Diisopropylethylamine → HCID 11977992, compound

Participants

Reaction Steps

A solution of 3-(3-chloro-benzenesulfonylamino)-benzoic acid (31.1 mg, 0.10 mmol) in DMF (0.5 ml) was added to 4-amino-2-fluoro-benzoic acid ethyl ester (20.1 mg, 0.11 mmol). Diisopropyl-ethyl-amine (0.035 ml) was added, followed by a solution of HATU (57.0 mg, 0.15 mmol) in DMF (0.5 ml). The mixture was shaken at room temperature overnight, then diluted with ethyl acetate (4.0 ml) and water (2.0 ml). The organic phase was separated and evaporated. The residue was dissolved in ethanol (0.60 ml) and treated with 3N KOH (0.40 ml). The mixture was shaken at room temperature overnight, then acidified to pH 2 with 3N HCl. Purification by preparative HPLC (ZORBAX Eclipse XDB-C18, 21.2×50 mm, 5 μm, gradient acetonitrile/water+0.1% formic acid) yielded the title compound (7.0 mg, 15%) as a white solid, MS (ISP): m/e=447.0 (M−H).

Provenance & Evidence