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4.3.8. N-[1-Methyl-4-(3-tolylamino)pyrrole-2-carbonyl]-
pyrrolidine (23). Yield: 21%; pale yellow crystals (n-hex-
ane–ethyl acetate); mp 165 ꢂC; 1H NMR (500 MHz,
CDCl3) d 7.05 (dd, 1H, J = 8.5, 7.6 Hz), 6.59–6.55 (m,
4H), 6.38 (d, 1H, J = 1.7 Hz), 3.84 (s, 3H), 3.63 (br s,
4H), 2.26 (s, 3H), 1.92 (m, 4H). MS; m/z 283 (M+). Anal.
Calcd for C17H21N3O: C, 72.06; H, 7.47; N, 14.83.
Found: C, 71.76; H, 7.49; N, 14.62.
1H, J = 8.1 Hz), 6.84 (d, 1H, J = 8.1 Hz), 6.68 (t, 1H,
J = 7.2 Hz), 6.59 (d, 1H, J = 1.7 Hz), 6.39 (d, 1H,
J = 1.7 Hz), 4.91 (s, 1H), 3.85 (s, 3H), 3.63 (br s, 4H),
2.23 (s, 3H), 1.92 (m, 4H). MS (FAB) m/z 283 (M+);
HRMS (FAB, M) C16H21N3O, calcd for 283.1685,
found 283.1695.
4.3.15. N-[4-(2-Methoxyphenylamino)-1-methylpyrrole-2-
carbonyl]pyrrolidine (30). Yield: 58%; yellow oil; 1H
NMR (500 MHz, CDCl3) 6.87 (dd, 1H, J = 7.6,
2.1 Hz), 6.87–6.79 (m, 2H), 6.69 (dt, 1H, J = 7.6,
1.7 Hz), 6.61 (d, 1H, J = 1.7 Hz), 6.41 (d, 1H,
J = 1.7 Hz), 5.65 (s, 1H), 3.88 (s, 3H), 3.63 (br s, 4H),
1.91 (m, 4H). MS (FAB) m/z 299 (M+); HRMS (FAB,
M) C17H21N3O2, calcd for 299.1634, found 299.1591.
4.3.9. N-[4-(3-Methoxyphenylamino)-1-methylpyrrole-2-
carbonyl]pyrrolidine (24). Yield: 67%; khaki needles (n-
1
hexane–ethyl acetate); H NMR (500 MHz, CDCl3) d
7.02 (d, 1H, J = 8.1 Hz), 6.59 (d, 1H, J = 1.7 Hz), 6.39
(d, 1H, J = 2.1 Hz), 6.38 (dd, 1H, J = 8.1, 2.1 Hz), 6.34
(t, 1H, J = 2.1 Hz), 6.31 (dd, 1H, J = 8.1, 2.1 Hz), 3.83
(s, 3H), 3.74 (s, 3H), 3.63 (br s, 4H), 1.91 (m, 4H).
MS; m/z 299 (M+). Anal. Calcd for C17H21N3O2: C,
68.20; H, 7.07; N, 14.04. Found: C, 68.36; H, 7.19; N,
13.90.
4.3.16. N-[1-Methyl-4-(2-nitrophenylamino)pyrrole-2-carb-
onyl]pyrrolidine (31). Yield: 39%; vermillion oil;
1H NMR (500 MHz, CDCl3) d 9.12 (s, 1H), 8.16 (dd,
1H, J = 8.5, 1.2 Hz), 7.33 (t, 1H, J = 7.2 Hz), 7.09 (dd,
1H, J = 8.5, 1.2 Hz), 6.69–6.67 (m, 2H), 6.66 (d, 1H,
J = 1.2 Hz), 6.42 (d, 1H, J = 1.7 Hz), 3.88 (s, 3H), 3.64
(br, 4H), 1.94 (m, 4H). MS 314 (M+), 315 (MH+);
HRMS (FAB, M) C16H18N4O3, calcd for:314.1379,
found 314.1343.
4.3.10. N-[1-Methyl-4-(3-nitrophenylamino)pyrrole-2-carb-
onyl]pyrrolidine (25). Yield: 9.6%; vermillion oil;
1H NMR (500 MHz, CDCl3) d 7.56 (dd, 1H, J = 2.1,
2.3 Hz), 7.53 (dd, 1H, J = 8.1, 2.1 Hz), 7.26 (t, 1H,
J = 8.1 Hz), 7.00 (dd, 1H, J = 8.1, 2.1 Hz), 6.63 (d, 1H,
J = 1.7 Hz), 6.39 (d, 1H, J = 1.7 Hz), 5.41 (s, 1H), 3.86
(s, 3H), 3.64 (br s, 4H), 1.93 (m, 4H). MS; m/z 314
(M+), 315 (MH+); HRMS (FAB, M) C16H18N4O3, calcd
for 314.1379, found 314.1348.
4.3.17. N-[4-(2-Cyanophenylamino)-1-methylpyrrole-2-
carbonyl]pyrrolidine (32). Yield: 31% yellow oil; 1H
NMR (500 MHz, CDCl3) 7.40 (d, 1H, J = 6.8 Hz),
7.29 (t, 1H, J = 8.1 Hz), 6.84 (d, 1H, J = 8.4 Hz), 6.69
(t, 1H, J = 7.6 Hz), 6.64 (d, 1H, J = 1.9 Hz), 6.39 (d,
1H, J = 1.7 Hz), 5.87 (s, 1H), 3.86 (s, 3H), 3.63 (br s,
4H), 1.93 (m, 4H). MS (FAB) m/z 294 (M+), 295
(MH+),HRMS (FAB, M); C17H18N4O, calcd for:
294.1481, found 294.1489.
