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

HRID 1744634

反応式

HRID 1744634 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6a2e29d848ec43788404ae9cea6b8b6c
出典データセット
uspto-grants-2006_03
特許番号
US07015218B1

関連ノート

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