HCID 21073265, compound → HCID 21073471, compound

Participants

Reaction Conditions

Reaction Steps

An intermediate compound, 2-Benzyloxy-7-{3-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-propoxy}-[1,8]naphthyridine, was produced as follows: To a suspension of 3-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-propan-1-ol hydrochloride (400 mg, 1.23 mmol) in THF (5 mL) cooled to −40° C. was added KOtBU (1 M in THF, 2.3 mL, 2.3 mmol, 1.9 equiv). The mixture became a cloudy solution. After stirring for 20 min at −40° C., 2-benzyloxy-7-chloro-[1,8]naphthyridine (333 mg, 1.23 mmol) was added as a solution in THF (8 mL) via cannula. The reaction was allowed to warm to 0° C. slowly over 1 h. The reaction was quenched with saturated NH4Cl and H2O and extracted with EtOAc. The organic layer was washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated. Purification by liquid chromatography (CH2Cl2 to 2% MeOH/CH2Cl2) gave the title compound as a clear oil/foam (367 mg, 0.701 mmol, 57%). MS: APCI: M+1: 523.0 (Exact Mass: 522.16).

Provenance & Evidence