p-Toluenesulfonic acid monohydrate → HCID 90025929, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5,8-dimethyl-2-(2-(1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)ethyl)-[1,2,4]triazolo[1,5-a]pyrazine (30 mg, 70.3 μmol, Eq: 1.00) in methanol (3 ml) was added p-toluenesulfonic acid monohydrate (669 μg, 3.52 μmol, Eq: 0.05), the resulting mixture was stirred for 2 hours at 25° C. under nitrogen atmosphere→nearly no reaction, another portion of p-toluenesulfonic acid monohydrate (13.4 mg, 70.3 μmol, Eq: 1.00) was added, stirring at 25° C. was continued overnight. The solvent was evaporated. The residue was diluted with ethyl acetate and washed with sat. sodium hydrogen carbonate. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. Purification by HPLC separation afforded 1-{5-[2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-ethyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-pyrrolidin-3-ol (2.05 mg, 8.51%) as a light yellow viscous oil. MS: m/z=323.5 (M+H+)

Provenance & Evidence