Dimethylformamide → Delafloxacin

HRID 610258ノート

反応式

HRID 610258 の反応式
CN(C)C=O.[NH2:6][C:7]1[N:12]=[C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([F:25])=[C:20](F)[C:21]=3[Cl:23])[C:16](=[O:26])[C:15]([C:27]([OH:29])=[O:28])=[CH:14]2)[C:10]([F:30])=[CH:9][C:8]=1[F:31].Cl.[OH:33][CH:34]1[CH2:37][NH:36][CH2:35]1.CN1CCCC1>C(O)C>[NH2:6][C:7]1[N:12]=[C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([F:25])=[C:20]([N:36]4[CH2:37][CH:34]([OH:33])[CH2:35]4)[C:21]=3[Cl:23])[C:16](=[O:26])[C:15]([C:27]([OH:29])=[O:28])=[CH:14]2)[C:10]([F:30])=[CH:9][C:8]=1[F:31]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 84541-MethylpyrrolidineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 154349011-(6-Amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

生成物 1

HCID 487101Delafloxacin収率 92.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
85 °C

実験手順

To 3.5 g of N,N-dimethylformamide were added 2.00 g of 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 1.00 g of 3-hydroxyazetidine hydrochloride, and 2.00 g of N-methylpyrrolidine together with 0.2 ml of ethanol, and the mixture was stirred at 85° C. for 10 minutes. The solvent and the like were distilled off under reduced pressure. After adding 10 ml of ethanol to the residue, the mixture was heated under reflux for 10 minutes and allowed to cool, and the precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 2.10 g of the title compound as a pale yellow powder.

後処理

  1. distillationThe solvent and the like were distilled off under reduced pressure
  2. additionAfter adding 10 ml of ethanol to the residue
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 10 minutes
  5. temperatureto cool
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with ethanol and diisopropylether successively

出典と根拠

ORDレコード
ord-dd23d7f72062449a8a7a7ae8d420014b
出典データセット
uspto-grants-1999_12
特許番号
US05998436

反応ノート

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