1,2-Dimethoxyethane → HCID 68079206, compound

Participants

Reaction Steps

The title compound was prepared in the same manner as described in example 74 using 6-chloro-1-(1,1-dimethylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.174 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzimidazol-2-one (58.9 mg, 0.226 mmol), DME (3 mL), water (1.00 mL), sodium carbonate (0.261 mL, 0.523 mmol) and PdCl2(dppf)-CH2Cl2 adduct (11.38 mg, 0.014 mmol) wherein the reaction time was 40 min. The crude product was purified by column chromatography (eluent: gradient of 0 to 15% (9:1 MeOH/NH4OH)/DCM). The final product was collected as a solid, 24 mg (27%). LCMS E-S (M+H)=500.2 1H NMR (400 MHz, DMSO-d6) δ ppm 1.77 (m, 9H), 2.12 (s, 3H), 2.24 (s, 3H), 2.40 (s, 3H), 4.38 (d, J=4.55 Hz, 2H), 5.89 (s, 1H), 7.06 (d, J=8.08 Hz, 1H), 7.59 (s, 1H), 7.72-7.86 (m, 2H), 8.73 (br. s., 2H), 10.74-10.92 (m, 1H), 11.53 (br. s., 1H).

Provenance & Evidence