Molecules 2016, 21, 772
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(DMSO-d6),
δ: 12.78 (d, 1H), 8.40 (d, J = 8.3 Hz, 2H), 7.96 (d, J = 8.3 Hz, 2H), 7.79–7.27 (m, 3H).
13C-NMR (DMSO-d6),
δ
: 162.79, 161.13, 139.35, 133.87, 131.03, 128.30, 126.47, 125.86, 123.14, 102.05.
ESI-HRMS: m/z [M + H]+, calculated for C13H8F3N3OS: 312.0418, found: 312.0414.
2-(3-(Trifluoromethyl)phenyl)-1H-thieno[3,4-d]imidazole-4-carboxamide (16g). The title compound was
˝
1
obtained similarly to compound 16a as a white solid (0.14 g, 21.8%). m.p.: 240–241 C. H-NMR
(DMSO-d6), : 12.79 (d, 1H), 8.56 (s, 1H), 8.50 (t, J = 10.9 Hz, 1H), 7.94 (t, J = 7.4 Hz, 1H), 7.83 (t,
J = 7.8 Hz, 1H), 7.74–7.33 (m, 3H). 1H-NMR (DMSO-d6, D2O), δ: 8.45–8.54 (m, 2H), 7.96 (d, J = 7.9 Hz,
δ
1H), 7.85 (t, J = 7.9 Hz, 1H), 7.49 (s, 1H). 13C-NMR (DMSO-d6),
δ: 162.93, 161.39, 152.06, 150.58,
139.41, 131.56, 130.73, 128.05, 124.07, 114.94, 110.86, 101.91. ESI-HRMS: m/z [M + H]+, calculated for
C13H8F3N3OS: 312.0418, found: 312.0413.
2-(2-(Trifluoromethyl)phenyl)-1H-thieno[3,4-d]imidazole-4-carboxamide (16h). The title compound was
obtained similarly to compound 16a as a yellow solid (0.14 g, 32.5%). m.p.: 241–243 ˝C. 1H-NMR
(DMSO-d6),
δ: 12.57 (d, 1H), 7.97 (t, J = 9.4 Hz, 1H), 7.91–7.75 (m, 3H), 7.65 (s, 1H), 7.40 (s, 1H), 7.20
(s, 1H). 13C-NMR (DMSO-d6),
δ
: 162.95, 161.28, 150.69, 138.99, 133.08, 132.27, 131.54, 129.62, 128.35,
127.26, 125.52, 122.80, 114.84, 111.14, 102.11. ESI-HRMS: m/z [M + H]+, calculated for C13H8F3N3OS:
312.0418, found: 312.0413.
2-(4-Nitrophenyl)-1H-thieno[3,4-d]imidazole-4-carboxamide (16i). The title compound was obtained
similarly to compound 16a as a yellow solid (0.12 g, 24.7%). m.p.: 278–279 ˝C. 1H-NMR (DMSO-d6),
δ
: 12.89 (d, 1H), 8.52–8.34 (m, 4H), 7.73–7.44 (m, 3H). 13C-NMR (DMSO-d6),
δ: 162.85, 160.65, 150.62,
149.14, 139.36, 135.78, 128.80, 124.71, 115.40, 111.84, 102.24. ESI-HRMS: m/z [M + H]+, calculated for
C12H8N4O3S: 289.0395, found: 289.0392.
2-(4-Methoxyphenyl)-1H-thieno[3,4-d]imidazole-4-carboxamide (16j). The title compound was obtained
˝
˝
similarly to compound 16a as a white solid (0.16 g, 45.2%). m.p.: 240 C–241 C. 1H-NMR (DMSO-d6),
δ
: 12.53 (d, 1H), 8.14 (d, J = 8.9 Hz, 2H), 7.47 (m, 2H), 7.27 (s, 1H), 7.13 (d, J = 8.9 Hz, 2H), 3.86 (s, 3H).
13C-NMR (DMSO-d6),
δ: 163.19, 160.12, 151.12, 139.51, 131.17, 130.67, 120.04, 117.59, 112.68, 101.45,
55.17. ESI-HRMS: m/z [M + H]+, calculated for C13H11N3O2S: 274.0650, found: 274.0651.
2-(3-Methoxyphenyl)-1H-thieno[3,4-d]imidazole-4-carboxamide (16k). The title compound was obtained
similarly to compound 16a as a white solid (0.15 g, 38.2%). m.p.: 230–242 ˝C. 1H-NMR (DMSO-d6),
δ
: 12.52 (d, 1H), 7.76 (d, J = 7.4 Hz, 2H), 7.46 (m, 4H), 7.14 (d, J = 8.0 Hz, 1H), 3.87 (s, 3H). 13C-NMR
(DMSO-d6), δ: 163.19, 159.98, 150.97, 139.42, 131.17, 130.67, 120.04, 117.59, 112.68, 101.24, 55.88.
ESI-HRMS: m/z [M + H]+, calculated for C13H11N3O2S: 274.0650, found: 274.0648.
2-(p-Tolyl)-1H-thieno[3,4-d]imidazole-4-carboxamide (16l). The title compound was obtained similarly
to compound 16a as a white solid (0.10 g, 19.8%). m.p.: 257–258 ˝C. 1H-NMR (DMSO-d6),
δ
: 12.65
(s, 1H), 8.08 (m, 2H), 7.66 (s, 1H), 7.53 (s, 1H), 7.39 (d, J = 8.1 Hz, 2H), 7.31 (s, 1H), 2.40 (s, 3H).
13C-NMR (DMSO-d6),
δ: 163.24, 151.18, 141.48, 139.48, 137.64, 130.04, 127.64, 113.79, 110.38, 101.27,
21.58. ESI-HRMS: m/z [M + H]+, calculated for C13H11N3OS: 258.0701, found: 258.0698.
2-(m-Tolyl)-1H-thieno[3,4-d]imidazole-4-carboxamide (16m). The title compound was obtained similarly to
˝
compound 16a as a white solid (0.12 g, 26.2%). m.p.: 254–255 C. 1H-NMR (DMSO-d6),
δ: 12.65 (s, 1H),
8.03 (s, 1H), 7.97 (d, J = 7.7 Hz, 1H), 7.63 (s, 1H), 7.46 (t, J = 7.6 Hz, 2H), 7.39 (d, J = 7.5 Hz, 2H), 2.42 (s,
3H). 13C-NMR (DMSO-d6),
δ: 163.03, 151.00, 139.41, 138.83, 132.30, 129.90, 129.40, 128.07, 124.78, 113.98,
110.50, 101.35, 21.51. ESI-HRMS: m/z [M + H]+, calculated for C13H11N3OS: 258.0701, found: 258.0696.
2-(o-Tolyl)-1H-thieno[3,4-d]imidazole-4-carboxamide (16n). The title compound was obtained similarly to
˝
compound 16a as a white solid (0.14 g, 31.5%). m.p.: 222–223 C. 1H-NMR (DMSO-d6),
δ
: 12.43 (s, 1H),
7.75 (d, J = 7.4 Hz, 1H), 7.63 (d, J = 12.3 Hz, 1H), 7.28–7.46 (m, 5H), 2.61 (s, 3H). 13C-NMR (DMSO-d6),
δ
:
163.98, 163.14, 152.79, 151.03, 138.94, 138.08, 131.93, 130.86, 130.00, 126.58, 114.24, 110.84, 101.45, 21.54.
ESI-HRMS: m/z [M + H]+, calculated for C13H11N3OS: 258.0701, found: 258.0700.