Ammonium Chloride → HCID 86687581, compound

Participants

Reaction Steps

To a flask containing ice cold suspension of N-(4-methoxybenzyl)thiazol-2-amine (147 mg, 0.665 mmol) in THF (2437 μl) was added lithium bis(trimethylsilyl)amide (1M in THF) (1267 μl, 1.267 mmol) faster than drop wise. The mixture was stirred for 15 min prior to the drop wise addition of a solution of 4-chloro-6-methylquinoline-7-sulfonyl chloride (175 mg, 0.634 mmol) in THF (2.0 ml, 0.5 ml wash). The solution was allowed to stir for 20 min (ice melt) providing a brown solution containing primarily product. The mixture was added to a flask containing sat. aq. NH4Cl and ice. The aqueous mixture was extracted 2× with EtOAc and the combined organics were dried with Na2SO4, filtered, and dried under reduced pressure. The crude material was purified with a 25 g HP Silicycle column ramping EtOAc in heptane (0-50%, 10% DCM throughout) to afford product, 4-chloro-N-(4-methoxybenzyl)-6-methyl-N-(thiazol-2-yl)quinoline-7-sulfonamide (162 mg, 0.352 mmol, 55.6% yield) as a yellow solid with about 15% impurity by LC-MS. m/z (ESI) 460.3 (M+H)+.

Provenance & Evidence