Water → 4-Biphenyl-3-yl-N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamide

HRID 1158704노트

반응식

HRID 1158704 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].[C:17]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:18]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:17]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[CH2:24][CH2:25][N:26]([C:5]([NH:6][C:7]3[O:11][N:10]=[C:9]([CH3:12])[C:8]=3[CH3:13])=[O:14])[CH2:27][CH2:28]2)[CH:18]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27567121-Biphenyl-3-yl-piperazineHCID 862452572,2,2-Trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate

생성물 1

HCID 159507444-Biphenyl-3-yl-N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamide수율 62.7%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixed solution of 2,2,2-trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate (265 mg, 0.923 mmol), 1-biphenyl-3-ylpiperazine (200 mg, 0.839 mmol) and diisopropylethylamine (0.292 ml, 1.68 mmol) in dimethylsulfoxide (2.5 ml) was stirred at 70° C. for 14 hours. To the reaction solution was added water, 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 (ethyl acetate:hexane=1:1), and then recrystallized from a mixed solvent of hexane and tetrahydrofuran to give the titled compound (198 mg, 62.6%) 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 (ethyl acetate:hexane=1:1)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

출처 및 근거

ORD 기록
ord-bcaa11f496414869bb89a6e361dc56f4
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812025B2

반응 노트

불러오는 중…