Dimethyl Sulfoxide → HCID 86676688, compound

Participants

Reaction Conditions

Reaction Steps

A solution containing 3-(6-fluoropyridin-3-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (0.070 g, 0.00019 mol) and (R)-tert-butyl piperidin-3-ylcarbamate (0.224 g, 0.00112 mol) in Dimethyl sulfoxide (1.40 mL, 0.0197 mol) was heated at 95° C. for 18 h. The reaction was quenched with water then filtered and washed with water. The crude product was dried under high vacuum overnight to give tert-butyl (3R)-1-(5-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ylcarbamate which was dissolved in Methylene chloride (1.4 mL, 0.022 mol) and treated with trifluoroacetic Acid (0.72 mL, 0.0093 mol). The reaction was stirred at RT 18 h. The reaction was concentrated then submitted for rHPLC to give 191 (50.6 mg, 73% yield). ESI MS m/z=372.1 (M+1). 1H NMR (400 MHz, DMSO) δ 9.40 (d, J=1.7 Hz, 1H), 9.18 (s, 1H), 8.88 (d, J=2.3 Hz, 1H), 8.60-8.53 (m, 3H), 8.21 (dd, J=8.9, 2.4 Hz, 1H), 7.50 (dd, J=7.7, 5.1 Hz, 1H), 6.97 (d, J=9.0 Hz, 1H), 4.27 (dd, J=23.6, 12.1 Hz, 2H), 2.88 (dd, J=17.5, 7.2 Hz, 2H), 2.73-2.56 (m, 2H), 1.89 (d, J=12.0 Hz, 1H), 1.73 (d, J=13.5 Hz, 1H), 1.47 (dd, J=24.5, 12.1 Hz, 1H), 1.25 (ddd, J=16.2, 12.6, 4.0 Hz, 1H)

Provenance & Evidence