4-Chlorophenol → HCID 66739481, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 4-chlorophenol (200 mg, 1.56 mmol) and triphosgene (460 mg, 1.56 mmol) in DCE (5 ml) was cooled to 0° C. and DIPEA (2.16 ml, 12.4 mmol) added. The resulting solution was stirred at 0° C. for 90 minutes then 1-(azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepane (367 mg, 1.56 mmol) in DCE (2 ml) was added. The resulting mixture was heated at 100° C. for 12 hours then cooled to room temperature and diluted with DCM (25 ml) and water (30 ml). The organic phase was separated and the aqueous phase extracted with DCM (3×25 ml). The organics were combined, dried (MgSO4), filtered and concentrated at reduced pressure. The residue was purified by FCC (98:2:1 DCM:MeOH:NH3) followed by preparative HPLC (Method 2) to yield the title compound (1.4 mg, 0.2% yield).

Provenance & Evidence