4-Methylmorpholine → HCID 16734977, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (±)-3-{[(3,5-difluorobenzyl)amino]methyl}-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step A (47.0 mg, 0.106 mmol) in DCM (1.5 mL) was added 4-methylmorpholine (32.2 mg, 0.320 mmol). This mixture was sonicated to provided a finely powdered suspension. After cooling to 0° C., trimethylacetyl chloride (23.0 mg, 0.190 mmol) was added and the cooling bath was removed. After 23 hours, additional 4methylmorpholine (2 drops) and trimethylacetyl chloride (23.0 mg, 0.190 mmol) were added. After 7 hours, the reaction was quenched by the addition of one drop of methanol. This reaction mixture was applied to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH—100:1 to 94:6, to give the title compound as a white solid. MS: m/z=527 (M+1). HRMS: m/z=527.2253; calculated m/z=527.2253 for C31H29F2N4O2.

Provenance & Evidence