Ammonia → HCID 178466592, compound

Participants

Reaction Conditions

Reaction Steps

Ammonia (0.06 mL of a 28-30% wt % solution in water) was added to a stirred mixture of (trans-4-{4-[({5-[(3-ethoxyphenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)acetic acid (Example 113, 65 mg), EDAC (32 mg), and HOBt (23 mg) in DMF (1 mL). The mixture was stirred for 16 h then was diluted with DMF (2 mL) and heated to 100° C. for 30 minutes in an Emrys Optimizer™ microwave. The crude mixture was purified directly by HPLC using a gradient of 25-75% acetonitrile/water with 1% ammonia as the eluent to give the title compound (10 mg) as a solid; 1H NMR δ 10.82 (2H, bs), 7.68 (2H, d), 7.22 (5H, m), 7.08 (1H, 1H), 6.67 (1H, s), 6.56 (1H, m), 4.00 (2H, quartet), 2.50 (1H+ DMSO, m), 1.96 (2H, d), 1.83-1.66 (5H, m), 1.42 (2H, m), 1.33(3H, t), 1.08 (2H, m); MS m/e MH+ 474.

Provenance & Evidence