Benzoyl chloride → N-[6-chloro-2-(4-cyanophenylamino)pyrimidin-4-yl]benzamide

HRID 243538

反応式

HRID 243538 の反応式
CN1CCCC1.[NH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([NH:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[N:9]=1.CN(C1C=CC=CN=1)C.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-]>O>[Cl:14][C:12]1[N:11]=[C:10]([NH:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[N:9]=[C:8]([NH:7][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:13]=1

参加物

7

反応物 5

HCID 7412Benzoyl chlorideHCID 84541-MethylpyrrolidineHCID 19660Carbonate IonHCID 218852-DimethylaminopyridineHCID 714650014-((4-Amino-6-chloropyrimidin-2-yl)amino)benzonitrile

生成物 1

HCID 71465002N-[6-chloro-2-(4-cyanophenylamino)pyrimidin-4-yl]benzamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
82.5 °C

実験手順

1400 ml of N-methylpyrrolidine and 140 g of 4-(4-Amino-6-chloropyrimidin-2-ylamino)benzonitrile was charged into a reaction vessel. To this were added 85.49 g of dimethylamino pyridine and 87.21 g of diazabicyclo undecene and stirred for 30 mins. To the reaction mixture was added 27.36 g of benzoyl chloride and stirred at RT for 30 mins. and heated to 80-85° C. and maintained the same for 4 hrs. After completion of the reaction, the reaction mass was cooled to RT and 1400 ml of water was added, followed by 1400 ml of 50% carbonate solution. The reaction mass was extracted with 1400 ml of dichloromethane and the dichloromethane layer was washed with 700 ml of water. The organic layers were separated and dried over anhydrous sodium sulfate and filtered; distilled off dichloromethane and the solid was isolated.

後処理

  1. stirringstirred at RT for 30 mins
  2. temperaturemaintained the same for 4 hrs
  3. customAfter completion of the reaction
  4. temperaturethe reaction mass was cooled to RT
  5. extractionThe reaction mass was extracted with 1400 ml of dichloromethane
  6. washthe dichloromethane layer was washed with 700 ml of water
  7. customThe organic layers were separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. distillationdistilled off dichloromethane
  11. customthe solid was isolated

出典と根拠

ORDレコード
ord-85f611c529154e2abe6e5538e9cbdacd
出典データセット
uspto-grants-2014_02
特許番号
US08653266B2

関連ノート

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