498 Schlitzer et al.
Arch. Pharm. Pharm. Med. Chem. 2004, 337, 493−501
n-hexane 1:1. Yield: 434 mg (70%). Mp 125°C. IR (KBr): ν =
1H), 7.87Ϫ7.89 (m, 1H), 10.02 (s, 1H), 10.16 (s, 1H). MS
(EI): m/z = 175 (100), 344 (40), 518 (90) M+, 519 (34) M++1.
Anal. calcd. for C33H30N2O4 : C, 76.42; H, 5.84; N, 5.40;
found: C, 76.40; H, 5.69; N, 5.41.
3260, 2960, 1670, 1640, 1630, 1595, 1550, 1500 cmϪ1 1H
.
NMR (CDCl3): δ 1.21 (d, J = 7 Hz, 6H), 2.30 (s, 3H), 2.87 (q,
J = 7 Hz, 1H), 3.67 (s, 2H), 6.43 (d, J = 16 Hz, 1H), 7.12Ϫ7.14
(m, 2H), 7.15Ϫ7.17 (m, 2H), 7.21Ϫ7.23 (m, 2H), 7.31Ϫ7.33
(m, 2H), 7.38Ϫ7.41 (m, 2H), 7.49Ϫ7.52 (m, 2H), 7.62 (d, J =
16 Hz, 1H), 7.65Ϫ7.67 (m, 2H), 8.06 (s, 1H), 8.18 (s, 1H),
8.44 (d, J = 9 Hz, 1H), 10.54 (s, 1H). MS (EI): m/z = 131 (43),
173 (47), 212 (32), 344 (48), 516 (100) M+, 517 (37) M++1.
Anal. calcd. for C34H32N2O3: C, 79.04; H, 6.24; N, 5.42;
found: C, 78.99; H, 6.18; N, 5.68.
N-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyl]-4-
propoxycinnamic acid amide (2j)
From 4-propoxycinnamic acid chloride (270 mg, 1.2 mmol),
according to general procedure. Purification: MPLC EtOAc:
n-hexane 1:1. Yield: 383 mg (60%). Mp 175°C. IR (KBr): ν =
3230, 1665, 1605, 1550, 1510 cmϪ1 1H NMR (DMSO-d6): δ
.
N-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyl]-4-tert-
butylcinnamic acid amide (2f)
0.93 (t, J = 7 Hz, 3H), 1.67Ϫ1.77 (m, 2H), 2.26 (s, 3H), 3.37
(s, 2H), 3.97 (t, J = 6 Hz, 2H), 6.60 (d, J = 16 Hz, 1H),
6.96Ϫ6.98 (m, 2H), 7.00Ϫ7.02 (m, 2H), 7.04Ϫ7.06 (m, 2H),
7.50Ϫ7.53 (m, 5H), 7.60Ϫ7.70 (m, 4H), 7.77 (s, 1H), 7.88 (d,
J=9 Hz, 1H), 10.02 (s, 1H), 10.16 (s, 1H). MS (EI): m/z = 43
(100), 60 (97), 73 (93), 83 (38), 189 (39), 532 (10) M+, 533
(4) M++1. Anal. calcd. for C34H32N2O4: C, 76.66; H, 6.07; N,
5.26; found: C, 76.26; H, 5.88; N, 5.56.
From 4-tert-butylcinnamic acid chloride (267 mg, 1.2 mmol),
according to general procedure. Purification: MPLC EtOAc:
n-hexane 1:1. Yield: 427 mg (67%). Mp 175°C. IR (KBr): ν =
3230, 2965, 1665, 1640, 1620, 1595, 1550, 1515 cmϪ1 1H
.
