Reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([O:15][C:16]2[CH:17]=[CH:18][C:19]3[N:20]([N:22]=[C:23]([NH:25][C:26]([CH:28]4[CH2:30][CH2:29]4)=[O:27])[N:24]=3)[CH:21]=2)[CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH:9]=1)[O:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([N:22]=[C:23]([NH:25][C:26]([CH:28]3[CH2:30][CH2:29]3)=[O:27])[N:24]=2)[CH:21]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
A mixture of tert-butyl[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)-4-methylphenyl]carbamate (1.50 g, 3.54 mmol) and trifluoroacetic acid (5 mL) was stirred at 0° C. for 30 min. The solvent was evaporated under reduced pressure, the residue was dissolved in water, and the solution was neutralized with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, the residue was collected by filtration and washed with ethyl acetate and hexane to give the title compound (1.04 g, 91%) as a white solid.
Workup
- customThe solvent was evaporated under reduced pressure
- dissolutionthe residue was dissolved in water
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationthe insoluble material was filtered off
- concentrationThe filtrate was concentrated under reduced pressure
- filtrationthe residue was collected by filtration
- washwashed with ethyl acetate and hexane
Sources & evidence
- ORD record
- ord-236585cb4c6c46109edd3c9ba713fe66
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344135B2
Linked notes
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