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

HRID 2391668Notes

Reaction equation

HRID 2391668 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[Cl:45])[O:11][C:12]1[CH:16]=[C:15]([N:17]2[C:25]3[CH:24]=[C:23]([CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[N:22]=[CH:21][C:20]=3[N:19]=[CH:18]2)[S:14][C:13]=1[C:35]([O:37]C)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:46]>CO>[Si:1]([O:8][CH2:9][C@@H:10]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[Cl:45])[O:11][C:12]1[CH:16]=[C:15]([N:17]2[C:25]3[CH:24]=[C:23]([CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[N:22]=[CH:21][C:20]=3[N:19]=[CH:18]2)[S:14][C:13]=1[C:35]([NH2:46])=[O:37])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68768690methyl 3-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-chlorophenyl)ethoxy]-5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]thiophene-2-carboxylate

Product 1

HCID 687661183-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-chlorophenyl)ethoxy]-5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner as described for example A5, 500 mg of methyl 3-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-chlorophenyl)ethoxy]-5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]thiophene-2-carboxylate and 40 ml of a saturated solution of ammonia in methanol yield the title compound.

Sources & evidence

ORD record
ord-6f9ef4ccd08a48e1b371445dddd72f10
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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