1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 5-(N-{[6-amino-5-({3-[(2-fluoro-5-methylbenzoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)pentanoate

Participants

Reaction Steps

To the mixture of methyl 5-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]pentanoate, (85.6 mg, 0.2 mmol, 1 eq) and 2-fluoro-5-methylbenzoic acid (32.7 mg, 1.05 eq) in dichloroethane (2 mL) at 60° C. was added catalytic amount of DMAP (5 mg, 0.2 eq) and EDCI (46.1 mg, 1.2 eq). The reaction was stirred at that temperature for 4 h and then cooled to room temperature. It was then partitioned between EtOAc and saturated aq NaHCO3. The organic layer was further washed with aq NH4Cl, brine and then dried with anhydrous sodium sulfate. The organic layer was decanted, concentrated, and the residue was subject to a gradient column chromatography (EtOAc-Hex 1:4 to neat EtOAc). The product containing fractions were concentrated to give the title compound as a white foam (92 mg).

Provenance & Evidence