Water → HCID 69200205, compound

Participants

Reaction Steps

To a solution of Intermediate 2 (250 mg, 0.712 mmol) in DCM (100 mL), was added 2M oxalyl chloride in DCM (0.427 μL, 0.854 mmol) and DMF (˜50 μL). The reaction mixture was stirred for 4 hr, and concentrated. The residue was put on high vacuum for 2 hr and dissolved in DCM (10 mL). The formed acid chloride was added into a solution of the product from Step D (267 mg, 0.854 mmol) and triethylamine (456 L, 3.28 mmol) in DCM (10 mL) at 0° C. The reaction mixture was stirred for 16 hr and concentrated. The residue was purified by flash column chromatography (silica gel, 8% [aq. NH4OH/MeOH 1/9]/DCM ) first and then by preparative TLC (100 micron) (developed by 5% MeOH/DCM) to yield the 7-(trifluoromethyl)-1,2,3,4-tetrahydropyrido[3,4-d]pyridazine amide (39.5 mg, 10.3%) and another structural isomer (42.3 mg, 11.1%). LC-MS calc. For C24H30F6N4O3: 536.22; Found: 537 (M+H).

Provenance & Evidence