Hydrochloric Acid → 5-{7-amino-4-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]furo[2,3-c]pyridin-2-yl}-2-chlorobenzoic acid hydrochloride

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-{4-[4-(7-amino-2-chlorofuro[2,3-c]pyridin-4-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone (125 mg, 0.347 mmol), 4-chloro-3-(methoxycarbonyl)phenylboronic acid (89.4 mg, 0.417 mmol), and Pd(PPh3)4 (40.1 mg, 0.0347 mmol) in 1.0 M aqueous sodium carbonate (1.74 mL, 1.74 mmol) and 1,4-dioxane (1.63 mL) was heated to 120° C. in a microwave for 30 min. The reaction mixture was then diluted with ethyl acetate (10 mL) and acidified with aqueous 1 N hydrochloric acid (5 mL), causing formation of a precipitate. The precipitate was collected by vacuum filtration and then triturated from DMSO and methanol (10 mL, ˜1:10) to afford 55 mg (29%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 8.45 (d, J=1.5 Hz, 1H), 8.29 (s, 1H), 8.22 (dd, J=1.8, 8.3 Hz, 1H), 8.00 (d, J=8.1 Hz, 2H), 7.91 (s, 1H), 7.75 (d, J=8.6 Hz, 1H), 6.56 (br s, 2H), 4.61-4.30 (m, 2H), 3.94 (br s, 1H), 3.24 (br s, 1H), 2.74 (br s, 1H), 2.26-1.63 (m, 7H); MS (ESI): 480.10 [M+H]+; HPLC tR=2.35 min (ZQ3, polar—4 min).

Provenance & Evidence