Dimethyl Sulfoxide → HCID 118208689, compound

Participants

Reaction Conditions

Reaction Steps

N-(6-Bromopyridin-2-yl)-4-(trifluoromethyl)pyrimidin-2-amine (0.015 g, 0.047 mmol), ethyl 3-(1H-pyrazol-4-yl)propanoate (0.008 g, 0.047 mmol), potassium phosphate tribasic (0.030 g, 0.14 mmol), and DMSO (0.48 mL) were added to a microwave vial. The reaction tube was sealed and heated to 130° C. for 12 hours. The completed reaction was diluted DMSO (0.5 mL) and passed through a syringe filtered where the eluent was collected and concentrated under reduced pressure. The residue was taken up in dichloromethane (1.0 mL), MeOH (0.5 mL), and NaOH (0.5 mL, 1.0 M) and was allowed to stir at ambient temperature for 4 hours. The reaction was concentrated under reduced pressure. The residue was taken up in DMSO (1.0 mL), passed through a syringe filter and purified by reverse phase preparative HPLC (0 to 95% ACN/H2O with 0.1% ammonium hydroxide modifier) to afford 3-(1-(6-((4-(trifluoromethyl)pyridin-2-yl)amino)pyridin-2-yl)-1H-pyrazol-4-yl)propanoic acid. MS ESI calc. for C12H15F3N5O2 [M+H]+ 378. found 378. 1H NMR (600 MHz, DMSO-d6) δ 10.35 (s, 1H), 8.48 (d, J=5.2, 1H), 8.19 (s, 1H), 8.18 (s, 1H), 7.80 (t, J=8.0, 1H), 7.60 (s, 1H), 7.49 (d, J=8.2, 1H), 7.34 (d, J=7.8, 1H), 7.20 (d, J=5.3, 1H), 2.62 (t, J=7.6, 2H), 2.23 (t, 2H).

Provenance & Evidence