W.-J. Zhou, L. Zhang, W. Xiao, H.-J. Chen, W.-N. Wu, and G.-P. Ouyang
Vol 000
NH), 2.21 (s, 3H, CH3), 2.56 (t, J= 4.85 Hz, 4H, piperazine-H),
2.80 (d, J=4.6Hz, 3H, CH3), 3.00(t, J=4.87Hz, 4H,
piperazine-H), 3. 12 (s, 2H, CH2), 7.26 (s, 1H, Ar–H), 7.27
(s, 1H, Ar–H), 9.78 (s, 1H, NH); 13C NMR (CDCl3,
125MHz): δ 170.1, 167.7, 138.0, 133.9, 132.2, 131.9, 131.6,
125.0, 62.5, 55.0, 46.2, 26.5, 19.0; MS (ESI) m/z: 325.1 ([M
+H]+); Anal. Calcd for C15H21ClN4O2: C 55.47, H 6.52 N
17.25; found C 55.83, H 6.71 N 17.38.
121.4, 48.7, 29.8, 16.4; MS (ESI) m/z: 307.1 ([M+H]+);
Anal. Calcd for C14H15ClN4O2: C 54.82, H 4.93, N
18.26; found C 54.47, H 4.67, N 18.52.
5-Chloro-N,3-dimethyl-2-(2-(pyrrolidin-1-yl)acetamido)
benzamide (6g). White solid; mp 123–125°C; yield 81%;
IR (KBr): v 3423, 2966, 2796, 1678, 1603, 1460, 1339,
1
878, 797, 746 cmÀ1; H NMR (DMSO-d6, 500MHz): δ
1.67–1.69 (m, 4H, 3,4-dipyrrole-H), 2.47 (s, 3H, CH3),
2.53 (t, J = 5.75Hz, 4H, 2,5-dipyrrole-H), 2.62 (s, 3H,
CH3), 3.73 (s, 2H, CH2), 7.68 (s, 1H, Ar–H), 7.85 (s, 1H,
Ar–H); 13C NMR (DMSO-d6, 125MHz): δ 161.4, 154.9,
144.6, 138.8, 134.7, 130.9, 123.1, 121.7, 60.3, 53.8,
30.7, 23.8, 17.2; MS (ESI) m/z: 310.2 ([M+H]+); Anal.
Calcd for C15H20ClN3O2: C 58.16, H 6.51, N 13.56;
found C 58.50, H 6.73, N 13.94.
5-Chloro-2-(2-(4-methylpiperazin-1-yl)acetamido)-N,3-dimethyl
benzamide (6c). Yellow solid; mp 136–138°C; yield 83%;
IR (KBr): v 3329, 2942, 1692, 1643, 1484, 1331, 1292,
1
1167, 1011, 878, 839, 770, 743 cmÀ1; H NMR (CDCl3,
500 MHz):
δ
2.26 (s, 3H, CH3), 2.39 (s, 3H,
methylpiperazine-H), 2.56 (s, 8H, methylpiperazine-H), 3.
60 (s, 2H, CH2), 3.72 (s, 3H, CH3), 7.46 (s, 1H, Ar–H),
8.02 (s, 1H, Ar–H); 13C NMR (CDCl3, 125MHz): δ 162.2,
152.2, 150.1, 144.1, 138.3, 134.7, 132.0, 123.6, 121.7,
62.9, 55.1, 53.1, 46.1, 30.6, 17.2; MS (ESI) m/z: 339.1 ([M
+H]+); Anal. Calcd for C16H23ClN4O2: C 56.72, H 6.84, N
16.54; found C 56.95, H 7.13, N 16.90.
5-Chloro-2-(2-(cyclohexylamino)acetamido)-N,3-dimethyl
benzamide (6h). White solid; mp 72–73°C; yield 78%; IR
(KBr): v 3433, 2924, 2851, 1669, 1602, 1465, 1340, 873, 794,
1
759 cmÀ1; H NMR (DMSO-d6, 500MHz): δ 1.09–1.89
(m, 6H, 3,4,5-tr-cyclohexane-H), 1.52 (s, 1H, NH), 1.65–1.86
(m, 4H, 2,6-dicyclohexane-H), 2.53 (s, 3H, CH3), 3.72–3.75
(m, 1H, 1-cyclohexane-H), 3.85 (s, 2H, CH2), 7.68 (s, 1H,
Ar–H), 7.83 (s, 1H, Ar–H); 13C NMR (DMSO-d6,
125 MHz): δ 166.1, 161.5, 149.2, 143.2, 139.4, 135.3,
127.8, 126.2, 61.2, 54.8, 45.0, 34.6, 31.1, 29.7, 21.9;
MS (ESI) m/z: 338.3 ([M+H]+); Anal. Calcd for
C17H24ClN3O2: C 60.44, H 7.16, N 12.44; found C 60.60,
H 7.38, N 12.61.
