Nitrogen → 1-[(3-Chloroquinoxalin-2-yl)amino]-4-methylpentan-2-one

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Reaction Steps

A mixture of 2a (6.96 g, 24.8 mmol), 28.4 ml Et3N and sulphur trioxide trimethylamine complex (7.9 g, 56.8 mmol) in 28.4 ml DMSO, is stirred overnight (under N2) at room temperature, then ice water (50 ml) is added. The aqueous phase is extracted in CH2Cl2 (3×30 ml). The collected organic phases are dried (CaCl2) and then evaporated under reduced pressure. The residues are purified by chromatography on a silica column, eluent: C6H12/Et2O (85:15) to give a beige solid (4.18 g, 61%); 1H NMR (100 MHz, CDCl3) δ: 0.93 (s, 3H), 1.00 (s, 3H), 2.34 (m, 1H), 2.40 (s, 2H), 4.38 (d, 2H), 6.39 (t, 1H), 7.59 (m, 4H); 13C NMR (25 MHz, CDCl3) δ: 22.56, 25.01, 49.28, 51.55, 125.34, 125.87, 127.98, 130.14, 136.65, 137.92, 140.99, 147.30, 205.01. Analysis calculated for C14H16N3OCl: C, 60.54; H, 5.81; N, 15.13. Experimental: C, 60.32; H, 6.06; N, 14.95.

Provenance & Evidence