Dimethylformamide → [8-chloro-3-(2-chloro-4-methanesulfonylbenzyl)-4-difluoromethoxy-2-methylquinolin-5-yloxy]acetic Acid Methyl Ester

HRID 2266508ノート

反応式

HRID 2266508 の反応式
[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8](=[O:30])[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][C:20]=1[Cl:29])=[C:10]([CH3:17])[NH:11]2.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[C:44](OC(=O)C)([F:46])[F:45]>O>[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:30][CH:44]([F:46])[F:45])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][C:20]=1[Cl:29])[C:10]([CH3:17])=[N:11]2

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 68780451HCID 68780451、化合物HCID 86613376Chlorodifluoromethyl acetate

生成物 1

HCID 68784446[8-chloro-3-(2-chloro-4-methanesulfonylbenzyl)-4-difluoromethoxy-2-methylquinolin-5-yloxy]acetic Acid Methyl Ester

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

A mixture of [8-chloro-3-(2-chloro-4-methanesulfonylbenzyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester (0.34 g), N,N-dimethylformamide (15 mL), potassium carbonate (0.58 g) and acetic acid chlorodifluoromethyl ester (0.4 mL) was stirred at 70° C. for 16 hours. The mixture was diluted with water, extracted with ethyl acetate and the combined extracts were dried over sodium sulfate and then the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (7:3 by volume) gave title compound, 0.37 g.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined extracts were dried over sodium sulfate
  3. customthe solvent removed under reduced pressure
  4. customPurification of the residue by column chromatography on silica gel
  5. washeluting with a mixture of cyclohexane and ethyl acetate (7:3 by volume)

出典と根拠

ORDレコード
ord-35dd80803ab44f03b90152995a133a21
出典データセット
uspto-grants-2010_12
特許番号
US07858640B2

反応ノート

読み込み中…