950
T. M. Abu Elmaati
Vol. 41
to afford compound 9 as yellow crystals, mp> 300 °C; yield 50 %;
Compound 16 was obtained as brown crystals from dioxan, mp
IR: ν
3448 (NH); 2221 (CN), 1710 (CO-ester) and 1660 (CO-
275 °C; yield 63 %; IR: ν
3548 (NH); 1700, 1685 (CO-
max
max
1
2
1
2
amide); H-NMR ([ H ] DMSO): δ 2.30 (s, 3 H, CH ); 3.81 (s, 3
amide); H-NMR ([ H ] DMSO): δ 2.22 (s, 3 H, CH ); 3.41 (s,
6
H
3
6 H 3
H, OCH ), 4.76 (s, 1H, CH), 6.68 (s, 1H, C H), 7.25-7.60 (m, 5
6 H, 2 NCH ), 7.00-7.50 (m, 5 H, arom. H), 8.20 (s, 1H, CH),
9.32 (br s, 1 H, NH); (m/z) 411.
3
(5)
3
13
H, arom. H), 8.2 (s, 1H, CH), 9.40 (br s, 1 H, NH); C-NMR
2
([ H ] DMSO): δ 166.2(CO), 138.2, 128.7, 128.7, 124.1, 120.4,
Anal. Calcd. for C H N O S (411.52); C, 61.29; H, 6.12; N,
6
C
21 25
5 2
120.4 (aromatic-carbons), 143.1, 113.7 (vinyl-carbons), 52.3
(OCH ), 11.6 (CH ), 119.2 (CN); MS (m/z) 381.
17.02 %. Found: C, 61.23; H, 6.00; N, 17.12.
3
3
4-Methyl-3-pyrrol-1-yl-4,7-dihydrothieno[2,3-b]pyridine-2,5-
dicarboxylicacid-2-dimethylamide-5-phenylamide (17).
Anal. Calcd. For C H N O S (381.41): C, 59.83; H, 3.96; N,
19 15
3 4
11.02 %. Found: C, 60.00; H, 3.91; N, 11.12.
Compound 17 was obtained as yellow crystals from
Reaction of Compound 3 with N,N-Dimethylchloroacetamide:
Formation of Compound 11.
EtOH/DMF, mp > 300 °C; yield 60 %; IR: ν
3548 (NH);
max:
1
2
1700, 1685 (CO-amide); H-NMR ([ H ] DMSO): δ 2.22 (s, 3
6
H
To a solution of compound 3 (2.65 g, 0.01 mol) in methanol
(30 ml) containing sodium methoxide was added 0.01 mol of
compound 10. The mixture was heated under reflux for 1 h. After
cooling, the reaction mixture was poured into ice-cold water. The
solid product deposited was collected by filtration and crystal-
lized from ethanol to afford compound 11 as yellow crystals, mp
H, CH ); 3.41 (s, 6 H, 2 N-CH ), 7.00-7.50 (m, 5 H, arom. H),
8.20 (s, 1H, CH), 9.32 (br s, 1 H, NH); MS (m/z) 406.
3
3
Anal. Calcd. for C H N O S (406.50): C, 65.00; H, 5.46; N,
22 22
4 2
13.78 %. Found: C, 65.13; H, 5.33; N, 13.72.
REFERENCES AND NOTES
220 °C; yield 60 %; IR: ν
(CO-amide); H-NMR ([ H ] DMSO): δ 2.30 (s, 3 H, CH );
3448, 3330 (NH , NH); 1700, 1680
max
2
1
2
6
H
3
[1] E. A. Hafez, M. H. Elnagdi, A. A. Elagamey and F. M. A.
El-Taweel, Heterocycles, 26, 903 (1987).
[2] F. A. Abu- Shanab, B. Wakfield, F. Al-Omran, M. M.
Abdel Khalek and M. H. Elnagdi, J. Chem. Res., (S) 488, (M) 2924
(1995).
