Dichloromethane → HCID 58662448、化合物

HRID 644812

反応式

HRID 644812 の反応式
[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]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 22397159Ethyl 4-Hydroxy-6,8-dimethyl-1,7-naphthyridine-3-carboxylate

生成物 1

HCID 58662448HCID 58662448、化合物収率 42%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-2ad6c20fb36049719137abacb75806ee
出典データセット
uspto-grants-2010_04
特許番号
US07700774B2

関連ノート

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