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J = 14.6 Hz), 4.02 (1H, d, J = 14.3 Hz), 4.36–4.48 (2H, qd, J = 7.0,
3.0 Hz), 5.17–5.23 (2H, d, J = 10.0 Hz), 5.81–5.96 (1H, m), 7.26–
7.32 (2H, m), 7.44 (1H, td, J = 7.6, 1.9 Hz), 7.85 (1H, d, J = 1.9 Hz);
13C NMR (270 MHz; CDCl3): d 25.82, 25.91, 26.53, 30.78, 36.43,
50.64, 52.22, 54.91, 117.80, 121.41, 126.05, 129.86, 131.10,
132.02, 133.03, 140.31, 167.45, 168.38; Anal. Calcd for
d, J = 8.0 Hz), 7.37 (1H, t, J = 7.6 Hz), 7.56 (1H, t, J = 7.7 Hz), 7.97
(1H, d, J = 7.7 Hz); 13C NMR (400 MHz; CDCl3): d 14.10, 25.68,
26.35, 30.61, 36.32, 50.12, 51.53, 54.71, 61.82, 120.98, 126.23,
129.55, 130.96, 132.12, 139.85, 167.21, 168.57, 168.63; Anal. Calcd
for C20H26N2O4: C, 67.01; H, 7.32; N, 7.81. Found: C, 67.04; H, 7.43;
N, 7.79.
C19H24N2O2: C, 73.03; H, 7.75; N, 8.96. Found: C, 73.03; H, 7.59;
N, 9.02.
3.6.12. Ethyl-2-(7-chloro-4-(cyclohexylmethyl)-2,5-dioxo-
2,3,4,5-tetrahydro benzo[e][1,4]diazepin-1-yl)acetate (5l)
Reagents 4l (1.52 g), cyclohexanemethylamine (0.74 g), bromo-
acetyl bromide (1.51 g) and DBU (0.90 g) gave 5l (1.53 g, 69%)
when recrystallised from ethylacetate/hexane: mp 120–122 °C;
1H NMR (270 MHz; CDCl3): d 1.02–1.08 (2H, m), 1.18–1.32 (6H,
m), 1.64–1.78 (6H, m), 3.37–3.45 (1H, dd, J = 13.5, 7.9 Hz), 3.55–
3.63 (1H, dd, J = 13.4, 6.9 Hz), 3.71 (1H, d, J = 14.7 Hz), 4.06 (1H,
d, J = 14.7 Hz), 4.21–4.29 (3H, m), 4.57 (1H, d, J = 17.4 Hz), 7.10
(1H, d, J = 8.8 Hz), 7.42 (1H, dd, J = 8.7, 2.6 Hz), 7.86 (1H, d,
J = 2.5 Hz); 13C NMR (400 MHz; CDCl3): d 14.10, 25.65, 25.70,
26.31, 30.58, 36.29, 50.07, 51.39, 54.82, 61.96, 122.56, 130.72,
130.93, 131.98, 132.09, 138.34, 165.92, 168.23, 168.40; Anal. Calcd
for C20H25N2O4Cl: C, 61.13; H, 6.42; N, 7.13; Cl, 9.02. Found: C
61.21; H, 6.60; N, 7.02; Cl, 8.86.
3.6.8. 1-Allyl-7-chloro-4-(cyclohexylmethyl)-3,4-dihydro-1H-
benzo[e][1,4]diazepine-2,5-dione (5h)
Reagents 4h (1.34 g), cyclohexanemethylamine (0.74 g), bromo-
acetyl bromide (1.51 g) and DBU (0.90 g) gave 5h (1.25 g, 64%)
when recrystallised from methanol: mp 101–102 °C; 1H NMR
(270 MHz; CDCl3): d 0.88–1.08 (2H, m), 1.30–1.24 (3H, m), 1.59–
1.80 (6H, m), 3.42–3.57 (2H, m), 3.69 (1H, d, J = 14.6 Hz), 3.99
(1H, d, J = 14.6 Hz), 4.34 (2H, qd, J = 14.3, 7.0 Hz), 5.14–5.19 (1H,
d, J = 12.2 Hz), 5.21–5.23 (1H, d, J = 5.7 Hz), 5.78–5.93 (1H, m),
7.23 (1H, d, J = 8.6 Hz), 7.39 (1H, dd, J = 8.7, 2.4 Hz), 7.83 (1H, d,
J = 2.4 Hz); 13C NMR (270 MHz; CDCl3): d 25.78, 25.87, 26.47,
30.74, 36.43, 50.60, 52.05, 54.99, 118.10, 122.90, 130.84, 131.19,
131.66, 132.02, 132.73, 138.74, 166.34, 167.94; Anal. Calcd for
C19H23N2O2Cl: C, 65.78; H, 6.69; N, 8.07; Cl, 10.22. Found: C,
66.07; H, 6.64; N, 7.98; Cl, 9.96.
