Medicinal Chemistry Research
N-[(2-trifluoromethyl-6-methylthiomethyl)phenyl]-2-(N,N-
N-[(2-trifluoromethyl-6-methylthiomethyl)phenyl]-2-(1-
diethylamine) acetylamide hydrochloride (10b)
propylamine) propionamide hydrochloride (11a)
1
1
Yield 83%; mp 163–167 °C; H-NMR (500 MHz, CD3OD)
Yield 93%; mp 134–138 °C; H-NMR (500 MHz, CD3OD)
δ 1.36 (6H, t, J = 7.5 Hz, 2′-CH3), 1.99 (3H, s, –SCH3),
3.30 (4H, m, 1′-NCH2), 3.69 (2H, m, Ar–CH2S-), 4.20 (2H,
m, 2-COCH2), 7.54 (1H, m, ArH), 7.70 (1H, m, ArH), 7.74
(1H, m, ArH); IRνmax (KBr, cm−1) 3116, 2982, 1696, 1546,
1469, 1389; ES-MS (m/z) [M + H] +: 335; anal. calcd for
C15H21F3N2OS.HCl: C, 48.58; H, 5.98; N, 7.55. Found C,
48.28; H, 5.82; N, 7.59.
δ 1.03 (3H, t, J = 7.5 Hz, 3′-CH3), 1.70 (3H, m, 3-CH3),
1.79 (2H, m, 2′-CH2), 2.01 (3H, s, –SCH3), 3.01 (2H, t, J =
8.0 Hz, 1′-NCH2), 3.66 (2H, m, Ar–CH2S-), 4.18 (1H, m, 2-
COCH), 7.54 (1H, m, ArH), 7.72 (2H, m, ArH); IRνmax
(KBr, cm−1) 3121, 2971, 1697, 1538, 1323, 1163; ES-MS
(m/z) [M + H]+: 335; anal. calcd for C15H21F3N2OS.HCl:
C, 48.50; H, 5.98; N, 7.55. Found C, 48.45; H, 5.99;
N, 7.40.
N-[(2-trifluoromethyl -6-methylthiomethyl)phenyl]-2-
pyrrolidino acetylamide hydrochloride (10c)
N-[(2-trifluoromethyl-6-methylthiomethyl)phenyl]-2-(N,N-
diethylamine) propionamide hydrochloride (11b)
1
Yield 75%; mp 183-185 °C; H-NMR (500 MHz, CD3OD)
1
δ 2.13 (3H, s, –SCH3), 2.22 (4H, m, 2′-CH2, 3′-CH2), 3.30
(2H, m, 1′-NCH, 4′-NCH), 3.82 (2H, m, Ar–CH2S-), 3.86
(2H, m, 1′-NCH, 4′-NCH), 4.45 (2H, m, 2-COCH2), 7.66
(1H, m, ArH), 7.81 (1H, m, ArH), 7.88 (1H, m, ArH);
IRνmax (KBr, cm-1) 3490, 2971, 1692, 1535, 1322, 1162;
ES-MS (m/z) [M + H]+: 333; anal. calcd for
C15H19F3N2OS.HCl: C, 46.57; H, 5.73; N, 7.24. Found C,
46.43; H, 6.00; N, 7.26.
Yield 81%; mp 145-148 °C; H-NMR (500 MHz, CD3OD)
δ 1.50 (6H, t, J = 7.5 Hz, 2′-CH3), 1.74 (3H, m, 3-CH3),
2.02 (3H, s, –SCH3), 3.40 (4H, m, 1′-NCH2), 3.66 (2H, m,
Ar–CH2S-), 4.28 (2H, m, 2-COCH2), 7.54 (1H, m, ArH),
7.73 (2H, m, ArH); IRνmax (KBr, cm−1) 3146, 2983, 1697,
1529, 1468, 1323; ES-MS (m/z) [M + H]+: 349; anal. calcd
for C16H23F3N2OS.HCl: C, 52.10; H, 6.56; N, 7.60. Found
C, 52.19; H, 6.56; N, 7.43.
