Triethylamine → HCID 86596852, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl N′-(3-amino-7-benzyloxyquinolin-4-yl)hydrazinecarboxylate (29.6 g, 77.8 mmol) in 250 mL of 1,2-dichloroethane was placed under an atmosphere of nitrogen. The mixture was treated with triethylamine (30.9 mL, 233 mmol). The mixture was then treated dropwise with ethoxyacetyl chloride (10.5 g, 85.6 mmol). After 2 h, the reaction was concentrated under reduced pressure to give a brown oil. The oil was dissolved in 200 mL of 1-butanol and treated with pyridinium p-toluenesulfonate (0.25 g, 1.0 mmol). The mixture was heated to 135° C. under an atmosphere of nitrogen. After 20 h, the reaction mixture was cooled to ambient temperature and concentrated under reduced pressure to give a brown oil. The oil was dissolved in 250 mL of CHCl3 and washed with saturated NaHCO3 solution (75 mL), water (75 mL) and brine (75 mL). The organic portion was then dried over Na2SO4, filtered and concentrated under reduced pressure to give an orange/brown oil. The oil was purified by chromatography (SiO2, 9:1 CHCl3:MeOH) to yield 14.4 g of tert-butyl (7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)carbamate as an orange/brown foam.

Provenance & Evidence