HCID 70558848, compound → HCID 86702023, compound

Participants

Reaction Steps

A solution of 3-(3-chloro-4-(2,2-diethoxyethoxy)-5-methylphenyl)-5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazole (1.01 g, 2.01 mmol) in dioxane (15 mL) and 2 M aq. H2SO4 (5 mL) is stirred at 80° C. for 3 h. The mixture is extracted with EA (100 mL) and the org. extract is washed twice with brine (2×35 mL), dried over MgSO4, filtered and concentrated to give crude 2-(2-chloro-4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)acetaldehyde (1.02 g) as a yellow oil; LC-MS: tR=1.11 min, [M+H]+=428.19. Part of this material (345 mg, 0.806 mmol.) is dissolved in DCM (10 mL), methanol (10 mL) and acetic acid (0.7 ml) before β-alanine (72 mg, 0.806 mmol) is added. The mixture is degassed and put under argon before Na(BH3CN) (23 mg, 0.364 mmol) is added. The clear solution is stirred at rt for 2 h before the reaction is quenched by adding water (2 mL). The mixture is concentrated and the crude product is purified by prep. HPLC to give the title compound (77 mg) as a brownish solid; LC-MS: tR=0.95 min, [M+H]+=501.23; 1H NMR (CDCl3): δ 8.53 (s br, 2H), 7.83 (s, 1H), 7.67 (s, 1H), 7.33 (s, 1H), 7.07 (s, 1H), 4.20-4.30 (m, 2H), 3.95 (s, 3H), 3.39-3.49 (m, 2H), 3.25-3.36 (m, 2H), 3.12-3.22 (m, 1H), 2.64-2.75 (m, 2H), 2.32 (s, 3H), 2.02-2.12 (m, 2H), 1.78-1.91 (m, 4H), 1.68-1.78 (m, 2H).

Provenance & Evidence