Chemistry & Biodiversity
10.1002/cbdv.201800550
Chem. Biodiversity
°
-1
1
Yield: 82%. Off white solid. M.p. 159-161 C. FT-IR (KBr cm ): 3275 (N-H), 1625 (C=O), 1537 (C=C), 1507 (C=C), 1211 (C-F), 831 (p-disubstituted benzene). H
NMR (400 MHz, DMSO-d
6
, δ in ppm): 10.11(s, 1H, N-H), 7.73-7.69(m, 2H, Ar-H), 7.65(s, 1H, thiophene ring-H), 7.36-7.32(m, 4H, Ar-H), 7.29-7.25(m, 1H, Ar-H),
.20-7.15(m, 2H, Ar-H), 3.69(s, 2H, N-CH ), 3.49(s, 2H, N-CH ), 2.84 (t, 2H, N-CH ), 2.74(t, 2H, Ar-CH , δ in ppm: 159.8 (C=C-F),
). 13C NMR (400 MHz, DMSO-d
59.8 (O=C-NH), 139.6 (C=C), 138.3, 136.4, 135.1, 128.2, 127.3, 121.9, 121.8, 115.3, 115.0 (C=C), 60.9 (N-CH ), 52.0 (N-CH ), 49.4 (N-CH ), 25.2 (Ar-CH ). HR-
7
1
2
2
2
2
6
2
2
2
2
+
+
MS: 367.1278 ([M + H] , C21H20FN2OS ; Calc. 367.1275).
-(2-fluorobenzyl)-N-(4-fluorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide (9)
5
°
-1
Yield: 79%. Brown solid. M.p. 176-179 C. IR (KBr cm ): 3269 (N-H), 1628 (C=O), 1538 (C=C), 1507 (C=C), 1319 (C-F), 1211 (C-F), 1153 (C-N), 831 (p-
1
disubstituted benzene), 757. H NMR (400 MHz, DMSO-d
6
, δ in ppm): 10.13(s, 1H, N-H), 7.73-7.68(m, 3H, Ar-H), 7.50-7.46(m, 1H, Ar-H), 7.35-7.32(m, 1H, Ar-
H), 7.22-7.16(m, 4H, Ar-H), 3.75(s, 2H, N-CH
2
), 3.54(s, 2H, N-CH
2
), 2.85(t, 2H, N-CH
2
), 2.77 (d, 2H, Ar-CH
2
). 13C NMR (400 MHz, DMSO-d
, δ in ppm: 162.0
6
(O=C-NH), 159.8 (C=C), 159.6, 159.4, 157.0, 139.5, 136.5, 135.2, 134.8, 131.4, 131.3, 129.2, 127.3, 124.7, 124.6, 124.2, 121.9, 121.8, 115.3, 115.1(C=C), 53.5
+
+
(
N-CH
2
), 51.8 (N-CH
2
), 49.4 (N-CH
2
), 25.3 (Ar-CH
2
). HR-MS: 385.1182 ([M + H] , C21H19F2N2OS ; Calc. 385.1181).
N-(4-fluorophenyl)-5-(4-nitrophenethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide(10)
°
-1
Yield: 86%. White solid. M.p. 145-148 C. IR (KBr cm ): 3294 (N-H), 1636 (C=O), 1509 (C=C), 1346 (N=O), 1210 (C-F), 1112 (C-N), 839 (p-disubstituted
1
benzene), 746, 700. H NMR (400 MHz, DMSO-d
6
, δ in ppm): 10.17(s, 1H, N-H), 8.17-8.15(m, 2H, Ar-H), 7.73-7.68(m, 3H, Ar-H), 7.58-7.56(m, 2H, Ar-H), 7.20-
), 3.34(s, 1H, N-CH ), 3.01-2.98(m, 2H, N-CH ), 2.83(s, 5H, N-CH , δ in ppm: 159.8 (O=C-
). 13C NMR (400 MHz, DMSO-d
NH), 159.4 (C=C), 157.0, 148.9, 145.9, 139.5, 136.5, 135.1, 134.6, 129, 127.3, 123.2, 121, 121.9, 115.2, 115.0 (C=C), 57.4 (N-CH ), 51.8 (N-CH ), 49.5 (N-CH ),
7
.16(m, 2H, Ar-H), 3.58(s, 2H, N-CH
2
2
2
2
6
2
2
2
+
+
32.4 (Ar-CH
2
), 25.1 (Ar-CH ). HR-MS: 426.1285 ([M + H] , C22H21FN3O3S ; Calc. 426.1282). Purity by HPLC: 96.09%.
