3-(Trifluoromethyl)-5,6,7,8-tetrahydro-(1,2,4)triazolo(4,3-a)pyrazine → 4-Desfluoro N-boc sitagliptin

Participants

Reaction Steps

The title compound was prepared from (3R)-3-[(1,1-dimethylethoxycarbonyl)-amino]-4-(2,5-difluorophenyl)butanoic acid (Intermediate 1, 50 mg, 0.16 mmol) and 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine (30 mg, 0.16 mmol) using a procedure analogous to that described for Example 1, Step C. The crude product was purified by preparative TLC (silica gel, 100% ethyl acetate, then 10% methanol/dichloromethane (2×)) to afford the title compound (38.1 mg) as a solid. 1H NMR (500 MHz, CDCl3) δ 1.38 (s, 9H), 2.57˜3.05 (m, 4H), 3.85˜4.30 (m, 5H), 4.90 (s, 1H), 4.95˜5.15 (m, 1H), 5.22˜5.40 (br, 1H), 6.86˜7.24 (m, 3H). LC/MS (M+1-t-Boc) 390.

Provenance & Evidence