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J. R. Brown et al. / Bioorg. Med. Chem. 19 (2011) 5585–5595
7.82–7.90 (1H, m), 8.38 (1H, s); ESI-HRMS m/z: [M+H]+ calcd:
327.1685, found: 327.1694.
4.2.16. 1-(2-Adamantyl)-3-tert-butylurea (16)
Yield: 185 mg (74%); Mp: >300 °C; 1H NMR (DMSO-d6): d 1.22
(9H, s), 1.49 (1H, s), 1.52 (1H, s), 1.65–1.86 (12H, m), 3.64 (1H, d,
J = 8.0 Hz), 5.70 (1H, s), 5.95 (1H, d, J = 8.5 Hz); ESI-HRMS m/z:
[M+H]+ calcd: 251.2124, found: 251.2121.
4.2.7. 1-Cyclooctyl-3-(2,3,4-trifluorophenyl)urea (7)
Yield: 371 mg (99%); Mp: 160–163 °C; 1H NMR (DMSO-d6): d
1.42–1.66 (13H, m), 1.76 (2H, t, J = 9.5 Hz), 6.63 (1H, d,
J = 8.0 Hz), 7.14–7.22 (1H, m), 7.84–7.93 (1H, m), 8.31 (1H, s);
ESI-HRMS m/z: [M+H]+ calcd: 301.1528, found: 301.1541.
4.2.17. 1-(2-Adamantyl)-3-propylurea (17)
Yield: 199 mg (84%); Mp: 194–196 °C; 1H NMR (DMSO-d6): d
0.84 (3H, t, J = 7.0 Hz), 1.37 (2H, sextuplet, J = 7.5 Hz), 1.49 (1H,
s), 1.52 (1H, s), 1.66–1.86 (12H, m), 2.94 (2H, q, J = 7.0 Hz), 3.66
(1H, d, J = 8.0 Hz), 5.81 (1H, t, J = 5.5 Hz), 6.02 (1H, d, J = 8.0 Hz);
ESI-HRMS m/z: [M+H]+ calcd: 237.1968, found: 237.1964.
4.2.8. 1-Cyclohexyl-3-(2,3,4-trifluorophenyl)urea (8)
Yield: 247 mg (63%); Mp: 188–191 °C; 1H NMR (DMSO-d6): d
1.30–1.28 (3H, m), 1.28–1.37 (2H, m), 1.48–1.57 (1H, m), 1.59–
1.70 (2H, m), 1.74–1.84 (2H, m), 3.42–3.52 (1H, m), 6.60 (1H, d,
J = 9.0 Hz), 7.15–7.23 (1H, m), 7.85–7.93 (1H, m), 8.33 (1H, s);
ESI-HRMS m/z: [M+H]+ calcd: 273.1215, found: 273.1203.
4.2.18. 1-(2-Adamantyl)-3-cyclohexylurea (18)
Yield: 234 mg (85%); Mp: >300 °C; 1H NMR (DMSO-d6): d 1.01–
1.32 (5H, m), 1.49 (1H, s), 1.52 (1H, s), 1.58–1.86 (17H, m), 3.65
(1H, d, J = 7.5 Hz), 5.75 (1H, d, J = 8.0 Hz), 5.98 (1H, d, J = 8.5 Hz);
ESI-HRMS m/z: [M+H]+ calcd: 277.2281, found: 277.2284.
4.2.9. 1-Cyclopentyl-3-(2,3,4-trifluorophenyl)urea (9)
Yield: 265 mg (71%); Mp: 184–186 °C; 1H NMR (DMSO-d6): d
1.30–1.43 (2H, m), 1.47–1.68 (4H, m), 1.77–1.89 (2H, m), 3.94
(1H, q, J = 6.5 Hz), 6.66 (1H, d, J = 7.5 Hz), 7.14–7.23 (1H, m),
7.84–7.94 (1H, m), 8.27 (1H, s); ESI-HRMS m/z: [M+H]+ calcd:
259.1059, found: 259.1046.
