Dichloromethane → HCID 24855564, compound

Participants

Reaction Steps

To 4-{[(3-butoxypyridin-2-yl)methyl]amino}-1H-imidazole-5-carboxamide (0.991 g, 3.43 mmol, obtained from Example 19(b)) was added dichloromethane (20 mL), ethoxycarbonyl isothiocyanate (0.47 mL, 4.11 mmol) and absolute ethanol (2 mL). After stirring o.n., more ethoxycarbonyl isothiocyanate (0.23 mL) was added and the solution was heated to reflux for 2 h upon, which more ethoxycarbonyl isothiocyanate (0.10 mL) was added and the solution was refluxed for 2 h more. The volatiles were removed in vacuo and 1 N sodium hydroxide (20 mL) was added and the suspension was heated to reflux for 4 h. After cooling to r.t. the solution was neutralized with 2 N hydrochloric acid. The resulting precipitate was filtered, washed with water and dried resulting in 0.699 g of crude product. Purification was achieved with a portion of the crude material (300 mg) by trituration with methanol and dichloromethane and then concentrating the organic layer followed by prep HPLC providing 0.103 g (16% yield, 0.231 mmol) of the title compound as its trifluoroacetic acid salt.

Provenance & Evidence