26.43, 24.46, 21.69. HRMS (ESI) calculated for C25H23N5O2
(M+H)+: 426.1929, found 426.1946.
46.51, 26.53, 24.44. HRMS (ESI) calculated for C25H22N4O2
(M+H)+: 411.1820, found 411.1817.
4.4.4. 2-(4-(6-(pyrrolidine-1-carbonyl)pyridin-3-yl)phenyl)-
1H-benzimidazole-4-carboxamide (10c). 1H NMR (400MHz,
DMSO-d6): δ 9.03 (bs, NH), 8.66 (bs, 1H), 8.37 (d, J=8.6, 2H),
8.33 (s, 1H), 8.07 (d, J=8.6, 2H), 7.95 (d, J=7.7, 1H), 7.90 (d,
J=8.1, 1H), 7.83 (bs, 1H), 7.53 (t, J=8.1, 1H), 3.62 (m, 2H), 3.49
(m, 2H), 1.82 (m, 4H). 13C NMR (100MHz, DMSO-d6): δ
166.90, 165.35, 153.71, 151. 07, 146.51, 140.53, 136.24, 134.03,
133.79, 129.98, 128.10, 125.30, 124.89, 124.25, 122.28, 117.00,
49.02, 46.97, 26.53, 23.98. HRMS (ESI) calculated for
4.5.1. 6-methyl-2-(4'-(pyrrolidine-1-carbonyl)-[1,1'-biphenyl]-
4-yl)-1H-benzimidazole-4-carboxamide (11a). 1H NMR
(400MHz, DMSO-d6): δ 13.33 (s, CONH2), 9.33 (s, NH), 8.31 (d,
J=8.5, 2H), 7.93 (d, J=8.3, 2H), 7.83 (d, J=8.3, 2H), 7.70 (s, 1H),
7.64 (d, J=8.1, 2H), 7.53 (s, 1H), 3.48-3.26 (m, 4H, overlap),
1.87-1.82 (m, 4H). 13C NMR (100MHz, DMSO-d6): δ 167.86,
166.20, 151.02, 140.95, 140.28, 139.77, 136.61, 135.72, 132.02,
128.59, 128.23, 127.90, 127.39, 126.51, 124.38, 121.90, 114.82,
48.95, 46.00, 25.99, 23.92, 21.29. HRMS (ESI) calculated for
C26H24N4O2 (M+H)+: 425.1977, found 425.1979.
C24H21N5O2 (M+H)+: 412.1773, found 412.1761.
4.4.5. 6-methyl-2-(4-(6-(pyrrolidine-1-carbonyl)pyridin-3-
yl)phenyl)-1H-benzimidazole-4-carboxamide (10d). 1H NMR
(400MHz, DMSO-d6): δ 9.10 (s, NH), 9.00 (s, 1H), 8.33 (d,
J=8.6, 2H), 8.30 (dd, J=2.3, 8.2, 1H), 8.01 (d, J=8.2, 2H), 7.82
(d, J=8.2, 1H), 7.70 (s, 1H), 7.55 (s, 1H), 3.64 (t, J=6.3, 2H),
4.5.2. 2-(4-(6-acetamidopyridin-3-yl)phenyl)-1H-
benzimidazole-4-carboxamide (11b). 1H NMR (400MHz,
DMSO-d6): δ 13.48 (s, CONH2), 10.67 (s, NH), 9.38 (s, NH),
8.77 (s, 1H), 8.34 (d, J=8.0, 2H), 8.21 (s, 2H), 7.97 (d, J=8.0,
2H), 7.89 (d, J=7.3, 1H), 7.81-7.75 (m, 1H), 7.36 (t, J=8.0, 1H),
2.13 (s, 3H). 13C NMR (100MHz, DMSO-d6): δ 169.96, 166.70,
152.32, 152, 03, 146.42, 142.03, 139.24, 136.72, 135.88, 130.42,
128.63, 128.06, 127.39, 123.54, 122.91, 115.54, 113.72, 24.46.
HRMS (ESI) calculated for C21H17N5O2 (M+H)+: 372.1460,
found 372.1461.
