Page 5 of 12
RSC Advances
DOI: 10.1039/C6RA01179A
2ꢀ(5ꢀcyclopentylꢀ1,3,4ꢀoxadiazolꢀ2ꢀyl)ꢀ6ꢀphenylꢀ4ꢀ
(trifluoromethyl)thieno[2,3ꢀb]pyridinꢀ3ꢀamine (5c). Yield: 25%; 60 162.14, 140.75, 131.36 (q, J = 33.0 Hz), 123.08 (q, J = 272.0 Hz),
(m, 4H). 13C NMR (100 MHz, CDCl3) δ 166.96, 163.60, 162.86,
1H NMR (400 MHz, CDCl3) δ 8.07 (d, J = 6.1 Hz, 2H), 7.98 (s,
1H), 7.49ꢀ7.45 (m, 3H), 5.98 (sbr, 2H), 3.38ꢀ3.21 (m, 1H), 2.12ꢀ
2.10 (m, 2H), 1.98ꢀ1.93 (m, 2H), 1.81ꢀ1.79 (m, 2H), 1.70ꢀ1.67
(m, 2H). 13C NMR (100 MHz, CDCl3) δ 168.26, 162.79, 162.01,
117.49, 114.96, 92.95, 30.37, 27.10, 18.90, 17.75, 11.52. ESIꢀMS
m/z 381.1[M + H]+.
5
2ꢀ(5ꢀcyclopentylꢀ1,3,4ꢀoxadiazolꢀ2ꢀyl)ꢀ6ꢀcyclopropylꢀ4ꢀ
(trifluoromethyl)thieno[2,3ꢀb]pyridinꢀ3ꢀamine (5g). Yield: 21%.
156.31, 140.52, 137.02, 132.36 (q, J = 33.0 Hz), 130.47, 129.15, 65 1H NMR (400 MHz, CDCl3) δ 7.44 (s, 1H), 6.24 (sbr, 2H), 3.42ꢀ
127.37, 123.49 (d, J = 272.0 Hz), 118.43, 113.32 (q, J = 6.2 Hz),
94.75, 35.91, 31.22, 25.50. ESIꢀMS: m/z 431.1 [M + H]+.
2ꢀ(5ꢀcyclohexylꢀ1,3,4ꢀoxadiazolꢀ2ꢀyl)ꢀ6ꢀphenylꢀ4ꢀ
3.34 (m, 1H), 2.22ꢀ1.70 (m, 9H), 1.25ꢀ1.14 (m, 4H). 13C NMR
(100 MHz, CDCl3) δ 167.99, 163.55, 162.85, 162.16, 140.67,
131.33 (q, J = 33.0 Hz), 123.09 (q, J = 272.0 Hz), 117.49, 114.95,
93.00, 35.88, 31.18, 25.48, 17.75, 11.50. ESIꢀMS m/z 395.1 [M +
10
(trifluoromethyl)thieno[2,3ꢀb]pyridinꢀ3ꢀamine (5d). Yield: 25%;
1H NMR (400 MHz, CDCl3) δ 8.03 (d, J = 6.2 Hz, 2H), 7.92 (s, 70 H]+.
1H), 7.45ꢀ7.41 (m, 3H), 6.21 (sbr, 2H), 3.12ꢀ2.91 (m, 1H), 2.10ꢀ
2ꢀ(5ꢀcyclohexylꢀ1,3,4ꢀoxadiazolꢀ2ꢀyl)ꢀ6ꢀcyclopropylꢀ4ꢀ
2.06 (m, 2H), 1.81ꢀ1.78 (m, 2H), 1.68ꢀ1.57 (m, 3H), 1.37ꢀ1.25
(trifluoromethyl)thieno[2,3ꢀb]pyridinꢀ3ꢀamine (5h). Yield: 22%.
1H NMR (400 MHz, CDCl3) δ 7.44 (s, 1H), 6.16 (sbr, 2H), 3.05ꢀ
2.92 (m, 1H), 2.29ꢀ2.09 (m, 3H), 1.94ꢀ1.76 (m, 2H), 1.75ꢀ1.57
15 (m, 3H). 13C NMR (100MHz, CDCl3) δ 167.99, 162.85, 161.75,
156.25, 140.49, 137.06, 132.26 (q, J = 33.0 Hz), 130.36, 129.07,
127.27, 123.08 (d, J = 272.0 Hz), 118.60, 113.51 (q, J = 6.2 Hz), 75 (m, 3H), 1.56ꢀ1.24 (m, 3H), 1.23ꢀ1.04 (m, 4H). 13C NMR (100
95.01, 35.09, 30.16, 25.60, 25.42. ESIꢀMS: m/z 445.2 [M + H]+.
