Potassium Carbonate → N-(2-chloro-4-(methylcarbamoyl)phenyl)-9-cyano-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 9-cyano-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid (300 mg) in toluene (10 mL) was added thionyl chloride (2 mL) and the reaction heated at 80° C. for 2 h. After cooling to room temperature, the solvent was reduced in vacuo and the residue redissolved in acetonitrile (10 mL). Potassium carbonate (306 mg) and 3-chloro-N-methyl-4-methylamino-benzamide from Example 21 (263 mg) were added and the reaction stirred at room temperature for 16 h. Water (20 mL) was added and the product extracted into ethyl acetate (2×20 mL). The organics were dried (MgSO4), reduced in vacuo and purified on silica to give 298. NMR: (CDCl3): 2.95-2.98 (5 H, m), 3.31 (3 H, s, Me), 4.19-4.21 (2 H, m), 6.10 (1 H, s, NH), 0.76 (1 H, s, Ar), 6.96 (1 H, d, J 8.4, Ar), 7.31-7.36 (2 H, m, Ar), 7.64-7.67 (2 H, m, Ar) and 7.87 (1 H, d, J 1.8, Ar). MS: (ESI+) MH+ 451.25

Provenance & Evidence