tert-butyl (3R)-3-aminopiperidine-1-carboxylate → HCID 89783981, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 50 mg, 0.168 mmol) and (R)-tert-butyl 3-aminopiperidine-1-carboxylate (Small Molecules, Inc., Hoboken, N.J.; 168 mg, 0.840 mmol) in DMSO (0.5 mL) was stirred under argon at 100° C. for 19 h, then 130° C. for 5 h, then 150° C. for 17 h. The mixture was cooled to 25° C. and partitioned between DCM (30 mL) and water (20 mL). The organic layer was separated, and the aq. layer was extracted with DCM (2×20 mL). The combined organic extracts were sequentially washed with water (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo to provide crude (R)-tert-butyl 3-((8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinolin-2-yl)amino)piperidine-1-carboxylate (179.7 mg) as a brown foam (used without further purification in the subsequent transformation): m/z (ESI, +ve) 462.4 (M+H)+.

Provenance & Evidence