3,4-Dichlorobenzaldehyde → HCID 135463504, compound

Participants

Reaction Conditions

Reaction Steps

1-(4-Fluorophenylsulfonyl)propan-2-one (150 mg, 0.69 mmol), 3-methyl-1H-pyrazol-5-amine (67 mg, 0.69 mmol) and 3,4-dichlorobenzaldehyde (121 mg, 0.69 mmol) were dissolved in THF (5 mL), to which was added a catalytic amount of piperidine (3 drops). The reaction in a sealed tube was stirred at 70° C. for about 48 hrs. After cooling to rt., solvent was removed and crude product was purified by HPLC (acetonitrile-water, 5% to 95% gradient) to provide pure Step B product 7-(3,4-dichlorophenyl)-6-(4-fluorophenylsulfonyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidine as a solid. LC-MS found: (M+1)+=452.17. The two enantiomers were readily separated on Chiral PAK AS using 15% EtOH-MeOH in heptane.

Provenance & Evidence