Sodium t-butoxide → HCID 178429375, compound

Participants

Reaction Conditions

Reaction Steps

To a glass microwave reaction vessel was added N-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-2-(3-chloropyrazin-2-yl)-2-methylpropanamide (0.3181 g, 0.791 mmol), RuPhos Precatalyst (0.035 g, 0.047 mmol, Strem Chemicals, Inc.), and sodium tert-butoxide (0.152 g, 1.583 mmol, Sigma-Aldrich Chemical Company, Inc.) in dry dioxane (0.791 ml) to stir at 80° C. for 5 h. The crude product was purified by reverse-phase preparative HPLC using 0.1% TFA in CH3CN/H2O, gradient 10% to 90% over 12 mins. The collected fractions were evaporated and the residue was taken up in DCM and filtered through a Silicycle Si-Carbonate cartridge to remove any salts to give the title compound (139.2 mg, 0.381 mmol, 48.1% yield). LCMS showed product peak at 1.607 min (m+1=366.0). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.35 (s, 6 H) 2.74 (qd, J=7.86, 2.64 Hz, 2 H) 3.00 (qd, J=9.13, 2.74 Hz, 2 H) 4.12-4.27 (m, 1 H) 4.55-4.69 (m, 1 H) 7.04 (td, J=7.58, 1.08 Hz, 1 H) 7.24 (td, J=7.68, 1.27 Hz, 1 H) 7.36-7.44 (m, 1 H) 7.69 (dd, J=7.83, 0.78 Hz, 1 H) 8.15-8.23 (m, 2 H) 8.49 (d, J=6.65 Hz, 1 H)

Provenance & Evidence