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

HRID 2215460Notes

Reaction equation

HRID 2215460 reaction equation
[CH2:1]([N:3]([CH2:37][CH3:38])[C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[N:16]=[CH:17][C:18]([OH:36])([C:32]([F:35])([F:34])[F:33])[CH2:19][C:20]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])([CH3:22])[CH3:21])[N:7]=1)=[O:5])[CH3:2].[BH4-].[Na+].[Cl-].C(OCC)(=O)C>C(O)C.[Ti]>[CH2:37]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[NH:16][CH2:17][C:18]([OH:36])([C:32]([F:34])([F:33])[F:35])[CH2:19][C:20]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])([CH3:21])[CH3:22])[N:7]=1)=[O:5])[CH3:38]

Participants

7

Reactant 4

HCID 312ChlorideHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 692051715-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino]quinoline-2-carboxylic acid diethylamide

Product 1

HCID 207862335-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylamino]quinoline-2-carboxylic acid diethylamideYield 92%

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 702EthanolSolvent

Procedure

A solution that consists of 230 mg (0.45 mmol) of 5-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentylidenamino]quinoline-2-carboxylic acid diethylamide and 0.132 ml (0.58 mmol) of titanium tetraethylate in 14 ml of ethanol is mixed with 135 mg (3.55 mmol) of sodium borohydride. After 6 hours at room temperature, the reaction is halted by adding saturated socium chloride solution and ethyl acetate. The precipitate that is produced is suctioned off on Celite. The filtrate is washed with saturated sodium chloride solution, and it is dried on sodium sulfate. After removal of the solvent and purification on silica gel with hexane-ethyl acetate (0–70%), 220 mg (92%) of the product is obtained.

Workup

  1. customThe precipitate that is produced
  2. washThe filtrate is washed with saturated sodium chloride solution, and it
  3. customis dried on sodium sulfate
  4. customAfter removal of the solvent and purification on silica gel with hexane-ethyl acetate (0–70%)

Sources & evidence

ORD record
ord-5bf47f9b6c2d44158b52999d91b8ade3
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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