Oxalyl chloride → 4'-Fluoro-biphenyl-4-carboxylic acid {2-[methyl-(1-methyl-pyrrolidin-3-yl)-amino]-benzothiazol-6-yl}-amide

Participants

Reaction Steps

The title compound is prepared by following Method C, using 4′-fluoro-biphenyl-4-carboxylic acid (3.46 g, 16.01 mmol), oxalyl chloride (4.65 mL, 53.36 mmol) and isomer-2 of N*2*-methyl-N*2*-(1-methyl-pyrrolidin-3-yl)-benzothiazole-2,6-diamine (2.80 g, 10.76 mmol) to give 4′-fluoro-biphenyl-4-carboxylic acid {2-[methyl-(1-methyl-pyrrolidin-3-yl)-amino]-benzothiazol-6-yl}-amide (2.41 g, 49%). The material is dissolved in THF (100 mL), and 1.0 M HCl in EtOH is added to adjusted the pH to 1. The resulting solid is collected and recrystallized from EtOH/Heptane to give 2.03 g (78%). LC/MS: Retention time=5.06 min; (m/z): calcd for, C26H25FN4OS (M+H)+: 461.6; found: 461.0.

Provenance & Evidence