Thionyl Chloride → HCID 57929981, compound

Participants

Reaction Conditions

Reaction Steps

A 125 mL flask was charged with N′-(6-(2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)pyridazin-3-yl)-1-methylcyclopropanecarbohydrazide (0.458 g, 0.614 mmol, prepared using General Procedure AR from Example #35, Step E with 1-methylcyclopropanecarboxylic acid) and 1,4-dioxane (20 mL) to give a brown suspension. To the suspension, thionyl chloride (0.3 mL, 4.11 mmol) was added and the mixture was stirred at about 80° C. After about 4 h, the reaction was concentrated under reduced pressure. The residue was redissolved in DCM and washed with saturated aqueous Na2CO3. The organic solution was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by silica gel chromatography using MeOH/DCM (gradient; 0:100 to 10:90) to give the title compound (0.140 g, 58% yield): LC/MS (Table 1, Method a) Rt=2.28 min; MS m/z: 393.3 (M+H)+.

Provenance & Evidence