Hydrochloric Acid → Ethyl 2-(5-(4-(6-fluorobenzo[d]thiazol-2-ylamino)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

Participants

Reaction Conditions

Reaction Steps

A solution of Methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 2, 150 mg) and 2-chloro-6-fluorobenzo[d]thiazole (101 mg) in EtOH (3 ml) was heated at 55-60° C. to get clear solution. 4M aqueous HCl in 1,4-Dioxane (0.11 ml) was added to it and the reaction mixture was refluxed at 80° C. for 20 hours. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc:Pet ether, 2:8). The solid was crystallized in EtOAc/pet ether to give the title compound. Yield: 120 mg (53%); 1HNMR (DMSO-d6, 300 MHz): δ 10.76 (s, 1H), 8.66 (d, 1H), 8.37 (s, 1H), 7.88 (d, 2H), 7.80 (d, 2H), 7.77 (d, 1H), 7.64 (dd, 1H), 7.2 (m, 1H), 4.29 (m, 1H), 4.16 (q, 2H), 2.27 (m, 1H), 1.22 (t, 3H), 0.95 (d, 6H); MS (ES+) m/z 499 (M+1).

Provenance & Evidence