3.49 (t, J=6.8, 2H), 2.50 (t, J=5.4, 3H), 1.85-1.83 (m, 4H). 13
C
NMR (100MHz, DMSO-d6): δ 166.81, 165.75, 153.97, 151.21,
146.66, 138.91, 136.09, 135.80, 135.64, 133.22, 128.69, 128.44,
128.16, 125.26, 124.17, 122.18, 115.83, 49.09, 47.03, 26.65,
24.07, 21.75. HRMS (ESI) calculated for C25H23N5O2 (M+H)+:
426.1929, found 426.1935.
4.5.3. 2-(4-(5-(pyrrolidin-1-ylmethyl)pyridin-3-yl)phenyl)-1H-
benzimidazole-4-carboxamide (11c). 1H NMR (400MHz,
CD3OD): δ 8.79 (s, 1H), 8.52 (s, 1H), 8.26 (d, J=8.3, 2H), 8.15
(s, 1H), 7.92 (bd, 1H), 7.83 (d, J=8.3, 2H), 7.71, (bd, J=7.5, 1H),
3.84 (s, 2H), 2.69 (bs, 4H), 1.87 (bs, 4H). 13C NMR (67MHz,
CD3OD): δ 68.45, 57.61, 55.03, 24.10, 22.13. HRMS (ESI)
calculated for C24H23N5O (M+H)+: 398.1980, found 398.1989.
4.4.6. 2-(4-(pyridin-2-yl)phenyl)-1H-benzimidazole-4-
carboxamide (10e). Compound reported by (Tong et al., 2009).
4.4.7. 2-(2'-acetamido-[1,1'-biphenyl]-4-yl)-1H-
benzimidazole-4-carboxamide (10f). 1H NMR (270MHz,
CD3OD): δ 8.19 (d, J=8.3, 2H), 7.92 (d, J=7.8, 1H), 7.68 (d,
J=7.8, 1H), 7.52 (d, J=8.3, 2H), 7.48 (d, J=8.1, 1H), 7.36-7.30
(m, 3H), 7.22 (t, J=7.5, 1H), 1.98 (s, 3H). 13C NMR (67MHz,
CD3OD): δ 172.54, 153.64, 143.00, 138.24, 135.64, 131.40,
130.63, 129.55, 129.47, 128.45, 128.08, 127.97, 124.39, 123.50,
123.27, 122.56, 118.58, 22.90. HRMS (ESI) calculated for
C22H18N4O2 (M+H)+: 371.1507, found 371.1505.
4.5.4. 2-(4'-(3-(piperidin-1-yl)propoxy)-[1,1'-biphenyl]-4-yl)-
1H-benzimidazole-4-carboxamide (11d). 1H NMR (400MHz,
DMSO-d6): δ 13.67 (s, CONH2), 9.39 (bs, NH), 8.33 (d, J=8.3,
1H), 7.96 (d, J=8.0, 2H), 7.85 (bs, 1H), 7.72 (d, J=8.0, 2H), 7.66
(d, J=8.3, 2H), 7.33 (bs, 1H), 7.03 (d, J=8.5, 2H), 4.09 (bs, 2H),
2.92 (bs, 2H), 2.11 (bs, 2H), 1.70 (bs, 4H), 1.48 (bs, 2H) . 13
C
4.4.8. 2-(3'-acetamido-[1,1'-biphenyl]-4-yl)-1H-
NMR (100MHz, DMSO-d6): δ 167.35, 158.64, 143.68, 131.43,
129.95, 129.35, 128.12, 126.06, 115.05, 65.44, 53.83, 52.57,
24.12, 23.27, 22.21. HRMS (ESI) calculated for C28H30N4O2
(M+H)+: 455.2446, found 455.2441.
benzimidazole-4-carboxamide (10g). 1H NMR (400MHz,
DMSO-d6): δ 13.49 (s, CONH2), 10.10 (s, NH), 9.38 (s, NH),
8.33 (d, J=8.3, 2H), 7.99 (s, 1H), 7.88 (d, J=7.7, 1H), 7.83 (d,
J=8.3, 2H), 7.74 (d, J=7.8, 1H), 7.60 (s, 1H), 7.42 (d, J=4.8, 2H),
7.34 (t, J=7.8, 1H), 2.07 (s, CH3). 13C NMR (100MHz, DMSO-
d6): δ 168.56, 166.22, 151.60, 142.07, 141.55, 140.02, 139.66,
135.41, 129.48, 128.17, 127.54, 127.26, 123.02, 122.42, 121.54,
118.35, 117.28, 115.05, 24.07. HRMS (ESI) calculated for
C22H18N4O2 (M+H)+: 371.1507, found 371.1509.
