Water → Methyl 3-{4-[(4-{[(2-phenylethyl)(4-propyl-1,3-thiazol-2-yl)amino]methyl}benzyl)oxy]phenyl}propanoate

HRID 732213Notes

Reaction equation

HRID 732213 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]2[S:11][CH:12]=[C:13]([CH2:15][CH2:16][CH3:17])[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:21][C:22]1[CH:41]=[CH:40][C:25]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.O>CN(C)C=O>[C:1]1([CH2:7][CH2:8][N:9]([CH2:21][C:22]2[CH:41]=[CH:40][C:25]([CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)[C:10]2[S:11][CH:12]=[C:13]([CH2:15][CH2:16][CH3:17])[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoateHCID 23143297N-(2-phenylethyl)-4-propyl-1,3-thiazole-2-amine

Product 1

HCID 23143271Methyl 3-{4-[(4-{[(2-phenylethyl)(4-propyl-1,3-thiazol-2-yl)amino]methyl}benzyl)oxy]phenyl}propanoateYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-phenylethyl)-4-propyl-1,3-thiazole-2-amine (246 mg) in N,N-dimethylformamide (2 mL) was added sodium hydride (40 mg), and the mixture was stirred at room temperature for 1 hr. Methyl 3-(4-{[4-(chloromethyl)benzyl]-oxy}phenyl)propanoate (318 mg) was added to the reaction mixture at room temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:1 in volume ratio) to give the title compound (380 mg) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:1 in volume ratio)

Sources & evidence

ORD record
ord-8fde406ae8944f8e8e584153504c90a5
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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