Ammonia → 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-[(2,5-diethoxybenzyl)oxy]thiophene-2-carboxamide

HRID 2391679Notes

Reaction equation

HRID 2391679 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]=[CH:17][N:18]([C:19]3[S:23][C:22]([C:24]([O:26]C)=O)=[C:21]([O:28][CH2:29][C:30]4[CH:35]=[C:34]([O:36][CH2:37][CH3:38])[CH:33]=[CH:32][C:31]=4[O:39][CH2:40][CH3:41])[CH:20]=3)[C:12]=2[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:42]>CO>[Si:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]=[CH:17][N:18]([C:19]3[S:23][C:22]([C:24]([NH2:42])=[O:26])=[C:21]([O:28][CH2:29][C:30]4[CH:35]=[C:34]([O:36][CH2:37][CH3:38])[CH:33]=[CH:32][C:31]=4[O:39][CH2:40][CH3:41])[CH:20]=3)[C:12]=2[CH:11]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68766692methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-[(2,5-diethoxybenzyl)oxy]thiophene-2-carboxylate

Product 1

HCID 687689785-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-[(2,5-diethoxybenzyl)oxy]thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner as described for example A9, 1.50 g of methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-[(2,5-diethoxybenzyl)oxy]thiophene-2-carboxylate and 250 ml of a saturated solution of ammonia in methanol yield the title compound.

Sources & evidence

ORD record
ord-7a1a3cbae1c940f69800893aff4794ad
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

Loading…