4-Methylmorpholine → Ammonium Hydroxide

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-oxo-3-pyridin-2-yl-2,3-dihydro-1H-benzimidazol-1-yl)acetic acid (11 mg, 0.040 mmol, described in Intermediate 7), (±)-3-amino-5,7-dihydrospiro[cyclopenta[c]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (10 mg, 0.040 mmol, described in Intermediate 3), HATU (19 mg, 0.050 mmol), and N-methylmorpholine (0.018 mL, 0.16 mmol) in DMF (1 mL) was stirred at 50° C. for 18 h. Additional HATU (19 mg, 0.050 mmol), and N-methylmorpholine (0.018 mL, 0.16 mmol) was added and the mixture was stirred at 50° C. for a further 6 h. The reaction mixture was purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided a crude product, which was further purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 95:5:1, to give the title compound. MS: m/z=504 (M+1). HRMS: m/z=504.1809; calculated m/z=504.1779 for C28H22N7O3.

Provenance & Evidence