Citric Acid → HCID 67198895, compound

Participants

Reaction Conditions

Reaction Steps

In a vial, 4-[4-(1-benzenesulfonyl-3-{2-fluoro-6-[(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amino]-pyridin-3-ylmethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (170, 0.137 g, 0.178 mmol) was dissolved in a solution of potassium hydroxide (0.392 g, 6.99 mmol) in 7.0 mL of methanol and the reaction was heated at 50° C. for 3 hours. Aqueous 1 M citric acid was added, then the reaction was extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. 4-[4-(3-{2-fluoro-6-[(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amino]-pyridin-3-ylmethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (P-1702, 56 mg, 0.0888 mmol) was combined with this and 10 mL of dichloromethane and trifluoroacetic acid (0.50 mL, 6.5 mmol) were added, then stirred at room temperature for 2 hours. Aqueous saturated sodium bicarbonate was added to pH=8, then concentrated under vacuum and ethyl acetate and water were added. The organic layer was isolated and washed with aqueous saturated sodium bicarbonate, then dried with magnesium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound as a yellow solid (P-1703, 74 mg). MS (ESI) [M+H+]+=631.1.

Provenance & Evidence