HCID 86629744, compound → HCID 57663767, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl (7-nitro-2-oxo-3-{[(7S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2-yl]methyl}-2,3-dihydro-1H-benzimidazol-1-yl)acetate from Step A (55 mg, 0.100 mmol) and iron powder (15 mg, 0.269 mmol) was heated to 80° C. in AcOH (1 mL) for 2 h. Iron powder (15 mg, 0.269 mmol) was added and the mixture was heated to 80° C. for 1 h, then more iron powder (15 mg, 0.269 mmol) was added and the mixture was heated to 100° C. for 1 h. The cooled mixture was filtered then partitioned between saturated aqueous NaHCO3 (20 mL) and CH2Cl2 (20 mL). The organic layer was removed and the aqueous layer was extracted further with CH2Cl2 (2×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified 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. The pure, product-containing fractions were combined and concentrated to give the title compound. MS: m/z=489 (M+1). HS: m/z=489.1662; calculated m/z=489.1670 for C28H21N6O3.

Provenance & Evidence