Medicinal Chemistry Research
Ar-6’, 6”-H), 7.13 (d, J = 6.3 Hz, 2H, Ar-5’, 5”-H), 4.17 (s,
Ar-6”-C), 53.82 (O-CH , Ar-4-O-CH ), 15.36 (2× CH , Ar-
3 3 3
13
+
3
H, Ar-4-OCH ), 1.43 (s, 6H, Ar-4’, 4”-CH ); C-NMR
2’,2”-CH ); MS (m/z): 532.9820 [M + H] .
3
3
3
1
3
(
101 MHz, CDCl ): δ = 163.49 (C, C = O), 162.39 (C, C =
N ,N -bis(3-bromo-2-methylphenyl)-4-methoxybenzene-
1,3-isophthalamide (1g)
3
O), 142.57 (C, Ar-4-C), 140.16 (C, Ar-1’-C), 138.63 (C,
Ar-1-C), 137.23 (C, Ar-3-C), 136.99 (C, Ar-1”-C), 135.59
White solid (The residue was recrystallized by acetone.);
(
C, Ar-2’-C), 134.92 (C, Ar-2”-C), 132.52 (C, Ar-2-C),
Yield = 64.7%; R : 0.22; m.p.: 211.3–212.3 °C; IR (KBr)
f
131.56 (C, Ar-6-C), 130.89 (CH, Ar-5-C), 130.21 (CH, Ar-
3’-C), 127.32 (CH, Ar-3”-C), 126.43 (CH, Ar-5”-C),
124.36 (CH, Ar-5’-C), 123.15 (CH, Ar-6’-C), 122.36 (CH,
υmax 3447.43, 3283.53, 1652.64, 1517.42, 1448.53,
1249.84, 1030.45, 767.32 cm ; H-NMR (400 MHz,
−
1
1
CDCl , TMS): δ = 10.57 (s, 2H, 2× -CONH-), 8.99 (s, 1H,
3
Ar-6”-C), 121.23 (C, Ar-4”-C), 119.52 (C, Ar-4’-C), 54.76
Ar-2-H), 8.86 (d, J = 6.8 Hz, 1H, Ar-6-H), 8.24 (d, J =
5.4 Hz, 1H, Ar-5-H), 8.10 (d, J = 5.4 Hz, 2H, Ar-4’,4”-H),
7.70 (t, J = 6.2 Hz, 2H, Ar-5’,5”-H), 7.13 (d,J = 5.8 Hz,
(
(
O-CH , Ar-4-O-CH ), 16.98 (2× CH , Ar-4’, 4”-CH ); MS
3 3 3 3
+
m/z): 532.9820 [M + H] .
1
3
N ,N -bis(4-fluoro-2-methylphenyl)-4-methoxybenzene-
2H, Ar-6’,6”-H), 4.04 (s, 3H, Ar-4-OCH ), 1.83 (s, 6H, Ar-
3
1
3
1
,3-isophthalamide (1e)
2’,2”-CH3); C-NMR (101 MHz, DMSO-d ): δ = 164.93
6
Yellow solid (The residue was recrystallized by acet-
(C, C = O), 160.45 (C, C = O), 142.68 (C, Ar-4-C), 141.76
(C, Ar-1’-C), 140.67 (C, Ar-1-C), 139.63 (C, Ar-3-C),
138.35 (C, Ar-1”-C), 137.65 (C, Ar-3’-C), 136.67 (C, Ar-
3”-C), 134.62 (C, Ar-2-C), 133.91 (C, Ar-6-C), 131.29
(CH, Ar-5-C), 130.15 (CH, Ar-4’-C), 128.49 (CH, Ar-4”-
C), 127.48 (CH, Ar-2’-C), 126.64 (C, Ar-2”-C), 125.64 (C,
Ar-5”-C), 120.62 (CH, Ar-5’-C), 118.63 (CH, Ar-6’-C),
117.95 (CH, Ar-6”-C), 62.82 (O-CH , Ar-4-O-CH ), 17.36
one.); Yield = 70.7%; R : 0.36; m.p.: 157.5–158.6 °C; IR
f
(
1
(
8
(
(
KBr) υmax 3436.34, 3344.54, 2980.34, 1670.34, 1601.54,
−
1
1
526.34, 1038.34, 809.54, 752.54 cm ;
H-NMR
400 MHz, CDCl , TMS): δ = 10.24 (s, H, 2× CONH-),
3
.85 (s, 1H, Ar-2-H), 8.52 (d, J = 7.8 Hz, 1H, Ar-6-H), 8.22
d, J = 8.6 Hz, 1H, Ar-5-H), 7.65 (s, 2H, Ar-3’, 3”-H), 7.06
d, J = 5.6 Hz, 2H, Ar-5’, 5”-H), 7.06 (d, J = 7.5 Hz, 2H,
3
3
+
Ar-6’, 6”-H), 4.03 (s, 3H, Ar-4-OCH ), 1.33 (s, 6H, Ar-
(2× CH , Ar-2’,2”-CH ); MS (m/z): 532.9820 [M + H] .
