Journal of Medicinal Chemistry
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7.28 (d, J = 8.4 Hz, 4H), 7.17 (q, J = 8.0 Hz, 4H), 6.50 (t, J = 7.6 Hz, 1H),
3.51 (s, 4H), 2.29 (s, 3H). LC−MS (ESI): m/z 441.3 (M + H)+.
N,N′-((4-Methoxyphenyl)methylene)bis(2-(4-chlorophenyl)-
acetamide) (37). Compound 37 was prepared from 2-(4-
chlorophenyl)acetamide and 4-methoxybenzaldehyde using method 1.
Yield: 91%. 1H NMR (400 MHz, DMSO-d6) δ 8.73 (d, J = 7.6 Hz, 2H),
7.34 (d, J = 8.8 Hz, 4H), 7.26 (d, J = 8.4 Hz, 4H), 7.21 (d, J = 8.8 Hz,
2H), 6.90 (d, J = 8.8 Hz, 2H), 6.46 (t, J = 8.0 Hz, 1H), 3.74 (s, 3H), 3.49
(s, 4H). LC−MS (ESI): m/z 457.2 (M + H)+.
N,N′-((2-(Trifluoromethyl)phenyl)methylene)bis(2-(4-
chlorophenyl)acetamide) (38). Compound 38 was prepared from 2-
(4-chlorophenyl)acetamide and 2-(trifluoromethyl)benzaldehyde using
method 1. Yield: 82%. 1H NMR (400 MHz, DMSO-d6) δ 8.04 (d, J = 6.0
Hz, 2H), 7.81 (d, J = 7.8 Hz, 1H), 7.72 (d, J = 7.8 Hz, 1H), 7.62 (t, J = 7.8
Hz, 1H), 7.52 (t, J = 7.8 Hz, 1H), 7.27−7.30 (m, 8H), 7.06 (t, J = 7.2 Hz,
1H), 3.52 (s, 4H). LC−MS (ESI): m/z 495.0 (M + H)+.
N,N′-((4-(Trifluoromethyl)phenyl)methylene)bis(2-(4-
chlorophenyl)acetamide) (39). Compound 39 was prepared from 2-
(4-chlorophenyl)acetamide and 4-(trifluoromethyl)benzaldehyde using
method 1. Yield: 85%. 1H NMR (400 MHz, DMSO-d6) δ 8.96 (d, J = 7.6
Hz, 2H), 7.73 (d, J = 8.4 Hz, 2H), 7.54 (d, J = 8.4 Hz, 2H), 7.35 (d, J =
8.4 Hz, 4H), 7.28 (d, J = 8.4 Hz, 4H), 6.57 (t, J = 7.6 Hz, 1H), 3.54 (s,
4H). LC−MS (ESI): m/z 495.2 (M + H)+.
N,N′-((4-Nitrophenyl)methylene)bis(2-(4-chlorophenyl)-
acetamide) (40). Compound 40 was prepared from 2-(4-
chlorophenyl)acetamide and 4-nitrobenzaldehyde using method 1.
Yield: 90%. 1H NMR (400 MHz, DMSO-d6) δ 9.02 (d, J = 8.0 Hz, 2H),
8.24−8.25 (m, 2H), 7.56−7.58 (m, 2H), 7.34−7.37 (m, 4H), 7.26−7.29
(m, 4H), 6.55 (t, J = 8.0 Hz, 1H), 3.53 (S, 4H). LC−MS (ESI): m/z
472.0 (M + H)+.
N,N′-(Phenylmethylene)bis(2-(4-(trifluoromethyl)phenyl)-
acetamide) (41). Compound 41 was prepared from 2-(4-
(trifluoromethyl)phenyl)acetamide and benzaldehyde using method 1.
