Dimethyl Sulfoxide → N-[4-(2-oxopropyl)phenyl]-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2263108노트

반응식

HRID 2263108 반응식
[O:1]=[C:2]([CH3:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:18])OCC(Cl)(Cl)Cl)=[CH:6][CH:5]=1.[C:20]1([C:26]2[N:30]=[C:29]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[S:28][N:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[O:1]=[C:2]([CH3:19])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([N:34]2[CH2:35][CH2:36][N:31]([C:29]3[S:28][N:27]=[C:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:30]=3)[CH2:32][CH2:33]2)=[O:18])=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 862450662,2,2-Trichloroethyl [4-(2-oxopropyl)phenyl]carbamate

생성물 1

HCID 68779937N-[4-(2-oxopropyl)phenyl]-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 2,2,2-trichloroethyl [4-(2-oxopropyl)phenyl]carbamate (200 mg, 0.616 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (152 mg, 0.616 mmol), diisopropylethylamine (0.107 ml, 0.616 mmol) and dimethylsulfoxide (4 ml) was stirred at 70° C. for 12 hours, the reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain the desired product as a solid. This was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (45.2 mg, 17.4%) 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)

출처 및 근거

ORD 기록
ord-3e742659e2194bec9ecd16605647da2f
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851473B2

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