p-Toluenesulfonic acid → HCID 53329179, compound

Participants

Reaction Steps

TsOH (0.109 g, 0.572 mmol) was added to a solution of (2-(2-(tert-butylamino)-3-(1,5-dihydroxypentyl)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone (0.070 g, 0.143 mmol) in toluene (2.0 mL) and the reaction was refluxed for 1.5 h. The reaction was concentrated and diluted with 10% sodium carbonate and extracted with dichloromethane. The combined organic extracts were washed with saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material which was purified by silica gel chromatography by eluting with 100% EtOAc followed by 1:20 2M NH3 in MeOH/dichloromethane, to provide (2-(2-amino-3-(tetrahydro-2H-pyran-2-yl)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone. MS (ESI, pos. ion) m/z: 416 (M+1).

Provenance & Evidence