L-Methionine → 2-(3-fluoro-4-(phenyl)phenyl)-6-hydroxy-7-methoxyquinazolin-4(3H)-one

HRID 61607ノート

反応式

HRID 61607 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[NH:23][C:22](=[O:24])[C:21]3[C:16](=[CH:17][C:18]([O:27][CH3:28])=[C:19]([O:25]C)[CH:20]=3)[N:15]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N[C@H](C(O)=O)CCSC>CS(O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[NH:23][C:22](=[O:24])[C:21]3[C:16](=[CH:17][C:18]([O:27][CH3:28])=[C:19]([OH:25])[CH:20]=3)[N:15]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

4

反応物 2

HCID 6137L-Methionine2 回HCID 1362032412-(3-fluoro-4-(phenyl)phenyl)-6,7-dimethoxyquinazolin-4(3H)-one

生成物 1

HCID 1362032402-(3-fluoro-4-(phenyl)phenyl)-6-hydroxy-7-methoxyquinazolin-4(3H)-one収率 87%

試薬・触媒・溶媒 1

HCID 6395Methanesulfonic Acid溶媒

反応条件

温度
110 °C

実験手順

A mixture of 2-(3-fluoro-4-(phenyl)phenyl)-6,7-dimethoxyquinazolin-4(3H)-one (3.83 g, 10.2 mmol) and methionine (2.1 g, 14.1 mmol) in methanesulfonic acid was heated 110° C. for 4 h. Additional methionine (0.75 g) was added and heating was continued for another 1.5 h. The mixture was allowed to cool to RT and was poured into ice-water (300 mL). A solid separated out, which was collected via filtration. The solid was suspended in sat. NaHCO3 and the after the effervescence subsided the solid was again collected via filtration. The solid was washed with water and EtOH to give the desired product 2-(3-fluoro-4-(phenyl)phenyl)-6-hydroxy-7-methoxyquinazolin-4(3H)-one (3.2 g, 8.83 mmol, 87%). HPLC retention time 7.06 mins.

後処理

  1. temperatureheating
  2. temperatureto cool to RT
  3. customA solid separated out
  4. filtrationwhich was collected via filtration
  5. filtrationwas again collected via filtration
  6. washThe solid was washed with water and EtOH

出典と根拠

ORDレコード
ord-c762351cf2ac428a950df7e205f178d5
出典データセット
uspto-grants-2016_09
特許番号
US09440961B2

反応ノート

読み込み中…