Ammonium Chloride → HCID 58934070, compound

Participants

Reaction Steps

A stirred solution of 3-amino-6-(4-benzylpiperazin-1-yl)-2-[(phenylsulfonyl)-methyl]pyridine (1.41 g, 3.34 mmol), p-toluenesulfonic acid monohydrate (63 mg, 0.33 mmol), triethyl orthoformate (2.78 mL, 16.7 mmol) in 1,2-dichloroethane is heated at reflux temperature under nitrogen for 7.5 h, stirred at room temperature for 16 h and in vacuo to afford an oil residue. The residue is stirred in dry THF, treated with 1.0M KO-t-Bu in THF (4.35 mL, 4.35 mmol) for 2 h, treated sequentially with saturated aqueous NH4Cl, saturated aqueous NaHCO3 and water and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo to give a yellow solid residue. This residue is chromatograped (silica gel, EtOAc as eluent to afford the title compound as a pale yellow solid, 1.18 g (79% yield), mp 238-239° C., identified by NMR and mass spectral analyses.

Provenance & Evidence