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

HRID 2262902노트

반응식

HRID 2262902 반응식
[C:1]1([C:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[O: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[O:10][CH:11]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=3)[CH2:13][CH2:14]2)=[O:29])=[N:19]1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 687757351-(4-Phenyl-1,3-oxazol-2-yl)piperazineHCID 86625471Bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate

생성물 1

HCID 68777876N-1,2-benzisoxazol-3-yl-4-(4-phenyl-1,3-oxazol-2-yl)piperazine-1-carboxamide

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

A mixture of 1-(4-Phenyl-1,3-oxazol-2-yl)piperazine (391 mg, 0.807 mmol), bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate (370 mg, 1.61 mmol), diisopropylethylamine (0.141 ml, 0.807 mmol) and dimethylsulfoxide (5 ml) was stirred at 70° C. for 2 hours. The reaction mixture was poured to water and 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=2:1) to give the desired product as a solid. The resulting solid was recrystallized from a mixed solvent of ethyl acetate and hexane to give 44.0 mg (14.1%) of the desired product. mp 171-172° C.

후처리

  1. extractionextracted 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=2:1)

출처 및 근거

ORD 기록
ord-9ae19a1ebc874e4193a4b0ba44e69f4c
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851473B2

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