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J1 = 8.61 Hz, J2 = 2.04 Hz, 1H), 6.67 (s, 1H), 4.01 (t, J = 6.96 Hz, 2H),
3.63 (t, J = 6.78 Hz, 2H), 2.63 (s, 3H), 2.23 (d, J = 0.9 Hz, 3H), 2.11
(quintet, J = 7.14 Hz, 2H). MS (ESI) m/z: 331 [M+H]+.
coupling procedure: 21% yield, white solid, mp = 184–185 °C. 1H
NMR (300 MHz, CD3OD): d 9.04 (s, 1H), 8.01 (d, J = 8.22 Hz, 1H),
7.79 (d, J = 8.04 Hz, 1H), 7.70 (d, J = 7.71 Hz, 1H), 7.64 (s, 1H),
7.52–7.47 (m, 1H), 7.31 (s, 1H), 6.64 (s, 1H), 4.11 (t, J = 7.14 Hz,
2H), 3.81 (t, J = 6.78 Hz, 2H), 2.25 (s, 3H), 2.23–2.10 (m, 2H). MS
(FAB) m/z: 326 [M+H]+.
4.1.7.52. 1-(Benzo[d]oxazol-6-yl)-3-(3-(5-methyl-1H-imidazol-
1-yl)propyl)thiourea (69).
Prepared from commercially
available 6-aminobenzoxazole by following the general thiourea
coupling procedure: 40% yield, pink solid, mp = 59–60 °C; 1H
NMR (300 MHz, CD3OD): d 8.46 (s, 1H), 7.83 (d, J = 2.01 Hz, 1H),
7.72 (d, J = 8.4 Hz, 1H), 7.60 (d, J = 1.08 Hz, 1H), 7.30 (dd,
J1 = 2.01 Hz, J2 = 8.58 Hz, 1H), 6.67 (s, 1H), 4.03 (t, J = 7.14 Hz, 2H),
3.65 (t, J = 7.14 Hz, 2H), 2.25 (d, J = 1.08 Hz, 3H), 2.14 (quintet,
J = 7.32 Hz, 2H). MS (ESI) m/z: 316 [M+H]+.
4.1.7.59. 1-(3-(5-Methyl-1H-imidazol-1-yl)propyl)-3-(quinolin-
3-yl)thiourea (76).
Prepared from commercially available
3-aminoquinoline by following the general thiourea coupling pro-
cedure: 62% yield, white solid, mp = 85–86 °C. 1H NMR (300 MHz,
CD3OD):
d 8.88 (d, J = 2.37 Hz, 1H), 8.38 (s, 1H), 7.97 (d,
J = 8.4 Hz, 1H), 7.90 (d, J = 8.07 Hz, 1H), 7.74–7.68 (m, 1H), 7.62
(s, 1H), 7.59–7.57 (m, 1H), 6.69 (s, 1H), 4.06 (t, J = 7.14 Hz, 2H),
3.65 (t, J = 7.14 Hz, 2H), 2.25 (d, J = 1.08 Hz, 3H), 2.13 (quintet,
J = 6.96 Hz, 2H). MS (FAB) m/z: 326 [M+H]+.
4.1.7.53. 1-(3-(5-Methyl-1H-imidazol-1-yl)propyl)-3-(2-meth-
ylbenzo[d]oxazol-6-yl)thiourea (70).
Prepared from com-
mercially available 2-methylbenzo[d]oxazol-6-amine by following
the general thiourea coupling procedure: 51% yield, white solid,
mp = 75–76 °C; 1H NMR (300 MHz, CD3OD): d 7.68 (d, J = 1.83 Hz,
1H), 7.60 (d, J = 1.08 Hz, 1H), 7.58 (d, J = 8.43 Hz, 1H), 7.22 (dd,
J1 = 1.83 Hz, J2 = 8.43 Hz, 1H), 6.67 (s, 1H), 4.02 (t, J = 7.32 Hz, 2H),
3.64 (t, J = 7.14 Hz, 2H), 2.62 (s, 3H), 2.23 (d, J = 0.93 Hz, 3H), 2.11
(quintet, J = 6.96 Hz, 2H). MS (ESI) m/z: 331 [M+H]+.
4.1.7.60. 1-(3-(5-Methyl-1H-imidazol-1-yl)propyl)-3-(quinolin-
2-yl)thiourea (77).
