Pyridine → N-{3-Cyano-4-[4-(5-methylisoxazol-4-ylcarbonyl)piperazin-1-yl]phenyl}-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide

HRID 1744593ノート

反応式

HRID 1744593 の反応式
[CH3:1][C:2]1[O:6][N:5]=[CH:4][C:3]=1[C:7](Cl)=[O:8].N1C=CC=CC=1.[C:16]([C:18]1[CH:19]=[C:20]([NH:30][C:31]([C:33]2[CH:34]=[N:35][N:36]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[C:37]=2[CH3:38])=[O:32])[CH:21]=[CH:22][C:23]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)#[N:17]>O>[C:16]([C:18]1[CH:19]=[C:20]([NH:30][C:31]([C:33]2[CH:34]=[N:35][N:36]([C:39]3[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=3)[C:37]=2[CH3:38])=[O:32])[CH:21]=[CH:22][C:23]=1[N:24]1[CH2:29][CH2:28][N:27]([C:7]([C:3]2[CH:4]=[N:5][O:6][C:2]=2[CH3:1])=[O:8])[CH2:26][CH2:25]1)#[N:17]

参加物

5

反応物 3

HCID 1049PyridineHCID 27599175-Methyl-1,2-oxazole-4-carbonyl chlorideHCID 22227929N-[3-cyano-4-(piperazin-1-yl)phenyl]-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide

生成物 1

HCID 22228167N-{3-Cyano-4-[4-(5-methylisoxazol-4-ylcarbonyl)piperazin-1-yl]phenyl}-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide収率 58.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5-Methylisoxazole-4-carbonyl chloride (1.4 g) synthesized according to the method described in J. Chem. Soc. Perkin Trans. I, pp. 1875–1879 (1988) was added to a pyridine solution (20 ml) containing N-[3-cyano-4-(piperazin-1-yl)phenyl]-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide (4 g) under ice-cooling, and the mixture was stirred for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under pressure. Diisopropyl ether was added to the obtained residue to allow crystallization. The crystals were recrystallized from hydrous dimethylformamide to give the title compound (2.9 g), melting point: 208° C.

後処理

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with dilute hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the solvent was evaporated under pressure
  6. additionDiisopropyl ether was added to the obtained residue
  7. customcrystallization
  8. customThe crystals were recrystallized from hydrous dimethylformamide

出典と根拠

ORDレコード
ord-7293ba7a70084518aab94ea179ea607f
出典データセット
uspto-grants-2006_03
特許番号
US07015218B1

反応ノート

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