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J = 8.4 Hz, 2H), 7.48–7.35 (m, 1H), 6.94 (d, J = 7.7 Hz, 2H), 6.90 (s,
1H), 6.83 (d, J = 8.5 Hz, 2H). LCMS: tR = 8.90 min. m/z = 257.1(M+H).
(dd, J = 13.3, 6.7 Hz, 2H), 2.73 (t, J = 7.6 Hz, 2H), 2.03–1.91 (m,
2H). LCMS: tR = 9.90 min. m/z = 256.2 (M+H).
4.2.10. 2-Hydroxy-N0-(4-methoxybenzylidene)benzohydrazide
TFA salt (A6)
4.2.17. 4-Hydroxy-N-(3-phenylpropyl)benzamide (A13)
General procedure B was used to couple 4-hydroxybenzoic acid
to 3-phenylpropylamine. The reaction was carried out at room
temperature overnight. A white solid was produced after purifica-
tion. 1H NMR (300 MHz, CDCl3) d 7.56–7.48 (m, 2H), 7.33–7.25 (m,
2H), 7.23–7.15 (m, 3H), 6.86–6.77 (m, 2H), 6.07 (s, 1H), 3.49 (dd,
J = 12.9, 6.9 Hz, 2H), 2.72 (t, J = 7.5 Hz, 2H), 2.03–1.90 (m, 2H).
LCMS: tR = 9.98 min. m/z = 256.3 (M+H).
General procedure A was used to form the imine bond using 4-
methoxybenzaldehyde. An off-white solid was produced after
purification. 1H NMR (300 MHz, DMSO) d 11.92 (s, 1H), 11.73 (s,
1H), 8.38 (s, 1H), 7.87 (d, J = 7.2 Hz, 1H), 7.68 (d, J = 8.9 Hz, 1H),
7.45–7.39 (m, 1H), 7.29–7.12 (m, 1H), 7.02 (d, J = 8.7 Hz, 2H),
6.94 (t, J = 7.8 Hz, 2H), 6.53 (s, 1H), 3.80 (s, 3H). LCMS:
tR = 10.34 min. m/z = 271.2 (M+H).
4.2.18. 2-Methyl-N-(3-phenylpropyl)benzamide (A14)
General procedure B was used to couple 2-methylbenzoic acid
to 3-phenylpropylamine. The reaction was carried out at room
temperature overnight and subsequently purified using HPLC, pro-
ducing an-off-white solid. 1H NMR (300 MHz, CDCl3) d 7.36–7.10
(m, 9H), 5.79 (s, 1H), 3.47 (dd, J = 13.6, 6.6 Hz, 2H), 2.73 (t,
J = 7.6 Hz, 2H), 2.43 (s, 3H), 2.00–1.89 (m, 2H). LCMS:
tR = 11.68 min. m/z = 254.2 (M+H).
4.2.11. 2-Hydroxy-N0-(4-nitrobenzylidene)benzohydrazide TFA
salt (A7)
General procedure A was used to form the imine bond using 4-
nitrobenzaldehyde and after purification, an off-white solid was
produced. 1H NMR (300 MHz, DMSO) d 12.30 (s, 1H), 11.69 (s,
1H), 10.96 (s, 1H), 8.03–7.90 (m, 1H), 7.90–7.82 (m, 1H), 7.71–
7.61 (m, 1H), 7.49–7.43 (m, 1H), 7.28–7.17 (m, 2H), 7.02–6.91
(m, 1H), 6.53 (s, 1H), 6.38 (d, J = 9.7 Hz, 1H). LCMS: tR = 10.68 min.
m/z = 285.9 (M+H).
4.2.19. 2-Methoxy-N-(3-phenylpropyl)benzamide (A15)
General procedure B was used to couple 2-methoxybenzoic acid
to 3-phenylpropylamine. The reaction was carried out at room
temperature overnight and produced a white solid. 1H NMR
(300 MHz, CDCl3) d 8.22 (dd, J = 7.8, 1.8 Hz, 1H), 7.90 (s, 1H),
7.48–7.40 (m, 1H), 7.34–7.24 (m, 2H), 7.25–7.15 (m, 3H), 7.13–
7.06 (m, 1H), 6.98 (d, J = 8.3 Hz, 1H), 3.96 (s, 3H), 3.50 (dd,
J = 12.9, 7.0 Hz, 2H), 2.74 (t, J = 7.5 Hz, 2H), 1.96 (dt, J = 14.7,
7.3 Hz, 2H). LCMS: tR = 11.90 min. m/z = 270.3 (M+H).
4.2.12. 2-Hydroxy-N-phenethylbenzamide (A8)
General procedure B was used to couple salicylic acid to phen-
ethylamine. The reaction was carried out at room temperature
overnight and after HPLC purification, a white solid was produced.
1H NMR (300 MHz, CDCl3) d 12.37 (s, 1H), 7.46–7.16 (m, 7H), 7.07–
6.98 (m, 1H), 6.89–6.79 (m, 1H), 6.33 (s, 1H), 3.81–3.71 (m, 2H),
2.98 (t, J = 6.8 Hz, 2H). LCMS: tR = 12.12 min. m/z = 242.3 (M+H).
4.2.13. 2-Hydroxy-N-(3-phenylpropyl)benzamide (A9)
General procedure B was used to couple salicylic acid to
3-phenylpropylamine. The reaction was carried out at room
temperature overnight. A white solid was produced after purifi-
cation. 1H NMR (300 MHz, CDCl3) d 12.42 (s, 1H), 7.44–7.17 (m,
6H), 7.12 (d, J = 7.9 Hz, 1H), 7.00 (d, J = 8.4 Hz, 1H), 6.82 (t,
J = 7.6 Hz, 1H), 6.29 (s, 1H), 3.53 (dd, J = 13.1, 6.4 Hz, 2H), 2.77
(t, J = 7.4 Hz, 2H), 2.02 (p, J = 7.2 Hz, 2H). LCMS: tR = 13.90 min.
m/z = 256.3 (M+H).
