Thionyl Chloride → HCID 67246988, compound

Participants

Reaction Steps

To a suspension of {5-[(7-chloroquinolin-4-yl)amino]-2-(morpholin-4-yl)phenyl}methanol hydrochloride (compound of step C of example 31) (0.100 g, 0.25 mmol) in 4 mL of NMP at 0° C. was added thionyl chloride (90 μL, 1.23 mmol). The reaction mixture was warmed up to room temperature and stirred for 3 h. The reaction mixture was then slowly added to N,N,N′-trimethylethylenediamine (1 mL, 7.50 mmol) in 1 mL of NMP at 0° C. and then stirred at room temperature for 2 h. This solution was diluted in 100 mL of CH2Cl2 and washed with a saturated aqueous solution of NaHCO3. The organic layer was dried over MgSO4, filtered, evaporated and purified by flash chromatography (DCM/MeOH/NH4OH//90/10/1 then 80/20/1) to yield expected compound as a yellow solid (97 mg, 85% yield). LC-MS: m/z (ESI) 454.4 [M+H]+.

Provenance & Evidence