N,N-Dimethyl-1,3-propanediamine → HCID 131727218, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(4-(2-chloropyridin-4-yloxy)-3-fluorophenyl)-2,6-difluorobenzamide (70 mg, 0.19 mmol), 3-(dimethylamino)propylamine (44 mL, 0.35 mmol), Cs2CO3 (85 mg, 0.26 mmol) and CuCl (17 mg, 0.17 mmol) in a screw capped vial was purged with N2. NMP and 2,2,6,6,-tetramethyl-3,5-heptanedione (31 mg, 0.17 mmol) were added to the mixture which was then heated at 120° C. for 4 h. The mixture was cooled, partitioned between EtOAc and saturated aq. NaHCO3 solution and the EtOAc phase was separated, dried (MgSO4) and concentrated in vacuo to give the crude product. Purification of the residue by preparative HPLC (Column C) and conversion to the hydrochloride salt was carried out in a similar manner as Step D of Example 33 to give the title compound (7 mg, 7%) as an off-white solid. MS (ESI+): m/z 517.37 (M+H)+.

Provenance & Evidence