3.6.13. 1-Cyclopropylmethyl-4-(cyclohexylmethyl)-3,4-dihydro-
1H-benzo[e][1,4]diazepine-2,5-dione (5m)
3.6.9. 1-Butyl-4-(cyclohexylmethyl)-3,4-dihydro-1H-benzo[e]
[1,4]diazepine-2,5-dione (5i)
Reagents 4m (1.23 g), cyclohexanemethylamine (0.74 g),
bromoacetyl bromide (1.51 g) and DBU (0.90 g) gave 5m (0.31 g,
17%) when purified by column chromatography, mobile phase
DCM: mp 123–125 °C; 1H NMR (400 MHz; CDCl3): d 0.15–0.23
(2H, m), 0.39–0.47 (2H, m), 0.91–0.99 (1H, m), 0.99–1.10 (2H, m),
1.14–1.33 (3H, m), 1.66–1.79 (5H,m), 1.79–1.86 (1H, m), 3.37
(1H, dd, J = 13.4, 6.1 Hz), 3.61 (1H, dd, J = 14.3, 6.1 Hz), 3.67 (1H,
dd, J = 13.4, 8.9 Hz), 3.68 (1H, d, J = 14.5 Hz), 4.01 (1H, d,
J = 14.5 Hz), 4.06 (1H, dd, J = 14.3, 8.0 Hz), 7.31 (1H, m), 7.32 (1H,
m), 7.50 (1H, dt, J = 8.2, 1.7 Hz), 7.89 (1H, dd, J = 8.1, 1.8 Hz); 13C
NMR (400 MHz; CDCl3): d 4.12, 4.20, 10.09, 25.85, 25.94, 26.55,
30.72, 30.88, 36.53, 51.59, 52.44, 54.99, 122.18, 126.05, 130.66,
131.08, 131.86, 140.01, 167.43, 168.75, 168.40; Anal. Calcd for
Reagents 4i (1.24 g), cyclohexanemethylamine (0.74 g), bromo-
acetyl bromide (1.51 g) and DBU (0.90 g) gave 5i (0.58 g, 31%)
when recrystallised from ethylacetate: mp 87–88 °C; 1H NMR
(400 MHz; CDCl3): d 0.82 (3H, t, J = 7.0 Hz), 0.93–1.09 (2H, m),
1.14–1.29 (5H, m), 1.41–1.59 (2H, sextet, J = 8.1 Hz), 1.63–1.85
(6H, m), 3.43 (1H, q, J = 6.7 Hz), 3.53–3.61 (2H, m), 3.64 (1H, d,
J = 14.5 Hz), 3.95 (1H, d, J = 14.5 Hz), 4.24 (1H, quintet, J = 7.0 Hz),
7.22 (1H, d, J = 7.8 Hz), 7.27 (1H, t, J = 7.7 Hz), 7.49 (1H, td, J = 7.9,
1.6 Hz), 7.84 (1H, dd, J = 7.8, 1.6 Hz); 13C NMR (400 MHz; CDCl3):
d 13.74, 19.93, 25.82, 26.42, 29.89, 30.70, 36.43, 46.77, 52.35,
54.82, 121.68, 125.92, 130.36, 130.98, 131.86, 139.72, 167.33,
168.59; Anal. Calcd for C20H28N2O2: C, 73.12; H, 8.60; N, 8.52.
Found: C, 73.08; H, 8.34; N, 8.57.
C20H26N2O2: C, 73.59; H, 8.03; N, 8.58. Found: C 73.62; H, 8.25;
N, 8.50.
