Chloroform → N3-(4-methoxybenzoyl)-N4-[4-methoxy-2-[3-(1-methylpyrrol-2-ylcarbonyl)aminopropoxy]benzoyl]-3,4-pyridinediamine

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Reaction Steps

1-Methyl-2-pyrrolecarboxylic acid (57.6 mg, 460 μmol) was dissolved in amylene stabilized chloroform (8 mL). Resin-supported carbodiimide (1.1 g, 0.85 mm ol/g, 920 μmol) was added. To the resin-acid slurry was added N3-(4-methoxybenzoyl)-N4-[4-methoxy-2-(3-aminopropoxy)benzoyl]-3,4-pyridinediamine (106 mg crude, 230 μmol) in amylene stabilized chloroform (5 mL). The vial was capped and the reaction was agitated overnight on an orbital platform shaker. The slurry was filtered. The filtrate was concentrated and then purified by semipreparative HPLC as described in Example 2-F to provide N3-(4-methoxybenzoyl)-N4-[4-methoxy-2-[3-(1-methylpyrrol-2-ylcarbonyl)aminopropoxy]benzoyl]-3,4-pyridinediamine (17.3 mg, 27%) as ivory needles.

Provenance & Evidence