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 1800660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1800660
[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]

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 77637Cyclopropanecarbonyl chlorideKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dfb9a3d6aa6a4bbb9ca62846c71300d6
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344135B2

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