methyl (2E,4S)-4-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-4-phenylbuta-2-enoate → methyl (4S)-4-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-4-phenylbutanoate

HRID 64471Notes

Reaction equation

HRID 64471 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@H:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)/[CH:23]=[CH:24]/[C:25]([O:27][CH3:28])=[O:26])=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(OCC)(=O)C.[C].[Pd]>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@H:22]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86713498methyl (2E,4S)-4-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-4-phenylbuta-2-enoate

Product 1

HCID 86713497methyl (4S)-4-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-4-phenylbutanoateYield 88.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 185 mg of methyl (2E,4S)-4-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-4-phenylbuta-2-enoate in 3.7 ml of ethyl acetate was added 20 mg of 10% palladium-carbon, followed by stirring for 8 hours under a hydrogen atmosphere. The reaction mixture was filtered over Celite and the solvent was evaporated under reduced pressure to obtain 165 mg of methyl (4S)-4-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-4-phenylbutanoate.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-467f81ec9fe7453c850b5551fdc041a7
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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