Lithium iodide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-oxo-2,7-naphthyridin-2(1H)-yl)benzo[d]thiazol-6-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-oxo-2,7-naphthyridin-2(1H)-yl)benzo[d]thiazol-6-yl)acetate (18.8 mg, 0.034 mmol)) in pyridine (0.8 mL) was added LiI (100 mg, excess). The reaction mixture was heating in a microwave at 170° C. for 90 min. The mixture was concentrated in vacuo 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 C28H25ClN3O4S: 534.1; found: 534.2. 1H NMR (400 MHz, CDCl3) δ 9.69 (s, 1H), 9.27 (d, J=7.6 Hz, 1H), 8.93 (s, 1H), 7.89 (s, 1H), 7.79 (s, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.58-7.50 (m, 3H), 6.93 (d, J=7.6 Hz, 1H), 5.36 (s, 1H), 2.59 (s, 3H), 1.01 (s, 9H).

Provenance & Evidence