Glycolic Acid → HCID 69046649, compound

Participants

Reaction Steps

To a mixture of 1-(3-chloro-3′,5′-dimethyl-2,2′-bipyridin-6-yl)piperidin-4-amine (hydrochloride salt) (60 mg, 0.13 mmol) and 2-hydroxyacetic acid (14.8 mg, 0.20 mmol) in DMF (1.3 mL) were added (in this order) NMM (105 mg, 1.0 mmol), HOBT (26.3 mg, 0.20 mmol), and EDCI (38.5 mg, 0.20 mmol). The resulting solution was stirred at rt for 3.5 h. Water was added, and the mixture was stirred at rt overnight. Filtered off the solid that had crashed out, washed with water, and dried to get 23 mg (47%) of the title compound as a white solid. m/z (APCI+) for C19H23N4O2Cl 375.10 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.26 (s, 1 H) 7.67 (d, J=9.09 Hz, 1 H) 7.62 (d, J=8.34 Hz, 1H) 7.53 (s, 1 H) 6.93 (d, J=9.35 Hz, 1 H) 5.37 (t, J=5.94 Hz, 1 H) 4.18 (d, J=13.64 Hz, 2H) 3.82-3.94 (m, 1 H) 3.78 (d, J=5.81 Hz, 2 H) 2.91 (t, J=11.49 Hz, 2 H) 2.32 (s, 3 H) 2.08 (s, 3 H) 1.72 (dd, J=12.76, 2.91 Hz, 2 H) 1.41-1.54 (m, 2 H).

Provenance & Evidence