Water → HCID 71526726, compound

Participants

Reaction Steps

To 3-[2′-{(1R,5S,8aS)-1-[3,5-bis(trifluoromethyl)phenyl]-3-oxohexahydro[1,3]oxazolo[3,4-a]pyridin-5-yl}-6-methoxy-4′-(trifluoromethyl)biphenyl-3-yl]propanehydrazide (10 mg, 0.015 mmol) in dioxane (1 mL) was added sodium bicarbonate (2.4 mg, 0.029 mmol) followed by water (0.2 mL). The system was sealed and cyanogen bromide (5.8 mL, 0.029 mmol) was added at room temperature. The reaction was complete in 5 minutes and the solvent was removed before the crude material was purified by HPLC to yield (1R,5S,8aS)-5-{5′-[2-(5-amino-1,3,4-oxadiazol-2-yl)ethyl]-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl}-1-[3,5-bis(trifluoromethyl)phenyl]hexahydro[1,3]oxazolo[3,4-a]pyridin-3-one (7 mg, 9.80 mmol). 1H NMR indicated that this compound exists as a pair of rotamers at 1:1 ratio. 1H NMR (500 MHz, CDCl3) δ8.45 (br s, 1H), 8.3 (br s, 1H), 7.90 (d, J=9.2 Hz, 1H), 7.75 (m, 5H), 7.38 (t, J=8.5 Hz) 7.2 (m, 2H), 7.0 (m, 2H), 5.55 (d, J=8.9 Hz, 1H), 5.40 (d, J=8.9 Hz, 1H), 5.38 (m, 1H), 5.25 (m, 1H), 4.2 (m, 1H), 3.95 (m, 1H), 3.82 (s, 3H), 3.8 (s, 3H), 3.2-3.1 (br s, 4H), 2.2 (m, 1H), 2.12 (m, 1H), 1.80 (m, 4H). MS ESI calc'd. for C33H28F9N4O4 [M+H]+ 715.2. found 715.3. RTA (95% HS): 1319 nM

Provenance & Evidence