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

HRID 2182667Notes

Reaction equation

HRID 2182667 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-a69a88ba80c346a39706d1dc10815a76
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

Loading…