2
5
-(3,4-difluorobenzoyl)-N-(4-fluorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide(11)
°
-1
Yield: 82%. Off white solid. M.p. 238-241 C. IR (KBr cm ): 3247 (N-H), 1640 (C=O), 1598 (C=O), 1509 (C=C), 1441 (C=C), 1283 (C-F), 1214 (C-F), 893 (p-
1
disubstituted benzene), 820, 748. H NMR (400 MHz, DMSO-d
6
, δ in ppm): 10.25(brs, 1H, N-H), 7.82-7.64(m, 3H, Ar-H), 7.64-7.51(m, 2H, Ar-H), 7.35(s, 1H,
), 3.72(d, 2H, Ar-CH ), 2.94(s, 2H, N-CH , δ in ppm: 167.7(O=C-F),
). 13C NMR (400 MHz, DMSO-d
59.7(O=C-F), 157.1(O=C-NH), 150.4(C=C), 139.2, 137.3, 135.1, 133.2, 132.6, 127.1, 124.1, 122.0, 116.7(C=C), 44.4(N-CH ), 25.3(N-CH ). HR-MS: 417.0855
thiophene ring-H), 7.20-7.16(m, 2H, Ar-H), 4.61(d, 2H, N-CH
2
2
2
6
1
2
2
+
+
(
[M + H] , C21H16F3N2O2S ; Calc. 417.0879).Purity by HPLC: 98.36%.
N-(4-fluorophenyl)-5-(furan-2-carbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide(12)
°
-1
Yield: 76%. Off white solid. M.p. 204-207 C. IR (KBr cm ): 3302 (N-H), 1646 (C=O), 1609 (C=O), 1540 (C=C), 1505 (C=C), 1208 (C-F), 823 (p-disubstituted
1
benzene), 740. H NMR (400 MHz, DMSO-d
6
, δ in ppm): 10.22(s, 1H, N-H), 7.89(dd, 1H, Ar-H), 7.77(s, 1H, Ar-H), 7.74-7.70(m, 2H, Ar-H), 7.21-7.16(m, 2H, Ar-
H), 7.09(dd, 1H, Ar-H), 6.67-6.66(m, 1H, furoic ring-H) 4.76(s, 2H, N-CH
2
), 3.96(s, 2H, N-CH
2
), 2.99(s, 2H, Ar-CH
2
). 13C NMR (400 MHz, DMSO-d
, δ in ppm:
6
159.7 (O=C-NH), 159.5 (O=C-NH), 159.0 (C=C), 157.1, 146.9, 145.05, 139.3, 137.3, 135.1, 132.9, 127.1, 122.0, 121.9, 115.8, 115.4, 115.1, 111.4 (C=C), 40.1 (N-
+
+
CH
2
), 39.9 (N-CH
2
), 38.8 (Ar-CH ). HR-MS: 371.0864 ([M + H] , C19H16FN2O3S ; Calc. 371.0860).