Prepared from commercially available
2-aminoquinoline by following the general thiourea coupling pro-
cedure: 64% yield, white solid, mp = 221–222 °C. 1H NMR
(500 MHz, CD3OD): d 8.19 (d, J = 8.9 Hz, 1H), 7.82 (t, J = 9.25 Hz,
2H), 7.70 (t, J = 7.25 Hz, 1H), 7.62 (s, 1H), 7.47 (t, J = 7.45 Hz, 1H),
7.12 (d, J = 8.85 Hz, 1H), 6.63 (s, 1H), 4.13 (t, J = 7.00 Hz, 2H), 3.84
(t, J = 6.7 Hz, 2H), 2.29 (quintet, J = 6.9 Hz, 2H), 2.21 (s, 3H). MS
(FAB) m/z: 326 [M+H]+.
4.1.7.54. 1-(Benzo[d]thiazol-5-yl)-3-(3-(5-methyl-1H-imidazol-
1-yl)propyl)thiourea (71). Prepared from commercially available
5-aminobenzothiazole by following the general thiourea coupling
procedure: 29% yield, white solid, mp = 78–79 °C. 1H NMR
(300 MHz, CD3OD): d 9.26 (s, 1H), 9.00 (s, 1H), 8.22 (d, J = 1.83 Hz,
1H), 8.04 (d, J = 8.61 Hz, 1H), 7.50 (dd, J1 = 1.65 Hz, J2 = 8.22 Hz,
1H), 7.30 (s, 1H), 4.30 (t, J = 6.96 Hz, 2H), 3.72 (t, J = 6.18 Hz, 2H),
2.38 (d, J = 1.08 Hz, 3H), 2.24–2.20 (m, 2H). MS (ESI) m/z: 333
[M+H]+.
4.1.7.61.
yl)propyl)thiourea (78).
1-(Isoquinolin-1-yl)-3-(3-(5-methyl-1H-imidazol-1-
Prepared from commercially
available 1-aminoisoquinoline by following the general thiourea
coupling procedure: 45% yield, white solid, mp = 136–137 °C. 1H
NMR (300 MHz, CD3OD): d 8.34 (d, J = 8.61 Hz, 1H), 8.10 (d,
J = 5.85 Hz, 1H), 7.91 (d, J = 8.22 Hz, 1H), 7.81 (t, J = 6.96 Hz, 1H),
7.71 (t, J = 7.14 Hz, 1H), 7.63 (s, 1H), 7.46 (d, J = 6.21 Hz, 1H), 6.64
(s, 1H), 4.12 (t, J = 7.14 Hz, 2H), 3.83 (t, J = 6.78 Hz, 2H), 2.25 (d,
J = 0.9 Hz, 3H), 2.25–2.21 (m, 2H). MS (FAB) m/z: 326 [M+H]+.
4.1.7.55. 1-(Benzo[d]thiazol-6-yl)-3-(3-(5-methyl-1H-imidazol-
1-yl)propyl)thiourea (72).
Prepared from commercially
available 6-aminobenzothiazole by following the general thiourea
coupling procedure: 44% yield, white solid, mp = 72–73 °C. 1H NMR
(300 MHz, CD3OD): d 9.20 (s, 1H), 8.13 (d, J = 2.19 Hz, 1H), 8.04 (d,
J = 8.61 Hz, 1H), 7.60 (s, 1H), 7.46 (dd, J1 = 2.04 Hz, J2 = 8.79 Hz, 1H),
6.67 (s, 1H), 4.03 (t, J = 7.14 Hz, 2H), 3.65 (t, J = 6.78 Hz, 2H), 2.23
(d, J = 1.08 Hz, 3H), 2.14 (quintet, J = 7.14 Hz, 2H). MS (ESI) m/z:
333 [M+H]+.
4.1.7.62. 1-(3-(5-Methyl-1H-imidazol-1-yl)propyl)-3-(quinolin-
6-yl)thiourea (79).
Prepared from commercially available
6-aminoquinoline by following the general thiourea coupling pro-
cedure: 46% yield, white solid, mp = 57–58 °C. 1H NMR (300 MHz,
CD3OD):
d 8.79 (dd, J1 = 1.65 Hz, J2 = 4.38 Hz, 1H), 8.32 (d,
J = 7.68 Hz, 1H), 8.01 (s, 1H), 7.97 (d, J = 8.97 Hz, 1H), 7.77 (dd,
J1 = 2.37 Hz, J2 = 8.97 Hz, 1H), 7.64 (s, 1H), 7.54 (dd, J1 = 4.38 Hz,
J2 = 8.22 Hz, 1H), 6.69 (s, 1H), 4.06 (t, J = 7.14 Hz, 2H), 3.67 (t,
J = 6.96 Hz, 2H), 2.25 (d, J = 0.93 Hz, 3H), 2.10 (quintet,
J = 6.96 Hz, 2H). MS (FAB) m/z: 326 [M+H]+.
