Water → HCID 69135242, compound

HRID 969517Notes

Reaction equation

HRID 969517 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:16]([CH2:17][CH2:18][CH2:19][C:20]2[CH2:21][C:22](=O)[CH:23]=[CH:24][CH:25]=2)=[C:15]([OH:27])[C:9]2[N:10]=[C:11]([CH3:14])[N:12]([CH3:13])[C:8]=2[CH:7]=1)=[O:5])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+].[OH2:32]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:16]([CH2:17][CH2:18][CH:19]([OH:32])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:15]([OH:27])[C:9]2[N:10]=[C:11]([CH3:14])[N:12]([CH3:13])[C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 69522549HCID 69522549, compound

Product 1

HCID 69135242HCID 69135242, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.6 g (12.5 mmol) 7-hydroxy-2,3-dimethyl-6-(3-oxo-phenylpropyl)-3H-benzimidazole-5-carboxylic acid ethyl ester in ethanol (200 ml) was treated with 570 mg (15.0 mmol) sodium borohydride and the reaction was stirred at room temperature for 3 h. A saturated ammonium chloride solution was added and the reaction was poured into water (200 ml). The precipitate was filtered off and dried in vacuo at 40° C. to afford 4.4 g (95%) of the title compound as a white solid. m.p. 193°-195° C.

Workup

  1. filtrationThe precipitate was filtered off
  2. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-16cd5ec1a05547f484e8702469a5dd99
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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