2-(1-(6-hydrazinyl-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-methyl-1H-benzo[d]imidazole → 2-(1-(6-(5-ethyl-3-methyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-methyl-1H-benzo[d]imidazole

Participants

Reaction Steps

A solution of Intermediate 11 (50 mg, 0.16 mmol) and A (46 mg, 0.32 mmol) in acetic acid (1.6 mL) was heated at 100° C. for 30 min. The solvent was removed in vacuo and the residue was purified by reverse phase chromatography (MeCN/H2O/0.1% TFA). The fractions containing the product were partitioned between EtOAc and saturated NaHCO3. The organic layer was washed with 50% saturated brine solution, dried over Na2SO4 and concentrated to provide Example 35 as an off-white solid. 1H NMR: (500 MHz, DMSO-d6) δ 7.60 (d, J=8 Hz, 1H), 7.53 (d, J=8 Hz, 1H), 7.21 (m, 2H), 6.52 (s, 1H), 4.58 (m, 2H), 4.45 (m, 3H), 3.74 (s, 3H), 3.22 (q, J=7.5 Hz, 2H), 2.44 (s, 3H), 2.30 (s, 3H) 1.25 (t, J=7.5 Hz, 3H). MS: m/z=389.5 (M+H).

Provenance & Evidence