Piperazine → HCID 86700430, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with a solution of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (10 mg), dioxane (500 μL), H2O (200 μL), Et3N (50 μL), and piperazine (40 mg). The reaction was heated to 60° C. for 1 h. Ethanol (absolute, 500 μL) and 5 M aq NaOH (500 μL) were added. The reaction was heated to 60° C. for 30 min. The reaction was cooled to 23° C. and directly purified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA) giving the title compound. 1H NMR (400 MHz, CD3OD) δ 8.49 (d, J=5.0 Hz, 1H), 8.03 (d, J=8.4 Hz, 1H), 7.81 (s, 1H), 7.68-7.44 (m, 3H), 7.41 (d, J=5.0 Hz, 1H), 5.08 (s, 1H), 3.92-3.69 (m, 4H), 2.85 (dd, J=18.8, 13.9 Hz, 4H), 2.66 (s, 3H), 0.91 (s, 9H). LCMS-ESI+: calc'd for C20H31ClN5O3S [M+H+]: 552.2, 554.2; Found: 552.4, 552.2 (M+H+).

Provenance & Evidence