Pyridine-2,6-dicarbonyl dichloride (1.0 g, 4.8 mmol) was dissolved in dry DCM (20 ml) under argon. S-(+)-1-methoxy-2-propylamine (1.08 ml, 10.2 mmol) was added dropwise and the mixture was stirred for 15 min. Dry TEA (~6 ml) was added and the mixture was stirred at ambient temperature overnight. The mixture was then washed with water (3 × 20 ml) and dried over sodium sulphate. The solvent was removed under reduced pressure and the residue was recrystallised from DCM/pentane. Yield 1.2 g (78%).

Elemental Analysis found (Calculated for C₁₅H₂₃N₃O₄) %: C 58.45 (58.24), H 7.60 (7.49), N 13.64 (13.58)

¹H NMR (400 MHz, 298 K, CDCl₃) δ_H 1.33 (6H, d, ³J_HH = 6.8 Hz, -CH₃), 3.42 (6H, s, -OCH₃), 3.46-3.56 (4H, m, CH₂), 4.29-4.42 (2H, m, CH), 7.92-8.05 (3H, m (s+t), NH, py), 8.32 (2H, d, ³J_HH = 7.8 Hz, pyr)

¹³C NMR (100 MHz, 298 K, CDCl₃) δ_C 17.7 (-CH3), 45.0 (CH), 59.1 (-OCH3), 75.4 (CH2), 124.8, 138.9, 148.8 (py), 162.8 (C=O)

MS (ESI⁺) m/z 332.1 ([M+Na]⁺); (ESI^-) m/z 308.1 ([M-H]^-)

IR (cm^-1) ν 3327, 2974, 2930, 2879, 2831, 1651, 1519, 1440, 1393, 1365, 1353, 1325, 1303, 1255, 1230, 1203, 1173, 1150, 1108, 1080, 1062, 997, 978, 925, 847, 758, 726