3.51 (s, 6 H, 2 N-CH ), 7.00-7.50 (m, 5 H, arom. H), 8.19 (s, 1H,
3
CH), 9.30 (br s, 1 H, NH); MS (m/z) 356.44.
Anal. Calcd. for C H N O S (356.44): C, 60.65; H, 5.66; N,
18 20
4 2
15.72 %. Found: C, 60.50; H, 5.61; N, 15.62.
General Procedure for the Reaction of Compound 11 with
Compounds 12, 13 and 14: Formation of Compounds 15, 16 and
17.
[3] H. Al-Awadhi, F. Al-Omran, M. H. Elnagdi, L. C. Infants,
C. Foces-Foces, N. Jagerovic and J. Elguero. Tetrahedron, 51, 12745
(1995).
[4] A. H. H. Elghandour, A. M. Hussein, M. H. Elnagdi, A. A.
Harb and S. A. Metwally J. Prakt. Chem., 334, 723 (1992).
[5] M. H. Mohamed, M. M. Abdel-Khalik and M. H. Elnagdi,
J. Heterocyclic Chem., 38, 685 (2001).
[6] S. Z. A. Swellim, F. M.A. El-Taweel and A. A. Elagamey,
Bull. Soc. Chim. Fr., 133, 229 (1996).
[7] A. M. Hussein, A. A. Atalla, A. M. Kamal El-Dean,
Pharmazie, 50, 788 (1995).
[8] T. M. Abu Elmaati and S. B. Said, N. S. Abu Elenein, M.
A. Sofan and M. N. Khodeir, Polish J. Chem., 76, 945 (2002).
[9] T. M. Abu Elmaati and F. M. A. El-Taweel, J. Chin. Chem.
Soc., 49, 1045 (2002).
To a solution of compound 11 (3.56 g, 0.01 mol) in POCl (15
3
ml) was added 0.01 mol of, as appropriate, reagents 12, 13 and 14.
The reaction mixture was heated under reflux for 2 h. After cool-
ing, the reaction mixture was poured into ice-cold water and then
neutralized with ammonia solution. The precipitate formed was
collected by filtration and crystallized from the proper solvent.
4-Methyl-3-[morphlino-4-ylmethylene)-amino]-4,7-dihydroth-
ieno[2,3-b]pyridine-2,5-dicarboxylic acid 2-dimethylamide-5-
phenylamide (15).
Compound 15 was obtained as yellow crystals from
[10] J. Becher and C. C. Stiden, Sulfur Reports, 8, 105 (1988).
[11] R. Lie and K. Undheim, Acta Chem. Scand., 27, 1756
(1973).
EtOH/DMF, mp 280 °C; yield 65 %; IR: ν
3548 (NH); 1700,
max:
1
2
1685 (CO-amide); H-NMR ([ H ] DMSO): δ 2.22 (s, 3 H,
6
H
CH ); 3.41 (s, 6 H, 2 NCH ), 7.00-7.50 (m, 5 H, arom. H), 8.20
3
3
[12] V. A.
Bakulev, V. S. Berseneva, N. P. Belskaia, Y. Y.
(s, 1H, CH), 9.32 (br s, 1 H, NH); MS (m/z) 453.
Anal. Calcd. For C H N O S (453.56): C, 60.91; H, 6.00;
Morzherin, A. Zaitsev, W. Dehaen, I Luyten and S. Tuppet, Org
Biomol. Chem., 1, 134 (2003).
[13] G. Wagner, H. Vieweg, S. Leistner, N. Bohm, U. Krasselt,
V. Hanfeld, J. Prantz and R. Grupe, Die Pharmazie, 45, 102 (1990).
[14] G. Wagner, H. Vieweg and S. Leistner, Die Pharmazie, 48,
464 (1993).
23 27
5 3
N, 15.44 %. Found: C, 60.83; H, 5.98; N, 15.42.
3-(Dimethylaminomethyleneamino)-4-methyl-4,7-dihydro-
thieno[2,3-b]pyridine-2,5-dicarboxy-2-dimethylamide-5-phenyl-
amide (16).