ACS Combinatorial Science
RESEARCH ARTICLE
and 1355 (NO2), 1324 and 1143 (SO2); 1H NMR (400.1 MHz,
DMSO-d6) δH 2.17 (3 H, s, CH3), 4.28ꢀ4.71 (4 H, m, CHꢀCH +
SO2CH2), 6.95ꢀ8.07 (16 H, m, arom.), 8.19 (1 H, s, dCHꢀO),
8.87 (1 H, t, 3JHH = 6.7 Hz, CH2NH), 10.25 and 10.41 (2 H, 2 s, 2
NH); 13C NMR (100.6 MHz, DMSO-d6) δC 176.7, 172.4, 170.4,
167.1, 166.3, 156.9, 156.8, 156.0, 145.6, 135.9, 135.7, 135.6,
135.2, 132.3, 130.7, 130.5, 129.7, 129.5, 126.8, 126.4, 126.3,
126.2, 126.1, 126.0, 124.5, 122.4, 119.7, 61.7, 55.2, 39.3, 37.7,
22.3; Anal. Calcd for C34H27N5O11S (713.67) C 57.22, H 3.81,
N 9.81%; Found C 57.37, H 3.80; N 9.77%.
CH3), 2.36ꢀ2.48 (7 H, m, 2 CH2CH3 + CH3), 4.38ꢀ4.48 (4 H,
2 m, CHꢀCH + SO2CH2), 6.91ꢀ7.76 (18 H, m, arom.), 8.21 (1
H, s, dCHꢀO), 8.58 (1 H, t, 3JHH = 5.4 Hz, NH), 9.58 and 9.81
(2 H, 2 br s, 2 NH); 13C NMR (100.6 MHz, DMSO-d6) δC
176.6, 171.3, 166.7, 166.2, 157.7, 154.9, 145.3, 140.4, 140.2,
137.8, 137.2, 136.6, 136.5, 136.0, 130.5, 129.4, 129.2, 129.1,
125.6, 124.3, 120.4, 120.3, 120.2, 119.4, 61.6, 55.5, 43.4, 28.8,
28.7, 22.2, 21.7, 17.0, 16.9; Anal. Calcd for C39H39N3O7S
(693.80) C 67.51, H, 5.67, N 6.06%; Found C 67.70, H 5.65;
N 6.02%.
N2-Cyclohexyl-2-(6-methyl-4-oxo-4H-chromen-3-yl)-N1,N1-
bis(4-methylphenyl)ethane-1,1,2-tricarboxamide (5{2,1,2}):
White powder (0.255 g, 88%); mp 294ꢀ296 °C; Rf (70% n-
hexane/EtOAc) 0.74; IR (KBr) (νmax, cmꢀ1) 3291 (NꢀH),
N2-Cyclohexyl-N1,N1-bis(4-ethylphenyl)-2-(6-methyl-4-oxo-
4H-chromen-3-yl)ethane-1,1,2-tricarboxamide (5{2,1,6}):
White powder (0.264 g, 87%); mp 270ꢀ272 °C; Rf (30% n-
hexane/EtOAc) 0.83; IR (KBr) (νmax, cmꢀ1) 3314 (NꢀH),
1
1
1677 and 1646 (CdO), 1600 (CdC); H NMR (400.1 MHz,
1675 and 1652 (CdO), 1609 (CdC); H NMR (400.1 MHz,
DMSO-d6) δH 0.87ꢀ1.58 (10 H, m, 5 CH2), 2.12, 2.20, and 2.38
CDCl3) δH 1.02ꢀ2.16 (10, m, 5 CH2), 1.11 (6 H, t, 2 CH2CH3),
(9 H, 3 s, 3 Me), 3.34ꢀ3.42 (1 H, m, NCH), 4.39 and 4.46 (2 H,
2.43ꢀ2.52 (4 H, m, 2 CH2CH3), 3.57 (1 H, s, NCH), 5.19 and
3
3
AB-system, JHH = 11.4 Hz, CHꢀCH), 6.95ꢀ7.55 (11 H, m,
5.29 (2 H, AB-system, JHH = 11.3 Hz, CHꢀCH), 6.79ꢀ7.57
arom.), 7.75 (1 H, br s, NH), 8.33 (1 H, s, dCHꢀO), 9.66 and
9.86 (2 H, 2 br s, 2 NH); 13C NMR (100.6 MHz, CDCl3) δC
176.9, 170.1, 167.2, 166.7, 157.4, 154.1, 137.8, 137.1, 136.5,
136.4, 133.9, 133.6, 130.3, 125.5, 124.2, 121.1, 120.4, 119.4, 56.5,
49.0, 43.8, 33.3, 26.4, 25.8, 25.7, 21.8, 21.7, 21.6; Anal. Calcd for
C35H37N3O5 (579.68) C 72.52, H 6.43, N 7.25%; Found C
72.23, H 6.40, N 7.29%.
