3-Aminobenzamide → HCID 87091804, compound

Participants

Reaction Conditions

Reaction Steps

Stir a solution of 3-aminobenzamide (51 mg, 0.362 mmol), CDI (60 mg, 0.362 mmol), and DMAP (45 mg, 0.362 mmol) in DMF (1.5 mL) at 90° C. for 30 min. A precipitate forms from the initial homogenous solution. Add N-(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-3-pyrrolidin-2-yl-benzamide di-HCl (100 mg, 0.241 mmol) to the hot reaction followed by more DMF (1 mL) and continue heating at 90° C. for 20 min. Cool the reaction to room temperature, dilute with water (1 mL), acidify with TFA (0.2 mL), and purify directly by reverse phase prep HPLC. Concentrate the fractions containing product to a solid which contains symmetric benzamide urea (30%). Suspend the solid in MeOH (4 mL) and sonicate—filter off the solid side product washing with MeOH (1 mL). Concentrate the filtrate, dry the residue in vacuo and triturate in EtOAc and hexane to give the title compound as a solid (97 mg). MS, electrospray 505.4 (M+H), rt 1.05 min.

Provenance & Evidence