4.2.20. 2-Nitro-N-(3-phenylpropyl)benzamide (A16)
General procedure B was used to couple 2-nitrobenzoic acid to
3-phenylpropylamine. The reaction was carried out at room tem-
perature overnight which produced
(300 MHz, CDCl3) 8.04 (dd, J = 8.1, 1.1 Hz, 1H), 7.60 (dtd,
a
white solid. 1H NMR
d
J = 17.2, 7.5, 1.4 Hz, 2H), 7.43 (dd, J = 7.4, 1.5 Hz, 1H), 7.35–7.24
(m, 2H), 7.26–7.14 (m, 3H), 5.83 (s, 1H), 3.49 (dd, J = 13.1, 6.9 Hz,
2H), 2.75 (t, J = 7.4 Hz, 2H), 2.04–1.91 (m, 2H). LCMS:
tR = 11.01 min. m/z = 285.2 (M+H).
4.2.14. 2-Hydroxy-N-(4-phenylbutyl)benzamide (A10)
General procedure B was used to couple salicylic acid to 4-
phenylbutylamine. The reaction was carried out at room tempera-
ture overnight. An off-white solid was produced following HPLC
purification. 1H NMR (300 MHz, CDCl3) d 7.39 (ddd, J = 8.7, 7.5,
1.5 Hz, 1H), 7.34–7.24 (m, 3H), 7.20 (t, J = 6.7 Hz, 3H), 6.98 (d,
J = 8.4 Hz, 1H), 6.87–6.78 (m, 1H), 6.27 (s, 1H), 3.47 (dd, J = 12.8,
6.8 Hz, 2H), 2.68 (t, J = 7.1 Hz, 2H), 1.79–1.62 (m, 4H). LCMS:
tR = 13.90 min. m/z = 270.4 (M+H).
4.2.21. 2-Fluoro-N-(3-phenylpropyl)benzamide (A17)
General procedure B was used to couple 2-fluorobenzoic acid to
3-phenylpropylamine. The reaction was carried out at room tem-
perature overnight which produced a white solid after purification.
1H NMR (300 MHz, CDCl3) d 8.10 (td, J = 7.9, 1.9 Hz, 1H), 7.52–7.42
(m, 1H), 7.34–7.27 (m, 3H), 7.24–7.16 (m, 3H), 7.15–7.06 (m, 1H),
6.75 (s, 1H), 3.52 (q, J = 5.8 Hz, 2H), 2.74 (t, J = 7.4 Hz, 2H), 1.98 (dt,
J = 14.7, 7.4 Hz, 2H). LCMS: tR = 12.34 min. m/z = 258.3 (M+H).
4.2.22. 2-Chloro-N-(3-phenylpropyl)benzamide (A18)
4.2.15. N-(3-Phenylpropyl)benzamide (A11)
General procedure B was used to couple 2-chlorobenzoic acid to
3-phenylpropylamine. The reaction was carried out at room tem-
perature overnight. After HPLC purification, a white solid was pro-
duced. 1H NMR (300 MHz, CDCl3) d 7.67–7.54 (m, 1H), 7.42–7.10
(m, 8H), 6.24 (s, 1H), 3.50 (q, J = 10.0 Hz, 2H), 2.75 (t, J = 7.3 Hz,
2H), 2.05–1.89 (m, 2H). LCMS: tR = 11.57 min. m/z = 274.1 (M+H).
General procedure B was used to couple benzoic acid to 3-phen-
ylpropylamine. The reaction was carried out at room temperature
overnight and produced an off-white solid after preparative HPLC.
1H NMR (300 MHz, CDCl3) d 7.75–7.67 (m, 2H), 7.58–7.40 (m, 3H),
7.38–7.29 (m, 2H), 7.29–7.20 (m, 3H), 6.17 (s, 1H), 3.55 (dd,
J = 13.4, 6.5 Hz, 2H), 2.77 (t, J = 7.5 Hz, 2H), 2.08–1.94 (m, 2H).
LCMS: tR = 11.34 min. m/z = 240.3 (M+H).
4.2.23. 2-Bromo-N-(3-phenylpropyl)benzamide (A19)
General procedure B was used to couple 2-bromobenzoic acid
to 3-phenylpropylamine. The reaction was carried out at room
temperature overnight and produced a white solid 1H NMR
(300 MHz, CDCl3) d 7.58 (d, J = 7.0 Hz, 1H), 7.49 (dd, J = 7.6,
1.8 Hz, 1H), 7.39–7.15 (m, 7H), 6.02 (s, 1H), 3.50 (dd, J = 13.4,
6.7 Hz, 2H), 2.76 (t, J = 7.4 Hz, 2H), 1.97 (dt, J = 14.6, 7.2 Hz, 2H).
LCMS: tR = 12.01 min. m/z = 320.1 (M+H).
4.2.16. 3-Hydroxy-N-(3-phenylpropyl)benzamide (A12)
General procedure B was used to couple 3-hydroxybenzoic acid
to 3-phenylpropylamine. The reaction was carried out at room
temperature overnight and produced a white solid. 1H NMR
(300 MHz, CDCl3) d 7.45 (s, 1H), 7.35–7.26 (m, 2H), 7.22 (d,
J = 6.3 Hz, 4H), 7.08–6.95 (m, 2H), 6.51 (s, 1H), 6.10 (s, 1H), 3.51