Hydrochloric Acid → HCID 58949445, compound

Participants

Reaction Steps

A round-bottomed flask was charged with 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (Example 104, Step C, 12.9 mg, 0.0549 mmol), EDCI (10.5 mg, 0.0549 mmol), HOBT-H2O (8.41 mg, 0.0549 mmol), tert-butyl 4-(4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (14.0 mg, 0.0275 mmol), Hunig's base (7.10 mg, 0.0549 mmol) and DMF (4 mL). After stirring for 18 hours, the reaction was diluted with water and extracted with EtOAc. The organics were dried over sodium sulfate, filtered and concentrated. Purification by preparative TLC (0.5 mm thickness) 9:1 EtOAc/MeOH gave a band at Rf 0.7 that was isolated, washed from silica with 9:1 EtOAc/MeOH and concentrated to get an oil. HCl (4 mL, 4N dioxane) was added and stirred for 18 hours. The mixture was concentrated to get an orange oil. MeOH (4 mL) was added and the formed precipitate filtered to give (4.2 mg, 23%) as an off white solid. LRMS (esi+) 626 m/z (M+1) detected.

Provenance & Evidence