Sodium borohydride → 5-[4-(4-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]-quinoline-2-carboxylic acid amide

HRID 2055009Notes

Reaction equation

HRID 2055009 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:32])([CH3:31])[CH2:9][C:10]([OH:30])([C:26]([F:29])([F:28])[F:27])[CH:11]=[N:12][C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][C:17]([C:23]([NH2:25])=[O:24])=[N:18]3)=[C:4]([O:33][CH3:34])[CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:31])([CH3:32])[CH2:9][C:10]([OH:30])([C:26]([F:29])([F:27])[F:28])[CH2:11][NH:12][C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][C:17]([C:23]([NH2:25])=[O:24])=[N:18]3)=[C:4]([O:33][CH3:34])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 692037995-[4-(4-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino]-quinoline-2-carboxylic acid amide

Product 1

HCID 207862225-[4-(4-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]-quinoline-2-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogously to Example 40, 340 mg (0.69 mmol) of 5-[4-(4-chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino]quinoline-2-carboxylic acid amide is dissolved in 10 ml of methanol and mixed several times with 110 mg (2.89 mmol) of sodium borohydride. After working-up and purification on silica gel with hexane-ethyl acetate (0-100%), 280 mg (82% of theory) of the product is obtained.

Workup

  1. custompurification on silica gel with hexane-ethyl acetate (0-100%), 280 mg (82% of theory) of the product
  2. customis obtained

Sources & evidence

ORD record
ord-55214cfdbdb842e2a3355fa036b7e4dd
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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