Sodium borohydride → 3-[1-(5-Fluoro-2-methoxyphenyl)cycloprop-1-yl]-1-(2-(hydroxymethyl)quinolin-5-ylamino)-2-(trifluoromethyl)propan-2-ol

HRID 2054996Notes

Reaction equation

HRID 2054996 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:15]=[CH:16][C:17]([OH:35])([C:31]([F:34])([F:33])[F:32])[CH2:18][C:19]2([C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3[O:29][CH3:30])[CH2:21][CH2:20]2)[N:6]=1)=O.[BH4-].[Na+]>>[F:28][C:26]1[CH:25]=[CH:24][C:23]([O:29][CH3:30])=[C:22]([C:19]2([CH2:18][C:17]([C:31]([F:32])([F:33])[F:34])([OH:35])[CH2:16][NH:15][C:11]3[CH:10]=[CH:9][CH:8]=[C:7]4[C:12]=3[CH:13]=[CH:14][C:5]([CH2:3][OH:2])=[N:6]4)[CH2:21][CH2:20]2)[CH:27]=1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 69205241HCID 69205241, compound

Product 1

HCID 219488603-[1-(5-Fluoro-2-methoxyphenyl)cycloprop-1-yl]-1-(2-(hydroxymethyl)quinolin-5-ylamino)-2-(trifluoromethyl)propan-2-ol

Procedure

Analogously to Example 40, 200 mg (0.41 mmol) of 5-{3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-hydroxy-2-(trifluoromethyl)propylidenamino}-quinoline-2-carboxylic acid methyl ester is reacted with 156 mg (4.1 mmol) of sodium borohydride. After working-up and purification on silica gel with hexane-ethyl acetate (0-75%), 119 mg (63% of theory) of the product is obtained.

Workup

  1. custompurification on silica gel with hexane-ethyl acetate (0-75%), 119 mg (63% of theory) of the product
  2. customis obtained

Sources & evidence

ORD record
ord-8b0bd5ec383b4e0e8047b5700740ca95
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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