1-Butanol → HCID 59385335, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4′-amino-3-methoxybiphenyl-4-carboxylate (0.27 g, 1.06 mmol) and 2-chloro-6-fluoro-1,3-benzothiazole (0.20 g, 1.06 mmol) in n-butanol (8 mL) was heated to 60-70° C., and then 4N HCl in 1,4-dioxane (0.12 mL, 0.48 mmol) was added dropwise with stirring. The reaction mixture was heated at 90° C. for 18 h. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (25% EtOAc in hexanes), yielding 0.209 g (44%) of butyl 4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methoxybiphenyl-4-carboxylate, and 0.132 g (30%) of methyl 4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methoxybiphenyl-4-carboxylate [LC/MS m/z 409.3 (MH+), retention time=3.67 min, m/z 451.3 (MH+), retention time=4.25 min. 1H NMR (400 MHz, CD2Cl2) δ 3.85 (s, 3H), 4.00 (s, 3H), 7.05-7.26 (m, 3H), 7.42 (d, 1H), 7.61-7.64 (m, 1H), 7.76 (s, 4H), 7.90 (d, 1H)].

Provenance & Evidence