Acetic Acid → HCID 58550619, compound

Participants

Reaction Steps

To a stirred suspension of 2′-oxo-1′,2′, 6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridine]-3-carbaldehyde (80.0 mg, 0.254 mmol, Intermediate 1) and HOAc (31 μL, 0.533 mmol) in dry chloroform (3 mL) was added a solution of methyl 1-[(3-amino-2-phenylpropyl)amino]cyclopentanecarboxylate dihydrochloride from Step D (106 mg, 0.304 mmol) and Hunig's base (106 μL, 0.609 mmol) in dry chloroform (2 mL). After 15 minutes, sodium triacetoxyborohydride (108 mg, 0.507 mmol) was added. After 4 hours of stirring, the mixture was diluted with DCM and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted once with DCM. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a residue. The residue was then was applied to a silica gel column for purification, eluting with a gradient of DCM:MeOH (with 10% NH4OH)—99:1 to 86:14 to give the title compound. MS: m/z=576 (M+1).

Provenance & Evidence