2
(
5-benzyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)(piperidin-1-yl)methanone (13)
-1
1
Yield: 71%. Viscous oil. IR (KBr cm ): 2933 (C-H), 2853 (C-H), 1603 (C=O), 1476 (C=C), 1429 (C=C), 1362 (C=C), 1255 (C-N), 988. H NMR (400 MHz, DMSO-d
6
,
δ in ppm): 7.39-7.26(m, 5H, Ar-H), 6.86(s, 1H, thiophene ring-H), 3.71-3.62(m, 6H, N-CH
2
x3), 3.51(t, 2H, Ar-CH
2
), 2.89-2.80(m, 4H, N-CH x2), 1.69-1.59(m,
2
6
H, -CH
0.68(N-CH
2
x3). 13C NMR (126 MHz, CDCl
), 51.82, 49.12, 39.92(N-CH
3
) δ in ppm: 162.74(O=C-NH), 137.09(C=C), 135.89, 133.55, 132.61, 127.60, 127.34, 127.03, 126.23, 125.27(C=C),
+
+
6
2
2
), 25.28(-CH
2
), 24.04, 23.12(-CH ). HR-MS: 341.1688 ([M + H] , C20H25N2OS ; Calc. 341.1682).
2
(
5-(2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl) (piperidin-1-yl) methanone (14)
-1
1
Yield: 74%. Oily liquid. IR (KBr cm ): 2932 (C-H), 2871 (C-H), 1619 (C=O), 1594 (C=C), 1418 (C=C), 1381 (C-F), 1261 (C-N), 736 (o-disubstituted benzene). H
NMR (400 MHz, DMSO-d , δ in ppm): 7.47-7.33(m, 1H, Ar-H), 7.22-7.17(m, 1H, Ar-H), 7.08-7.04(m, 1H, Ar-H), 6.99-6.97(m, 1H, AR-H), 6.67(s, 1H, Thiazole
ring-H), 3.72-3.50(m, 8H, N-CH
5-(4-nitrophenethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)(piperidin-1-yl)methanone (15)
6
+
+
2
x4), 2.83-2.78(m, 3H), 1.62-1.49(m, 7H) -CH x5. HR-MS: 359.1592 ([M + H] , C20H24FN2OS ; Calc. 359.1588).
2
(
°
-1
Yield: 74%. Yellow solid. M.p. 140-143 C. IR (KBr cm ): 2932 (C-H), 1599 (C=O), 1511 (C=C), 1477 (C=C), 1424 (C=C), 1341 (N=O), 1263 (C-N), 852 (p-
1
disubstituted benzene). H NMR (400 MHz, DMSO-d
6
, δ in ppm): 8.16(d, 2H, Ar-H), 7.39(d, 2H, Ar-H), 6.92(s, 1H, thiophene ring-H), 3.66-3.61(m, 6H, N-CH
x3). 13C NMR (400 MHz, DMSO-d
, δ in ppm: 167.6(O=C-NH), 149.1(C=C-NO ), 145.8(C=C), 136.5, 134.3,
), 52.0, 49.7(Ar-CH -N), 45.8, 32.5(-CH ), 25.7, 24.9, 24.0(-CH
2
x3), 3.01-2.82(m, 8H, -CH
2
x4), 1.71-1.61(m, 6H, -CH
33.9, 129.9, 126, 123.2(C=C), 57.6(N-CH
00.1689).
2
6
2
+
+
1
4
2
2
2
2
). HR-MS: 400.1688 ([M + H] , C21H26N3O3S ; Calc.
(
5-(3,4-difluorobenzoyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)(piperidin-1-yl) methanone (16)
°
-1
Yield: 81%. White solid. M.p: 96-98 C. IR (KBr cm ): 2933 (C-H), 2860 (C-H), 1604 (C=O), 1512 (C=C), 1432 (C=C), 1268 (C-F), 1190 (C-F), 1107 (C-N), 838 (p-
1
disubstituted benzene), 780 (o-disubstituted benzene). H NMR (400 MHz, DMSO-d
6
, δ in ppm): 7.34-7.30(m, 1H, Ar-H), 7.25-7.20(m, 2H, Ar-H), 6.91(s, 1H,
thiophene ring-H), 4.75-4.50(m, 2H, N-CH
2
), 4.03-3.5(m, 6H, N-CH
2
x3), 2.95-2.67(m, 2H, Ar-CH ), 1.70-1.62(m, 6H, -CH
2
2
x3). HR-MS: 391.1291 ([M + H]+,
+
C20H21F2N2O2S ; Calc. 391.1286).
(
5-(furan-2-carbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)(piperidin-1-yl) methanone (17)
8
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