Yield: 83%. 1H NMR (400 MHz, DMSO-d6) δ 8.94 (d, J = 7.8 Hz, 2H),
7.63 (d, J = 7.8 Hz, 4H), 7.48 (d, J = 8.4 Hz, 4H), 7.29−7.37 (m, 5H),
6.55 (t, J = 7.8 Hz, 1H), 3.63 (s, 4H). LC−MS (ESI): m/z 495.1 (M +
H)+.
N,N′-((2-Fluorophenyl)methylene)bis(2-(4-(trifluoromethyl)-
phenyl)acetamide) (42). Compound 42 was prepared from 2-(4-
(trifluoromethyl)phenyl)acetamide and 2-fluorobenzaldehyde using
method 1. Yield: 86%. 1H NMR (400 MHz, DMSO-d6) δ 8.99 (d, J =
7.2 Hz, 2H), 7.63 (d, J = 7.8 Hz, 4H), 7.46 (d, J = 7.8 Hz, 5H), 7.36−7.40
(m, 1H), 7.21 (t, J = 7.8 Hz, 2H), 6.74 (t, J = 7.8 Hz, 1H), 3.60 (s, 4H).
LC−MS (ESI): m/z 513.0 (M + H)+.
N,N′-((4-Fluorophenyl)methylene)bis(2-(4-(trifluoromethyl)-
phenyl)acetamide) (43). Compound 43 was prepared from 2-(4-
(trifluoromethyl)phenyl)acetamide and 4-fluorobenzaldehyde using
method 1. Yield: 90%. 1H NMR (400 MHz, DMSO-d6) δ 8.95 (d, J =
8.4 Hz, 2H), 7.63 (d, J = 8.4 Hz, 4H), 7.47 d, J = 8.4 Hz, 4H), 7.37 (dd, J
= 5.4, 8.4 Hz, 2H), 7.19 (t, J = 8.4 Hz, 2H), 6.51 (t, J = 7.8 Hz, 1H), 3.62
(s, 4H). LC−MS (ESI): m/z 513.2 (M + H)+.
N,N′-((4-Chlorophenyl)methylene)bis(2-(4-(trifluoromethyl)-
phenyl)acetamide) (44). Compound 44 was prepared from 2-(4-
(trifluoromethyl)phenyl)acetamide and 4-chlorobenzaldehyde using
method 1. Yield: 85%. 1H NMR (400 MHz, DMSO-d6) δ 8.96 (d, J = 7.8
Hz, 2H), 7.63 (d, J = 7.2 Hz, 4H), 7.46 (d, J = 7.8 Hz, 4H), 7.43 (dd, J =
1.8, 8.4 Hz, 2H), 7.34−7.35 (m, 2H), 6.50 (t, J = 7.2 Hz, 1H), 3.62 (s,
4H). LC−MS (ESI): m/z 529.0 (M + H)+.
Hz, 2H), 6.91 (d, J = 8.4 Hz, 2H), 6.48 (t, J = 7.8 Hz, 1H), 3.74 (s, 3H),
3.61(s, 4H). LC−MS (ESI): m/z 525.1 (M + H)+.
N,N′-((4-(Trifluoromethyl)phenyl)methylene)bis(2-(4-
(trifluoromethyl)phenyl)acetamide) (47). Compound 47 was prepared
from 2-(4-(trifluoromethyl)phenyl)acetamide and 4-(trifluoromethyl)-
benzaldehyde using method 1. Yield: 74%. 1H NMR (400 MHz,
DMSO-d6) δ 9.08 (d, J = 7.2 Hz, 2H), 7.73 (d, J = 7.8 Hz, 2H), 7.63 (d, J
= 7.8 Hz, 4H), 7.56 (d, J = 7.8 Hz, 2H), 7.48 (d, J = 7.8 Hz, 4H), 6.60 (t, J
= 7.8 Hz, 1H), 3.35−3.43 (m, 4H). LC−MS (ESI): m/z 562.9 (M +
H)+.
N,N′-((4-(Diethylamino)phenyl)methylene)dibenzamide (51).
