Ammonium Chloride → HCID 86687586, compound

Participants

Reaction Steps

To a flask containing ice cold suspension of N-(4-methoxybenzyl)thiazol-2-amine (171 mg, 0.776 mmol) in THF (2844 μl) was added lithium bis(trimethylsilyl)amide (1M in THF) (1479 μl, 1.479 mmol) faster than drop wise. The mixture was stirred for 15 mins prior to the drop wise addition of a solution of 4-chloro-6-methoxyquinoline-7-sulfonyl chloride (216 mg, 0.739 mmol) in THF (2.0 ml, 0.4 ml wash). The solution was allowed to stir for 4 hr (ice melt) providing a brown solution containing primarily product according to LC-MS. The mixture was added to a flask containing sat. aq. NH4Cl. 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 40 g HP silicycle column ramping EtOAc in heptane (0-50%, 10% DCM throughout) affording product, 4-chloro-6-methoxy-N-(4-methoxybenzyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (128 mg, 0.269 mmol, 36.4% yield) as a yellow solid. m/z (ESI) 476.1 (M+H)+.

Provenance & Evidence