Triethylamine → 5-(6-Cyano-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 2382732Notes

Reaction equation

HRID 2382732 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:14])[C:10]=1[C:11](Cl)=[O:12])=[O:5])[CH3:2].[NH2:15][C:16]1[C:21]([C:22]#[N:23])=[CH:20][N:19]2[CH:24]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:26]=[C:18]2[CH:17]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:14])[C:10]=1[C:11](=[O:12])[NH:15][C:16]1[C:21]([C:22]#[N:23])=[CH:20][N:19]2[CH:24]=[C:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:26]=[C:18]2[CH:17]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60136485Ethyl 5-(chlorocarbonyl)-1-methyl-1H-pyrazole-4-carboxylateHCID 670415967-Amino-2-phenylimidazo[1,2-A]pyridine-6-carbonitrile

Product 1

HCID 510343645-(6-Cyano-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl esterYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chlorocarbonyl-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (940 mg, 4.33 mmol) was added slowly to a solution of 7-amino-2-phenyl-imidazo[1,2-a]pyridine-6-carbonitrile (410 mg, 1.8 mmol) and triethylamine (363 mg) in dichloromethane (8 ml), and the mixture was stirred at r.t. overnight. The mixture was extracted with dichloromethane, the combined organic layers were dried (Na2SO4), and evaporated. The title compound (310 mg, 42%) was obtained by column chromatography (silica gel, heptane:ethyl acetate=80:20-60:40). MS (m/e)=413.3 [M−H+].

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialthe combined organic layers were dried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-23a752db54004adcaf2e0c9618916ee4
Source dataset
uspto-grants-2012_09
Patent number
US08263584B2

Reaction notes

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