Dimethylformamide → HCID 59200361, compound

Participants

Reaction Conditions

Reaction Steps

A DMF (3 mL) suspension of 4-chloropicolinic acid (0.160 g, 1.01 mmol) and sodium hydrogensulfide hydrate (0.225 g, 3.03 mmol, 3 eq) was heated to 100° C. After 3 h, the suspension was diluted with methanol (10 mL), 5-bromo-N-(pyridine-2-yl)thiazol-2-amine (0.256 g, 1.0 mmol, 1 eq, described in the synthesis of thiazoles Example A) was added followed by a solution of sodium methoxide 25% (2 mL). The resulting mixture was heated at 80° C. for 15 min., concentrated to remove most of the methanol, diluted with DMF and acidified with acetic acid. The resulting solution was purified on preparative HPLC (ammonium acetate/water/acetonitrile) and freeze dried to give the title compound as a solid (0.094 mg, 28%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.00 (1H, dd, J=6.69, 5.68 Hz), 7.12 (1H, d, J=8.34 Hz), 7.34 (1H, dd, J=5.31, 1.77 Hz), 7.68 (1H, d, J=1.52 Hz), 7.73-7.83 (2H, m), 8.31 (1H, d, J=4.04 Hz), 8.48 (1H, d, J=5.31 Hz), 11.80 (1H, s). LC/MS (M+H)+: 331, (M−H)−: 329.

Provenance & Evidence