N-Methyl-o-phenylenediamine → HCID 71547301, compound

Participants

Reaction Conditions

Reaction Steps

A slurry of 2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropanecarboxylic acid (2-5, 1.50 g, 5.49 mmol, 1.0 eq.), n-methyl-2-phenylenediamine (1.006 g, 8.23 mmol, 1.0 eq.), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.473 g, 7.68 mmol, 1.3 eq.), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (1.046 g, 7.68 mmol) and diisopropylethyl amine (2.88 mL, 16.47 mmol) in tetrahydrofuran (20 mL) was allowed to stir for 16 hours. The solvent was removed by roto-evaporation to afford a dark brown oil. The oil was dissolved in acetic acid (3 mL) and heated at 90° C. for 30 minutes. The solvent was removed by roto-evaporation and the resulting yellow oil was purified by reverse phase liquid chromatography (H2OCH3CN gradient w/ 0.1% NR4OH present) to afford 2-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (2-6) as a white powder. 1H NMR (500 MHz, CDCl3) δ 7.69 (m, 2H), 7.28 (m, 3H), 3.82 (s, 3H), 2.90 (s, 3H), 2.83 (m, 2H), 2.68 (s, 3H), 2.41 (s, 3H), 2.19 (m, 2H). HRMS m/z (M+H) 360.1937 found, 360.1931 required.

Provenance & Evidence