Sodium t-butoxide → HCID 178481620, compound

Participants

Reaction Steps

Following the procedure described for Example 44 (MethOD B6), using methyl (2-bromophenyl)(methyl)carbamate, INTERMEDIATE 74 (0.510 g, 2.089 mmol), trans-N1-(benzo[d]thiazol-2-yl)cyclobutane-1,3-diamine, INTERMEDIATE 11 (0.400 g, 1.824 mmol), tris(dibenzylideneacetone)dipalladium (o) (0.042 g, 0.046 mmol), 2-(dicyclohexylphosphino)-3,6-dimethoxy-2′-4′-6′-triisopropyl-1,1′biphenyl (0.049 g, 0.091 mmol), and sodium tert-butoxide (0.351 g, 3.65 mmol) in dry dioxane (5 mL) afforded the title compound 1-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one (0.0811 g, 0.231 mmol, 12.69% yield) m/z: 351.0 (M+1); 1H NMR (400 MHz, CHLOROFORM-d) δ: ppm 2.55-2.65 (m, 2 H) 3.38-3.47 (m, 5 H) 4.47-4.55 (m, 1 H) 5.22 (quin, J=8.51 Hz, 1 H) 6.97-7.01 (m, 1 H) 7.06-7.16 (m, 4 H) 7.27-7.33 (m, 1 H) 7.57 (d, J=8.02 Hz, 1 H) 7.60 (dd, J=7.92, 0.68 Hz, 1 H).

Provenance & Evidence