Acetic Acid → HCID 86732042, compound

Participants

Reaction Steps

To the mixture of trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)cyclopropanecarbaldehyde (16-6, 280 mg, 0.899 mmol, 1.0 eq.) and N1-methylbenzene-1,2-diamine (0.11 mL, 0.989 mmol, 1.1 eq.) in anhydrous ethanol (5.0 mL) at room temperature was added glacial AcOH (0.062 mL, 1.08 mmol, 1.2 eq.) followed by anhydrous CuSO4 (158 mg, 0.989 mmol, 1.1 eq.). The resulting brownish mixture was stirred at room temperature for 4 hours under an atmosphere of nitrogen gas. The mixture was concentrated in vacuo and neutralized with 7 M NH3 in methanol (1.0 mL). Then it was filtered and concentrated to dryness. The resulting residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes) to give trans-2-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (16-7) as a light brown solid. 1H NMR (300 MHz, CDCl3) 8.07 (s, 1H), 7.74-7.66 (m, 1H), 7.35-7.22 (m, 3H), 3.84 (s, 3H), 3.08-2.99 (m, 1H), 2.98-2.88 (m, 1H), 2.93 (s, 3H), 2.42 (s, 3H), 2.13-2.02 (m, 2H). LRMS m/z (M+H) 414 found, 414 required. m.p. 151-153° C.

Provenance & Evidence