NMR (CDCl3): δ 1.29 (s, 9H), 2.31 (s, 3H), 3.67 (s, 2H), 6.44
(d, J = 16 Hz, 1H), 7.13Ϫ7.15 (m, 2H), 7.21Ϫ7.23 (m, 2H),
7.32Ϫ7.34 (m, 2H), 7.35Ϫ7.37 (m, 2H), 7.40Ϫ7.43 (m, 2H),
7.51Ϫ7.54 (m, 2H), 7.63 (d, J = 16 Hz, 1H), 7.66Ϫ7.68 (m,
2H), 8.02 (s, 1H), 8.06 (s, 1H), 8.47 (d, J = 9 Hz, 1H), 10.54
(s, 1H). MS (EI): m/z = 187 (36), 344 (47), 530 (100) M+, 531
(39) M++1. Anal. calcd. for C35H34N2O3: C, 79.22; H, 6.46; N,
5.28; found: C, 79.33; H, 6.40; N, 5.48.
N-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyl]-4-
butoxycinnamic acid amide (2k)
From 4-butoxycinnamic acid chloride (286 mg, 1.2 mmol),
according to general procedure. Purification: MPLC EtOAc:
n-hexane 1:1. Yield: 466 mg (71%). Mp 152°C. IR (KBr): ν =
3230, 1665, 1650, 1620, 1605, 1550, 1510 cmϪ1 1H NMR
.
N-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyl]-4-
(CDCl3): δ 0.96 (t, J = 7 Hz, 3H), 1.42Ϫ1.52 (m, 2H),
1.71Ϫ1.80 (m, 2H), 2.30 (s, 3H), 3.67 (s, 2H), 3.93 (t, J = 6
Hz, 2H), 6.32 (d, J = 16 Hz, 1H), 6.79Ϫ6.81 (m, 2H),
7.12Ϫ7.14 (m, 2H), 7.21Ϫ7.23 (m, 2H), 7.31Ϫ7.33 (m, 2H),
7.40Ϫ7.42 (m, 3H), 7.50Ϫ7.52 (m, 2H), 7.58 (d, J = 16 Hz,
1H), 7.65Ϫ7.67 (m, 2H), 8.05 (s, 1H), 8.47 (d, J = 9 Hz, 1H),
10.53 (s, 1H). MS (EI): m/z = 147 (40), 203 (100), 344 (36),
546 (62) M+. Anal. calcd. for C35H34N2O4: C, 76.89; H, 6.27;
N, 5.13; found: C, 76.50; H, 6.12; N, 5.33.
methylthiocinnamic acid amide (2g)
From 4-methylsulfonylcinnamic acid (192 mg, 1 mmol), ac-
cording to general procedure. Purification: recrystallization
from toluene. Yield: 315 mg (61%). Mp 210°C. IR (KBr): ν =
3229, 3057, 2922, 1681, 1627, 1615, 1554, 1506, 1289, 1171
1
cmϪ1. H NMR (DMSO-d6): δ 2.26 (s, 3H), 2.49 (s, 3H), 3.37
(s, 2H), 6.71 (d, J = 16 Hz, 1H), 7.00Ϫ7.06 (m, 4H), 7.30 (m,
2H), 7.48Ϫ7.53 (m, 5H), 7.63 (m, 2H), 7.68 (m, 2H), 7.77 (m,
1H), 7.87 (m, 1H), 10.01 (s, 1H), 10.20 (s, 1H). MS (EI): m/
z = 105 (51), 177 (100), 212 (32), 344 (25), 520 (36) M+. Anal.
calcd. for C32H28N2O3S: C, 73.82; H, 5.42; N, 5.38; found: C,
73.84; H, 5.46; N, 5.27.
N-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyl]-4-
fluorocinnamic acid amide (2q)
From 4-fluorocinnamic acid (166 mg, 1 mmol), according to
general procedure. Purification: recrystallization from toluene.
