Hydrochloric Acid → HCID 66811616, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl cis-2-[(2-{2-(methyl[(trans-2-methylcyclopropyl)methyl]amino)-6-[methyl(methylsulfonyl)amino]isonicotinoyl}hydrazino)carbonyl]-3-phenylpiperidine-1-carboxylate (93.7 mg, 0.15 mmol) in 1,2-dichloroethane (1.5 ml) was added Burgess reagent (162 mg, 0.60 mmol). The reaction vessel was sealed and heated to 120° C. for 10 min in an Emry's Optimizer microwave reactor. The reaction was concentrated in vacuo and purified via reverse phase HPLC to yield the cyclodehydration product. A solution of the material in EtOAc (15 ml) at 0° C. was saturated with HCl gas and allowed to stir for 1 h. The reaction was concentrated in vacuo and purified via reverse phase HPLC to yield title example N-methyl-N-(6-(methyl[(trans-2-methylcyclopropyl)methyl]amino)-4-[5-(cis-3-phenylpiperidin-2-yl)-1,3,4-oxadiazol-2-yl]pyridin-2-yl)methanesulfonamide. HRMS (ES, M+H), cal'd for C26H34N6O3S: 511.2486. found: 511.2475. 1H NMR (400 MHz, CD3OD) δ 7.32 (m, 3H), 7.19 (d, J=7.3 Hz, 2H), 6.78 (m, 1H), 6.55 (m, 1H), 5.45 (d, J=5.1 Hz, 1H), 3.99 (m, 1H), 3.62 (m, 1H), 3.54 (m, 2H), 3.38 (m, 1H), 3.34 (s, 3H), 3.14 (s, 3H), 3.10 (s, 3H), 2.43-2.27 (m, 2H), 2.03 (m, 2H), 1.04 (d, J=5.7 Hz, 3H), 0.73 (m, 2H), 0.46 (m, 1H), 0.26 (m, 1H).

Provenance & Evidence