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 triethylamine salt

HRID 1415939

反应方程式

HRID 1415939 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].Cl.Cl.[NH2:33][C@H:34]1[CH2:38][CH2:37][NH:36][CH2:35]1.[CH2:39]([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH3:40]>C(O)C>[CH:34]([O:27][CH:18]([CH3:17])[CH3:19])([CH3:38])[CH3:35].[CH2:39]([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH3:40].[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:36]4[CH2:37][CH2:38][C@H:34]([NH2:33])[CH2:35]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 110899701-(3-Amino-4,6-difluorophenyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acidHCID 13500644(3S)-(+)-3-Aminopyrrolidine Dihydrochloride

产物 2

HCID 7914异丙醚HCID 699605351-(3-amino-4,6-difluorophenyl)-7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid triethylamine salt收率 142%

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 1,000 mg of N,N-dimethylformamide were added 220 mg of 1-(3-amino-4,6-difluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid, 210 mg of (3S)-3-aminopyrrolidine dihydrochloride, and 400 mg of triethylamine. The solution was stirred at 90° C. for 1.5 hours. The reaction solution was allowed to cool down, combined with 10 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 220 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-8325b659aecf44de9f6a0364c03a3721
来源数据集
uspto-grants-1999_06
专利号
US05910498

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