Oxalyl chloride → HCID 58458939, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-(benzyloxy)-2-cyclopentyl-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid (0.33, 1 mmol) in CH2Cl2 (3 mL) was added a catalytic amount of DMF followed by 3 mL of a 2M solution of oxalyl chloride dissolved in CH2Cl2. The resulting yellow reaction mixture was stirred for 1 h and concentrated to give a yellow oil. The yellow oil was dissolved in 1,4-dioxane (9 mL) and added to a stirred solution of 2-(4-fluorophenyl)-N-hydroxyacetimidamide (0.18 g, 1.1 mmol) and DIEA (0.2 mL) in 1,4-dioxane (1 mL). After 4 h at room temperature, the reaction mixture was heated at 90° C. for 14 h. The mixture was cooled to room temperature and purified by flash column chromatography on a silica gel column using 7:1 hexanes/EtOAc as eluant to afford the title compound (0.29 g, 63% yield) as an off-white solid. 1HNMR (500 MHz, CDCl3) δ: 7.43-7.39 (2H, m), 7.33 (2H, dd, J=8.6, 5.2 Hz), 7.28-7.23 (3H, m), 7.00 (2H, t, J=8.6 Hz), 5.34 (2H, s), 4.14 (2H, s), 3.63 (3H, s), 3.21-3.14 (1H, m), 2.05-1.99 (4H, m), 1.88-1.80 (2H, m), 1.71-1.62 (2H, m). HRMS (M+H) calcd for C26H26N4O3F: 461.1989. found: 461.1979.

Provenance & Evidence