Sodium Hydroxide → (S)-2-(2-(2-(1H-indazol-1-yl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (S)-ethyl 2-(2-(2-(1H-indazol-1-yl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (6.8 mg, 0.011 mmol) in THF (0.4 mL) and methanol (0.4 mL) was added 1N NaOH solution (0.4 mL, excess). The reaction mixture was stirred at 50° C. for 2 h and then purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C32H28ClN4O3S: 583.2; found: 583.3. 1H NMR (400 MHz, CDCl3) δ 8.86 (d, J=8.8 Hz, 1H), 8.63 (d, J=4.8 Hz, 1H), 8.57 (s, 1H), 8.23 (s, 1H), 7.97 (s, 1H), 7.81-7.77 (m, 2H), 7.73 (d, J=7.6 Hz, 1H), 7.58-7.50 (m, 4H), 7.30 (t, J=7.2 Hz, 1H), 5.35 (s, 1H), 2.61 (s, 3H), 1.02 (s, 9H).

Provenance & Evidence