Triethylamine → HCID 58949536, compound

Participants

Reaction Steps

A mixture of 7-(2-fluoro-4-(2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamido)phenoxy)thieno[3,2-b]pyridine-2-carboxylic acid (12 mg, 0.023 mmol), EDCI (13.3 mg, 0.069 mmol), and HOBt (9.4 mg, 0.069 mmol) in DMF (1 mL) was stirred at room temperature for 30 minutes. 1-Methylpiperazine (6.9 mg, 0.069 mmol) was added followed by Et3N (7 mg, 0.069 mmol). After stirring for 2 hours, the reaction mixture was diluted with EtOAc and washed with saturated aqueous NH4Cl, saturated aqueous NaHCO3, and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (5% MeOH in CH2Cl2) to afford 11 mg (79%) of the desired product. LRMS (APCI pos) m/e 603.3 (M+1). 1H-NMR (400 MHz, CD3OD) δ 8.87 (d, 1H), 8.37 (d, 1H), 8.32 (d, 1H), 8.14 (d, 1H), 8.03 (s, 1H), 7.68 (m, 2H), 7.57 (m, 2H), 7.24-7.32 (m, 3H), 3.61 (m, 4H), 2.98 (s, 3H); 19F-NMR (376 MHz, CD3OD) δ −114.7, −129.3.

Provenance & Evidence