p-(Trifluoromethoxy)benzaldehyde → HCID 44629182, compound

Participants

Reaction Steps

1′-(4-Trifluoromethoxybenzyl)-1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl-6-carboxylic acid cyclopropylamide (9) was prepared by adding diisopropyl ethyl amine to a suspension of compound 5 (72 mg, 0.25 mmol), 4-trifluoromethoxybenzaldehyde (8) (Aldrich) and 3 Å molecular sieves (200 mg, Aldrich). The mixture was stirred for 12 hours and NaCNBH3 was added. The crude product was filtered and then purified on Prep TLC (10% MeOH in dichloromethane with 1% NH4OH) to provide the title compound 9 (25 mg, yield 23%): 1H NMR (400 MHz, CD3OD, HCl-salt): δ 8.48 (bd, 1 h, NH), 7.88 (d, 1H, J=7.6 Hz), 7.83 (t, 1H, J=7.6 Hz), 7.65 (d, 1H, J=7.6 Hz), 7.57 (m, 2H), 7.32 (d, 2H, J=8.8 Hz), 6.68 (m, 1H), 4.39 (m, 2H), 3.85 (m, 2H), 3.68 (m, 1H), 3.26 (m, 1H), 3.12 (m, 1H), 2.82 (m, 1H), 2.71 (m, 1H), 0.72 m, 2H), 0.54 (m, 2H); MS: 418.

Provenance & Evidence