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isophth); 7.83 (t, J ¼ 7.8, HꢂC(5), isophth). ESI-MS (pos.): 248.8 (100, [M þ H]þ), 249.9 (13.6, [M þ
2 H]þ).
4,5-Dihydro-2-{[3-(4,5-dihydro-1H-imidazol-2-ylcarbamoyl)benzoyl]amino}-1H-imidazol-3-ium
Chloride (2). 1H-NMR ((D6)DMSO, 250 MHz): 13 (br. s, 2 CONH); 9.1 (s, 2 NH, dhIm); 8.67 (t, J ¼ 1.57,
HꢂC(2), isophth); 8.45 (dd, HꢂC(4) and HꢂC(6), isophth); 7.84 (t, J ¼ 7.8, HꢂC(5), isophth); 3.8 (s, 4
CH2, dhIm). ESI-MS (pos.): 301.1 (100, [M þ H]þ), 302.1 (51.7, [M þ 2 H]þ), 303.2 (33.3, [M þ 3 H]þ),
337.2 (5.3, [M þ Cl]þ).
2-{[3-(1H-Imidazol-2-ylcarbamoyl)benzoyl]amino}-1H-imidazol-3-ium Chloride (3). 1H-NMR
((D6)DMSO, 250 MHz): 13.3 (br. s, 4 H), 8.77 (s, HꢂC(2), isophth); 8.47 (dd, J ¼ 8.1, 1.8, HꢂC(4) and
HꢂC(6), isophth); 7.79 (t, J ¼ 7.8, HꢂC(5), isophth); 7.34 (s, 4 CH of Im). ESI-MS (pos.): 296.9 (100,
[M þ H]þ), 298 (17.3, [M þ 2 H]þ), 332.9 (8.1, [M þ Cl]þ).
2-{[3-(1H-Benzimidazol-2-ylcarbamoyl)benzoyl]amino}-1H-3,1-benzimidazol-3-ium Chloride (4).
1H-NMR ((D6)DMSO, 250 MHz): 13.3 (br. s, 4 H), 8.87 (t, J ¼ 1.57, HꢂC(2), isophth); 8.46 (dd, J ¼ 7.9,
1.8, HꢂC(4) and HꢂC(6), isophth); 7.83 (t, J ¼ 7.8, HꢂC(5), isophth); 7.67 (q, J ¼ 4.5, 1.4, 2 HꢂC(4) and 2
HꢂC(7), BnIm), 7.37 (q, J ¼ 4, 1.4, 2 HꢂC(5) and 2 HꢂC(6), BnIm). ESI-MS (pos.): 397.3 (100, [M þ
H]þ), 398.1 (25.5, [M þ 2 H]þ), 433 (11, [M þ Cl]þ).
Pyridine Derivatives as HCl Salts. Amino({[6-(carbamimidoylcarbamoyl)pyridin-2-yl]carbonyl}-
amino)methaniminium Chloride (5). 1H-NMR ((D6)DMSO, 250 MHz): 12.16 (br. s, 2 CONH); 8.86 (br.
d, J ¼ 41, 8 H, Gua); 8.56 (d-like, J ¼ 8.4, HꢂC(3) and HꢂC(5), Py); 8.44 (q-like, J ¼ 7.3, 1.2, HꢂC(4),
Py). ESI-MS (pos.): 250 (100, [M þ H]þ), 251 (14, [M þ 2 H]þ), 285.8 (28.3, [M þ Cl]þ).
4,5-Dihydro-2-({[6-(4,5-dihydro-1H-imidazol-2-ylcarbamoyl)pyridin-2-yl]carbonyl}amino)-1H-imi-
dazol-3-ium Chloride (6). 1H-NMR ((D6)DMSO, 250 MHz): 12.77 (s, 2 CONH); 9.31 (s, 2 NH, dhIm);
8.56 (d-like, J ¼ 6.9, HꢂC(3) and HꢂC(5), Py); 8.46 (q-like, J ¼ 7.8, 1.3, HꢂC(4), Py); 3.86 (s, 4 CH2,
dhIm). ESI-MS (pos.): 301.9 (100, [M þ H]þ), 303 (43, [M þ 2 H]þ) 304.2 (23.5, [M þ 3 H]þ), 338.1 (12,
[M þ Cl]þ).
2-({[6-(1H-Imidazol-2-ylcarbamoyl)pyridin-2-yl]carbonyl}amino)-1H-imidazol-3-ium Chloride (7).
