Ammonium Chloride → HCID 86687591, compound

Participants

Reaction Steps

To a flask containing ice cold suspension of N-(4-methoxybenzyl)thiazol-2-amine (557 mg, 2.53 mmol) in THF (9.0 ml) was added lithium bis(trimethylsilyl)amide (1M in THF) (4816 μl, 4.82 mmol) faster than drop wise. The mixture was stirred for 15 mins prior to the drop wise addition of a solution of 4-chloro-8-methylquinoline-7-sulfonyl chloride (665 mg, 2.408 mmol) in THF (6.0 ml, 1.0 ml wash). The solution was allowed to stir for 20 mins (ice melt) providing a brown solution containing primarily product according to LC-MS. 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) affording product, 4-chloro-N-(4-methoxybenzyl)-8-methyl-N-(thiazol-2-yl)quinoline-7-sulfonamide (326 mg, 0.709 mmol, 29.4% yield) as a yellow solid. m/z (ESI) 460.3 (M+H)+.

Provenance & Evidence