4.5.5. 2-(4'-(2-(piperidin-1-yl)ethoxy)-[1,1'-biphenyl]-4-yl)-
1H-benzimidazole-4-carboxamide (11e). 1H NMR (400MHz,
DMSO-d6): δ 13.61 (bs, CONH2), 9.42 (s, NH), 8.28 (d, J=7.5,
2H), 7.87 (d, J=6.8, 1H), 7.77 (d, J=8.3, 2H), 7.73 (d, J=7.5, 1H),
7.63 (d, J=8.3, 2H), 7.31 (t, J=7.5, 1H), 6.98 (d, J=8.3, 2H), 4.06
(t, J=5.3, 2H), 2.68 (t, J=5.3, 2H), 1.46 (t, J=5.3, 4H), 1.31 (bs,
2H). 13C NMR (100MHz, DMSO-d6): δ 166.88, 159.01, 152.30,
142.30, 135.97, 131.92, 130.43, 129.52, 128.37, 128.01, 127.82,
127.38, 127.08, 126.86, 123.44, 122.78, 115.54, 65.75, 57.51,
54.67, 25.66, 24.08, 21.74. HRMS (ESI) calculated for
4.4.9. 2-(4'-acetamido-[1,1'-biphenyl]-4-yl)-1H-
benzimidazole-4-carboxamide (10h). 1H NMR (270MHz,
DMSO-d6): δ 8.32 (d, J=8.4, 2H), 8.22 (d, J=7.8, 1H), 8.14 (d,
J=8.1, 1H), 7.93 (d, J=8.4, 2H), 7.75 (d, J=8.6, 2H), 7.69 (d,
J=8.6, 2H), 7.54 (bs, 1H), 2.21 (s, 3H). 13C NMR (100MHz,
CD3OD): δ 168.98, 167.10, 153.10, 142.02, 139.85, 133.94,
129.92, 129.04, 128.67, 127.79, 127.48, 126.84, 126.31, 125.17,
122.55, 119.85, 116.65, 24.54. HRMS (ESI) calculated for
C22H18N4O2 (M+H)+: 371.1507, found 371.1508.
C27H28N4O2 (M+H)+: 441.2290, found 441.2291.
4.5.6. 2-(4'-(cyclopropanecarboxamido)-2',3-difluoro-[1,1'-
biphenyl]-4-yl)-6-fluoro-1H-benzimidazole-4-carboxamide
(11f). 1H NMR (400MHz, DMSO-d6): δ 10.60 (s, NH), 9.26 (s,
NH), 8.35 (t, J=7.8, 1H), 7.99-7.60 (m, 5H), 7.43 (s, 1H), 7.41 (s,
1H), 1.80-1.75 (m, 1H), 0.84-0.81 (m, 4H). 13C NMR (100MHz,
DMSO-d6): δ 172.46, 165.10, 160.45, 160.42, 158.00, 157.97,
147.99, 141.44, 141.32, 138.44, 130.82, 130.50, 125.30, 124.05,
120.11, 116.39, 115.77, 115.27, 110.78, 106.43, 102.10, 14.84,
7.75. HRMS (ESI) calculated for C24H17N4F3O2 (M+H)+:
451.1381, found 451.1378.
4.5.0. 2-(4'-(pyrrolidine-1-carbonyl)-[1,1'-biphenyl]-4-yl)-1H-
benzimidazole-4-carboxamide (10i). 1H NMR (400MHz,
DMSO-d6): δ 9.38 (bs, NH), 8.37 (d, J=8.4, 2H), 7.96 (d, J=8.4,
2H), 7.90 (d, J=7.2, 1H), 7.84 (d, J=8.4, 2H), 7.78 (d, J=8.0, 1H),
7.65 (d, J=8.0, 2H), 7.37 (t, J=7.2, 1H), 3.51-3.48 (m, 4H), 1.90-
1.83 (m, 4H). 13C NMR (100MHz, DMSO-d6): δ 168.34, 166.79,
152.07, 141.63, 140.77, 137.14, 128.99, 128.75, 128.43, 128.36,
128.08, 127.94, 127.16, 127.05, 123.48, 122.92, 115.68, 49.10,
4.5.7. 6-fluoro-2-(4'-propionamido-[1,1'-biphenyl]-4-yl)-1H-
benzimidazole-4-carboxamide (11g). 1H NMR (400MHz,
10