Sodium Hydroxide → 1-(5-{2-[(ethylcarbamoyl)amino]-5-(1H-pyrazol-1-yl)[1,2,4]triazolo[1,5-a]pyridin-7-yl}pyrimidin-2-yl)-4-methylpiperidine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A 2N aqueous solution of NaOH (5 mL) was added to a solution of ethyl 1-(5-{2-[(ethylcarbamoyl)amino]-5-(1H-pyrazol-1-yl)[1,2,4]triazolo[1,5-a]pyridin-7-yl}pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate (88 mg, 0.17 mmol) in EtOH (15 mL) at rt and was heated at 70° C. After 2 h the reaction mixture was cooled to rt and concentrated in vacuo to ˜⅓ volume. Water (10 mL) was added and the resultant solution extracted with EtOAc (2×10 mL). The aqueous was then acidified to pH 1-2 and extracted with 10% IPA/DCM (3×10 mL). The organic layers were combined and dried (MgSO4), filtered and concentrated in vacuo to give a off white solid which was purified by semi preparative HPLC to give Compound 227 as a cream solid (20 mg, 24%). 1H NMR (DMSO) δ 10.01 (s, 1H), 9.00 (d, J=2.4 Hz, 1H), 8.94 (s, 2H), 8.16-8.06 (m, 1H), 8.01 (s, 2H), 7.81 (s, 1H), 6.77-6.73 (m, 1H), 4.35 (d, J=13.5 Hz, 2H), 3.25 (s, 2H), 2.05 (d, J=12.9 Hz, 2H), 1.38 (s, 2H), 1.25 (s, 2H), 1.19 (s, 3H), 1.14 (d, J=7.2 Hz, 3H). MS: 491.1 [M+H]+.

Provenance & Evidence