Ammonia → 2-[6-(Tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyridin-3-yl]-acetamide

HRID 402895Notes

Reaction equation

HRID 402895 reaction equation
[NH3:1].C([O:4][C:5](=O)[CH2:6][C:7]1[N:11]2[CH:12]=[C:13]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:17][SiH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:14]=[CH:15][C:10]2=[N:9][C:8]=1[CH3:35])C>>[C:19]([SiH2:18][O:17][C:16]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:13]1[CH:14]=[CH:15][C:10]2[N:11]([C:7]([CH2:6][C:5]([NH2:1])=[O:4])=[C:8]([CH3:35])[N:9]=2)[CH:12]=1)([CH3:21])([CH3:22])[CH3:20]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 131729756[6-(Tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyridin-3-yl]-acetic acid ethyl ester

Product 1

HCID 1317297552-[6-(Tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyridin-3-yl]-acetamideYield 90%

Procedure

At −78° C., ammonia (25 ml) is added to [6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyridin-3-yl]-acetic acid ethyl ester (950 mg, 1.85 mmol) in a glass autoclave. The reaction mixture is stirred at room temperature for 48 hours. After removal of volatiles, the residue is recrystallized from diethylether to afford the title compound (800 mg, 90%). MS (ES+): 458 (M+H)+.

Workup

  1. customAfter removal of volatiles
  2. customthe residue is recrystallized from diethylether

Sources & evidence

ORD record
ord-7cd31d4c29f845f9b02a5ee155624269
Source dataset
uspto-grants-2014_06
Patent number
US08742132B2

Reaction notes

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