3.6.10. 1-Butyl-7-chloro-4-(cyclohexylmethyl)-3,4-dihydro-1H-
benzo[e][1,4]diazepine-2,5-dione (5j)
3.6.14. 1-Cyclopropylmethyl-7-chloro-4-(cyclohexylmethyl)-
3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione (5n)
Reagents 4j (1.43 g), cyclohexanemethylamine (0.74 g), bromo-
acetyl bromide (1.51 g) and DBU (0.90 g) gave 5j (1.07 g, 52%)
when recrystallised from ethylacetate/hexane: mp 80–82 °C; 1H
NMR (270 MHz CDCl3): d 0.81–0.86 (3H, t, J = 7.3 Hz), 0.97–1.08
(2H, quintet, J = 6.0 Hz), 1.13–1.29 (4H, sextet, J = 7.4 Hz), 1.39–
1.56 (2H, m), 1.68–1.79 (7H, m), 3.40–3.58 (3H, m), 3.65 (1H, d,
J = 14.5 Hz), 3.93 (1H, d, J = 14.5 Hz), 4.21–4.32 (1H, quintet,
J = 7.0 Hz), 7.17 (1H, d, J = 8.8 Hz), 7.42 (1H, dd, J = 8.8, 2.6 Hz),
7.83 (1H, d, J = 2.6 Hz); 13C NMR (270 MHz; CDCl3): d 14.26,
20.50, 26.25, 26.36, 26.94, 30.39, 31.24, 36.97, 47.35, 52.77,
55.47, 123.73, 131.33, 131.60, 131.70, 132.45, 138.80, 165.80,
168.72; Anal. Calcd for C20H27N2O2 Cl: C, 66.19; H, 7.51; N, 7.72;
Cl, 9.77. Found: C, 65.88; H, 7.48; N, 7.61; Cl, 10.06.
Reagents 4n (1.42 g), cyclohexanemethylamine (0.74 g), bromo-
acetyl bromide (1.51 g) and DBU (0.90 g) gave 5n (71%) when
purified by column chromatography, mobile phase DCM: mp
123–125 °C; 1H NMR (400 MHz; CDCl3): d 0.15–0.23 (2H, m),
0.39–0.47 (2H, m), 0.91–0.99 (1H, m), 0.99–1.10 (2H, m), 1.14–
1.33 (3H, m), 1.66–1.79 (5H,m), 1.79–1.86 (1H, m), 3.37 (1H, dd,
J = 13.4, 6.1 Hz), 3.61 (1H, dd, J = 14.3, 6.1 Hz), 3.67 (1H, dd,
J = 13.4, 8.9 Hz), 3.68 (1H, d, J = 14.5 Hz), 4.01 (1H, d, J = 14.5 Hz),
4.06 (1H, dd, J = 14.3, 8.0 Hz), 7.31 (1H, m), 7.32 (1H, m), 7.50
(1H, dt, J = 8.2, 1.7 Hz), 7.89 (1H, dd, J = 8.1, 1.8 Hz); 13C NMR
(400 MHz; CDCl3): d 4.12, 4.20, 10.09, 25.85, 25.94, 26.55, 30.72,
30.88, 36.53, 51.59, 52.44, 54.99, 122.18, 126.05, 130.66, 131.08,
131.86, 140.01, 167.43, 168.75, 168.40; Anal. Calcd for
C20H26N2O2: C, 66.56; H, 6.98; N, 7.76; Cl, 9.82; Found: C 66.10;
3.6.11. Ethyl-2-(4-(cyclohexylmethyl)-2,5-dioxo-2,3,4,5-tetra-
hydrobenzo[e][1,4]diazepin-1-yl)acetate (5k)
H, 6.84; N, 7.82, Cl, 10.35.
Reagents 4k (1.33 g), cyclohexanemethylamine (0.74 g), bromo-
acetyl bromide (1.51 g) and DBU (0.90 g) gave 5k (0.65 g, 32%)
when recrystallised from ethylacetate/hexane: mp 96–98 °C; 1H
NMR (270 MHz; CDCl3): d 1.12–1.15 (2H, m), 1.28–1.41 (6H, m),
1.77 (6H, m), 3.51–3.71 (1H, dd, J = 13.4, 8.1 Hz), 3.64–3.72 (1H,
dd, J = 13.4, 6.9 Hz), 3.80 (1H, dd, J = 14.6 Hz), 4.18 (1H, dd,
J = 14.6 Hz), 4.31–4.40 (3H, m), 4.69 (1H, d, J = 13.6 Hz), 7.24 (1H,
3.6.15. 1-Benzyl-4-(cyclohexylmethyl)-3,4-dihydro-1H-benzo[e]
[1,4]diazepine-2,5-dione (5o)
Reagents 4o (1.43 g), cyclohexanemethylamine (0.74 g), bromo-
acetyl bromide (1.51 g) and DBU (0.90 g) gave 5o (0.90 g, 44%)
when recrystallised from ethylacetate/hexane: mp 132–133 °C
(lit. 117–120 °C14); 1H NMR (270 MHz; CDCl3): d 0.91–1.08 (2H,
quintet, J = 11.8 Hz), 1.13–1.21 (3H, m), 1.54–1.82 (6H, m),