Water → HCID 67150313, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 2, 250 mg) in acetone (8 ml) was added potassium carbonate (155 mg, 1.5 eq) and 1-(bromomethyl)-4-fluorobenzene (0.112 ml, 1.2 eq). The reaction mixture was stirred for 8 hours at 60-65° C. Water was added after the completion of the reaction, and the reaction mixture was extracted with ethyl acetate. Organic layer was washed with water and concentrated. The compound was purified by column chromatography using 10-15% ethylacetate in petroleum ether to give the title compound. Yield: 130 mg (39%). 1H NMR (CDCl3; 300 MHz): δ 7.87 (s, 1H), 7.66 (d, 1H), 7.44 (d, 2H), 7.37 (m, 2H), 7.08 (t, 2H), 6.68 (d, 2H), 4.74 (m, 1H), 4.37 (s, 2H), 3.79 (s, 3H), 2.37 (m, 1H), 1.05 (t, 6H); MS (ESI) m/z 442.1 [M+H]+, 464.1 [M+Na]+.

Provenance & Evidence