1,2-Dichloroethane → MK-3697

Participants

Reaction Conditions

Reaction Steps

Potassium 5′-methyl-5-(1,3-thiazol-2-yl)-2,3′-bipyridine-4-carboxylate (7-4, 980 mg, 2.9 mmol, 1 equiv), 1-(5,6-dimethoxypyridin-2-yl)methanamine (3-6, 490 mg, 2.9 mmol, 1 equiv), EDC (670 mg, 3.5 mmol, 1.2 equiv), 1-hydroxy-7-azabenzotriazole (480 mg, 3.5 mmol, 1.2 equiv) and diisopropylethylamine (2.0 mL, 12 mmol, 4 equiv) were suspended in DMF (14.6 mL) and the reaction mixture was heated for 2 hours at 65° C. The reaction mixture was then partitioned between DCM (50 mL) and water (50 mL). The layers were separated and the organic layer was dried over MgSO4 and concentrated. The residue was purified by normal phase column chromatography (0-20% MeOH in EtOAc) to afford a white solid that was recrystallized from chloroform/hexanes to give the title compound (7-5) as a crystalline solid (970 mg, 75% yield). 1H NMR (CDCl3, 300 MHz) δ 9.08 (s, 2H), 8.53 (s, 1H), 8.22 (s, 1H), 8.11 (s, 1H), 7.81 (dd, J=3.1 and 1.1 Hz, 1H), 7.78 (t, J=4.8 Hz, 1H), 7.43 (dd, J=3.3 and 1.1 Hz, 1H), 7.02 (d, J=7.9 Hz, 1H), 6.85 (d, J=7.7 Hz, 1H), 4.58 (d, J=5.3 Hz, 2H), 3.91 (s, 3H), 3.88 (s, 3H), 2.45 (s, 3H). HRMS (M+H)C23H21N5O3S calc'd 448.1438. found 448.1443

Provenance & Evidence