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Water → 4-[4-(3-cyanophenyl)-1,3-thiazol-2-yl]-N-pyridin-3-ylpiperazine-1-carboxamide

HRID 2263281
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인쇄 미리보기

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HRID 2263281 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[CH:2]=1.Cl[C:17]1[CH:18]=[C:19]([C:23]2[N:24]=[C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[S:26][CH:27]=2)[CH:20]=[CH:21][CH:22]=1.[CH:34]([N:37](C(C)C)CC)(C)C.O>CS(C)=O>[C:34]([C:17]1[CH:18]=[C:19]([C:23]2[N:24]=[C:25]([N:28]3[CH2:33][CH2:32][N:31]([C:8]([NH:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:15])[CH2:30][CH2:29]3)[S:26][CH:27]=2)[CH:20]=[CH:21][CH:22]=1)#[N:37]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 617805201-[4-(3-Chlorophenyl)-1,3-thiazol-2-yl]piperazineHCID 685753802,2,2-Trichloroethyl pyridin-3-ylcarbamate

생성물 1

HCID 687781214-[4-(3-cyanophenyl)-1,3-thiazol-2-yl]-N-pyridin-3-ylpiperazine-1-carboxamide수율 26.5%

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

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온도
70 °C

실험 절차

A mixture of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (219 mg, 0.814 mmol), 1-[4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperazine (200 mg, 0.740 mmol) and diisopropylethylamine (0.258 ml, 1.48 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 70° C. for 15 hours. 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), and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 76.6 mg (26.5%) of the desired product as a solid.

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)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

출처 및 근거

ORD 기록
ord-bb2ee7bd9ce14819903ed24481e22b63
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07851473B2

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