Water → HCID 21906691, compound

Participants

Reaction Conditions

Reaction Steps

N-(2-Hydroxyethyl)-ethylenediamine (0.208 g) was added to a mixture of N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide (0.192 g, Example 1(ii)) and potassium carbonate (0.14 g) in anhydrous N-methyl-2-pyrrolidinone (3 ml). The resulting solution heated in a MARS microwave for 10 minutes (300 Watts, 150° C.). The mixture was cooled and poured into water (50 ml) and extracted into ethyl acetate (3×10 ml). The combined organic extracts were washed with brine (2×10 ml), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was dissolved into ethyl acetate 30 ml and di-tert-butylcarbonate (0.218 g) added. The resulting mixture was left to stand at room temperature for 2 hours and was then concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with ethyl acetate to afford tert-butyl 2-[(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)(2-hydroxyethyl)amino]ethylcarbamate (0.013 g).

Provenance & Evidence