Methoxyacetic Acid → (3S,4S)-benzyl 3-((3-carbamoyl-6-(6-((2-methoxyacetamido)methyl)pyridin-3-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-4-ethylpyrrolidine-1-carboxylate

Participants

Reaction Steps

A mixture of (3S,4S)-benzyl 3-((6-(6-(aminomethyl)pyridin-3-yl)-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-4-ethylpyrrolidine-1-carboxylate (29 mg, 0.056 mmol), 2-methoxyacetic acid (9.56 μl, 0.124 mmol), BOP (54.9 mg, 0.124 mmol) and diisopropylethylamine (0.039 mL, 0.226 mmol) in DMF (0.5 mL) was stirred at rt overnight. The reaction mixture was partitioned between EtOAc (20 ml) and 10% LiCl solution (20 ml). The organic layer was washed with 10% LiCl solution (2×20 ml) and brine (20 ml). After drying (MgSO4) and filtration, the organic layer was concentrated to afford (3S,4S)-benzyl 3-((3-carbamoyl-6-(6-((2-methoxyacetamido)methyl)pyridin-3-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-4-ethylpyrrolidine-1-carboxylate (22 mg, 0.038 mmol, 66.5% yield) as a yellow semisolid. The material will be used as is in the next step. MS (ES+) m/z: 586.22 (M+H); LC retention time: 2.370 min (analytical HPLC Method O).

Provenance & Evidence