Dimethylformamide → HCID 70558848, compound

Participants

Reaction Steps

To a solution of 2-cyclopentyl-6-methoxy-isonicotinic acid (704 mg, 3.18 mmol) in DMF (5 mL) TBTU (1.43 g, 4.45 mmol) and Hünig's base is added. The mixture is stirred at rt for 15 min before 3-chloro-4-(2,2-diethoxyethoxy)-N-hydroxy-5-methylbenzimidamide (907 mg, 2.86 mmol) is added. Stirring is continued for 18 h before another portion of 3-chloro-4-(2,2-diethoxyethoxy)-N-hydroxy-5-methylbenzimidamide (503 mg, 1.59 mmol) and TBTU (510 mg, 1.59 mmol) is added. Stirring is continued for 4 h. The mixture is diluted with EA (100 mL) and washed with water (50 mL). The washing is extracted three times with EA (3×50 mL). The combined org. extracts are dried over MgSO4, filtered and concentrated. The residue is dissolved in dioxane (35 mL) and the resulting solution is stirred at 110° C. for 18 h. The solvent is evaporated and the crude product is purified by MPLC on silica gel eluting with heptane:EA 7:3 to give 3-(3-chloro-4-(2,2-diethoxyethoxy)-5-methylphenyl)-5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazole (1.01 g) as a yellow oil; LC-MS: tR=1.43 min, [M+H]+=502.29; 1H NMR (CDCl3): δ 8.06 (d, J=1.9 Hz, 1H), 7.92 (d, J=1.4 Hz, 1H), 7.50 (d, J=0.9 Hz, 1H), 7.29 (d, J=1.1 Hz, 1H), 4.94 (t, J=5.3 Hz, 1H), 4.08 (d, J=5.3 Hz, 2H), 4.02 (s, 3H), 3.77-3.86 (m, 2H), 3.64-3.73 (m, 2H), 3.19-3.29 (m, 1H), 2.44 (s, 3H), 2.08-2.14 (m, 2H), 1.83-1.94 (m, 4H), 1.71-1.77 (m, 2H), 1.28 (t, J=7.1 Hz, 6H).

Provenance & Evidence