Cesium carbonate → 5-(1h-Benzoimidazol-2-ylamino)-3-cyclohexylmethoxy-isothiazole-4-carboxylic acid amide monoformate salt

Participants

Reaction Conditions

Reaction Steps

3-Cyclohexylmethoxy-5-methylsulfanyl-isothiazole-4-carboxylic acid amide (5) (30 mg, 0.094 mmol) is dissolved in DMF (0.3 mL) and the solution is agitated on a shaker plate. 1H-Benzoimidazol-2-ylamine (25 mg, 0.188 mmol) and cesium carbonate (61 mg, 0.188 mmol) are then added and the reaction mixture is heated to 100° C. and agitated for 4 hrs. The resulting solution is then filtered and the mother liquor is purified by preparative HPLC to provide 5-(1H-Benzoimidazol-2-ylamino)-3-cyclohexylmethoxy-isothiazole-4-carboxylic acid amide monoformate salt (1.0 mg). 1H NMR (d6 DMSO): δ 12.09 (1H, s), 11.88 (1H, s), 7.77 (1H, s), 7.45–7.47 (1H, m), 7.36–7.38 (1H, m), 7.05–7.10 (2H, m), 7.01 (1H, s), 4.19 (2H, d, J=6.4 Hz), 1.61–1.83 (6H, m), 1.14–1.31 (3H, m), 0.97–1.11 (2H, m); LRMS (M+): 372.1.

Provenance & Evidence