(12 H, m, dCHꢀO + arom.), 9.03, 10.07, and 10.51 (3 H, 3 br s,
3 NH); 13C NMR (100.6 MHz, CDCl3) δC 178.2, 171.9, 167.6,
167.1, 158.2, 155.5, 140.7, 140.1, 137.2, 137.0, 135.7, 135.6,
128.6, 128.3, 125.9, 124.2, 121.3, 121.2, 121.0, 118.7, 56.0, 49.7,
45.3, 33.3, 33.2, 29.1, 26.2, 25.5, 25.4, 21.5, 16.59; Anal. Calcd for
C37H41N3O5 (607.73) C 73.12, H 6.80, N 6.91%; Found C
72.88, H 6.83, N 6.95%.
2-(6-Methyl-4-oxo-4H-chromen-3-yl)-N1,N1-bis(4-methylphenyl)-
N2-{[(4-methylphenyl)sulfonyl]methyl}ethane-1,1,2-tricarboxamide
(5{2,3,2}): White powder (0.283 g, 85%); mp 252ꢀ254 °C;
Rf (25% n-hexane/EtOAc) 0.70; IR (KBr) (νmax, cmꢀ1) 3319
(NꢀH), 1688, 1647, and 1630 (CdO), 1600 (CdC), 1321 and
1143 (SO2); 1H NMR (400.1 MHz, DMSO-d6) δH 1.94 (12 H, 4
s, 4 Me), 4.40ꢀ4.50 and 4.67ꢀ4.70 (4 H, 2 m, CHꢀCH + CH2),
6.94ꢀ7.79 (15 H, m, arom.), 8.23 (1 H, s, dCHꢀO), 8.60 (1 H,
N1,N1-Bis(2,4-dimethoxyphenyl)-2-(6-methyl-4-oxo-4H-chr-
omen-3-yl)-N2-(1,1,3,3-tetramethylbutyl)ethane-1,1,2-tricarb-
oxamide (5{2,7,7}): Dark violet powder (0.263 g, 75%); mp
238ꢀ240 °C; Rf (50% n-hexane/EtOAc) 0.46; IR (KBr)
(νmax, cmꢀ1) 3218 (NꢀH), 1658 and 1614 (CdO), 1574
1
(CdC); H NMR (400.1 MHz, CDCl3) δH 0.78 (9 H, s,
C(Me)3), 1.24 and 1.25 (6 H, 2 s, C(Me)2), 1.50 and 1.72 (2
3
H, AB-system, JHH = 14.8 Hz, CH2), 2.40 (3 H, s, Me), 3.68,
t, 3JHH = 6.0 Hz, NH), 9.59 and 9.82 (2 H, 2 br s, 2 NH); 13
C
3.70, 3.76, and 3.78 (12 H, 4 s, 4 OMe), 4.26 and 4.71 (2 H, AB-
system, 3JHH = 12.0 Hz, CHꢀCH), 6.26ꢀ8.21 (9 H, m, arom.),
6.51 (1 H, br s, NH), 8.25 (1 H, s, dCHꢀO), 8.44 and 8.81 (2 H,
2 br s, 2 NH); 13C NMR (100.6 MHz, CDCl3) δC 178.1, 169.7,
167.6, 165.8, 157.7, 155.9, 155.2, 151.3, 150.7, 136.0, 135.9,
126.0, 124.0, 122.4, 121.9, 121.7, 121.3, 119.8, 118.9, 104.5,
104.3, 99.4, 99.3, 57.8, 56.6, 56.5, 56.3, 56.2, 52.1, 45.3, 32.2, 32.0,
29.8, 29.6, 21.7; Anal. Calcd for C39H47N3O9 (701.80) C 66.74,
H 6.75, N 5.99%; Found C 66.50, H 6.79, N 6.01%.
NMR (100.6 MHz, DMSO-d6) δC 176.6, 171.4, 166.7, 157.7,
155.0, 145.3, 137.7, 137.0, 136.7, 136.5, 136.0, 134.0, 133.7,
130.5, 130.4, 130.3, 129.4, 125.6, 124.3, 120.3, 120.2, 119.4, 61.6,
55.6, 43.4, 22.3, 21.8, 21.7, 21.6; Anal. Calcd for C37H35N3O7S
(665.75) C 66.75, H 5.30, N 6.31%; Found C 66.94, H 5.33,
N 6.26%.
