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

HRID 2263322노트

반응식

HRID 2263322 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:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[C:24]1[N:25]=[C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[S:27][CH:28]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[Cl:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[C:24]1[N:25]=[C:26]([N:29]2[CH2:34][CH2:33][N:32]([C:8]([NH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[O:15])[CH2:31][CH2:30]2)[S:27][CH:28]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 685753802,2,2-Trichloroethyl pyridin-3-ylcarbamateHCID 68776332HCID 68776332, 화합물

생성물 1

HCID 116189214-[4-(2,3-dichlorophenyl)-1,3-thiazol-2-yl]-N-pyridin-3-ylpiperazine-1-carboxamide수율 24.8%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
70 °C

실험 절차

A mixture of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (94.3 mg, 0.350 mmol), 1-[4-(2,3-dichlorophenyl)-1,3-thiazol-2-yl]piperazine (100 mg, 0.318 mmol) and diisopropylethylamine (0.111 ml, 0.636 mmol) in dimethyl sulfoxide (1.0 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), and recrystallized from a mixed solvent of hexane and ethyl acetate to give 34.3 mg (24.8%) of the desired product as a solid. mp 132-133° 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)
  6. customrecrystallized from a mixed solvent of hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-3b157c9d82c3428893d06d2e3f312508
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851473B2

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