5ꢀ(3ꢀaminoꢀ6ꢀphenylꢀ4ꢀ(trifluoromethyl)thieno[2,3ꢀb]pyridinꢀ
20 2ꢀyl)ꢀNꢀcyclohexylꢀ1,3,4ꢀoxadiazolꢀ2ꢀamine (6a). Yield: 20%. 1H
NMR (400 MHz, CDCl3)) δ 8.05 (d, J = 6.1 Hz, 2H), 7.96 (s, 1H),
MHz, CDCl3) δ 167.84, 163.45, 162.44, 161.86, 140.62, 131.55
(q, J = 33.0 Hz), 123.00 (q, J = 272.0 Hz), 117.68, 114.89, 93.17,
35.07, 30.16, 25.59, 25.40, 17.67, 11.66. ESIꢀMS m/z 409.2 (M +
H)+.
7.45ꢀ7.41 (m, 3H), 6.23 (s, 1H), 6.02 (sbr, 2H), 3.75ꢀ3.60 (m, 1H), 80 2ꢀ(5ꢀcyclohexylꢀ1,3,4ꢀoxadiazolꢀ2ꢀyl)ꢀ6ꢀcyclopentylꢀ4ꢀ
2.06ꢀ1.98 (m, 2H), 1.74ꢀ1.59 (m, 2H), 1.35ꢀ1.18 (m, 6H). 13C
NMR (100 MHz, CDCl3) δ 166.36, 162.81, 162.43, 155.99,
25 139.42, 137.16, 132.65 (q, J = 33.0 Hz), 130.33, 129.11,
12155.74, 139.49, 137.06, 132.46 (q, J = 33.0 Hz), 130.41,
(trifluoromethyl)thieno[2,3ꢀb]pyridinꢀ3ꢀamine (5i). Yield: 30%.
1H NMR (400 MHz, DMSOꢀd6) δ 7.48 (s, 1H), 6.27 (s, 2H),
3.40ꢀ3.32 (m, 1H), 3.02ꢀ2.95 (m, 1H), 2.17ꢀ2.15 (m, 4H), 1.95ꢀ
1.82 (m, 6H), 1.81ꢀ1.61 (m, 5H), 1.49ꢀ1.31 (m, 3H). 13C NMR
129.12, 127.41, 123.18 (d, J = 271.0 Hz), 118.45, 113.59 (q, J = 85 (100 MHz, CDCl3) δ 167.86, 166.01, 162.40, 161.90, 140.59,
6.2 Hz), 99.93, 53.43, 33.03, 29.76, 24.55. ESIꢀMS: m/z 458.3
[M ꢀ H]+.
131.68 (q, J = 33.0 Hz), 123.10 (q, J = 272.0 Hz), 117.93, 115.15,
93.56, 35.07, 33.57, 30.16, 29.69, 25.86, 25.59, 25.40. ESIꢀMS
m/z 437.2 (M + H)+.
30 5ꢀ(3ꢀaminoꢀ6ꢀphenylꢀ4ꢀ(trifluoromethyl)thieno[2,3ꢀb]pyridinꢀ2ꢀ
1
yl)ꢀNꢀcyclopentylꢀ1,3,4ꢀoxadiazolꢀ2ꢀamine (6b). Yield: 23%. H
5ꢀ(3ꢀaminoꢀ6ꢀcyclopropylꢀ4ꢀ(trifluoromethyl)thieno[2,3ꢀ
NMR (400 MHz, CDCl3) δ 8.05 (d, J = 6.1 Hz, 2H), 7.95 (s, 1H), 90 b]pyridinꢀ2ꢀyl)ꢀNꢀcyclohexylꢀ1,3,4ꢀoxadiazolꢀ2ꢀamine
(6d).
1
7.46ꢀ7.42 (m, 3H), 6.13 (s, 1H), 6.03 (sbr, 2H), 3.95ꢀ3.84 (m, 1H),
1.97ꢀ1.93 (m, 2H), 1.65ꢀ1.75 (m, 2H), 1.53ꢀ1.62 (m, 4H).13C
35 NMR (100 MHz, CDCl3) δ 166.36, 162.81, 162.43, 155.99,
139.42, 137.16, 132.65 (q, J = 33.0 Hz), 130.33, 129.11, 127.26,
Yield: 20%. H NMR (400 MHz, DMSOꢀd6) δ 7.87 (d, J = 7.2,
1H), 7.82 (s, 1H), 6.16 (sbr, 2H), 3.49ꢀ3.38 (m, 1H), 2.46ꢀ2.40
(m, 1H), 2.05ꢀ1.92 (m, 2H), 1.72ꢀ1.67 (m, 2H), 1.42ꢀ1.25 (m,
6H), 1.19ꢀ1.04 (m, 4H). 13C NMR (100 MHz, DMSOꢀd6) δ
123.30 (d, J = 270.0 Hz), 118.57, 113.40 (q, J = 6.2 Hz), 55.83, 95 163.00, 161.08, 160.91, 154.82, 138.34, 129.93 (q, J = 33.0 Hz),
33.24, 29.71, 23.60. ESIꢀMS: m/z 446.2 [M + H]+.
5ꢀ(3ꢀaminoꢀ6ꢀphenylꢀ4ꢀ(trifluoromethyl)thieno[2,3ꢀb]pyridinꢀ
40 2ꢀyl)ꢀNꢀphenylꢀ1,3,4ꢀoxadiazolꢀ2ꢀamine (6c). Yield: 20%. 1H
NMR (400 MHz, DMSOꢀd6) δ 10.84 (s, 1H), 8.36 (s, 1H), 8.29
122.79 (q, J = 272.0 Hz), 117.10, 115.53, 92.45, 51.83, 32.11,
25.14, 24.24, 16.92, 11.39. ESIꢀMS m/z 424.2 (M + H)+.
