Dimethyl Sulfoxide → N-1,2-Benzisoxazol-3-yl-4-(4-phenyl-2-thienyl)piperazine-1-carboxamide

HRID 2263055노트

반응식

HRID 2263055 반응식
[C:1]1([C:7]2[CH:8]=[C:9]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[C:20]([N:27](C(OCC(Cl)(Cl)Cl)=O)[C:28](OCC(Cl)(Cl)Cl)=[O:29])=[N:19]1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[O:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[C:20]([NH:27][C:28]([N:15]2[CH2:16][CH2:17][N:12]([C:9]3[S:10][CH:11]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:8]=3)[CH2:13][CH2:14]2)=[O:29])=[N:19]1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 687773121-(4-Phenyl-2-thienyl)piperazineHCID 86625471Bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate

생성물 1

HCID 68779482N-1,2-Benzisoxazol-3-yl-4-(4-phenyl-2-thienyl)piperazine-1-carboxamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 1-(4-phenyl-2-thienyl)piperazine (240 mg, 0.984 mmol), bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate (239 mg, 0.492 mmol), diisopropylethylamine (0.0857 ml, 0.492 mmol) and dimethylsulfoxide (3 ml) was stirred at 70° C. for 2 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 (hexane:ethyl acetate=1:1) 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 (42.5 mg, 21.4%) 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 (hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-f20fc80628b34866bd9f2eca4bc2389a
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851473B2

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