1H-NMR ((D6)DMSO, 250 MHz): 13.21 (br. s, 4 H); 8.58 (d-like, J ¼ 6.6, HꢂC(3) and HꢂC(5), Py); 8.48
(q-like, J ¼ 1.2, 7.6, HꢂC(4), Py); 7.45 (s, 4 CH, Im). ESI-MS (pos.): 298 (100, [M þ H]þ), 299 (17.3, [M þ
2 H]þ), 333.9 (10, [M þ Cl]þ).
2-({[6-(1H-Benzimidazol-2-ylcarbamoyl)pyridin-2-yl]carbonyl}amino)-1H-3,1-benzimidazol-3-ium
Chloride (8). 1H-NMR ((D6)DMSO, 250 MHz): 13.7 (br. s, 4 H); 8.65 (d-like, J ¼ 8.1, HꢂC(3) and
HꢂC(5), Py); 8.52 (t-like, J ¼ 7.8, HꢂC(4), Py); 7.79 (q, J ¼ 1.5, 4.5, 2 HꢂC(4) and 2 HꢂC(7), BnIm), 7.45
(m, 2 HꢂC(5) and 2 HꢂC(6), BnIm). ESI-MS (pos.): 398 (100, [M þ H]þ), 399 (25.1, [M þ 2 H]þ), 434
(18.2, [M þ Cl]þ).
Monomethyl Isophthalates. Amino{[3-(methoxycarbonyl)benzoyl]amino}methaniminium Chloride
(9). 1H-NMR ((D6)DMSO, 250 MHz): 12.1 (br. s, 1 CONH); 8.66 (br. s, 4 H, Gua (overlaps with HꢂC(2)
of isophth)); 8.6 (s, HꢂC(2), isophth); 8.45 (d, J ¼ 8.4, HꢂC(6), isophth); 8.26 (d, J ¼ 8.1, HꢂC(4),
isophth); 7.77 (t, J ¼ 7.8, HꢂC(5), isophth); 3.9 (s, MeO). ESI-MS (pos.): 221.8 (100, [M þ H]þ), 222.9
(12.3, [M þ 2 H]þ).
4,5-Dihydro-2-{[3-(methoxycarbonyl)benzoyl]amino}-1H-imidazol-3-ium Chloride (10). 1H-NMR
((D6)DMSO, 250 MHz): 12.95 (br. s, CONH); 9.14 (s, 2 NH, diIm); 8.6 (t, J ¼ 1.7, HꢂC(2), isophth); 8.43
(dt, J ¼ 8.7, 1, HꢂC(6), isophth); 8.26 (dt, J ¼ 8.1, 1.4, HꢂC(4), isophth); 7.77 (t, J ¼ 7.8, HꢂC(5), isophth);
3.92 (s, MeO), 3.8 (s, 2 CH2, diIm). ESI-MS (pos.): 247.8 (100, [M þ H]þ), 248.9 (15.8, [M þ 2 H]þ).
2-{[3-(Methoxycarbonyl)benzoyl]amino}-1H-imidazol-3-ium Chloride (11). 1H-NMR ((D6)DMSO,
250 MHz): 13.1 (br. s, 2 H); 8.62 (s, HꢂC(2), isophth); 8.36 (d, J ¼ 8.1, HꢂC(6), isophth); 8.26 (d, J ¼ 7.8,
HꢂC(4), isophth); 7.79 (t, J ¼ 7.8, HꢂC(5), isophth); 7.33 (s, 2 CH, Im); 3.93 (s, MeO). ESI-MS (pos.):
246 (100, [M þ H]þ), 247 (14.8, [M þ 2 H]þ), 491.3 (6.1, [2 M þ H]þ).
2-{[3-(Methoxycarbonyl)benzoyl]amino}-1H-3,1-benzimidazol-3-ium Chloride (12). 1H-NMR
((D6)DMSO, 250 MHz): 12.48 (br. s, 2 H); 8.77 (t, J ¼ 1.6, HꢂC(2), isophth); 8.4 (dt, J ¼ 7.8, 1.57,
HꢂC(6), isophth); 8.16 (dt, J ¼ 7.7, 1.4, HꢂC(4), isophth); 7.69 (t, J ¼ 7.6, HꢂC(5), isophth), 7.5 (q, J ¼ 4.5,
1.4, HꢂC(4) and HꢂC(7), BnIm); 7.23 (q, J ¼ 4.5, 1.4, HꢂC(5) and HꢂC(6), BnIm); 3.93 (s, MeO). ESI-
MS (pos.): 296 (100, [M þ H]þ), 297 (18.7, [M þ 2 H]þ), 591.4 (11.3, [2 M þ H]þ).