5ꢀ(3ꢀaminoꢀ6ꢀcyclopropylꢀ4ꢀ(trifluoromethyl)thieno[2,3ꢀ
b]pyridinꢀ2ꢀyl)ꢀNꢀcyclopentylꢀ1,3,4ꢀoxadiazolꢀ2ꢀamine
(6e).
1
(d, J = 7.6 Hz, 2H), 7.63(d, J = 7.5 Hz, 2H), 7.40ꢀ7.37 (m, J = 8.0 100 Yield: 22%. H NMR (400 MHz, CDCl3) δ 7.35 (s, 1H), 6.03
Hz, 3H), 7.06ꢀ7.02 (m, 3H), 6.39 (sbr, 2H). 13C NMR (100 MHz,
DMSOꢀd6) δ 161.14, 158.10, 155.24, 155.19, 139.25, 138.38,
45 136.24, 132.74 (q, J = 33.0 Hz), 130.49, 129.05, 127.24, 124.13,
123.50 (d, J = 271.0 Hz), 121.95, 118.11, 117.03, 113.73 (q, J =
6.2 Hz), 93.50. ESIꢀMS m/z 476.3[M + Na]+.
(sbr, 2H), 4.05(s, 1H), 2.17ꢀ1.96 (m, 2H), 1.80ꢀ1.51(m, 4H),
1.29ꢀ1.11(m, 8H). 13C NMR (100 MHz, CDCl3) δ 162.01,
161.28, 159.57, 155.04, 138.32, 129.94 (q, J = 33.0 Hz), 122.06
(q, J = 272.0 Hz), 116.62, 113.90, 92.19, 54.64, 32.17, 28.68,
105 22.57, 16.64, 10.38. ESIꢀMS m/z 410.1 (M + H)+.
6ꢀcyclopropylꢀ2ꢀ(5ꢀcyclopropylꢀ1,3,4ꢀoxadiazolꢀ2ꢀyl)ꢀ4ꢀ
2ꢀ(5ꢀcyclopropylꢀ1,3,4ꢀoxadiazolꢀ2ꢀyl)ꢀ4ꢀ(trifluoromethyl)ꢀ
6,7ꢀdihydroꢀ5Hꢀcyclopenta[b]thieno[3,2ꢀe]pyridinꢀ3ꢀamine (10a).
Yield: 21%. H NMR (400 MHz, CDCl3) δ 6.05 (sbr, 2H), 3.23
(trifluoromethyl)thieno[2,3ꢀb]pyridinꢀ3ꢀamine (5e). Yield: 25%.
50 1H NMR (400 MHz, CDCl3) δ 7.44 (s, 1H), 6.21 (sbr, 2H), 2.17ꢀ
2.25 (m, 2H), 1.12ꢀ1.25 (m, 8H). 13C NMR (100 MHz, CDCl3) δ
1
(sbr, 2H), 3.10 (t, J = 7.6 Hz, 2H), 2.18 (m, 3H), 1.15ꢀ1.11 (m,
166.29, 163.54, 162.78, 161.53, 140.54, 131.30 (q, J = 33.0 Hz), 110 4H). 13C NMR (100 MHz, CDCl3) δ 167.92, 166.32, 161.49,
122.93(q, J = 272.0 Hz), 117.48, 114.97, 92.88, 17.74, 11.50,
8.55, 6.29. ESIꢀMS m/z 367.1 [M + H]+.
160.82, 140.84, 132.29, 127.83 (q, J = 33.0 Hz), 124.02 (q, J =
273.0 Hz), 118.59, 93.46, 33.80, 31.09, 23.00, 8.57, 6.29. ESIꢀ
MS m/z 367.1 (M + H)+.
55
2ꢀ(5ꢀcyclobutylꢀ1,3,4ꢀoxadiazolꢀ2ꢀyl)ꢀ6ꢀcyclopropylꢀ4ꢀ
(trifluoromethyl)thieno[2,3ꢀb]pyridinꢀ3ꢀamine (5f) Yield: 18%.
2ꢀ(5ꢀcyclobutylꢀ1,3,4ꢀoxadiazolꢀ2ꢀyl)ꢀ4ꢀ(trifluoromethyl)ꢀ6,7ꢀ
1H NMR (400 MHz, CDCl3) δ 7.44 (s, 1H), 6.26 (sbr, 2H), 3.82ꢀ 115 dihydroꢀ5Hꢀcyclopenta[b]thieno[3,2ꢀe]pyridinꢀ3ꢀamine
(10b).
1
3.75 (m, 1H), 2.58ꢀ2.47 (m, 4H), 2.22ꢀ2.05 (m, 3H), 1.22ꢀ1.11
Yield: 21%; H NMR (400 MHz, CDCl3) δ 6.33 (sbr, 2H), 3.87ꢀ
4
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