8
94
BURYI et al.
(
(
2Н, NH ), 7.28 br. s [2Н, C(O)NH ], 7.47–7.52 m
p. 2053. doi 10.1007/BF02494257
2
2
5
3H, Ar), 7.57–7.58 m (5H, Ph), 7.76 s (1Н, Н ), 8.21
4. Litvinov, V.P., Krivokolysko, S.G., and Dyachenko, V.D.,
Chem. Heterocycl. Compd., 1999, vol. 35, no. 5, p. 509.
doi 10.1007/BF02324634
. Litvinov, V.P., Russ. Chem. Rev., 2006, vol. 75, no. 7,
p. 577. doi 10.1070/RC2006v075n07ABEH003619
2
6
3
13
d (2H, H , H , Ar, J = 6.9 Hz). С NMR spectrum
DEPTQ, δ , ppm: 98.5 (C ), 118.2* (C ), 121.1 (C ),
1
1
1
1
spectrum, δ , ppm: 69.2 (NH ), 105.3 (CONH ), 286.8
(
3
3
2
5
3a
C
5
27.1* (CH, Ar), 128.7* (CH, Ar), 128.8* (CH, Ar),
28.9* (CH, Ar), 129.2* (CH, Ar), 129.8* (CH, Ar),
1
1
3
4
6
. Bakhite, E.A.-G., Phosphorus, Sulfur, Silicon, Relat.
Elem., 2003, vol. 178, p. 929. doi 10.1080/
36.6 (C , Ph), 137.5 (C , Ph), 145.5 (C ), 147.5 (C ),
6
7а
15
55.5 (C ), 159.7 (C ), 166.9 (CONH ). N NMR
2
1
0426500390208820
N
2
2
7
8
. Litvinov, V.P., Dotsenko, V.V., and Krivokolysko, S.G.,
Russ. Chem. Bull., 2005, vol. 54, no. 4, p. 864. doi
N ). Mass spectrum (HRMS ESI-TOF), m/z:
Py
+
68.0833 [M + Na] (calculated for C H N NaOS:
20 15 3
1
0.1007/s11172-005-0333-1
68.0828).
-Amino-6-(4-tert-butylphenyl)-4-phenylthieno-
2,3-b]pyridine-2-carboxamide (13b). Yield 83%,
. Litvinov, V.P., Dotsenko, V.V., and Krivokolysko, S.G.,
Adv. Heterocycl. Chem., 2007, vol. 93, p. 117. doi
10.1016/S0065-2725(06)93003-7
3
[
–
1
yellow powder, mp 262°С. IR spectrum, ν, cm : 3488,
3
NMR spectrum, δ, ppm: 1.31 s [9Н, С(СН ) ], 5.87 br.
s (2Н, NH ), 7.25 br. s [2Н, C(O)NH ], 7.52 d (2H, H ,
H , Ar, J = 8.3 Hz), 7.57–7.58 m (5H, Ph), 7.71 s (1Н,
Н ), 8.13 d (2H, H , H , Ar, J = 8.3 Hz). С NMR
spectrum, δ , ppm: 31.0* [С(СН ) ], 34.5 [С(СН ) ],
9
1
1
9. Litvinov, V.P., Dotsenko, V.V., and Krivokolysko, S.G.,
Khimiya tiyenopiridinov rodstvennykh sistem
Chemistry of Thienopyridines and Related Systems),
Moscow: Nauka, 2006, p. 6.
1
464, 3340, 3109 (N–H), 1647, 1591 (C=N, С=С). Н
i
(
3
3
3
2
2
5
3
1
0. El-Sayed, H. A., J. Iran. Chem. Soc., 2014, vol. 11,
5
2
6
3
13
no. 1, p. 131. doi 10.1007/s13738-013-0283-8
1
1. Eurtivong, C., Semenov, V., Semenova, M., Konyush-
kin, L., Atamanenko, O., Reynisson, J., and Kiselyov, A.,
Bioorg. Med. Chem., 2017, vol. 25, no. 2, p. 658. doi
10.1016/j.bmc.2016.11.041
C
3 3
3a
3 3
2
5
8.3 (C ), 117.9* (C ), 120.9 (C ), 125.7* (CH, Ar),
26.9* (CH, Ar), 128.7* (CH, Ar), 128.8* (CH, Ar),
29.2* (CH, Ar), 134.8 (C , Ar), 136.7 (C , Ar), 145.5
C ), 147.4 (C ), 152.5 (C-Bu-t), 155.6 (C ), 159.7
C ), 166.9 (CONH ). N NMR spectrum, δ , ppm:
1
1
3
4
6
12. Allais, C., Grassot, J.M., Rodriguez, J., and Con-
(
(
6
7
a
15
stantieux, T., Chem. Rev., 2014, vol. 114, no. 21,
2 N
p. 10829. doi
10.1021/cr500099b
9.9 (NH ), 105.9 (CONH ), 287.1 (N ). Mass
2 2 Py
1
1
1
3. Sharanin, Yu.A., Rodinovskaya, L.A., Shestopalov, A.M.,
Promonenkov, V.K., and Litvinov, V.P., J. Org. Chem.
USSR, 1986, vol. 22, no. 1, p. 223.
4. Chen, Z., Cirillo, P.F., Disalvo, D., Liu, W., Marshall, D.R.,
Wu, L., and Young, E.R.R., WO Patent 2005056562,
+
spectrum (HRMS ESI-TOF), m/z: 424.1449 [M + Na]
(
calculated for C H N NaOS: 424.1454).
2
4
23
3
FUNDING
2
005.
This work was financially supported by the Ministry
of Education and Science of the Russian Federation
project MON no. 4.5547.2017/8.9, V.V. Dotsenko and
5. Cywin, C.L., Chen, Z., Emeigh, J., Fleck, R.W., Hao, M.,
Hickey, E., Liu, W., Marshall, D.R., Morwick, T., Nemoto, P.,
Sorcek, R.J., Sun, S., and Wu, J. WO Patent
2003103661, 2003.
6. Liu, W., Hickey, E.R., Cywin, C.L., Fleck, R.W.,
Spero, D.M., Morwick, T.M., and Proudfoot, J.R., WO
Patent 2005035537, 2005.
7. Obydennov, K.L., Klimareva, E.L., Kosterina, M.F.,
Slepukhin, P.A., and Morzherin, Yu.Yu., Tetrahedron
Lett., 2013, vol. 54, no. 36, p. 4876. doi 10.1016/
j.tetlet.2013.06.127
(
I.V. Aksenova; project MON no. 4.1196.2017/4.6,
N.A. Aksenov).
1
1
CONFLICT OF INTEREST
No conflict of interest was declared by the authors.
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 5 2019