1,2-Dichloroethane → (7S)-2-{[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]carbonyl}-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Participants

Reaction Steps

A mixture of (S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridine]-2-carboxylic acid (15 mg, 0.045 mmol, described in Intermediate 9), 1-piperidin-4-yl-1,4-dihydro-2H-3,1-benzoxazin-2-one (12 mg, 0.045 mmol), EDC (10 mg, 0.050 mmol), HOIST (7 mg, 0.050 mmol), and N,N,N-triethylamine (0.006 mL, 0.045 mmol) was stirred in DMF (2.5 mL) at ambient temperature for 18 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. The pure, product-containing fractions were combined and concentrated to give the title compound. MS: m/z=546 (M+1). HRMS: m/z=546.2132; calculated m/z=546.2136 for C32H28N5O4.

Provenance & Evidence