Water → N-(3,4-Dimethylisoxazol-5-yl)-4-[3-(3-thienyl)phenyl]piperazine-1-carboxamide

HRID 1158720

반응식

HRID 1158720 반응식
ClC(Cl)(Cl)CO[C:5](=[O:14])[NH:6][C:7]1[O:11][N:10]=[C:9]([CH3:12])[C:8]=1[CH3:13].[S:17]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[C:24]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:25]=[CH:26][CH:27]=2)=[CH:18]1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH3:12][C:9]1[C:8]([CH3:13])=[C:7]([NH:6][C:5]([N:31]2[CH2:32][CH2:33][N:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([C:19]4[CH:20]=[CH:21][S:17][CH:18]=4)[CH:23]=3)[CH2:29][CH2:30]2)=[O:14])[O:11][N:10]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 589851401-[3-(3-Thienyl)phenyl]piperazineHCID 86245257HCID 86245257, 화합물

생성물 1

HCID 16113933N-(3,4-Dimethylisoxazol-5-yl)-4-[3-(3-thienyl)phenyl]piperazine-1-carboxamide수율 19.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixed solution of 2,2,2-trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate (129 mg, 0.450 mmol), 1-[3-(3-thienyl)phenyl]piperazine (100 mg, 0.409 mmol) and diisopropylethylamine (0.143 ml, 0.818 mmol) in dimethylsulfoxide (1.5 ml) was stirred at 70° C. for 15 hours. Water was poured into the reaction solution, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduce pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:7), and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give the titled compound 30.7 mg (19.6%) as solid product.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:7)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

출처 및 근거

ORD 기록
ord-88c75a60a9314b91b8af8dc7309bc0e7
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812025B2

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