Trifluoroacetic acid → N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide
Reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:16]=[CH:17][C:18]3[N:19]([N:21]=[C:22]([NH:24][C:25]([CH:27]4[CH2:29][CH2:28]4)=[O:26])[N:23]=3)[CH:20]=2)[CH:9]=1)(C)(C)C.COC1C=CC=CC=1.FC(F)(F)C(O)=O>>[NH2:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][C:15]1[CH:16]=[CH:17][C:18]2[N:19]([N:21]=[C:22]([NH:24][C:25]([CH:27]3[CH2:29][CH2:28]3)=[O:26])[N:23]=2)[CH:20]=1Participants
4
Procedure
To a mixture of tert-butyl[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]carbamate (1.79 g, 4.39 mmol) and methoxybenzene (0.5 mL) was added trifluoroacetic acid (8.0 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and 5% aqueous sodium hydrogen carbonate solution (200 mL) was added to the residue. The obtained precipitate was collected by filtration, and washed with water, diisopropyl ether and hexane to give the title compound (1.13 g, 83%) as a pale-yellow powder. The obtained compound was used for the next reaction without further purification.
Workup
- temperaturecooling
- concentrationThe reaction mixture was concentrated under reduced pressure, and 5% aqueous sodium hydrogen carbonate solution (200 mL)
- additionwas added to the residue
- filtrationThe obtained precipitate was collected by filtration
- washwashed with water, diisopropyl ether and hexane
Sources & evidence
- ORD record
- ord-7980237f0886463abbb05cbc663b7ccc
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344135B2
Reaction notes
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