Sodium Hydroxide → 1-(2-Aminoquinolin-5-ylamino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-ol

HRID 2054948Notes

Reaction equation

HRID 2054948 reaction equation
C([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:15][CH2:16][C:17]([C:32]([F:35])([F:34])[F:33])([OH:31])[CH2:18][C:19]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[O:29][CH3:30])([CH3:21])[CH3:20])[N:6]=1)(=O)C.[OH-].[Na+]>CCO.C1COCC1.[Na+].[Cl-]>[NH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:15][CH2:16][C:17]([C:32]([F:35])([F:33])[F:34])([OH:31])[CH2:18][C:19]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[O:29][CH3:30])([CH3:21])[CH3:20])[N:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 219488711-(2-Acetylaminoquinolin-5-ylamino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-ol

Product 1

HCID 219488431-(2-Aminoquinolin-5-ylamino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-olYield 80.2%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 535 mg (1.05 mmol) of 1-(2-acetylaminoquinolin-5-ylamino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-ol in 18 ml of EtOH-THF (2:1) is refluxed with 12 ml of 3N sodium hydroxide solution for 90 minutes. The batch is diluted with saturated NaCl and extracted with ethyl acetate. The extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with ethyl acetate yields 380 mg of the product as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts are dried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-35a3368ccd5943479fc20d5081fb7066
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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