Hydrochloric Acid → 2-(5-(4-(6-Fluorobenzo[d]thiazol-2-ylamino)phenyl)thiazole-2-carboxamido)-3-methylbutanoic acid

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Reaction Steps

To a solution of Ethyl 2-(5-(4-(6-fluorobenzo[d]thiazol-2-ylamino)phenyl)thiazole-2-carboxamido)-3-methylbutanoate (Example 19, 80 mg) in THF (1.6 ml) was added 1 M aqueous solution of Lithium hydroxide monohydrate (0.32 ml) and the mixture was stirred at RT for 4 hours. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to get yellow solid, which was crystallized in ethyl acetate to give the title compound. Yield: 58 mg (77%); 1HNMR (DMSO-d6, 300 MHz): δ 12.99 (bs, 1H), 10.76 (s, 1H), 8.36 (s, 1H), 8.34 (d, 1H), 7.88 (d, 2H), 7.8 (d, 2H), 7.77 (d, 1H), 7.65 (dd, 1H), 7.2 (m, 1H), 4.32, (m, 1H), 2.27 (m, 1H), 0.97 (d, 6H); MS (ES+): m/z 471 (M+1).

Provenance & Evidence