mmol), and 2-(2-bromoethoxy)tetrahydro-2H-pyran (840 mg, 4 mmol) in 1-methyl-2-pyrrolidinone (10 ml), was heated at 60 C. for 4 hours, followed by a further 18 hours at room temperature. The mixture was diluted with ethyl acetate and washed with water (*3), then brine, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate as the eluant to afford the title compound as a white foam, 1.20 g. 1H-NMR (CDCl3, 400 MHz) delta: 1.37 (m, 2H), 1.46 (m, 2H), 1.61 (m, 4H), 1.76 (m, 4H), 1.92 (m, 4H), 2.33 (s, 3H), 2.43 (m, 2H), 2.72 (m, 4H), 3.39 (m, 1H), 3.72 (m, 1H), 3.86 (m, 1H), 4.13 (m, 3H), 4.30 (t, 2H), 4.54 (m, 1H), 5.24 (m, 1H), 6.87 (d, 1H), 7.21 (d, 1H), 8.04 (m, 3H), 8.13 (d, 1H), 8.26 (dd, 1H). LRMS: m/z APCI- 614 [M-H-]
  • 10
  • [ 107-20-0 ]
  • [ 14667-47-1 ]
  • [ 133427-07-3 ]
YieldReaction ConditionsOperation in experiment
In ethanol; for 18h;Heating / reflux; [0306] A mixture of methyl 2-aminonicotinate (prepared according to the method of WO 89/01488 at page 33, prep 17) (1 g, 6.56 mmol), and chloroacetaldehyde (1.05 mL, 6.56 mmol) in ethanol (5 mL) was heated under reflux for 18 hours. The cooled mixture was diluted with water (10 mL), 0.88 ammonia (1 mL) added and the solution concentrated in vacuo. The residue was dissolved in methanol and the dark solution treated with charcoal, the mixture filtered and the filtrate concentrated in vacuo. The residue was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (97:2.5:0.5) as eluant, and the product triturated with ether, to afford the title compound, 768 mg. [0307] 1HNMR (CDCl3, 400 MHz): 4.02 (s, 3H), 6.83 (s, 1H), 7.63 (s, 1H), 7.79 (s, 1H), 8.00 (d, 1H), 8.31 (d, 1H). [0308] MS TSP+ m/z 177.2 [MH+]
In ethanol; for 18h;Heating / reflux; [0302] [C00008] [00008] [0303] A mixture of methyl 2-aminonicotinate (WO 89/01488 pg33, prep 17) (1 g, 6.56 mmol), and chloroacetaldehyde (1.05 mL, 6.56 mmol) in ethanol (5 mL) was heated under reflux for 18 hours. The cooled mixture was diluted with water (10 mL), 0.88 ammonia (1 mL) added and the solution concentrated in vacuo. The residue was dissolved in methanol and the dark solution treated with charcoal, the mixture filtered and the filtrate concentrated in vacuo. The residue was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (97:2.5:0.5) as eluant, and the product triturated with ether, to afford the title compound, 768 mg. [0304] 1H NMR (CDCl3, 400MHz): delta:4.02 (s, 3H), 6.83 (s, 1H), 7.63 (s, 1H), 7.79 (s, 1H), 8.00 (d, 1H), 8.31 (d, 1H). [0305] MS TSP+m/z 177.2 [MH+]
With sodium hydrogencarbonate; In ethanol; water; for 18h;Reflux; Inert atmosphere; [0154] To a solution of methyl 2-amino-pyridine-3-carboxylate (5 g, 35 mmol, 1.0 eq) in ethanol (250 mL) was added NaHC03 (5.08 g) and chloroacetaldehyde in water (35 mL of 45% in water, 148 mmol, 4.5 eq). The reaction mixture was heated at reflux for 18 h. Solvent was removed and the residue was basified with Na2C03 and then extracted with DCM. Organic layers were combined and evaporated to give a residue, which was purified by column to give the titled compound.
