二氯甲烷 → HCID 58662448，化合物

HRID 644812

反应方程式

HRID 644812 反应方程式
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([CH3:18])[N:11]=[C:12]([CH3:17])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].ClCCl.C(N(CC)CC)C.Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>O>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([CH3:18])[N:11]=[C:12]([CH3:17])[CH:13]=2)[N:8]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH:7]=1)=[O:5])[CH3:2]

参与物

6

反应物 4

HCID 6344二氯甲烷HCID 8471三乙胺HCID 10387氯甲酸苄酯HCID 22397159Ethyl 4-Hydroxy-6,8-dimethyl-1,7-naphthyridine-3-carboxylate

产物 1

HCID 58662448HCID 58662448，化合物收率 42%

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

反应条件

温度
0 °C

实验过程

6,8-Dimethyl-4-oxo-1,4-dihydro-[1,7]naphthyridine-3-carboxylic acid ethyl ester (0.2 g, 0.628 mmol), prepared in step (ii), and dichloromethane (10 mL) were added to a 50 mL round bottom flask. This mixture was cooled to 0° C. and stirred, and triethylamine (0.19 g, 1.88 mmol) was then added to the mixture dropwise. Stirring of the reaction mixture was continued at the same temperature for another 0.5 h, after which time benzyl chloroformate (0.16 g, 0.943 mmol) was added to the mixture. The temperature was allowed to increase to RT, and stirring was continued at this temperature for 2 h. Water was added to the reaction mixture and the mixture was extracted with dichloromethane (2×25 mL). The combined organic phase was washed with brine, dried over sodium sulfate, and the organic solvent was evaporated to provide a residue. This residue was purified by column chromatography over 100-200 mesh silica gel, used 5% MeOH and chloroform as eluent, to provide the compound as a yellow solid (0.1 g, 42%).

后处理

  1. additionwere added to a 50 mL round bottom flask
  2. stirringStirring of the reaction mixture
  3. temperatureto increase to RT
  4. stirringstirring
  5. waitwas continued at this temperature for 2 h
  6. extractionthe mixture was extracted with dichloromethane (2×25 mL)
  7. washThe combined organic phase was washed with brine
  8. dry with materialdried over sodium sulfate
  9. customthe organic solvent was evaporated
  10. customto provide a residue
  11. customThis residue was purified by column chromatography over 100-200 mesh silica gel

来源与证据

ORD记录
ord-2ad6c20fb36049719137abacb75806ee
来源数据集
uspto-grants-2010_04
专利号
US07700774B2

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