4.2.19. 1-(2-Adamantyl)-3-pentylurea (19)
Yield: 246 mg (93%); Mp: 151–153 °C; 1H NMR (CDCl3): d 0.93
(3H, t, J = 6.5 Hz), 1.30–1.39 (4H, m), 1.53 (2H, quintet, J = 7.5 Hz),
1.62 (2H, s), 1.76 (2H, s), 1.80 (1H, s), 1.86 (7H, t, J = 11.0 Hz),
1.93 (2H, s), 3.19 (2H, q, J = 7.0 Hz), 3.81 (1H, s), 4.26 (1H, s), 4.64
(1H, s); ESI-HRMS m/z: [M+H]+ calcd: 265.2281, found: 265.2297.
4.2.10. 1-(2-Adamantyl)-3-(4-cyanophenyl)urea (10)
Yield: 265 mg (90%); Mp: 217–219 °C; 1H NMR (DMSO-d6): d
1.57 (1H, s), 1.60 (1H, s), 1.68–1.89 (12H, m), 3.78 (1H, d,
J = 7.5 Hz), 6.67 (1H, d, J = 7.5 Hz), 7.55 (2H, d, J = 8.5 Hz), 7.67
(2H, d, J = 8.5 Hz), 8.92 (1H, s); ESI-HRMS m/z: [M+H]+ calcd:
296.1764, found: 296.1769.
4.2.20. 1-(2-Adamantyl)-3-hexylurea (20)
Yield: 200 mg (71%); Mp: 95–98 °C; 1H NMR (DMSO-d6): d 0.87
(3H, t, J = 6.5 Hz), 1.21–1.39 (8H, m), 1.49 (1H, s), 1.52 (1H, s), 1.66–
1.86 (12H, m), 2.97 (2H, q, J = 6.5 Hz), 3.65 (1H, d, J = 8.0 Hz), 5.78
(1H, t, J = 5.5 Hz), 6.01 (1H, d, J = 8.5 Hz); ESI-HRMS m/z: [M+H]+
calcd: 279.2437, found: 279.2443.
4.2.11. 1-(2-Adamantyl)-3-phenethylurea (11)
Yield: 229 mg (77%); Mp: 115–117 °C; 1H NMR (DMSO-d6): d
1.49 (1H, s), 1.51 (1H, s), 1.65–1.86 (12H, m), 2.68 (2H, t,
J = 7.0 Hz), 3.24 (2H, q, J = 7.0 Hz), 3.67 (1 H, d, J = 8.0 Hz), 5.82
(1H, t, J = 5.5 Hz), 6.11 (1H, d, J = 8.5 Hz), 7.21 (3H, d, J = 6.0 Hz),
7.30 (2H, t, J = 7.5 Hz); ESI-HRMS m/z: [M+H]+ calcd: 299.2124,
found: 299.2128.
4.2.21. 1-(2-Adamantyl)-3-heptylurea (21)
Yield: 292 mg (85%); Mp: 83–86 °C; 1H NMR (CDCl3): d 0.90
(3H, t, J = 6.0 Hz), 1.24–1.38 (8H, m), 1.52 (2H, t, J = 6.5 Hz), 1.48–
1.56 (2H, m), 1.75 (2H, s), 1.77 (1H, s), 1.86 (7H, t, J = 11.0 Hz),
1.93 (2H, s), 3.18 (2H, q, J = 6.5 Hz), 3.81 (1H, s), 4.34 (1H, s),
4.70 (1H, s); ESI-HRMS m/z: [M+H]+ calcd: 293.2594, found:
293.2582.
4.2.12. 1-(3-Acetylphenyl)-3-(2-adamantyl)urea (12)
Yield: 212 mg (72%); Mp: 213–215 °C; 1H NMR (DMSO-d6): d
1.57 (1H, s), 1.60 (1H, s), 1.69–1.91 (13H, m), 2.55 (3H, s), 3.79
(1H, d, J = 7.5 Hz), 6.50 (1H, d, J = 7.5 Hz), 7.38 (1H, t, J = 8.0 Hz),
7.50 (1H, d, J = 8.0 Hz), 7.58 (1H, d, J = 8.0 Hz), 8.00 (1H, s); ESI-
HRMS m/z: [M+H]+ calcd: 313.1917, found: 313.1909.
