O-(萘-1-基甲基)羟胺 → HCID 58989906，化合物

HRID 1663148笔记

反应方程式

HRID 1663148 反应方程式
FC1C(O[C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=C(F)C(F)=C(F)C=1F.[C:29]1([CH2:39][O:40][NH2:41])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[C:29]1([CH2:39][O:40][NH:41][C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1

参与物

4

反应物 2

HCID 15009996O-(萘-1-基甲基)羟胺HCID 58989934HCID 58989934，化合物

产物 1

HCID 58989906HCID 58989906，化合物

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
50 °C

实验过程

2-[(Pyridin-4-ylmethyl)-amino]-benzoic acid pentafluorophenyl ester (preparation 7C, 150 mg) and O-naphthalen-1-ylmethyl-hydroxylamine (preparation 53, 1.05 eq.) was dissolved in DMF and the stirred mixture was heated to 50° C. The reaction mixture was stirred at this temperature for 15 hours. The mixture was cooled to room temperature and partitioned between EtOAc and water. The organic layer washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc) and gave the title compound. 13C-NMR (DMSO-d6) δ 167.3, 149.5, 149.1, 148.4, 133.2, 132.5, 131.9, 131.4, 129.3, 128.4, 128.2, 126.3, 126.1, 125.9, 125.2, 124.8, 121.9, 114.8, 113.4, 111.5, 75.3, 44.8.

后处理

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. washThe organic layer washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (petroleum ether/EtOAc)

来源与证据

ORD记录
ord-d603c02062204037ae9215d247527a86
来源数据集
uspto-grants-2011_10
专利号
US08034811B2

反应笔记

加载中…