HCID 91206831, compound → N-[5-(5-amino-2-chloro-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide
Reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:25]([CH:27]4[CH2:29][CH2:28]4)=[O:26])=[N:23][C:18]3=[CH:17][CH:16]=2)[C:11]([Cl:30])=[CH:10][C:9]=1[F:31])(C)(C)C>FC(F)(F)C(O)=O>[NH2:7][C:8]1[C:9]([F:31])=[CH:10][C:11]([Cl:30])=[C:12]([CH:13]=1)[O:14][C:15]1[N:20]=[C:19]2[S:21][C:22]([NH:24][C:25]([CH:27]3[CH2:28][CH2:29]3)=[O:26])=[N:23][C:18]2=[CH:17][CH:16]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of tert-butyl[4-chloro-5-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-2-fluorophenyl]carbamate (1.20 g, 2.51 mmol) and trifluoroacetic acid (10 mL) was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (100 mL). The solution was washed successively with saturated aqueous sodium hydrogen carbonate solution (50 mL×2) and saturated brine (10 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (886 mg, 93%) as a white powder.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutionthe residue was dissolved in ethyl acetate (100 mL)
- washThe solution was washed successively with saturated aqueous sodium hydrogen carbonate solution (50 mL×2) and saturated brine (10 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8a65c1d707464b19a60d6f38ba30bd77
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344135B2
Reaction notes
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