Compound 51 was prepared from benzamide and 4-(diethylamino)-
benzaldehyde using method 1. Yield: 73%. 1H NMR (400 MHz,
CD3OD) δ 9.24 (d, J = 7.6 Hz, 1H), 7.88−7.93 (m, 4H), 7.81 (d, J = 8.8
Hz, 2H), 7.46−7.65 (m, 9H), 7.20 (m, 1H), 3.70−3.81 (m, 4H), 1.17 (t,
J = 7.2 Hz, 6H). LC−MS (ESI): m/z 402.2 (M + H)+. HRMS (ESI) for
C25H28N3O2 (MH+): calcd, 402.2176; found, 402.2167.
N,N′-((4-(Diethylamino)phenyl)methylene)bis(3-phenylpropana-
mide) (52). Compound 52 was prepared from 3-phenylpropanamide
1
and 4-(diethylamino)benzaldehyde using method 1. Yield: 66%. H
NMR (400 MHz, CD3OD) δ 8.29−8.30 (m, 2H), 7.17−7.29 (m, 10H),
6.92 (d, J = 8.4 Hz, 2H), 6.56 (d, J = 8.4 Hz, 2H), 6.46 (t, J = 8.0 Hz, 1H),
2.82 (t, J = 7.6 Hz, 4H), 2.42−2.47 (m, 4H), 1.07 (t, J = 6.8 Hz, 6H).
LC−MS (ESI): m/z 458.2 (M + H)+. HRMS (ESI) for C29H36N3O2
(MH+): calcd, 458.2802; found, 458.2795.
N,N′-((4-(Diethylamino)phenyl)methylene)bis(3-phenylacryla-
mide) (53). Compound 53 was prepared from cinnamamide and 4-
1
(diethylamino)benzaldehyde using method 1. Yield: 68%. H NMR
(400 MHz, CD3OD) δ 8.68−8.70 (m, 2H), 7.38−7.58 (m, 12H), 7.19
(d, J = 8.8 Hz, 2H), 6.79 (d, J = 16.0 Hz, 2H), 6.66−6.68 (m, 3H), 3.29−
3.35 (m, 4H), 1.08 (t, J = 7.2 Hz, 6H). LC−MS (ESI): m/z 454.2 (M +
H)+. HRMS (ESI) for C29H32N3O2 (MH+): calcd, 454.2489; found,
454.2487.
N,N′-((4-(Diethylamino)phenyl)methylene)bis(2-methylpropana-
mide) (56). Compound 56 was prepared from isobutyramide and 4-
1
(diethylamino)benzaldehyde using method 1. Yield: 80%. H NMR
(400 MHz, CD3OD) δ 7.18 (d, J = 8.4 Hz, 2H), 6.70−6.73 (m, 2H),
6.56 (s, 1H), 3.35−3.50 (m, 2H), 2.47−2.54 (m, 4H), 1.13−1.16 (m,
12H). LC−MS (ESI): m/z 334.2 (M + H)+. HRMS (ESI) for
C19H32N3O2 (MH+): calcd, 334.2489; found, 334.2483.
N,N′-((4-(Diethylamino)phenyl)methylene)bis(2,2-dimethylpro-
panamide) (57). Compound 57 was prepared from pivalamide and 4-
1
(diethylamino)benzaldehyde using method 1. Yield: 77%. H NMR
(400 MHz, DMSO) δ 7.70 (d, J = 8.8 Hz, 2H), 7.03 (d, J = 8.8 Hz, 2H),
6.62 (d, J = 8.8 Hz, 2H), 6.52 (t, J = 8.4 Hz, 1H), 3.30−3.33 (m, 4H),
1.12 (s, 18H), 1.05−1.08 (m, 6H). LC−MS (ESI): m/z 262.2 (M + H)+.
HRMS (ESI) for C21H36N3O2 (MH+): calcd, 362.2802; found,
362.2795.
N,N′-((4-(Diethylamino)phenyl)methylene)dipentanamide (58).
