HCID 86669822, compound → HCID 68182226, compound

Participants

Reaction Steps

To a stirred solution of N-(2-((3-formyl-6-methoxyquinolin-2-yl)amino)ethyl)acetamide SLA 41086 (147 mg, 512 μmol) in THF (20 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added sodium borohydride NaBH4 (19 mg, 502 μmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 1 N aq. HCl solution (40 mL). After stirring for 15 min at that temperature, the mixture was basified to pH=9 with a 2 N aq. NaOH solution. THF was then removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (100 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4, filtered and concentrated under vacuum to give N-(2-((3-(hydroxymethyl)-6-methoxyquinolin-2-yl)amino)ethyl)acetamide SLA 41088 as an orange solid (113 mg, 76% yield).

Provenance & Evidence