Hydrochloric Acid → Ethyl 3-[2-fluoro-4-({4-[((2-phenylethyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]-benzyl}oxy)phenyl]propanoate

HRID 732223Notes

Reaction equation

HRID 732223 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:28][C:29]1[CH:50]=[CH:49][C:32]([CH2:33][O:34][C:35]2[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])=[C:37]([F:48])[CH:36]=2)=[CH:31][CH:30]=1.Cl>CN(C)C=O>[F:48][C:37]1[CH:36]=[C:35]([O:34][CH2:33][C:32]2[CH:49]=[CH:50][C:29]([CH2:28][N:9]([CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:10]3[S:11][CH:12]=[C:13]([C:15]4[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:19][CH:20]=4)[N:14]=3)=[CH:30][CH:31]=2)[CH:40]=[CH:39][C:38]=1[CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 23143241Ethyl 3-(4-([4-(chloromethyl)benzyl]oxy}-2-fluorophenyl)propanoateHCID 23143279N-(2-phenylethyl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole-2-amine

Product 1

HCID 23143236Ethyl 3-[2-fluoro-4-({4-[((2-phenylethyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]-benzyl}oxy)phenyl]propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-phenylethyl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole-2-amine (500 mg, 1.43 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (50 mg, in oil, 1.3 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hr. Ethyl 3-(4-{[4-(chloromethyl)benzyl]oxy}-2-fluorophenyl)propanoate (350 mg, 1.0 mmol) was added, and the mixture was further stirred at room temperature for 2 hr. The reaction mixture was poured into 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-3:2 in volume ratio) to give the title compound as a yellow oil.

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-3:2 in volume ratio)

Sources & evidence

ORD record
ord-9406cc8c63ac435ca948c7e6d7aa8044
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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