Water → 6-Chloro-N-(3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl)-N-isobutylnicotinamide

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Reaction Steps

To a solution of 6-chloronicotinic acid (34.1 mg, 0.22 mmol) in DMF (4 mL) were added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (60 mg, 032 mmol), HOBt.H2O (30 mg, 0.20 mmol) and 3,5-dichloro-N-(3-chloro-5-((isobutylamino)methyl)benzyl)-2-hydroxy-N-isobutylbenzenesulfonamide (100 mg, 0.20 mmol). The resulting reaction mixture was stirred at rt. for 18 h. The mixture was diluted with saturated NaHCO3 solution and ethyl acetate. The organic layer was concentrated. The residue was dissolved in 1 N NaOH solution and THF for 2 h. The mixture was concentrated and dissolved in MeOH, purified by preparative HPLC. Fractions containing the desired product were combined, concentrated, and lyophilized to give the desired product as white solid (62 mg, 40%). 1H NMR (CD3OD): δ 8.50-8.35 (m 1H), 8.0-7.8 (m, 1H), 7.70-7.49 (m, 3H), 7.34 (m, 1H), 7.16 (m, 1H), 7.10 (m, 1H), 4.72-4.45 (m, 4H), 3.30-3.03 (m, 4H), 2.1-1.6 (m, 2H), 0.96-0.71 (m, 12H); MS (ESI): (M−H)−=646.0.

Provenance & Evidence