4.1.7.56. 1-(3-(5-Methyl-1H-imidazol-1-yl)propyl)-3-(pyridin-2-
yl)thiourea (73).
Prepared from commercially available
2-aminopyridine by following the general thiourea coupling proce-
dure: 53% yield, white solid, mp = 146–147 °C; 1H NMR (300 MHz,
CD3OD):
d 8.23–8.20 (m, 1H), 7.75–7.69 (m, 1H), 7.62 (d,
J = 0.93 Hz, 1H), 7.03–6.99 (m, 1H), 6.97 (d, J = 8.43 Hz, 1H), 6.65
(s, 1H), 4.13 (t, J = 7.14 Hz, 2H), 3.76 (t, J = 6.96 Hz, 2H), 2.23 (d,
J = 0.93 Hz, 3H), 2.19 (quintet, J = 7.14 Hz, 2H). MS (FAB) m/z: 276
[M+H]+.
4.1.7.63. 1-(3-(5-Methyl-1H-imidazol-1-yl)propyl)-3-(quinolin-
7-yl)thiourea (80).
Prepared from commercially available
7-aminoquinoline by following the general thiourea coupling pro-
cedure: 30% yield, white solid, mp = 100–101 °C. 1H NMR
(300 MHz, CD3OD): d 8.80 (dd, J1 = 4.38 Hz, J2 = 1.65 Hz, 1H), 8.33
(d, J = 7.86 Hz, 1H), 8.13 (s, 1H), 7.92 (d, J = 8.97 Hz, 1H), 7.69–
7.63 (m, 2H), 7.49–7.44 (m, 1H), 6.68 (s, 1H), 4.07 (t, J = 7.14 Hz,
2H), 3.68 (t, J = 6.57 Hz, 2H), 2.25 (d, J = 0.9 Hz, 3H), 2.14 (quintet,
J = 7.14 Hz, 2H). MS (ESI) m/z: 326 [M+H]+.
4.1.7.57. 1-(3-(5-Methyl-1H-imidazol-1-yl)propyl)-3-(pyridin-3-
yl)thiourea (74).
Prepared from commercially available
3-aminopyridine by following the general thiourea coupling proce-
dure: 55% yield, white solid, mp = 51–52 °C; 1H NMR (300 MHz,
CD3OD):
d 8.55 (d, J = 2.55 Hz, 1H), 8.30 (dd, J1 = 1.29 Hz,
J2 = 4.77 Hz, 1H), 8.00–7.96 (m, 1H), 7.61 (s, 1H), 7.42–7.37 (m,
1H), 6.69 (s, 1H), 4.04 (t, J = 7.14 Hz, 2H), 3.64 (t, J = 6.96 Hz, 2H),
2.24 (d, J = 0.72 Hz, 3H), 2.08 (quintet, J = 6.96 Hz, 2H). MS (FAB)
m/z: 276 [M+H]+.
4.1.7.64.
yl)propyl)thiourea (81).
1-(Isoquinolin-6-yl)-3-(3-(5-methyl-1H-imidazol-1-
Prepared from commercially avail-
able 6-aminoisoquinoline by following the general thiourea cou-
pling procedure: 68% yield, white solid, mp = 95–96 °C. 1H NMR
(300 MHz, CD3OD): d 9.10 (s, 1H), 8.35 (d, J = 5.85 Hz, 1H), 8.12
(s, 1H), 8.04 (d, J = 8.79 Hz, 1H), 7.72–7.69 (m, 2H), 7.63 (s, 1H),
6.68 (s, 1H), 4.06 (t, J = 7.14 Hz, 2H), 3.68 (t, J = 6.78 Hz, 2H), 2.24
(s, 3H), 2.17 (quintet, J = 6.96 Hz, 2H). MS (FAB) m/z: 326 [M+H]+.
4.1.7.58.
yl)propyl)thiourea (75).
able 3-aminoisoquinoline by following the general thiourea
1-(Isoquinolin-3-yl)-3-(3-(5-methyl-1H-imidazol-1-
Prepared from commercially avail-