DYACHENKO
1580
3339, 3211, 3190 [ν(NH, NH2)], 1684 [ν(C=O)], 1639
[δ(NH2)]. H NMR spectrum, δ, ppm: 2.28 s (3H,
[M + 2]+, 354 (8) [M + 1]+, 353 (32) [M]+, 219 (100)
[M – АсС6H4NH]+, 191 (16) [M – АсС6H4NHСО]+,
169 (12), 147 (8), 120 (7), 73 (9), 65 (5), 44 (11)
[C=S]+. Found, %: C 64.42; H 5.30; N 11.77.
C19H19N3O2S. Calculated, %: C64.57; H5.42; N11.89.
M 353.446.
1
Me), 2.54 s (3H, Me), 2.69 s (3H, Me), 6.90 br.s
(2H, NH2), 7.35 d (2Harom, J 8.8 Hz), 7.68 d (2Harom, J
8.8 Hz), 9.21 br.s (1H, NH). Mass spectrum, m/z
(Irel, %): 392 (3) [M + 2]+, 391 (19) [M + 1]+, 390 (4)
[M]+, 389 (20) [M – 1]+, 219 (100) [M – BrC6H4NH2]+,
205 (6), 191 (14), 171 (3) [M – BrC6H4NH2]+, 155
(7), 91 (6) [C6H4NH]+, 65 (4), 45 (3) [CHS]+, 44 (6)
[S=S]+. Found, %: C 52.18; H 4.01; N 10.62.
C17H16BrN3OS. Calculated, %: C 52.32; H 4.13; N
10.77. M 390.305.
Octyl 3-amino-4,5,6-trimethylthieno[2,3-b]pyri-
dine-2-carboxylate (5g). Yield 2.4 g (68%), colorless
powder, mp 121–123°C (EtOH). IR spectrum, cm–1:
3333, 3280, 3008 [ν(NH2)], 1714 [ν(C=O)], 1641
1
[δ(NH2)]. H NMR spectrum, δ, ppm: 0.88 t (3H, Me,
J 6.2 Hz), 1.26-1.49 m (10H, 5СH2), 1.67–1.78 m (2H,
СH2), 2.28 s (3H, Me), 2.54 s (3H, Me), 2.69 s (3H,
Me), 4.20 t (2H, ОСH2, J 5.8 Hz), 6.63 br.s (2H, NH2).
Mass spectrum, m/z (Irel, %): 350 (5) [M + 2]+, 349
(18) [M + 1]+, 348 (89) [M]+, 334 (10), 236 (48) [M –
NH3 – Me(СH2)7О]+, 218 (100) [M – Me(СH2)7ОH]+,
204 (18), 190 (26), 149 (13), 77 (6), 55 (12), 41 (28).
Found, %: C 65.33; H 7.96; N 7.91. C19H28N2O2S.
Calculated, %: C 65.48; H 8.10; N 8.04. M 348.511.
3-Amino-4,5,6-trimethylthieno[2,3-b]pyridine-2-
carboxamide (5d). Yield 1.8 g (77%), colorless powder,
mp 283–285°C (BuOH), sublimates at 200°C. IR spec-
trum, cm–1: 3360, 3295, 3004 [ν(NH2)], 1670 [ν(C=O)],
1631 [δ(NH2)]. 1H NMR spectrum, δ, ppm: 2.23 s (3H,
Me), 2.52 s (3H, Me), 2.64 s (3H, Me), 6.86 br.s (2H,
NH2), 7.07 br.s (2H, СОNH2). Mass spectrum, m/z
(Irel, %): 237 (5) [M + 2]+, 236 (13) [M + 1]+, 235 (100)
[M]+, 218 (85) [M – NH3]+, 204 (9), 190 (63) [M – NH3 –
СО]+, 175 (13), 163 (17), 146 (12), 131 (9), 118 (10),
104 (7), 91 (7), 77 (14), 65 (6), 53 (8), 45 (13) [CHS]+,
44 (19) [S=S]+, 39 (12). Found, %: C 52.00; H 5.40; N
17.71. C11H13N3OS. Calculated, %: C 52.16; H 5.57; N
17.86. M 235.310.
Nonyl 3-amino-4,5,6-trimethylthieno[2,3-b]pyri-
dine-2-carboxylate (5h). Yield 2.5 g (70%), colorless
powder, mp 113–115°C (MeOH). IR spectrum, cm–1:
3342, 3277, 3118 [ν(NH2)], 1706 [ν(C=O)], 1639
1
[δ(NH2)]. H NMR spectrum, δ, ppm: 0.87 t (3H, Me,
J 6.4 Hz), 1.23-1.46 m (12H, 6СH2), 1.66-1.78 m (2H,
СH2), 2.29 s (3H, Me), 2.55 s (3H, Me), 2.68 s (3H,
Me), 4.21 t (2H, ОСH2, J 5.1Hz), 6.53 br.s (2H, NH2).
