Methyl N-(triethylammoniosulfonyl)carbamate → HCID 71735907, compound

Participants

Reaction Steps

To a mixture of 2-cyclopropyl-N′-(4-((((1S,2S)-2-(4-fluorophenyl)cyclopropyl)methyl)amino)-3-(trifluoromethyl)pyridin-2-yl)acetohydrazide (0.06 g, 0.142 mmol) in THF (4 mL) was added Burgess reagent (0.068 g, 0.284 mmol) and the resulting mixture was refluxed stirring for 6 hours. The reaction mixture diluted with EtOAc and extracted with aqueous sodium bicarbonate. The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers were washed with aqueous sodium bicarbonate (2×10 mL) and brine (10 mL), dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography to give 3-(cyclopropylmethyl)-N-(((1S,2S)-2-(4-fluorophenyl)cyclopropyl)methyl)-8-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-amine as a white solid (0.045 g, 74% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.98 (d, J=7.5 Hz, 1H), 7.09-7.01 (m, 2H), 7.00-6.92 (m, 2H), 6.64 (d, J=7.8 Hz, 1H), 5.49 (d, J=4.0 Hz, 1H), 3.39 (tdd, J=19.0, 12.8, 5.6 Hz, 2H), 3.01 (d, J=6.8 Hz, 2H), 1.92 (dt, J=9.1, 4.9 Hz, 1H), 1.46-1.34 (m, 1H), 1.19-0.94 (m, 3H), 0.65-0.54 (m, 2H), 0.37-0.27 (m, 2H). LCMS M+1=405.05.

Provenance & Evidence