Water → N-Pyridin-4-yl-4-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamide

HRID 2263028노트

반응식

HRID 2263028 반응식
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)=[CH:3][CH:2]=1.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]1[N:25]=[C:24]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[S:23][N:22]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[N:1]1[CH:2]=[CH:3][C:4]([NH:7][C:8]([N:29]2[CH2:28][CH2:27][N:26]([C:24]3[S:23][N:22]=[C:21]([C:17]4[S:16][CH:20]=[CH:19][CH:18]=4)[N:25]=3)[CH2:31][CH2:30]2)=[O:15])=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 142572942,2,2-Trichloroethyl pyridin-4-ylcarbamateHCID 687780151-[3-(Thiophen-2-yl)-1,2,4-thiadiazol-5-yl]piperazine

생성물 1

HCID 68780013N-Pyridin-4-yl-4-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamide수율 18.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixed solution of 2,2,2-trichloroethyl pyridin-4-ylcarbamate (235 mg, 0.872 mmol), 1-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine (200 mg, 0.793 mmol) and diisopropylethylamine (0.152 ml, 0.872 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 80° C. for 3.5 hours. Water was poured to the reaction mixture, and the resulting solution 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, followed by methanol:ethyl acetate=1:9) and recrystallized from a mixed solvent of hexane and ethyl acetate to give 54.9 mg (18.6%) of the desired product as a solid.

후처리

  1. extractionthe resulting solution 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, followed by methanol:ethyl acetate=1:9)
  6. customrecrystallized from a mixed solvent of hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-77cfdb764d514997864e63caf0846972
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851473B2

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