Water → HCID 59571056, compound

HRID 2192957Notes

Reaction equation

HRID 2192957 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6](/[C:16](=[CH:26]\[C@H:27]3[CH2:31][CH2:30][C:29](=[O:32])[CH2:28]3)/[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1.[BH4-].[Na+].O>C(O)C.C(Cl)(Cl)Cl>[CH:1]1([C:4]2[CH:5]=[C:6](/[C:16](=[CH:26]\[C@H:27]3[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28]3)/[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 44129689HCID 44129689, compound

Product 1

HCID 59571056HCID 59571056, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of (2E)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-N-(1-methyl-1H-pyrazol-3-yl)-3-[(1S)-3-oxocyclopentyl]acrylamide (140 mg) in ethanol (2 mL) was added sodium borohydride (12 mg) at 0° C., followed by stirring for 15 minutes. The reaction mixture was diluted with chloroform and the reaction was stopped with water. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated to obtain (2E)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1S)-3-hydroxycyclopentyl]-N-(1-methyl-1H-pyrazol-3-yl)acrylamide (140 mg) as a colorless amorphous substance.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-57c173715c9549048ff638c54817a166
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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