Hydrochloric Acid → HCID 10126802, compound

Participants

Reaction Steps

A solution of [6-ethyl-3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid ethyl ester (0.474 g, 1.10 mmol) and BHT (2 mg) in 1,2-dimethoxyethane (10 mL, 1 M) is cooled to 0° C. and treated with 1 N NaOH (5 mL, 5 mmol). After stirring 30 min, the soln is acidified to pH 3-4 with 1 N HCl and extracted with ethyl acetate (3×). The combined organic layers are washed with saturated aq NaCl, dried over MgSO4 and filtered through a layered pad of celite, charcoal and florisil to give [6-ethyl-3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid (0.25 g, 56%). mp 155-157° C.; Rf 0.63 (50% methanol in chloroform) 1H NMR (DMSO-d6, 300 MHz) δ 12.98 (br s, 1 H), 7.87 (d, J=8.1 Hz, 1 H), 7.73-7.64 (m, 1 H), 7.53 (s, 1 H), 6.98 (d, J=8.1 Hz, 1 H), 4.99 (s, 2 H), 4.64 (s, 2 H), 2.76 (q, J=7.8 Hz, 2 H), 1.21 (t, J=7.8 Hz, 3 H); LRMS calcd for C19H14F3N3O2S: 405.4; found 405.0 (M)+. Anal. Calcd for C19H14F3N3O2S: C, 56.29; H, 3.48; N, 10.37; S, 7.91. Found C, 56.12; H, 3.40; N, 10.27; S, 7.91.

Provenance & Evidence