5-Chloro-2-(2-(piperidin-1-yl)acetamido)-N,3-dimethylbenzamide
(6d). White solid; mp 208–210°C; yield 85%; IR (KBr): v
3305, 2934, 1667, 1556, 1486, 1316, 1159, 1127, 878, 797,
1
745cmÀ1; H NMR (DMSO-d6, 500MHz): δ 1.36–1.57
(m, 6H, 3,4,5-tr-piperidine-H), 2.11 (s, 3H, CH3), 2.38
(d, J=5.72Hz, 4H, 2,6-dipiperidine-H), 2.66 (s, 3H, CH3),
2.95 (s, 2H, CH2), 7.29 (s, 1H, Ar–H), 7.39 (s, 1H, Ar–H),
8.41 (s, 1H, NH), 9.72 (s, 1H, NH); 13C NMR (DMSO-d6,
125 MHz): δ 169.1, 167.2, 138.4, 134.7, 133.2, 131.8,
130.1, 125.3, 63.0, 55.0, 26.5, 26.1, 23.9, 19.0; MS
(ESI) m/z: 324.1 ([M+H]+); Anal. Calcd for C16H22ClN3O2:
C 59.35, H 6.85, N 12.98; found C 59.47, H 7.11, N
13.32.
5-Chloro-2-(2-(cyclopentylamino)acetamido)-N,3-dimethyl
benzamide (6i). White solid; mp 79–81°C; yield 85%; IR
(KBr): v 3425, 2958, 1680, 1664, 1601, 1464, 1341, 874,
797, 741, 713cmÀ1 1H NMR (DMSO-d6, 500 MHz):
;
δ 1.33–1.44 (m, 4H, 3,4-dicyclopentane-H), 1.60–1.70
(m, 4H, 2,5-dicyclopentane-H), 2.32 (s, 1H, NH), 2.46
(s, 3H, CH3), 3.09–3.93 (m, 1H, 1-cyclopentane-H), 3.54
(s, 3H, CH3), 3,82 (s, 3H, CH2), 7.68 (s, 1H, Ar–H), 7.83
(s, 1H, Ar–H); 13C NMR (DMSO-d6, 125MHz): δ 161.3,
156.4, 144.5, 138.5, 134.7, 130.6, 123.1, 121.4, 59.7, 51.7,
33.1, 30.0, 24.0, 17.1; MS (ESI) m/z: 325.1 ([M+H]+);
Anal. Calcd for C16H22ClN3O2: C 59.35, H 6.85, N 12.98;
found C 59.09, H 6.66, N 13.15.
5-Chloro-2-(2-(cyclopropylamino)acetamido)-N,3-dimethyl
benzamide (6e). White solid; mp 175–177°C; yield 86%;
IR (KBr): v 3292, 1667, 16,376.6, 1513, 132, 1228, 1207,
1
1010, 871, 725 cmÀ1; H NMR (DMSO-d6, 500 MHz): δ
0.34–0.35 (m, 4H, 2,3-di-cy-H), 2.14 (s, 3H, CH3), 2.18
(s, 1H, NH), 2.71 (s, 3H, CH3), 2.53 (s, 2H, CH2), 7.32
(s, 1H, Ar–H), 7.43 (s, 1H, Ar–H), 8.37 (s, 1H, NH); 13C
NMR (DMSO-d6, 125MHz): δ 171.2, 167.2, 138.4,
135.0, 133.5, 131.7, 130.1, 125.5, 53.0, 31.2, 26.6, 19.0,
6.6; MS (ESI) m/z: 296.1 ([M+H]+); Anal. Calcd for
C14H18ClN3O2: C 56.85, H 6.13, N 14.21; found C
56.59, H 6.42, N 14.54.
5-Chloro-N,3-dimethyl-2-(2-(4-oxopiperidin-1-yl)acetamido)
benzamide (6j). White solid; mp 82–84°C; yield 86%; IR
(KBr): v 3442, 2975, 1682, 1598, 1464, 1338, 1099,
1
900.0, 798, 745, 715 cmÀ1; H NMR (CDCl3, 500 MHz):
2-(2-(1H-imidazol-1-yl)acetamido)-5-chloro-N,3-dimethyl
benzamide (6f). White solid; mp 174–176°C; yield 86%;
IR (KBr): v 3361, 3132, 1684, 1611, 1462, 1331,1244,
δ 1.26 (t, J = 5.62 Hz, 4H, 3,5-dipiperidine-H), 2.57
(s, 3H, CH3), 3.63 (t, J=5.72Hz, 4H, 2,6-dipiperidine-H),
3.70 (s, 3H, CH3), 4.61 (s, 2H, CH2), 7.52 (s, 1H,
Ar–H), 8.08 (s, 1H, Ar–H); 13C NMR (CDCl3,
125MHz): δ 162.0, 151.8, 144.1, 138.5, 134.8, 133.1,
132.4, 123.6, 121.9, 77.4, 72.5, 30.7, 17.2, 15.2; MS
(ESI) m/z: 338.3 ([M+H]+); Anal. Calcd for
C16H20ClN3O3: C 56.89, H 5.97, N 12.44; found C 56.63,
H 5.62, N 12.81.
1077, 882, 796, 739 cmÀ1
;
1H NMR (DMSO-d6,
500MHz): δ 2.19 (s, 3H, CH3), 2.52 (s, 3H, CH3), 5.49
(s, 2H, CH2), 6.93 (s, 1H, 2-imidazole-H), 7.16 (s, 1H,
Ar–H), 7.63 (d, J= 8.0 Hz, 2H, 4,5-imidazole-H), 7.83
(s, 1H, Ar–H); 13C NMR (DMSO-d6, 125MHz): δ 161.0,
153.3, 144.2, 139.1, 138.6, 134.8, 131.0, 128.4, 123.1,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet