1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 46178836, compound

Participants

Reaction Steps

To a solution of potassium 1-{[(3S)-3-({[(7S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclo-penta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-3-yl]methyl}amino)-3-phenylpropyl]amino}cyclopentanecarboxylate from step B (˜50 mg, ˜0.87 mmol) in DMF (4.5 mL) was added HOAt (18 mg, 0.13 mmol) and EDCI (150 mg, 0.80 mmol, in 4 portions). After 5 hours at ambient temperature, the reaction mixture was placed into a 60° C. bath for 16 hours. After the reaction was allowed to cool back to ambient temperature, the bulk of the DMF was removed in vacuo, before being diluted with chloroform (20 mL) and half-saturated sodium bicarbonate (5 mL). The aqueous layer was separated and extracted once with chloroform. The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue. This residue was applied to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH—99:1 to 92:8. Product-containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=544 (M+1). HRMS: m/z=544.2762; calculated m/z=544.2707 for C34H34N5O2.

Provenance & Evidence