Triethylamine → 4-({5-[(2-ethoxy-2-oxoethyl)carbamoyl]adamantan-2-yl}amino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Benzyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (55 mg), ethyl {[(4-amino-1-adamantyl) carbonyl]amino}acetate (54 mg) and triethylamine (80 μl) were dissolved in N-methyl-2-pyrrolidone (0.55 ml) and stirred at 180° C. for 1 hour using a microwave reaction system. To the reaction solution were added ethyl acetate and water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate), the obtained compound was dissolved in dioxane (1.1 ml) and methanol (1.1 ml), 10% palladium on carbon (50% wet) was added, and catalytic reduction was performed for 4 hours at ambient temperature at 1 atm. Methanol, dioxane, and 1M hydrochloric acid were added, and the precipitated solid was dissolved and filtered to remove the catalyst. The filtrate was concentrated under reduced pressure to obtain 4-({5-[(2-ethoxy-2-oxoethyl)carbamoyl]adamantan-2-yl}amino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (18 mg).

Provenance & Evidence