Chloroacetyl chloride → HCID 89761950, compound

Participants

Reaction Steps

(+/−)-4-(2-methoxy-4-(trifluoromethyl)phenyl)-2-methyl-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide was prepared in a similar fashion to Example 223, starting from 3-hydroxy-4-((2-methoxy-4-(trifluoromethyl)phenyl)amino)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)benzenesulfonamide) (from Step 1, Example 223) and 2-chloropropanoyl chloride instead chloroacetyl chloride. Purification was achieved using reverse-phase HPLC with a Waters-Xbridge C18, 19×100 mm, 10 m column with a gradient 5-95% acetonitrile and water with 0.1% ammonium hydroxide modifier. 1H NMR (500 MHz, DMSO-d6) δ 1.53 (dd, J=16.93, 6.73 Hz, 3 H) 2.54 (s, 3 H) 3.79 (s, 1 H) 4.97-5.04 (m, 1 H) 6.40 (d, J=8.48 Hz, 1 H) 6.83 (d, J=4.58 Hz, 1H) 7.26 (d, J=4.52 Hz, 1 H) 7.30-7.42 (m, 2 H) 7.45-7.63 (m, 3 H). m/z ESI 500.0 (M+H)+.

Provenance & Evidence