Triethylamine → (R)-(7-Chlorothieno[3,2-b]pyridin-2-yl)(3-(dimethylamino)pyrrolidin-1-yl)methanone

Participants

Reaction Conditions

Reaction Steps

HATU (4.99 g, 26.25 mmol) and Et3N (7.23 mL, 52.50 mmol) was added to a solution of (3R)-N,N-dimethylpyrrolidin-3-amine (1.0 g, 17.5 mmol) and 7-chlorothieno[3,2-b]pyridine-2-carboxylic acid lithium salt (3.85 g, 17.5 mmol) in 30 mL DMF at 0° C. The reaction mixture was stirred at 0° C. for 15 min and solvent was concentrated. The residue was partition between H2O and 10% CH3OH in EtOAC. The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash column chromatography (5-7% CH3OH in CH2Cl2) to give a white solid (1.74 g, 32%). 1H NMR (CD3OD) δ 8.57 (1H, d, J=5.2 Hz), 7.90 (1H, d, J=7.9 Hz), 7.48 (1H, d, J=5.2 Hz), 4.11-3.97 (1H, m), 3.90-3.36 (3H, m), 2.99-2.90 (1H, m), 2.30 (3H, s), 2.26 (3H, s), 1.97-1.72 (2H, m). ESIMS (MH+): 310.10.

Provenance & Evidence