Water → HCID 69135091, compound

HRID 969518Notes

Reaction equation

HRID 969518 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]([C:5]1[C:18]([CH2:19][CH2:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:17]([OH:29])[C:8]2[N:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4].[BH4-].[Na+].[Cl-].[NH4+].O>C(O)C>[CH3:30][N:2]([CH3:1])[C:3]([C:5]1[C:18]([CH2:19][CH2:20][CH:21]([OH:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:17]([OH:29])[C:8]2[N:9]=[C:10]([C:13]([F:16])([F:14])[F:15])[N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 69136057HCID 69136057, compound

Product 1

HCID 69135091HCID 69135091, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.0 g (7.2 mmol) 7-hydroxy-3-methyl-6-(3-oxo-3-phenyl-propyl)-2-trifluoromethyl-3H-benzimidazole-5-carboxylic acid dimethylamide in ethanol (100 ml) was treated with 324 mg (8.6 mmol) sodium borohydride and the reaction was stirred at room temperature for 3 h. A saturated ammonium chloride solution was added, the reaction was poured into water (100 ml) and extracted with dichloromethane. The organic layers were dried over magnesium sulphate and concentrated in vacuo to afford 3.0 g (98%) of the title compound as a brown foam.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layers were dried over magnesium sulphate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53c98a3f2ac94aef82d1459e48c79f57
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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