Water → 8-(2,6-Dichloro-3,5-dimethoxy-phenyl)-2-[(2-dimethylamino-ethyl)-methyl-amino]-quinoxaline-5-carboxylic acid

HRID 43108

反応式

HRID 43108 の反応式
[OH-:1].[K+].[Cl:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[C:6]([Cl:14])[C:5]=1[C:15]1[C:24]2[N:23]=[C:22]([N:25]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH3:26])[CH:21]=[N:20][C:19]=2[C:18]([C:32]#N)=[CH:17][CH:16]=1.[OH2:34]>C(O)CO.CCOCC.O>[Cl:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([O:12][CH3:13])=[C:6]([Cl:14])[C:5]=1[C:15]1[C:24]2[N:23]=[C:22]([N:25]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH3:26])[CH:21]=[N:20][C:19]=2[C:18]([C:32]([OH:34])=[O:1])=[CH:17][CH:16]=1

参加物

6

反応物 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 592929388-(2,6-Dichloro-3,5-dimethoxy-phenyl)-2-[(2-dimethylamino-ethyl)-methyl-amino]-quinoxaline-5-carbonitrile

生成物 1

HCID 866411428-(2,6-Dichloro-3,5-dimethoxy-phenyl)-2-[(2-dimethylamino-ethyl)-methyl-amino]-quinoxaline-5-carboxylic acid

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 21584184Diethylether water溶媒

反応条件

温度
150 °C

実験手順

A solution of KOH (268 mg, 4.79 mmol, 10 equiv) in H2O (2 mL) was added to 8-(2,6-dichloro-3,5-dimethoxy-phenyl)-2-[(2-dimethylamino-ethyl)-methyl-amino]-quinoxaline-5-carbonitrile (Step 85.2) (220 mg, 0.48 mmol) in ethylene glycol (2 mL). The reaction mixture was stirred at 150° C. for 48 h, allowed to cool to rt, diluted with Et2O/H2O, and extracted with Et2O. The aqueous phase was acidified to pH 5 by addition of 6 N HCl. Vacuum filtration of the resulting suspension afforded 450 mg of the title compound as an impure yellow solid, which was used without further purification: ESI-MS: 479.0/480.9 [M+H]+; tR=3.75 min (System 1).

後処理

  1. temperatureto cool to rt
  2. extractionextracted with Et2O
  3. additionThe aqueous phase was acidified to pH 5 by addition of 6 N HCl
  4. filtrationVacuum filtration of the resulting suspension

出典と根拠

ORDレコード
ord-63823ff003bc4ae2abef6175612c8ef2
出典データセット
uspto-grants-2013_09
特許番号
US08536175B2

関連ノート

読み込み中…