Dimethyl Sulfoxide → 1-(4-Chlorophenyl)-5-methyl-N-[4-(4-morpholinopiperidin-1-yl)-3-nitrophenyl]pyrazole-4-carboxamide

HRID 1744634

반응식

HRID 1744634 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20](Cl)=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=3)=[O:15])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[O:27]1[CH2:32][CH2:31][N:30]([CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:29][CH2:28]1.CS(C)=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N:36]4[CH2:37][CH2:38][CH:33]([N:30]5[CH2:31][CH2:32][O:27][CH2:28][CH2:29]5)[CH2:34][CH2:35]4)=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=3)=[O:15])[CH:10]=[N:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 7957244-MorpholinopiperidineHCID 222280911-(4-Chlorophenyl)-N-(4-chloro-3-nitrophenyl)-5-methylpyrazole-4-carboxamide

생성물 1

HCID 222279621-(4-Chlorophenyl)-5-methyl-N-[4-(4-morpholinopiperidin-1-yl)-3-nitrophenyl]pyrazole-4-carboxamide수율 32.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

1-(4-Chlorophenyl)-N-(4-chloro-3-nitrophenyl)-5-methylpyrazole-4-carboxamide (1.6 g) and 4-morpholinopiperidine (2.4 g) were added to dimethyl sulfoxide (20 ml) and the mixture was stirred at a refluxing temperature for 1.5 h. After cooling to room temperature, water was added and the precipitated solid was collected by filtration and extracted with chloroform. The organic layer was washed with 30% potassium carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase:chloroform/methanol) and recrystallized from hydrous dimethylformamide to give the title compound (0.7 g), melting point: 195–200° C.

후처리

  1. filtrationthe precipitated solid was collected by filtration
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with 30% potassium carbonate and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (mobile phase:chloroform/methanol)
  7. customrecrystallized from hydrous dimethylformamide

출처 및 근거

ORD 기록
ord-6a2e29d848ec43788404ae9cea6b8b6c
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015218B1

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