[(S)-1-(5-fluoro-1,2,3,4-tetrahydroquinolin-8-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester → [(S)-1-(7-Fluoro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl)ethyl]carbamic acid tert-butyl ester

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Reaction Steps

A solution of [(S)-1-(5-fluoro-1,2,3,4-tetrahydroquinolin-8-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester (15 mg, 0.044 mmol) in AcOH (1 mL) was stirred at 100° C. for 2 h, then concentrated in vacuo. A further portion of [(S)-1-(5-fluoro-1,2,3,4-tetrahydroquinolin-8-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester (90 mg, 0.267 mmol) in AcOH (5 mL) was stirred at 100° C. for 1 h, then concentrated in vacuo. The combined residues were purified by column chromatography (Si—PCC, gradient 30-60% EtOAc in cyclohexane) affording the title compound as a colourless gum (78 mg, 79%). LCMS (Method J): RT 2.19 min [M+H]+ 320

Provenance & Evidence