Ammonia → 7-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 469201ノート

反応式

HRID 469201 の反応式
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[CH:13]1([NH:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24](=[O:38])[C:25]([C:35]([OH:37])=O)=[CH:26][N:27]3[CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:22][C:21]=2[F:39])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.N>CN(C=O)C>[CH:13]1([NH:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24](=[O:38])[C:25]([C:35]([NH2:3])=[O:37])=[CH:26][N:27]3[CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:22][C:21]=2[F:39])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

参加物

5

反応物 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 666369197-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

生成物 1

HCID 666369957-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide収率 92.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

2.6 g of 1,1′-carbonyldiimidazole was added to a 30 ml DMF suspension of 4.0 g 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, followed by stirring at 100° C. for 13.5 hours. 10 ml of 28% aqueous ammonia was added thereto under ice-cooling, followed by stirring under ice-cooling for 75 minutes and at room temperature for 5 hours. After evaporation of the solvent under a reduced pressure, ethanol was added, and heating under reflux was carried out. After cooling to room temperature, the insoluble materials were collected by filtration and dried to obtain 3.7 g of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide.

後処理

  1. temperatureunder ice-cooling
  2. stirringby stirring under ice-
  3. temperaturecooling for 75 minutes and at room temperature for 5 hours
  4. customAfter evaporation of the solvent under a reduced pressure, ethanol
  5. additionwas added
  6. temperatureheating
  7. temperatureunder reflux
  8. temperatureAfter cooling to room temperature
  9. filtrationthe insoluble materials were collected by filtration
  10. customdried

出典と根拠

ORDレコード
ord-28da3a5eeb4d4e54a9f1dc0e2f17777f
出典データセット
uspto-grants-2014_01
特許番号
US08629126B2

反応ノート

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