Benzophenone imine → HCID 59651108, compound

Participants

Reaction Steps

To a solution of N-(4-[5-(1-aminoethyl)-1,3,4-oxadiazol-2-yl]-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylmethanesulfonamide (0.544 g, 1.26 mmol, example 22) in 10 mL CH2Cl2 was added benzophenone imine (0.25 mL, 1.51 mmol). A white precipitate appeared gradually through the course of the reaction. The reaction was allowed to proceed for 15 h, when a further aliquot of benzophenone imine was added (0.160 mL, 0.894 mmol). After a further 24 h, the reaction was diluted with H2O and EtOAc, and the layers were separated. The aqueous layer was washed with EtOAc(2×), the combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by normal phase chromatography (2->35% EtOAc/hexanes) to afford N-(4-(5-{1-[(diphenyl methylene)amino]ethyl}-1,3,4-oxadiazol-2-yl)-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N -methylmethanesulfonamide as a yellow foam. 1H NMR (CDCl3, 400 MHz) δ 7.63 (m, 4H), 7.54-7.50 (m, 4H), 7.48 (m, 2H), 7.05 (s, 1H), 6.99 (s, 1H), 4.95 (q, J=6.5 Hz, 1H), 3.52 (dd, J=14.3, 6.2 Hz, 1H), 3.38 (s, 3H), 3.34 (dd, J=14.3, 6.3 Hz, 1H), 3.14 (s, 3H), 3.12 (s, 3H), 1.67 (d, J=6.6 Hz, 3H), 1.01 (d, J=6.0 Hz, 3H), 0.74 (m, 1H), 0.65 (m, 1H), 0.40 (m, 1H), 0.25 (m, 1H); LCMS [M+H]+=559.

Provenance & Evidence