Diisopropylethylamine → 8-(4-Fluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

To a solution of hydroxylamine hydrochloride (370 mg, 5.32 mmol) and N,N-diisopropylethylamine (543 μL, 3.19 mmol) in MeOH (2 mL) and EtOH (2 mL) was added a solution of N-(3-(4-fluoro-phenyl)-pyridin-2-yl)-N′-ethoxycarbonyl-thiourea (340 mg, 1.06 mmol) in MeOH (2 mL) and EtOH (2 mL). The reaction mixture was stirred at room temperature for 1 hour and then at 60° C. for 3 hours. The solvents were evaporated and saturated aqueous NaHCO3 solution was added to the residue. The aqueous phase was extracted with CH2Cl2, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using dichloromethane/methanol (with 10% ammonia) as eluent. The title compound was obtained as a white solid (205 mg, 84%).

1. waitat 60° C. for 3 hours
2. customThe solvents were evaporated
3. additionsaturated aqueous NaHCO3 solution was added to the residue
4. extractionThe aqueous phase was extracted with CH2Cl2
5. dry with materialthe combined organic phases were dried over sodium sulfate
6. customthe solvent was evaporated
7. customthe residue purified by silica gel chromatography

ORD record

ord-29d9231e17a749198e71ed964e17d6a6

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486967B2