Diisopropylethylamine → HCID 69675260, compound

Participants

Reaction Steps

2,7-bis(2-((2S,4S)-4-methylpyrrolidin-2-yl)-1H-imidazol-5-yl)-5,10-dihydrochromeno[5,4,3-cde]chromene was obtained as in Example OY. A mixture of (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (124 mg, 0.706 mmol), (R)-2-(tert-butoxycarbonylamino)-2-phenylacetic acid (177 mg, 0.706 mmol), COMU (665 mg, 1.55 mmol) in 3.7 mL DMF was allowed to preactivate for 20 minutes before it was added to 449 mg of the crude amine in 3.7 mL DMF with 0.74 mL DIPEA. Once starting material was consumed, by LCMS monitoring, the reaction mixture was neutralized with formic acid, diluted with methanol and purified by reverse phase HPLC three products, two homodimers and the heterodimer (S)-2-(methoxycarbonylamino)-1-((2S,4S)-2-(5-(7-(2-((2S,4S)-1-((R)-2-(t-butoxycarbonylamino)-2-phenylacetyl)-4-methylpyrrolidin-2-yl)-1H-imidazol-5-yl)-5,10-dihydrochromeno[5,4,3-cde]chromen-2-yl)-1H-imidazol-2-yl)-4-methylpyrrolidin-1-yl)-3-methylbutan-1-one as the trifluoroacetate salts. The eluted fractions were concentrated under reduced pressure, basified with saturated sodium bicarbonate solution and extracted into dichloromethane. Concentration under reduced pressure gave product (86 mg).

Provenance & Evidence