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

HRID 2055002Notes

Reaction equation

HRID 2055002 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-].[Na+].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 5234Sodium ChlorideHCID 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 sodium 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-02a2837ec8fe43869a4248370d98b847
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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