N,N-二甲基甲酰胺 → 1-(3-amino-4,6-difluorophenyl)-7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 1415938

反应方程式

HRID 1415938 反应方程式
CN(C)C=O.[NH2:6][C:7]1[CH:8]=[C:9]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:26])=[C:22](Cl)[N:23]=3)[C:18](=[O:27])[C:17]([C:28]([OH:30])=[O:29])=[CH:16]2)[C:10]([F:14])=[CH:11][C:12]=1[F:13].[NH2:31][C@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1.C(N(CC)CC)C>C(O)C>[CH:32]([O:27][CH:18]([CH3:17])[CH3:19])([CH3:36])[CH3:33].[NH2:6][C:7]1[CH:8]=[C:9]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:26])=[C:22]([N:34]4[CH2:35][CH2:36][C@H:32]([NH2:31])[CH2:33]4)[N:23]=3)[C:18](=[O:27])[C:17]([C:28]([OH:30])=[O:29])=[CH:16]2)[C:10]([F:14])=[CH:11][C:12]=1[F:13]

参与物

7

反应物 4

HCID 6228N,N-二甲基甲酰胺HCID 8471三乙胺HCID 1519351(S)-3-氨基吡咯烷HCID 110899701-(3-Amino-4,6-difluorophenyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

产物 2

HCID 7914异丙醚HCID 110371721-(3-amino-4,6-difluorophenyl)-7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid收率 191.2%

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

反应条件

温度
90 °C

实验过程

To 6,500 mg of N,N-dimethylformamide were added 1,300 mg of 1-(3-amino-4,6-difluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid, 600 mg of (3S)-3-aminopyrrolidine, and 1,000 mg of triethylamine. The solution was stirred at 90° C. for 1 hour. The reaction solution was allowed to cool down, combined with 25 ml of ethanol, heated at reflux for 5 minutes, and allowed to cool down. The precipitate was collected by filtration and washed with ethanol and then with diisopropyl ether to give 1,410 mg of the title compound.

后处理

  1. temperatureto cool down
  2. temperatureheated
  3. temperatureat reflux for 5 minutes
  4. temperatureto cool down
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with ethanol

来源与证据

ORD记录
ord-b023eee62d134e96bb708fa16541416f
来源数据集
uspto-grants-1999_06
专利号
US05910498

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