Mass spectrum, m/z (Irel, %): 364 (5) [M + 2]+, 363
(23) [M + 1]+, 362 (100) [M]+, 348 (12), 236 (49) [M –
Me(СH2)7СH]+, 219 (36) [M – Me(СH2)8О]+, 218 (91)
[M – Me(СH2)8ОH]+, 204 (13), 190 (21), 55 (11), 43
(20), 41 (21). Found, %: C 66.18; H 8.22; N 7.60.
C20H30N2O2S. Calculated, %: C 66.26; H 8.34; N 7.73.
M 362.538.
3-Amino-N-phenyl-4,5,6-trimethylthieno[2,3-b]-
pyridine-2-carboxamide (5e). Yield 2.5 g (81%),
colorless powder, mp 275–277°C (BuOH). IR spectrum,
cm–1: 3337, 3270, 2980 [ν(NH, NH2)], 1668 [ν(C=O)],
1642 [δ(NH2)]. 1H NMR spectrum, δ, ppm: 2.27 s (3H,
Me), 2.55 s (3H, Me), 2.70 s (3H, Me), 6.88 br.s (2H,
NH2), 7.04 t (1H, Ph, J 7.6 Hz), 7.28 t (2H, Ph, J
7.6 Hz), 7.67 d (2H, Ph, J 7.7 Hz), 9.26 br.s (1H, NH).
Mass spectrum, m/z (Irel, %): 313 (3) [M + 2]+, 312 (7)
[M + 1]+, 311 (38) [M]+, 219 (100) [M – PhNH2]+, 205
(7), 191 (16), 147 (8), 93 (11) [PhNH3]+, 77 (8) [Ph]+,
65 (6), 45 (4) [CHS]+, 44 (8) [S=S]+. Found, %: C
65.42; H 5.41; N 13.33. C17H17N3OS. Calculated, %: C
65.57; H 5.50; N 13.49 M 311.408.
(3-Amino-4,5,6-trimethylthieno[2,3-b]pyridin-2-
yl)(biphenyl-4-yl)methanone (5i). Yield 3.2 g (85%),
yellow powder, mp 259–261°C (АсOH). IR spectrum,
cm–1: 3321, 3295, 3204 [ν(NH2)], 1699 [ν(C=O)],
1636 [δ(NH2)]. 1H NMR spectrum, δ, ppm: 2.32 s (3H,
Me), 2.56 s (3H, Me), 2.78 s (3H, Me), 7.47 br.s (2H,
NH2), 7.61-7.78 m (5Harom), 7.86 d (2Harom, J 7.7 Hz),
8.06 d (2Harom, J 7.1 Hz). Mass spectrum, m/z (Irel, %):
374 (4) [M + 2]+, 373 (16) [M + 1]+, 372 (57)
[M]+, 371 (100) [M – 1]+, 355 (61) [M – NH3]+, 295
(4), 181 (9), 172 (8), 152 (39) [PhC6H3]+, 73 (8), 44
(15) [C=S]+. Found, %: C 74.06; H 5.32; N 7.40.
C23H20N2OS. Calculated, %: C 74.16; H 5.41; N 7.52.
M 372.491.
3-Amino-N-(4-acetylphenyl)-4,5,6-trimethyl-
thieno[2,3-b]pyridine-2-carboxamide (5f). Yield 2.6 g
(75%), yellow powder, mp 265–267°C (BuOH). IR
spectrum, cm–1: 3319, 3280, 3004 [ν(NH, NH2)], 1670
1
[ν(C=O)], 1633 [δ(NH2)]. H NMR spectrum, δ, ppm:
2.31 s (3H, Me), 2.43 s (3H, Me), 2.54 s (3H, Me),
2.71 s (3H, MeСО), 6.96 br.s (2H, NH2), 7.85 d
(2Harom, J 7.2 Hz), 7.94 d (2Harom, J 7.2 Hz), 9.34 br.s
(1H, NH). Mass spectrum, m/z (Irel, %): 355 (2)
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 11 2015