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

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-oxo-2,6-naphthyridin-2(1H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (15.5 mg, 0.024 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 C33H28ClN4O4S: 611.2; found: 611.2. 1H NMR (400 MHz, CDCl3) δ 9.32 (s, 1H), 8.81 (d, J=6.0 Hz, 1H), 8.75-8.71 (m, 2H), 8.60 (s, 1H), 8.27 (d, J=7.6 Hz, 1H), 7.99 (d, J=3.6 Hz, 1H), 7.94 (s, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.53-7.48 (m, 3H), 6.94 (d, J=8.0 Hz, 1H), 5.32 (s, 1H), 2.59 (s, 3H), 1.00 (s, 9H).

Provenance & Evidence