ACCEPTED MANUSCRIPT
1.3 Hz, Py), 8.36 (1 H, dd, 8.2 Hz, 2.1 Hz, Py), 7.80 (1 H, d, 8.1 Hz, Py), 3.81-3.78 (8 H, m, O-CH2), 3.72-
3.68 (4 H, m, N-CH2), 3.62-3.58 (2 H, m, N-CH2), 3.46-3.42 (2 H, m, N-CH2); δC (125.7 MHz, CDCl3) 188.5,
166.1, 163.8, 158.2, 149.9, 138.0, 129.1, 124.3, 66.9, 66.7, 66.6, 66.4, 47.7, 46.3, 42.8, 41.9; IR (KBr, ν (cm-
1)): 1678 (CO), 1644 (CON); MS m/z (rel int.): 333 (18, M+), 305 (1), 247 (18), 220 (16), 191 (1), 161 (1), 134
(1), 114 (18), 86 (100)
2,5-Bis-(N-(1’-methoxycarbonylethyl)carboxamido)pyridine (2f). Yield: 29.7 mg (9%); yellow viscous
oil; [Found: C, 53.26; H, 5.50; N, 12.15; C15H19N3O6 requires C, 53.41; H, 5.68; N, 12.46%];Rf (50% EtOAc,
50% CHCl3) 0.31; δH (500 MHz, CDCl3) 8.99 (1 H, d, 1.3 Hz, Py), 8.50 (1 H, d, 7.7 Hz, NH); 8.24 (1 H, dd,
8.1 Hz, 2.1 Hz, Py), 8.1 (1 H, d, 8.1 Hz, Py), 7.17 (1 H, d, 7.1 Hz, NH); 4.81 (overlapping, 2x quintets, 2 H, m,
N-CH); 3.81 (3 H, s, O-CH3), 3.79 (3 H, s, O-CH3),1.56 (overlapping, 2x doublets, 6 H, t, 6.6 Hz, CHCH3); δC
(125.7 MHz, CDCl3) 173.4, 173.1, 164.4, 163.1, 151.5,147.3, 136.3, 131.8, 122.0, 52.7, 52.6, 48.7, 48.2, 18.3,
18.2; IR (KBr, ν (cm-1)): 3342 (NH), 1747 (COO), 1663 (CON); MS m/z (rel int.): 337 (1, M+), 322 (1), 306
(1), 278 (100), 235 (30), 207 (31), 192 (1), 175 (1), 162 (1), 148 (8), 133 (1), 120 (2), 77 (8), 59 (1).
2-(N-(1’-Methoxycarbonylethyl)carboxamido)-5-(N-(1’-methoxycarbonylethyl)glyoxylamido)pyridine
(3f). Yield: 45 mg (12%); yellow viscous oil; [Found: C, 52.40; H, 5.48; N, 11.25; C16H19N3O7 requires C,
52.60; H, 5.24; N, 11.50%]; Rf (50% EtOAc, 50% CHCl3) 0.57; δH (500 MHz, CDCl3) 9.49 (1 H, d, 1.3 Hz,
Py), 8.79 (1 H, dd, 8.1 Hz, 2.0 Hz, Py), 8.55 (1 H, d, 7.7 Hz, NH), 8.30 (1 H, d, 8.1 Hz, Py), 7.69 (1 H, d, 7.5
Hz, NH),4.82 (1 H, quintet, 7.4 Hz, N-CH), 4.69 (1 H, qi, 7.4 Hz, N-CH), 3.82 (3 H, s, O-CH3), 3.81 (3 H, s,
O-CH3),1.58(3 H, d, 7.3 Hz, CHCH3), 1.56(3 H, d, 7.3 Hz, CHCH3); δC (125.7 MHz, CDCl3) 185.3, 172.9,
172.2, 162.8, 159.9, 152.7, 150.9, 140.1, 130.9, 121.9, 52.8, 52.6, 48.3, 48.2, 18.4, 18.0. IR (KBr, ν (cm-1)):
3371 (NH), 1744 (overlapping COO, CO), 1676 (CON); MS m/z (rel int.): 365 (1, M+), 334 (1), 306 (100),
288 (1), 263 (2), 235 (25), 208 (2), 192 (1), 175 (2), 148 (17), 120 (2), 102 (17), 77 (17), 59 (10).
2-(N-(1’-methoxycarbonylethyl)carboxamido)-5-iodopyridine (4f). Yield: 45 mg (13%) off-white
viscous oil; [Found: C, 35.81; H, 3.57; N, 8.25; C10H11IN2O3 requires C, 35.95; H, 3.32; N, 8.38%]; Rf (20%
EtOAc, 80% CHCl3) 0.78; δH (500 MHz, CDCl3) 8.80 (1 H, d, 1.7 Hz, Py), 8.37 (1 H, d, 7.1 Hz, NH); 8.19 (1
H, dd, 8.1 Hz, 2.0 Hz, Py), 7.95 (1 H, d, 8.1 Hz, Py), 4.79 (1 H, qi, 7.4 Hz, N-CH); 3.79 (3 H, s, O-
CH3),1.55(3 H, d, 7.3 Hz, CHCH3); δC (125.7 MHz, CDCl3) 173.1, 163.4, 154.3, 148.3, 145.8, 124.0, 97.3,
52.5, 48.1, 18.4; IR (KBr, ν (cm-1)): 3384 (NH), 1743 (COO), 1683 (CON); MS m/z (rel int.): 334 (1, M+),
319 (1), 306 (1), 291 (1), 275 (100), 257 (1), 232 (43), 204 ( 40), 191 (1), 177 (1), 164 (1), 148 (2), 133 (1),
120 (1), 105 (1), 92 (1), 77 (17), 64 (1), 50 (2).
2,3-Bis-(N-tert-butylcarboxamido)pyridine (6a). Yield: 134 mg (48 %); cream-colored crystals; [Found:
C, 64.77; H, 8.18; N, 15.02; C15H23N3O2 requires C, 64.95; H, 8.36; N, 15.15%]; mp. 113 ˚C; Rf (3 % MeOH,
97 % CHCl3) 0.58; δH (500 MHz, CDCl3) 8.54 (1 H, dd, 4.9 Hz, 1.4 Hz, Py), 8.16 (1 H, dd, 7.7 Hz, 1.4 Hz,
Py), 7.68 (1 H, brs, NH), 7.45 (2 H, overlapping dd és brs, 7.7 Hz, 4.9 Hz, Py, NH), 1.49 (9 H, s, C(CH3)3),
1.48 (9 H, s, C(CH3)3); δC (125.7 MHz, CDCl3)165.9, 165.2, 148.8, 148.5, 139.0, 133.2, 125.3, 51.6, 51.5,
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