4.2.22. 1-(1-(1-Adamantyl)methyl)-3-(3-chloro-4-methyl-
phenyl)urea (22)
Yield: 301 mg (91%); Mp: 183–185 °C; 1H NMR (DMSO-d6): d
1.45 (5H, s), 1.56–1.76 (7H, m), 1.95 (3H, s), 2.23 (3H, s), 2.79
(2H, d, J = 6.0 Hz), 6.30–6.38 (1H, m), 7.04–7.10 (1H, m), 7.17
(1H, d, J = 8.0 Hz), 7.65–7.71 (1H, m), 8.46 (1H, s); ESI-HRMS m/z:
[M+H]+ calcd: 333.1734, found: 333.1730.
4.2.13. 1-(2-Adamantyl)-3-benzylurea (13)
Yield: 234 mg (81%); Mp: 205–207 °C; 1H NMR (DMSO-d6): d
1.51 (1H, s), 1.53 (1H, s), 1.66–1.88 (12H, m), 3.70 (1H, d,
J = 8.0 Hz), 4.21 (2H, d, J = 6.0 Hz), 6.18 (1H, d, J = 8.0 Hz), 6.27
(1H, t, J = 6.0 Hz), 7.24 (3H, q, J = 7.5 Hz), 7.33 (2H, t, J = 7.5 Hz);
ESI-HRMS m/z: [M+H]+ calcd: 285.1968, found: 285.1974.
4.2.23. 1-(3-Chloro-4-methylphenyl)-3-heptylurea (23)
Yield: 266 mg (90%); Mp: 99–101 °C; 1H NMR (CD3OD): d 0.93
(3H, t, J = 6.5 Hz), 1.29–1.42 (8H, m), 1.50–1.58 (2H, m), 2.30 (3H,
s), 3.19 (2H, t, J = 6.5 Hz), 7.09–7.17 (2H, m), 7.53 (1H, s); ESI-HRMS
m/z: [M+H]+ calcd: 283.1578, found: 283.1566.
4.2.14. 1-(2-Adamantyl)-3-(3-chloro-2-methylphenyl)urea (14)
Yield: 261 mg (82%); Mp: 254–257 °C; 1H NMR (DMSO-d6): d
1.57 (1H, s), 1.59 (1H, s), 1.70–1.86 (10H, m), 1.91 (2H, d,
J = 12.5 Hz), 2.26 (3H, s), 3.79 (1H, d, J = 7.5 Hz), 6.91 (1H, d,
J = 8.0 Hz), 7.03 (1H, d, J = 7.5 Hz), 7.10 (1H, t, J = 8.0 Hz), 7.84–
7.91 (2H, m); ESI-HRMS m/z: [M+H]+ calcd: 319.1578, found:
319.1569.
4.2.24. 1-(3-Chloro-4-methylphenyl)-3-cyclooctylurea (24)
Yield: 277 mg (94%); Mp: 179–182 °C; 1H NMR (DMSO-d6): d
1.42–1.68 (14H, m), 2.23 (3H, s), 3.65–3.73 (1H, m), 6.13 (1H, d,
J = 8.0 Hz), 7.05 (1H, d, J = 8.0 Hz), 7.16 (1H, d, J = 8.0 Hz), 7.65
(1H, s), 8.35 (1H, s); ESI-HRMS m/z: [M+H]+ calcd: 295.1578, found:
295.1555.
4.2.15. 1-(2-Adamantyl)-3-isopropylurea (15)
Yield: 162 mg (69%); Mp: 240–242 °C; 1H NMR (DMSO-d6): d
1.02 (6H, d, J = 6.5 Hz), 1.49 (1H, s), 1.52 (1H, s), 1.66–1.85 (12H,
m), 3.59–3.68 (2H, m), 5.66 (1H, d, J = 7.5 Hz), 5.95 (1H, d,
J = 8.0 Hz); ESI-HRMS m/z: [M+H]+ calcd: 237.1968, found:
237.1964.
4.2.25. 1-(3-Chloro-4-methylphenyl)-3-(3-fluorobenzyl)urea
(25)
Yield: 235 mg (80%); Mp: 146–148 °C; 1H NMR (CD3OD): d 2.30
(3H, s), 4.40 (2H, s), 7.00 (1H, t, J = 8.5 Hz), 7.08 (1H, d, J = 10.0 Hz),