Iodo benzene diacetate → HCID 71005110, compound

Participants

Reaction Steps

A solution of 8-(cyclopropylmethoxy)quinoline-2-carbaldehyde (0.14 g, 0.62 mmol) and tert-butyl methyl((3S)-1-(2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-yl)carbamate (0.20 g, 0.51 mmol) in ethanol (10 mL) was stirred at ambient temperature for 16 hours. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (10 mL) and treated with iodobenzene diacetate (0.20 g, 0.62 mmol) and stirred at ambient temperature for 4 hours. The mixture was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate solution (10 mL). The organic layer was separated, washed with brine, dried (MgSO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (Biotage SP4, C-18 25M; 10-90% CH3CN/water gradient). The residue was dissolved in dichloromethane (1 mL), treated with TFA (4 mL) and stirred at ambient temperature for 1 hour. The solution was concentrated under reduced pressure and the residue was purified by reverse phase chromatography (Biotage SP4, C-18 25M; 10-70% CH3CN/water gradient). The TFA salt was dissolved in methanol (0.50 mL) and treated with 2N HCl in diethyl ether (4 mL) and stirred for 10 minutes. The solvent was removed under reduced pressure and the solid obtained suspended in MeCN (5 mL) and stirred for 10 minutes. The solid was collected by filtration to afford (3S)-1-(1-(3-(8-(cyclopropylmethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)-N-methylpyrrolidin-3-amine (0.129 g, 44%). LCMS APCI (+) m/z 497 (M+H).

Provenance & Evidence