4-Pyridineacetic acid → HCID 60207819, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-amine (51 mg, 0.163 mmol, 1.0 equiv) and 2-(pyridin-4-yl)acetic acid (56 mg, 0.323 mmol, 2.0 equiv) in DMF (1 mL) was added HBTU (51 mg, 0.179 mmol, 1.1 equiv) and DIEA (91 μL, 0.520 mmol, 3.2 equiv) and heated to 40° C. and let stir for 15 h. The reaction was diluted with saturated NaHCO3 solution (15 mL) and extracted with a solution of 30% IPA in CHCl3 (3×20 mL). The organic layer dried (sodium sulfate), concentrated, and the residue was purified by silica gel flash column chromatography (10% methanol in dichloromethane) afford 35 (45 mg, 64% yield) as an off-white amorphous solid. 1H NMR (400 MHz, CD3OD) δ 8.65 (s 1H), 8.51 (d, J=5.6 Hz, 2H), 7.91 (d, J=4.4 Hz, 2H), 7.75 (d, J=5.2 Hz, 1H), 7.48 (d, J=5.6 Hz, 2H), 7.27 (t, J=4.0 Hz, 1H), 3.83 (s, 2H), 3.22 (t, J=7.6 Hz, 2H), 2.60 (s, 3H), 1.48 (quint, J=7.6 Hz, 2H), 1.25 (sex, J=7.2 Hz, 2H), 0.77 (t, J=7.2 Hz, 3H). LCMS (ES+) m/z 433 (M+1).

Provenance & Evidence