tert-Butyl isocyanate → HCID 68980364, compound

Participants

Reaction Steps

To a solution of 7-o-tolyl-benzo[1,2,4]triazine-3,6-diamine (compound 16 on scheme (CCLXIX)) (0.12 mmol, 30 mg) in 5 mL anhydrous 1,4-dioxane was added potassium bis(trimethylsilyl)amide (53 mg, 0.26 mmol) and the mixture was stirred at room temperature under argon for 1.5 h. To the red solution was added tert-butylisocyanate (28.5 μl, 0.36 mmol) and stirring was continued for 2 h at room temperature. The product was poured into saturated aqueous NaHCO3 solution (40 mL) and was extracted with EtOAc (100 mL). The combined organic phases were dried (Na2SO4) and the solvent was evaporated to give 1-(3-amino-7-o-tolyl-benzo[1,2,4]triazin-6-yl)-3-tert-butyl-urea (28 mg, 67%). The title product was prepared as a red solid (27.8 mg, 48%) from the above intermediate and 4-bromo-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide following the above-described coupling procedure and was purified by reverse phase preparative HPLC. 1H NMR DMSO-d6: δ 1.37 (s, 9H), 1.87 (m, 2H); 2.01 (m, 2H), 2.16 (s, 3H), 3.04 (m, 4H), 3.24 (td, J=6.1 Hz, J=6.1 Hz, 2H), 3.56 (m, 2H), 7.21 (s, 1H), 7.33-7.40 (m, 4H), 7.50 (d, J=9.0 Hz, 2H), 7.75 (d, J=9.0 Hz, 2H), 7.88 (t, J=6.1 Hz, 1H), 7.99 (s, 1H), 8.34 (s, 1H), 8.83 (s, 1H), 9.53 (br s, 1H), 10.21 (s, 1H). MS (ESI+) m/z=603.

Provenance & Evidence