Oxalyl chloride → HCID 86664398, compound

Participants

Reaction Steps

4-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation B; 100 mg, 0.265 mmol) was diluted with dichloromethane (5 mL) followed by the addition of oxalyl chloride in dichloromethane (2M) (146 μL, 0.292 mmol) and dimethylformamide (1 drop). After stirring for 30 minutes a small aliquot was diluted with methanol for 5 minutes. Thin layer chromatography of this aliquot showed complete conversion to methyl ester. 6-(Trifluoromethyl)benzo[d]thiazol-2-amine (63.7 mg, 0.292 mmol) and diisopropyl ethylamine (116 μL, 0.664 mmol) were added and the reaction was stirred at 35° C. for 1 hour. The reaction was loaded directly onto a Biotage 25 cartridge and eluted with 5% ethyl acetate/hexanes to 70% ethyl acetate/hexanes to yield ethyl 6-chloro-7-(4-(6-(trifluoromethyl)benzo[d]thiazol-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (50 mg, 0.0867 mmol, 32.7% yield).

Provenance & Evidence