(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → (2S,4R)-1-(2-(1H-benzo[d][1,2,3]triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Participants

Reaction Steps

Proceeding as in Example 1, but substituting 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 176, (2S,4R)-1-(2-(1H-benzo[d][1,2,3]triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (17 mg, 12%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.95 (s, 1H), 8.04 (d, 1H), 7.77-7.64 (m, 1H), 7.59-7.49 (m, 3H), 7.44-7.12 (m, 8H), 7.07-6.90 (m, 4H), 5.80 (q, 2H), 4.56-4.48 (m, 1H), 4.02-3.93 (m, 1H), 3.55-3.46 (m, 1H), 2.85-2.69 (m, 3H), 2.08-1.94 (m, 2H). MS (EI) for C32H28FN5O3. found 549.9 (MH+).

Provenance & Evidence