N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amine → HCID 90110743, compound

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Reaction Steps

To a solution of N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amine (0.61 g, 2.44 mmol, 1.1 equiv) in THF (5.55 mL) at −78° C. was added LIHMDS (2.441 mL, 2.44 mmol, 1.1 equiv) and stirred for 0.5 h followed by the slow addition of 6-fluoro-1-(2-iodobenzyl)-1H-indazole-5-sulfonyl chloride (2-2, 1.0 g, 2.22 mmol, 1.0 equiv) in THF (1.85 mL) and stirred overnight as the system approached ambient temperature. The reaction was quenched with ammonium chloride and extracted with EtOAc. The organic phase was dried over Na2SO4, filtered and concentrated and the residue was purified by normal phase chromatography (0→40% EtOAc in hexanes). ESI+ MS [M+H]+ C25H21FIN5O4S2: 666.1 found, 666.5 required.

Provenance & Evidence