Water → HCID 69135223, compound

HRID 969519Notes

Reaction equation

HRID 969519 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]([C:5]1[C:17]([CH2:18][CH2:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:16]([OH:28])[C:8]2[N:9]=[C:10]([CH:13]3[CH2:15][CH2:14]3)[N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4].[BH4-].[Na+].[Cl-].[NH4+].O>C(O)C>[CH3:29][N:2]([CH3:1])[C:3]([C:5]1[C:17]([CH2:18][CH2:19][CH:20]([OH:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:16]([OH:28])[C:8]2[N:9]=[C:10]([CH:13]3[CH2:15][CH2:14]3)[N:11]([CH3:12])[C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 69135069HCID 69135069, compound

Product 1

HCID 69135223HCID 69135223, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.5 g (4.0 mmol) 2-cyclopropyl-7-hydroxy-3-methyl-6-(3-oxo-3-phenyl-propyl)-3H-benzoimidazole-5-carboxylic acid dimethylamide in ethanol (22 ml) was treated with 283 mg (6.3 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 and extracted with dichloromethane (3×100 ml). The organic layers were dried over magnesium sulphate and concentrated in vacuo to afford 1.5 g (100%) of the title compound as a orange-brown solid. m.p. 92+-94° C.

Workup

  1. extractionextracted with dichloromethane (3×100 ml)
  2. dry with materialThe organic layers were dried over magnesium sulphate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7515c39580e34875a8ecffe46a7df657
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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