Acetic Acid → HCID 70945244, compound

Participants

Reaction Steps

Methyl-6-(4-(3-oxopropyl)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (200 mg), (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (221 mg) was dissolved in a mixed solvent of DCM (3 ml) and methanol (5 ml) containing acetic acid (0.4 ml). Sodium triacetoxyborohydride (350 mg) was then added in portions and the mixture was stirred at rt for further 3 hours. After diluting with ethyl acetate (100 ml), washed with sodium carbonate (30 ml), brine (20 ml), dried over sodium sulphate, solvent removed under vacuum, residue was then columned on silica gel using DCM:MeOH (20:1) as eluant to give (1S,4S)-tert-butyl 5-(3-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoro-methyl)phenyl)propyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (220 mg). 1H NMR (CDCl3) δ: 8.33 (s, 1H), 8.26 (d, 1H), 8.04 (s, 1H), 7.55 (d, 1H), 4.46 (s, 3H), 4.40 (br, 0.4H), 4.25 (br, 0.6H), 3.4-3.6 (m, 2H), 3.18 (m, 1H), 2.8-3.0 (m, 3H), 2.5-2.75 (m, 3H), 1.5-1.9 (m, 4H), 1.46 (s, 9H). MS m/z 542 (M+H).

Provenance & Evidence