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 1800660노트

반응식

HRID 1800660 반응식
[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]

참가 물질

8

반응물 4

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 57387326HCID 57387326, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 77637Cyclopropanecarbonyl chloride촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dfb9a3d6aa6a4bbb9ca62846c71300d6
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

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