N-[(2-trifluoromethyl-6-methylthiomethyl)phenyl]-2-
N-[(2-trifluoromethyl-6-methylthiomethyl)phenyl]-2-
piperidino acetylamide hydrochloride (10d)
pyrrolidino propionamide hydrochloride (11c)
1
1
Yield 97%; mp 92–95 °C; H-NMR (500 MHz, CD3OD) δ
Yield 88%; mp 23–25 °C; H-NMR (500 MHz, CD3OD) δ
1.60 (2H, m, 2′-CH2), 1.88 (4H, m, 3′-CH2, 4′-CH2), 2.01
(3H, s, –SCH3), 3.15 (2H, m, 1′-NCH, 5‘-NCH), 3.63 (2H,
m, 1′-NCH, 5′-NCH), 3.71 (2H, m, Ar–CH2S-), 4.21 (2H,
m, 2-COCH2), 7.53 (1H, m, ArH), 7.69 (1H, m, ArH), 7.76
(1H, m, ArH); IRνmax (KBr, cm−1) 3490, 2971, 1692, 1535,
1322, 1162; ES-MS (m/z) [M + H] +: 347; anal. calcd for
C16H21F3N2OS.HCl: C, 47.94; H, 6.03; N, 6.99. Found C,
48.24; H, 6.32; N, 7.10.
1.77 (3H, m, 3-CH3), 2.05 (3H, s, –SCH3), 2.20 (4H, m, 2′-
CH2, 3′-CH2), 3.28 (2H, m, 1′-NCH, 4′-NCH), 3.66 (2H,
m, Ar–CH2S–), 3.67 (2H, m, 1′-NCH, 4′-NCH), 4.24 (2H,
m, 2-COCH2), 7.51 (1H, m, ArH), 7.72 (2H, m, ArH);
IRνmax (KBr, cm-1) 3416, 2963, 1693, 1536, 1322, 1163;
ES-MS (m/z) [M + H]+: 347; anal. calcd for
C16H21F3N2OS.HCl: C, 50.19; H, 5.79; N, 7.32. Found C,
50.45; H, 6.05; N, 7.34.
N-[(2-trifluoromethyl-6-methylthiomethyl)phenyl]-2-
N-[(2-trifluoromethyl-6-methylthiomethyl)phenyl]-2-
piperidino acetylamide hydrochloride (10e)
piperidino propionamide hydrochloride (11d)
1
Yield 85%; mp 98–101 °C; 1H-NMR (500 MHz, CD3OD) δ
2.01 (3H, s, –SCH3), 3.37 (2H, m, 1′-NCH), 3.60 (2H, m,
5′-NCH2), 3.72 (2H, m, Ar–CH2S–), 3.85 (2H, m, 2′-
OCH2), 4.05 (2H, m, 4′-OCH2), 4.32(2H, m, 2-COCH2),
7.54 (1H, m, ArH), 7.70 (1H, m, ArH), 7.76 (1H, m, ArH);
Yield 79%; mp 185-187 °C; H-NMR (500 MHz, CD3OD)
δ 1.60 (2H, m, 2′-CH2), 1.70 (3H, m, 3-CH3), 1.88 (4H, m,
3′-CH2, 4′-CH2), 2.02 (3H, s, –SCH3), 3.08 (2H, m, 1′-
NCH, 5‘-NCH), 3.63 (2H, m, 1′-NCH, 5‘-NCH), 3.70 (2H,
m, Ar–CH2S–), 4.20 (2H, m, 2-COCH2), 7.55 (1H, m,
ArH), 7.73 (2H, m, ArH); IRνmax (KBr, cm-1) 3111, 2980,
1692, 2543, 1702, 1532; ES-MS (m/z) [M + H]+: 362; anal.
calcd for C17H23F3N2OS.HCl: C, 49.94; H, 6.28; N, 7.28.
Found C, 49.67; H, 6.58; N, 7.06.
IRνmax (KBr, cm−1) 3434, 2974, 1693, 1537, 1323, 1164;
+
ES-MS (m/z) [M + H]
:
349; anal. calcd for
C15H19F3N2O2S.HCl: C, 45.74; H, 5.37; N, 7.11. Found C,
45.75; H, 5.66; N, 7.16.