  • 11
  • [ 133427-07-3 ]
  • [ 133427-08-4 ]
YieldReaction ConditionsOperation in experiment
The solution was concentrated under reduced pressure to remove the methanol, the aqueous solution acidified using 2N hydrochloric acid, and the mixture evaporated under reduced pressure to give the title compound as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz) delta: 7.60 (dd, 1H), 8.10 (s, 1H), 8.41 (d, 1H), 8.55 (s, 1H), 9.18 (d, 1H) LRMS: m/z ES+ 163 [MH]+
[0310] Lithium hydroxide solution (2.5 mL, 1M in water) was added to a solution of the ester from preparation 8 (400 mg, 2.27 mmol) in methanol (5 mL) and the solution stirred at room temperature for 90 minutes. The solution was concentrated in vacuo to remove the methanol, the aqueous solution acidified using 2M hydrochloric acid, and the mixture concentrated in vacuo to give the title compound as a yellow solid. [0311] 1HNMR (DMSO-D6, 400 MHz): 7.60 (dd, 1H), 8.10 (s, 1H), 8.41 (d, 1H), 8.55 (s, 1H), 9.18 (d, 1H) [0312] MS TSP+ m/z 163 [MH]+
[0306] [C00009] [00009] [0307] Lithium hydroxide solution (2.5 ml, 1M in water) was added to a solution of the ester from preparation 3 (400 mg, 2.27 mmol) in methanol (5 ml) and the solution stirred at room temperature for 90 minutes. The solution was concentrated in vacuo to remove the methanol, the aqueous solution acidified using 2M hydrochloric acid, and the mixture evaporated under reduced pressure to give the title compound as a yellow solid. [0308] 1H NMR (DMSO-D6, 400 MHz): delta: 7.60 (dd, 1H), 8.10 (s, 1H), 8.41 (d, 1H), 8.55 (s, 1H), 9.18 (d, 1H) [0309] MS TSP+m/z 163 [MH]+
  • 12
  • [ 14667-47-1 ]
  • [ 133603-12-0 ]
  • [ 133427-07-3 ]
YieldReaction ConditionsOperation in experiment
55% With hydrogen bromide; sodium hydrogencarbonate; In ethanol; Example 1 Syntheses of methyl imidazo[1,2-a]pyridine-8-carboxylate (Compound No. 1-1) 47% Hydrogen bromide (2.5ml, 14.4 m moles) was added to diethoxybromoethane (2.0ml, 13.2 m moles), and the mixture was stirred at 50 C. for 2 hours. The reaction mixture was cooled to room temperature, and ethanol (7.0 ml) and sodium bicarbonate (1.0 g, 11.9 m moles) were added thereto. The mixture was stirred, and insoluble substance was filtered off. To the filtrate were added methyl 2-aminonicotinate (1.0 g, 6.6 m moles), sodium bicarbonate (2.0 g, 13.8 m moles) and ethanol (7.0 ml), and the mixture was refluxed under heating for 4 hours. The reaction mixture was cooled to room temperature, and saturated aqueous solution of sodium bicarbonate was added thereto. The mixture was extracted with dichloromethane (100 ml*3), and the extract was washed with water, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure. The concentrate was purified by column chromatography on silica gel (eluent: chloroform and then chloroform/methanol=9/1) to give the object compound (0.6 g, yield 55%) as yellow crystals. m.p. 67-69 C.
  • 13
  • [ 5345-47-1 ]
  • [ 133427-07-3 ]
  • 14
  • [ 133427-07-3 ]
  • [ 885276-95-9 ]
YieldReaction ConditionsOperation in experiment
With N-iodo-succinimide; In acetonitrile; at 20℃; for 2h; A mixture of imidazo[l,2-a]pyridine-8-carboxylic acid methyl ester (3.24 g, 18.3 mmol) and N-iodosuccinimide ( S) (4.11 g, 18.3 mmol) in acetonitrile (50 mL) is stirred at room temperature. After 2 hours, the reaction mixture is quenched with saturated aqueous Na2S2C>3 and extracted with EtOAc (3 x 100 mL). The combined organic layers are washed with water, brine, dried over Na2S04 and concentrated. The crude material is purified by silica gel chromatography eluting with 80% EtOAc in hexanes to afford 3-iodo-imidazo[l,2-a]pyridine-8-carboxylic acid methyl ester. Mp: 99-110C.
  • 15
  • [ 133427-07-3 ]
  • [ 1300022-42-7 ]
  • 16
  • [ 67-56-1 ]
  • [ 133427-08-4 ]
  • [ 133427-07-3 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 8h;Reflux; To a stirred solution of imidazo[l,2-a]pyridine-8-carboxylic acid (3.8 g, 23 mmol) in methanol (100 mL) is added thionylchloride (8.36 g, 70.3 mmol) and the mixture is warmed at reflux. After 8 hours, the reaction mixture is cooled to room temperature and quenched with saturated aqueous NaHCC>3, and extracted with EtOAc (3 x 250 mL). The combined organic layers are washed with water, brine, dried over Na2S04 and concentrated. The crude material is purified by silica gel chromatography eluting with 3% MeOH in CH2CI2 to afford imidazo[l,2-a]pyridine-8-carboxylic acid methyl ester. Mp: 71-73C.
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