Picolinic acid → HCID 44201107, compound

Participants

Reaction Steps

To a solution of picolinic acid (10 mg, 0.09 mmol) in DMF (1 mL) were added DIPEA (16 μL, 0.09 mmol) and HATU (33 mg, 0.09 mmol). After stirring at rt for 15 min, 17a (30 mg, 0.09 mmol) was added as a solution in DMF (0.5 mL). The reaction was stirred at rt until complete consumption of 17a was determined by LC/MS and then heated at 100° C. for 1 h. Subsequently the reaction was cooled to rt, filtered and purified by preparative LC/MS to give 7-ethyl-1-methyl-3-(2-methyl-5-(5-(pyridin-2-yl)-1,2,4-oxadiazol-3-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (A105). 1H NMR (400 MHz, d6-DMSO) δ 10.13 (s, 1H), 9.09 (s, 1H), 8.81 (s, 1H), 8.18 (d. J=8 Hz, 1H), 8.10 (m, 2H), 7.75 (s, 1H), 7.71 (m, 1H), 7.47 (d, J=8 Hz, 1H), 7.41 (s, 1H), 7.28 (d, J=8 Hz, 1H), 3.72 (s, 3H), 3.01 (q, J=7.6 Hz, 2H), 2.10 (s, 3H), 1.36 (t, J=7.6 Hz, 3H). MS m/z 439.3 (M+1).

Provenance & Evidence