Sodium Chloride → 5-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]-quinoline-2-carboxylic acid methylamide

HRID 2182707Notes

Reaction equation

HRID 2182707 reaction equation
[CH3:1][NH: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]([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:4].[BH4-].[Na+].[Cl-].[Na+].C(OCC)(=O)C>C(O)C.[Ti]>[CH3:1][NH:2][C:3]([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]([OH:35])([C:31]([F:32])([F:33])[F:34])[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:4]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 692048185-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino]quinoline-2-carboxylic acid methylamide

Product 1

HCID 207862265-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]-quinoline-2-carboxylic acid methylamide

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 702EthanolSolvent

Procedure

155 mg (0.315 mmol) of 5-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino]quinoline-2-carboxylic acid methylamide is dissolved in 10 ml of ethanol and mixed with 0.09 ml (0.4 mmol) of titanium tetraethylate as well as 94 mg (2.6 mmol) of sodium borohydride. The reaction is halted after 5 hours by adding saturated sodium chloride solution and ethyl acetate. Insoluble components are filtered. The filtrate is extracted with ethyl acetate, the combined organic phases are dried on sodium sulfate, and the solvent is removed in a vacuum. After chromatography on silica gel with hexane-ethyl acetate (0-50%), 110 mg (71% of theory) of the product is obtained.

Workup

  1. filtrationInsoluble components are filtered
  2. extractionThe filtrate is extracted with ethyl acetate
  3. customthe combined organic phases are dried on sodium sulfate
  4. customthe solvent is removed in a vacuum
  5. customAfter chromatography on silica gel with hexane-ethyl acetate (0-50%), 110 mg (71% of theory) of the product is obtained

Sources & evidence

ORD record
ord-1b8ddc74693246c6a287e7911316da76
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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