3
3
3
3
1
3
1
2
’,2”-CH3); C-NMR (101 MHz, CDCl ): δ = 164.56 (C,
N ,N -bis(3-fluoro-2-methylphenyl)-4-methoxybenzene-
3
C = O), 160.65 (C, C = O), 142.59 (C, Ar-4-C), 141.56 (C,
Ar-1’-C), 137.65 (C, Ar-1-C), 135.33 (C, Ar-3-C), 134.53
1,3-isophthalamide (1h)
White solid (The residue was recrystallized by acetone.);
(
1
C, Ar-1”-C), 133.23 (C, Ar-2’-C), 132.22 (C, Ar-2”-C),
31.52 (C, Ar-2-C), 130.56 (C, Ar-6-C), 129.89 (CH, Ar-5-
C), 127.41 (d, J = 43 Hz, 2C, Ar-4’, 4”-C), 126.21 (CH, Ar-
Yield = 67.1%; R : 0.22; m.p.: 275.5–277.6 °C; IR (KBr)
f
υmax 3358.34, 3067.45, 2984.36, 2223.31, 1658.34,
−
1
1
1264.86, 1145.43, 889.25, 830.53 cm ;
H-NMR
3
’-C), 125.32 (CH, Ar-3”-C), 123.43 (CH, Ar-5”-C),
(400 MHz, CDCl , TMS): δ = 10.32 (s, 2H, 2× -CONH-),
3
1
21.36 (CH, Ar-5’-C), 118.15 (CH, Ar-6’-C), 116.36 (CH,
8.77 (s, 1H, Ar-2-H), 8.54 (d, J = 6.0 Hz, 1H, Ar-6-H), 8.28
(d, J = 6.8 Hz, 1H, Ar-5-H), 7.99 (d, J = 7.0 Hz, 2H, Ar-
4’,4”-H), 7.67 (t, J = 8.2 Hz, 2H, Ar-5’,5”-H), 7.35 (d, J =
Ar-6”-C), 54.86 (O-CH , Ar-4-O-CH ), 18.76 (2× CH , Ar-
2
3
3
3
+
’,2”-CH ); MS (m/z): 411.0099 [M + H] .
3
1
3
N ,N -bis(4-bromo-2-methylphenyl)-4-methoxybenzene-
,3-isophthalamide (1f)
5.6 Hz, 2H, Ar-6’,6”-H), 4.06 (s, 3H, Ar-4-OCH ), 1.53 (s,
3
1
3
1
6H, Ar-2’,2”-CH3); C-NMR (101 MHz, DMSO-d ): δ =
6
White solid (The residue was recrystallized by acetone.);
165.15 (C, C = O), 165.07 (C, C = O), 143.37 (C, Ar-4-C),
142.36 (C, Ar-1’-C), 140.34 (C, Ar-1-C), 139.69 (C, Ar-3-
C), 138.37 (C, Ar-1”-C), 136.83 (d, J = 58 Hz, 2C, Ar-
3’,3”-C), 135.38 (C, Ar-2-C), 134.65 (C, Ar-6-C), 133.29
(CH, Ar-5-C), 131.26 (CH, Ar-4’-C), 129.37 (CH, Ar-4”-
C), 127.34 (CH, Ar-2’-C), 125.67 (C, Ar-2”-C), 123.34 (C,
Ar-5”-C), 121.35 (CH, Ar-5’-C), 119.64 (CH, Ar-6’-C),
116.57 (CH, Ar-6”-C), 61.37 (O-CH , Ar-4-O-CH ), 14.38
Yield = 56.5%; R : 0.37; m.p.: 251.4–252.4 °C; IR (KBr)
f
υmax 3445.34, 2360.54, 1657.56, 1552.23, 1509.76,
−
1 1
1
(
8
(
338.56, 1240.75, 1036.34, 844.62, 781.63 cm ; H-NMR
400 MHz, CDCl , TMS): δ = 10.07 (s, 2H, 2× -CONH-),
3
.74 (s, 1H, Ar-2-H), 8.44 (d, J = 7.8 Hz, 1H, Ar-6-H), 8.22
d, J = 5.8 Hz, 1H, Ar-5-H), 8.04 (s, 2H, Ar-3’,3”-H), 7.69
d, J = 8.8 Hz, 2H, Ar-5’, 5”-H), 7.46 (d, J = 7.8 Hz, 2H,
(
3
3
±+
Ar-6’, 6”-H), 3.96 (s, 3H, Ar-4-OCH ), 1.63 (s, 6H, Ar-
(2× CH , Ar-2’,2”-CH ); MS (m/z): 411.0099 [M ± H]
N ,N -bis(4-bromo-3-methylphenyl)-4-methoxybenzene-
1,3-isophthalamide (1i)
.
3
3
3
3
1
3
1
2
’,2”-CH3); C-NMR (101 MHz, CDCl ): δ = 163.92 (C,
3
C = O), 162.29 (C, C = O), 142.98 (C, Ar-4-C), 141.99 (C,
Ar-1’-C), 139.65 (C, Ar-1-C), 138.36 (C, Ar-3-C), 137.36
Brown solid (The residue was recrystallized by acetone.);
(
1
C, Ar-1”-C), 136.56 (C, Ar-2’-C), 135.68 (C, Ar-2”-C),
34.29 (C, Ar-2-C), 133.56 (C, Ar-6-C), 132.19 (CH, Ar-5-
Yield = 71.9%; R : 0.31; m.p.: 273.4–275.5 °C; IR (KBr)
f
υmax 3398.08, 3258.45, 2984.45, 1677.03, 1604.15,
−
1
1
C), 131.96 (C, Ar-4’-C), 130.95 (C, Ar-4”-C), 129.64 (CH,
Ar-3’-C), 124.63 (CH, Ar-3”-C), 121.65 (CH, Ar-5”-C),
1280.02, 1072.78, 740.43 cm ; H-NMR (400 MHz,
CDCl , TMS): δ = 10.72 (s, 2H, 2× -CONH-), 8.87 (s, 1H,
3
1
19.67 (CH, Ar-5’-C), 117.84 (CH, Ar-6’-C), 115.67 (CH,
Ar-2-H), 8.55 (d, J = 7.0 Hz, 1H, Ar-6-H), 8.06 (d, J =