1,2-Dichloroethane → HCID 10282444, compound

Participants

Reaction Steps

To a solution of 0.035 g (0.1 mmol) (5-chloro-2-{[2,2-difluoro-2-(2-pyridinyl)ethyl]amino}-3-fluoro-4-pyridinyl)acetic acid 1-9 (mixed with LiCl) in 1 mL DMF was added 0.029 g (0.1 mmol) tert-butyl 2-[2-(aminomethyl)-4-chlorophenyl]ethylcarbamate, 0.03 g (0.15 mmol) EDC and 0.014 g (0.1 mmol) HOAt and the reaction mixture stirred at room temperature 4 h, then diluted with 50 mL EtOAc, washed with 50 mL saturated aqueous sodium bicarbonate solution, brine, then dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography (2×12 cm silica gel, linear gradient 2-6% MeOH (containing 10% saturated ammonium hydroxide solution)/CH2Cl2 afforded tert-butyl 2-[4-chloro-2-({[(5-chloro-2-{[2,2-difluoro-2-(2-pyridinyl)ethyl]amino}-3-fluoro-4-pyridinyl)acetyl]amino}methyl)phenyl]ethylcarbamate 1-10. 1H NMR (400 mHz, CD3OD) δ8.60 (d, 1H, J=4.58 Hz); 7.89 (ddd, J=7.7, 7.7, and 1.47 Hz); 7.72 (s, 1H); 7.67 (d, 1H, J=7.87 Hz); 7.46 (dd, 1H, J=7.51 and 4.58); 7.29(d, 1H, J=1.83 Hz); 7.18 (m, 2H); 4.42 (s, 2H); 4.32 (t, 2H, J=13.9 Hz); 3.74 (d, 2H, J=1.46 Hz); 3.21 (t, 2H, J=7.14 Hz); 2.80 (t, 2H, J=7.4 Hz); 1.40 (s, 9H). Mass Spectrum (electrospray) M+H=612.3.

Provenance & Evidence