2-(6-Methyl-4-oxo-4H-chromen-3-yl)-N1,N1-bis(2-methylp-
henyl)-N2-2-naphthylethane-1,1,2-tricarboxamide (5{2,6,5}):
White powder (0.280 g, 90%); mp 274ꢀ276 °C; Rf (25% n-
hexane/EtOAc) 0.79; IR (KBr) (νmax, cmꢀ1) 3281 (NꢀH),
N2-Butyl-2-(6-methyl-4-oxo-4H-chromen-3-yl)-N1,N1-di-1-
naphthylethane-1,1,2-tricarboxamide (5{2,8,8}): Light pink
powder (0.281 g, 90%); mp 240ꢀ242 °C; Rf (30% n-hexane/
EtOAc) 0.72; IR (KBr) (νmax, cmꢀ1) 3280 (NꢀH), 1675, 1649,
and 1623 (CdO), 1600 (CdC); 1H NMR (400.1 MHz, DMSO-
d6) δH 0.73 (3 H, t, 3JHH = 7.2 Hz, Me), 1.14 (2 H, sex., 3JHH = 7.1
Hz, CH2CH3), 1.28 (2 H, quin., 3JHH = 7.1 Hz, CH2CH2CH3),
2.39 (3 H, s, Me), 3.00 (2 H, q, 3JHH = 6.4 Hz, NCH2), 4.48 and
5.05 (2 H, 2 d, 3JHH = 11.2 Hz, CHꢀCH) 7.14ꢀ8.18 (18 H, m,
arom. +NH), 8.46 (1 H, s, dCHꢀO), 9.93 and 10.07 (2 H, 2 br s,
2 NH); 13C NMR (100.6 MHz, DMSO-d6) δC 177.1, 171.1,
168.4, 168.1, 157.8, 155.2, 136.6, 136.4, 135.0, 134.9, 134.7,
134.1, 129.5, 129.4, 129.0, 127.4, 127.3, 127.2, 127.1, 127.0,
126.9, 126.8, 126.7, 125.6, 124.5, 123.9, 123.3, 122.8, 122.6,
121.3, 119.4, 55.7, 44.4, 39.9, 32.4, 21.7, 20.6, 14.9; Anal. Calcd
for C39H35N3O5 (625.71) C 74.86, H 5.64, N 6.72%; Found C
74.63, H 5.62, N 6.75%.
1
1672 and 1641 (CdO), 1600 (CdC); H NMR (400.1 MHz,
DMSO-d6) δH 1.88, 2.20, and 2.36 (9 H, 3 s, 3 Me), 4.61 and 4.90
(2 H, AB-system, 3JHH = 11.2 Hz, CHꢀCH), 7.04ꢀ8.14 (18 H,
m, arom.), 8.48 (1 H, s, dCHꢀO), 9.40, 9.43, and 9.92 (3 H, 3 s,
3 NH); 13C NMR (100.6 MHz, DMSO-d6) δC 177.1, 170.3,
167.7, 167.2, 158.5, 155.1, 137.9, 137.3, 136.9, 136.7, 136.5,
134.5, 132.7, 132.5, 131.7, 131.6, 131.0, 129.4, 128.7, 128.5,
127.6, 127.3, 126.8, 126.5, 125.8, 125.7, 125.6, 125.5, 124.4,
121.6, 120.4, 119.4, 116.9, 54.9, 45.7, 21.7, 19.0, 18.6; Anal. Calcd
for C39H33N3O5 (623.69) C 75.10, H 5.33 N 6.74%; Found C
74.87, H 5.35, N 6.71%.
N1,N1-Bis(4-ethylphenyl)-2-(6-methyl-4-oxo-4H-chromen-
3-yl)-N2-{[(4-methylphenyl)sulfonyl]methyl}ethane-1,1,2-tri-
carboxamide (5{2,3,6}): White powder (0.270 g, 78%); mp
254ꢀ256 °C; Rf (30% n-hexane/EtOAc) 0.65; IR (KBr)
(νmax, cmꢀ1) 3308 (NꢀH), 1677, 1655, and 1640 (CdO),
2-(6-Methyl-4-oxo-4H-chromen-3-yl)-N1,N1-bis(3-nitrophe-
nyl)-N2-(1,1,3,3-tetramethylbutyl)ethane-1,1,2-tricarboxamide
(5{2,7,3}): White powder (0.309 g, 92%); mp 276ꢀ278 °C; Rf
1
1603 (CdC), 1328 and 1144 (SO2); H NMR (400.1 MHz,
DMSO-d6) δH 0.97ꢀ1.08 (6 H, m, 2 CH2CH3), 2.14 (3 H, s,
663
dx.doi.org/10.1021/co200125a |ACS Comb. Sci. 2011, 13, 659–666