Hydrochloric Acid → HCID 178435049, compound

Participants

Reaction Steps

A solution of (2-methylthien-3-yl)-1-trityl-imidazol-4-yl-methanol (1.5 g, 3.5 mmol) was combined with HCl (3.4 mmol) and Pd(OH)2 (1.5 g) in EtOH and hydrogenated (55 psi) at 55° C. for 48 hrs. The catalyst was removed by filtration through Dicalite and the solvent was evaporated in vacuo. The residue was dissolved in water, washed twice with Et2 O, and then basified with Na2CO3 and extracted twice with EtOAc. The combined extracts were dried (K2CO3), filtered and solvent evaporated. The residue was chromatographed on flash silica gel (99:0.75:0.25 EtOAc/MeOH/NH4OH) to give a thick syrup which was dissolved in 2-PrOH and combined with fumaric acid (116 mg). The solvent was evaporated and the residue recrystallized from acetone to give the target compound, m.p. 140°-141° C. 1H NMR (DMSO-d6) supported the assigned structure: δ6 2.3 (s, 3H), 3.75 (s, 2H), 6.6 (s, 2H), 6.75 (s, 1H), 6.85 (d, J=5.3 Hz, 1H), 7.15 (d, 1H), 7.65 (s, 1H). Elemental Analysis: Calc. for C9H10N2 S.C4H4O4C, 53.05; H, 4.79; N, 9.52. Found C, 53.22; H, 4.87; N, 9.50.

Provenance & Evidence