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

HRID 216676Notes

Reaction equation

HRID 216676 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-c7aaad74e02c4ff9abfd1efec9710f1f
Source dataset
uspto-grants-2012_06
Patent number
US08193236B2

Reaction notes

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