Sodium Bicarbonate → HCID 52934042, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-N4-(2-pyridinylmethyl)-3,4-quinolinediamine (for a preparation see Intermediate 38, 0.5 g, 1.33 mmol) in DCM (20 ml) was added tetrahydro-2H-pyran-4-carbonyl chloride (1.1 eq., 1.46 mmol, 0.15 g, Apollo Scientific) at 0° C., the mixture was stirred at 0° C. for 30 minutes. The reaction mixture was hydrolysed with saturated aqueous Sodium hydrogen carbonate and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated to give the crude product which was used in the next step without purification. AcOH (5 ml) was added to the crude product and the mixture was stirred at 100° C. overnight. The reaction mixture was concentrated under reduce pressure, hydrolised with sodium hydroxide 1N and extracted with DCM. The organic phase was dried over over Na2SO4, evaporated under reduce pressure. The residue was purified by flash chromatography on silica gel (DCM/MeOH, 95:5) and the compound was re-crystallised from acetonitrile to give the title compound as an off-white powder (0.13 g, 21%)

Provenance & Evidence