Dimethylformamide → HCID 68684046, compound

Participants

Reaction Steps

4-amino-2-fluoro-5-methoxybenzoic acid (Intermediate 183; 0.75 g, 4.07 mmol), HATU (1.70 g, 4.48 mmol) and DIPEA (2.1 mL, 12.21 mmol) were stirred together in DMF (10 mL) for 10 minutes. Endo-9-methyl-9-azabicyclo[3,3,1]-nonan-3-amine (Chempacific; 0.69 g, 4.48 mmol) in DMF (1 mL) was added and the brown solution stirred at ambient temperature for 2 hours. The solvent was evaporated and the residue dissolved in MeOH and loaded onto an SCX-2 (20 g) column pre-wet with MeOH. The column was washed with MeOH (2 column volumes) and the product eluted with 2M NH3/MeOH (2 column volumes). Product containing fractions were combined and evaporated and the resultant material purified on a silica column eluting with 0-10% 2M NH3/MeOH/DCM). Product containing fractions were combined and evaporated to yield the title compound as a dark brown gum (897 mg, 69%).

Provenance & Evidence