Water → Methyl 4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzoate

HRID 1691528Notes

Reaction equation

HRID 1691528 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:10]=1.[H-].[Na+].Br[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1.O>CN(C)C=O>[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][N:5]([CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)[C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:20])[F:19])=[CH:13][CH:12]=2)[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 23143261N-(3-Methylbutyl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine

Product 1

HCID 23157327Methyl 4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzoateYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-methylbutyl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole-2-amine (1.20 g, 3.82 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (60% in oil, 0.229 g, 5.73 mmol). The mixture was stirred for 30 min, and methyl 4-(bromomethyl)benzoate (1.05 g, 4.58 mmol) was added. The mixture was stirred at 60° C. for 1.5 hr, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:97-40:60) to give the title compound (1.34 g, yield 76%) as a yellow oil.

Workup

  1. stirringThe mixture was stirred at 60° C. for 1.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:97-40:60)

Sources & evidence

ORD record
ord-cb8da1d16deb44b5941f8d11cfb933ee
Source dataset
uspto-grants-2012_04
Patent number
US08153694B2

Reaction notes

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