Yield: 441 mg (90%). Mp 193°C. IR (KBr): ν = 3358, 2961,
1675, 1629, 1597, 1559, 1511 cmϪ1. 1H NMR (CDCl3): δ 2.25
(s, 3H), 3.61 (s, 2H), 6.31 (d, J = 16 Hz, 1H), 6.96 (m, 2H),
7.09 (m, 2H), 7.17 (m, 2H), 7.34Ϫ7.47 (m, 4H), 7.49 (m, 2H),
7.55 (d, J = 16 Hz, 1H), 7.62 (m, 3H), 7.95 (s, 1H), 8.43 (m,
1H), 10.45 (s, 1H). MS (EI): m/z = 149 (48), 212 (53), 360
(47), 492 (100) M+. Anal. calcd. for C31H25FN2O3: C, 75.59;
H, 5.12; N, 5.69; found: C, 75.34; H, 5.15; N, 5.76.
N-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyl]-4-
methoxycinnamic acid amide (2h)
From 4-methoxycinnamic acid (214 mg, 1.2 mmol), according
to general procedure. Purification: recrystallization from tolu-
ene. Yield: 60 mg (10%). Mp 89°C. IR (KBr): ν = 3274, 1664,
1603, 1549, 1510 cmϪ1. 1H NMR (DMSO-d6): δ 2.25 (s, 3H),
3.36 (s, 2H), 3.79 (s, 3H), 6.60 (d, J = 16 Hz, 1H), 6.99 (m,
4H), 7.04 (m, 2H), 7.47Ϫ7.54 (m, 5H), 7.57Ϫ7.64 (m, 2H),
7.68 (m, 2H), 7.76 (m, 1H), 7.85Ϫ7.88 (m, 1H), 10.02 (s, 1H),
10.18 (s, 1H). MS (EI): m/z = 105 (30), 161 (100), 212 (29),
504 (21) M+. Anal. calcd. for C32H28N2O4: C, 76.17; H, 5.59;
N, 5.55; found: C, 75.85; H, 5.55; N, 5.52.
N-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyl]-4-
chlorocinnamic acid amide (2r)
From 4-chlorocinnamic acid chloride (223 mg, 1.2 mmol), ac-
cording to general procedure. Purification: recrystallization
from toluene. Yield: 70 mg (11%). Mp 85°C. IR (KBr): ν =
3358, 1673, 1632, 1563, 1510 cmϪ1. 1H NMR (CDCl3): δ 2.25
(s, 3H), 3.63 (s, 2H), 6.36 (d, J = 16 Hz, 1H), 7.08 (m, 2H),
7.16 (m, 2H), 7.24 (m, 2H), 7.29 (m, 2H), 7.37Ϫ7.41 (m, 2H),
7.46Ϫ7.52 (m, 2H), 7.56 (m, 1H), 7.63 (m, 3H), 7.95 (s, 1H),
8.43 (m, 1H), 10.45 (s, 1H). MS (EI): m/z = 105 (89), 165
N-[3-Benzoyl-4-[(4-methylphenyl)acetylamino]phenyl]-4-
ethoxycinnamic acid amide (2i)
From 4-ethoxycinnamic acid chloride (253 mg, 1.2 mmol),
according to general procedure. Purification: MPLC EtOAc:
n-hexane 3:2. Yield: 392 mg (63%). Mp 175°C. IR (KBr): ν =
3310, 1680, 1670, 1645, 1620, 1605, 1515 cmϪ1 1H NMR
.
(DMSO-d6): δ 1.33 (t, J = 7 Hz, 3H), 2.25 (s, 3H), 3.38 (s, 2H),
4.07 (q, J = 7 Hz, 2H), 6.60 (d, J = 16 Hz, 1H), 6.95Ϫ6.97 (m,
2H), 7.00Ϫ7.02 (m, 2H), 7.04Ϫ7.06 (m, 2H), 7.48Ϫ7.53 (m,
5H), 7.61Ϫ7.64 (m, 2H), 7.68Ϫ7.70 (m, 2H), 7.76Ϫ7.78 (m,
(64), 212 (100), 508 (43) M+ 510 (18) M+. Anal. calcd. for
,
C31H25N2O3Cl: C, 73.15; H, 4.95; N, 5.50; found: C, 72.89;
H, 4.92; N, 5.22.
2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim