Water → HCID 59766923, compound

HRID 2389725Notes

Reaction equation

HRID 2389725 reaction equation
[C:1]([O:5][C:6](=[O:48])[N:7]([CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([C:36]([C:38]2[S:42][C:41]3[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=3[C:39]=2[Cl:47])=[O:37])[CH2:16][C:17]2[CH:18]=[C:19]([C:24]3[CH:29]=[CH:28][C:27]([C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=3)[CH:20]=[CH:21][C:22]=2[F:23])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>CCO.C(Cl)Cl>[C:1]([O:5][C:6](=[O:48])[N:7]([CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([C:36]([C:38]2[S:42][C:41]3[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=3[C:39]=2[Cl:47])=[O:37])[CH2:16][C:17]2[CH:18]=[C:19]([C:24]3[CH:25]=[CH:26][C:27]([CH:30]([OH:35])[C:31]([F:33])([F:32])[F:34])=[CH:28][CH:29]=3)[CH:20]=[CH:21][C:22]=2[F:23])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 59766908(4-{(3-Chloro-benzo[b]thiophene-2-carbonyl)-[4-fluoro-4'-(2,2,2-trifluoro-acetyl)-biphenyl-3-ylmethyl]-amino}-cyclohexyl)-methyl-carbamic acid tert-butyl ester

Product 1

HCID 59766923HCID 59766923, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetophenone (265) (90 mg, 0.13 mmol) was dissolved in EtOH (0.9 mL) with a little DCM. Sodium borohydride (8 mg, 0.21 mmol) was added portionwise and the reaction stirred at RT until complete. H2O (5 mL) was added and the product extracted with EtOAc (2×5 mL). Drying (MgSO4), filtration, reduction in vacuo and chromatography with EtOAc/heptanes gave the title compound.

Workup

  1. extractionthe product extracted with EtOAc (2×5 mL)
  2. customDrying
  3. filtration(MgSO4), filtration, reduction in vacuo and chromatography with EtOAc/heptanes

Sources & evidence

ORD record
ord-5ba0c4a2d4fd44b596cd0973088dfe74
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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