Pyridine → 2-Chloro-3-(1-Cyanocyclopropyl)-N-[5-({2-[(Cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-B]pyridin-5-Yl}oxy)-2-Fluorophenyl]benzamide

HRID 1800660ノート

反応式

HRID 1800660 の反応式
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[CH:14][C:15]([F:33])=[C:16]([NH:18][C:19](=[O:32])[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]4([C:29]#[N:30])[CH2:28][CH2:27]4)[C:21]=3[Cl:31])[CH:17]=1)[N:5]=2.N1C=CC=CC=1.[CH:40]1([C:43](Cl)=[O:44])[CH2:42][CH2:41]1.C(=O)([O-])O.[Na+]>O1CCCC1.C1(C(Cl)=O)CC1.O>[Cl:31][C:21]1[C:22]([C:26]2([C:29]#[N:30])[CH2:28][CH2:27]2)=[CH:23][CH:24]=[CH:25][C:20]=1[C:19]([NH:18][C:16]1[CH:17]=[C:12]([O:11][C:6]2[N:5]=[C:4]3[S:3][C:2]([NH:1][C:43]([CH:40]4[CH2:42][CH2:41]4)=[O:44])=[N:10][C:9]3=[CH:8][CH:7]=2)[CH:13]=[CH:14][C:15]=1[F:33])=[O:32]

参加物

8

反応物 4

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 57387326HCID 57387326、化合物

生成物 1

HCID 252061852-Chloro-3-(1-Cyanocyclopropyl)-N-[5-({2-[(Cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-B]pyridin-5-Yl}oxy)-2-Fluorophenyl]benzamide収率 96%

試薬・触媒・溶媒 3

HCID 77637Cyclopropanecarbonyl chloride触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-fluorophenyl}-2-chloro-3-(1-cyanocyclopropyl)benzamide (9.0 g, 18.8 mmol) and pyridine (2.3 mL, 28.1 mmol) in tetrahydrofuran (90 mL) was added dropwise cyclopropanecarbonyl chloride (1.89 mL, 20.8 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. Cyclopropanecarbonyl chloride (63 μL, 0.69 mmol) was further added and the mixture was stirred at room temperature for 12 hr. Water (100 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL) were added to the reaction mixture to give a suspension, and the mixture was stirred at room temperature for 30 min. The precipitate was collected by filtration, repeatedly washed with water, and dried under reduced pressure to give the title compound (9.85 g, 96%) as a white powder.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 12 hr
  3. customto give a suspension
  4. stirringthe mixture was stirred at room temperature for 30 min
  5. filtrationThe precipitate was collected by filtration
  6. washrepeatedly washed with water
  7. customdried under reduced pressure

出典と根拠

ORDレコード
ord-dfb9a3d6aa6a4bbb9ca62846c71300d6
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

反応ノート

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