Tert-butyl(5-{[2-(cyclopropylcarbonyl)amino[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)carbamate → N-[5-(3-amino-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide

HRID 2366787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366787
[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([O:16][C:17]2[CH:18]=[CH:19][C:20]([F:31])=[C:21]([NH:23]C(=O)OC(C)(C)C)[CH:22]=2)[N:10]=3)=[O:5])[CH2:3][CH2:2]1>FC(F)(F)C(O)=O>[NH2:23][C:21]1[CH:22]=[C:17]([CH:18]=[CH:19][C:20]=1[F:31])[O:16][C:11]1[N:10]=[C:9]2[S:8][C:7]([NH:6][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])=[N:15][C:14]2=[CH:13][CH:12]=1

Komponenten

3

Edukt 1

HCID 70688667Tert-butyl(5-{[2-(cyclopropylcarbonyl)amino[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)carbamate

Produkt 1

HCID 86646022N-[5-(3-amino-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamideAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (5-{[2-(cyclopropylcarbonyl)amino[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)carbamate (0.78 g, 1.75 mmol) in trifluoroacetic acid (5 mL) was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate (100 mL), washed with 0.1N aqueous sodium hydroxide solution (100 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with diethyl ether to give the title compound (0.60 g, quantitative) as a colorless powder.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate (100 mL)
  3. washwashed with 0.1N aqueous sodium hydroxide solution (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0b225768fbed43d0876fca066a1494f3
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697874B2

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