Picolinic acid → HCID 59463234, compound

Participants

Reaction Steps

A mixture of 2-(1-{[5-(aminomethyl)-2-thienyl]carbonyl}-3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (0.080 g, 0.21 mmol), EDCI (0.070 g, 0.36 mmol), DIPEA (0.150 mL, 0.86 mmol), and picolinic acid (0.31 g. 0.25 mmol) in DCM (4 mL) was allowed to stir at rt overnight. The reaction mixture was diluted with water and extracted with DCM. The organic solutions were combined, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give N-[(5-{[5-(2-hydroxyphenyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-1-yl]carbonyl}-2-thienyl)methyl]pyridine-2-carboxamide (I-136) (0.033 g) as a clear oil. LCMS: (FA) ES+ 484.2. 1H NMR (400 MHz, d6-DMSO) δ: 9.53-9.59 (m, 1H), 9.05-9.09 (m, 1H), 8.72-8.76 (m, 1H), 8.65-8.69 (m, 1H), 8.36-8.41 (m, 1H), 8.06-8.11 (m, 1H), 7.98-8.05 (m, 1H), 7.88 (d, 1H), 7.60-7.67 (m, 2H), 7.02-7.12 (m, 2H), 6.86-6.91 (m, 1H), 6.82 (d, 1H), 6.69 (t, 1H), 5.82 (dd, 1H), 4.70 (d, 2H), 3.82-3.92 (m, 1H), and 3.17 (dd, 1H).

Provenance & Evidence