Compound 58 was prepared from pentanamide and 4-(diethylamino)-
benzaldehyde using method 1. Yield: 69%. 1H NMR (400 MHz,
CD3OD) δ 7.18 (d, J = 8.8 Hz, 2H), 6.71 (d, J = 8.8 Hz, 2H), 6.58 (t, J =
8.4 Hz, 1H), 3.33−3.41 (m, 4H), 2.25 (t, J = 7.2 Hz, 4H), 1.58−1.66 (m,
4H), 1.33−1.43 (m, 4H), 1.14 (t, J = 7.2 Hz, 6H), 0.95 (t, J = 2.8 Hz,
6H). LC−MS (ESI): m/z 362.2 (M + H)+. HRMS (ESI) for
C21H36N3O2 (MH+): calcd, 362.2802; found, 362.2792.
N,N′-((4-(Diethylamino)phenyl)methylene)dihexanamide (59).
Compound 59 was prepared from hexanamide and 4-(diethylamino)-
benzaldehyde using method 1. Yield: 76%. 1H NMR (400 MHz,
CD3OD) δ 7.19 (d, J = 8.8 Hz, 2H), 6.71 (d, J = 8.8 Hz, 2H), 6.58 (t, J =
8.4 Hz, 1H), 3.35−3.41 (m, 4H), 2.19−2.26 (m, 4H), 1.61−1.68 (m,
4H), 1.32−1.35 (m, 8H), 1.14 (t, J = 6.8 Hz, 6H), 0.94 (t, J = 2.8 Hz,
6H). LC−MS (ESI): m/z 390.3 (M + H)+. HRMS (ESI) for
C23H40N3O2 (MH+): calcd, 390.3115; found, 390.3108.
N,N′-((4-(Diethylamino)phenyl)methylene)dioctanamide (60).
Compound 60 was prepared from octanamide and 4-(diethylamino)-
benzaldehyde using method 1. Yield: 68%. 1H NMR (400 MHz,
DMSO) δ 8.21 (d, J = 8.0 Hz, 2H), 7.07 (d, J = 8.8 Hz, 2H), 6.61 (d, J =
8.8 Hz, 2H), 6.42 (t, J = 8.0 Hz, 1H), 3.29−3.31 (m, 4H), 2.06−2.14 (m,
4H), 1.47−1.50 (m, 4H), 1.08−1.24 (m, 16H), 1.06 (t, J = 7.2 Hz, 6H),
N,N′-(p-Tolylmethylene)bis(2-(4-(trifluoromethyl)phenyl)-
acetamide) (45). Compound 45 was prepared from 2-(4-
(trifluoromethyl)phenyl)acetamide and 4-methylbenzaldehyde using
method 1. Yield: 81%. 1H NMR (400 MHz, DMSO-d6) δ 8.87 (d, J = 8.4
Hz, 2H), 7.63 (d, J = 7.8 Hz, 4H), 7.47 (d, J = 8.4 Hz, 4H), 7.20 (d, J =
8.4 Hz, 2H), 7.15 (d, J = 7.8 Hz, 2H), 6.49 (t, J = 7.8 Hz, 1H), 3.61 (s,
4H), 2.28 (s, 3H). LC−MS (ESI): m/z 509.1 (M + H)+.
N,N′-((4-Methoxyphenyl)methylene)bis(2-(4-(trifluoromethyl)-
phenyl)acetamide) (46). Compound 46 was prepared from 2-(4-
(trifluoromethyl)phenyl)acetamide and 4-methoxybenzaldehyde using
method 1. Yield: 86%. 1H NMR (400 MHz, DMSO-d6) δ 8.85 (d, J = 7.8
Hz, 2H), 7.63 (d, J = 7.8 Hz, 4H), 7.47 (d, J = 7.8 Hz, 4H),7.24 (d, J = 9.0
9983
dx.doi.org/10.1021/jm301212u | J. Med. Chem. 2012, 55, 9973−9987