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Water → 4-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-pyridin-2-ylpiperazine-1-carboxamide

HRID 2262968
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HRID 2262968 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl.[C:16]1([C:22]2[N:26]=[C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[S:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:16]1([C:22]2[N:26]=[C:25]([N:27]3[CH2:32][CH2:31][N:30]([C:8]([NH:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[O:15])[CH2:29][CH2:28]3)[S:24][N:23]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 116876422,2,2-Trichloroethyl pyridin-2-ylcarbamate

생성물 1

HCID 159792504-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-pyridin-2-ylpiperazine-1-carboxamide수율 55.5%

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

실험 절차

A mixed solution of 2,2,2-trichloroethyl pyridin-2-ylcarbamate (270 mg, 0.610 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and diisopropylethylamine (0.129 ml, 0.738 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 70° C. for 3 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 (hexane:ethyl acetate=3:7) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 124 mg (55.4%) 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 (hexane:ethyl acetate=3:7)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

출처 및 근거

ORD 기록
ord-6e135b2878b64f26aa56e56112a6bc80
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07851473B2

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