Water → 4-[4-(2,3-Dichlorophenyl)-1,3-thiazol-2-yl]-N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamide

HRID 2263323노트

반응식

HRID 2263323 반응식
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][C:9](=[O:16])OCC(Cl)(Cl)Cl)[O:4][N:3]=1.[Cl:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[C:25]1[N:26]=[C:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[S:28][CH:29]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[Cl:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[C:25]1[N:26]=[C:27]([N:30]2[CH2:35][CH2:34][N:33]([C:9]([NH:8][C:5]3[O:4][N:3]=[C:2]([CH3:1])[C:6]=3[CH3:7])=[O:16])[CH2:32][CH2:31]2)[S:28][CH:29]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 68776332HCID 68776332, 화합물HCID 862452572,2,2-Trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate

생성물 1

HCID 115832774-[4-(2,3-Dichlorophenyl)-1,3-thiazol-2-yl]-N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamide수율 15.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
70 °C

실험 절차

A mixture of 2,2,2-trichloroethyl (3,4-dimethylisoxazol-5-yl)carbamate (121 mg, 0.420 mmol), 1-[4-(2,3-dichlorophenyl)-1,3-thiazol-2-yl]piperazine (120 mg, 0.382 mmol) and diisopropylethylamine (0.133 ml, 0.764 mmol) in dimethyl sulfoxide (1.2 ml) was stirred at 70° C. for 3 days. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1), and recrystallized from a mixed solvent of hexane and ethyl acetate to give 27.0 mg (15.6%) of the desired product as a solid. mp 175-176° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)
  6. customrecrystallized from a mixed solvent of hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-390c0a7f7ce6464a9c19ec86e85b21f4
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851473B2

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