4.3.11. N-[4-(3-Cyanophenylamino)-1-methylpyrrole-2-carb-
onyl]pyrrolidine (26). Yield: 9.3%; yellow oil; 1H
NMR (500 MHz, CDCl3) 7.20 (dd, 1H, J = 8.1,
7.7 Hz), 6.97–6.90 (m, 3H), 6.60 (d, 1H, J = 1.7 Hz),
6.35 (d, 1H, J = 1.7 Hz), 5.32 (s, 1H), 3.85 (s, 3H),
3.63 (br s, 4H), 1.93 (m, 4H). MS; m/z 294 (M+), 295
(MÀH+); HRMS (FAB, M) C17H18N4O, calcd for
294.1481, found 294.1491.
4.3.18. N-[4-(2-Fluorophenylamino)-1-methylpyrrole-2-carb-
onyl]pyrrolidine (33). Yield: 22%; khaki crystals (n-
hexane–ethyl acetate); mp 105 ꢂC; 1H NMR
(500 MHz, CDCl3) d 7.01–6.97 (m, 1H), 6.94–6.88 (m,
2H), 6.67–6.63 (m, 1H), 6.62 (d, 1H, J = 1.7 Hz), 6.40
(d, 1H, J = 2.1 Hz), 5.30 (s, 1H), 3.85 (s, 3H), 3.64 (br
s, 4H), 1.92 (m, 4H). MS (FAB) m/z 287 (M+); HRMS
(FAB, M); C16H18N3OF, calcd for: 287.1434, found
287.1400.
4.3.12. N-[4-(3-Fluorophenylamino)-1-methylpyrrole-2-carb-
onyl]pyrrolidine (27). Yield: 32%; khaki crystals (n-
hexane–ethyl acetate); mp 117 ꢂC; 1H NMR
(500 MHz, CDCl3) 7.08 (ddd, 1H, J = 8.1, 8.1, 6.0 Hz),
6.60 (d, 1H, J = 1.7 Hz), 6.50 (dd, 1H, J = 8.1, 2.1 Hz),
6.46–6.37 (m, 4H), 3.85 (s, 3H), 3.63 (br s, 4H), 1.92
(m, 4H). MS (FAB) m/z 287 (M+). Anal. Calcd for
C16H18N3OF: C, 66.88; H, 6.31; N, 14.62. Found: C,
66.82; H, 6.50; N, 14.36.
4.3.19.
N-[4-(2-Clorophenylamino)-1-methylpyrrole-2-
carbonyl]pyrrolidine (34). Yield: 27%; khaki crystals (n-
hexane–ethyl acetate); mp 124 ꢂC; 1H NMR
(500 MHz, CDCl3) d 7.25 (dd, 1H, J = 7.2, 1.2 Hz),
7.04 (dt, 1H, J = 8.1, 1.2 Hz), 6.85 (dd, 1H, J = 8.5,
1.2 Hz), 6.66–6.63 (m, 2H), 6.40 (d, 1H, J = 2.1 Hz),
5.64 (s, 1H), 3.85 (s, 3H), 3.63 (br s, 4H), 1.92 (m,
4H). MS (FAB) m/z 303, 305 (M+), 304, 306 (MÀH+).
Anal. Calcd for C16H18N3OCl: C, 63.26; H, 5.97; N,
13.83. Found: C, 62.99; H, 5.98; N, 13.78.
4.3.13. N-[4-(3-Clorophenylamino)-1-methylpyrrole-2-carb-
onyl]pyrrolidine (28). Yield: 18%; khaki crystals (n-
hexane–ethyl acetate); mp 157 ꢂC; 1H NMR
(500 MHz, CDCl3) d 7.04 (dd, 1H, J = 8.14, 7.93 Hz),
6.72 (dd, 1H, J = 2.1, 2.1 Hz), 6.67 (ddd, 1H, J = 7.9,
1.8, 0.9 Hz), 6.60 (ddd, 1H, J = 8.2, 2.1, 0.9 Hz), 6.58
(d, 1H, J = 1.8 Hz), 6.36 (d, 1H, J = 2.1 Hz), 3.84 (s,
3H), 3.62 (br s, 4H), 1.92 (m, 4H). MS (FAB) m/z 303,
305 (M+), 304, 306 (MÀH+); HRMS (FAB, M)
C16H18N3OCl, calcd for 303.1138, found 303.1151.
4.3.20. N-[4-(3,5-Dimethylphenylamino)-1-methylpyrrole-
2-carbonyl]pyrrolidine (35). Yield: 23%; white crystals (n-
1
hexane–ethyl acetate); mp 134 ꢂC; H NMR (500 MHz,
4.3.14. N-[1-Methyl-4-(2-tolylamino)pyrrole-2-carbonyl]-
pyrrolidine (29). Yield: 6.0%; yellow oil; 1H NMR
(500 MHz, CDCl3) 7.07 (d, 1H, J = 7.7 Hz), 7.04 (t,
CDCl3) d 6.91 (s, 1H), 6.50–6.47 (m, 3H), 6.40 (s, 1H),
3.84 (s, 3H), 3.68 (br s, 4H), 2.22 (s, 3H), 1.91 (br s,
4H). MS (FAB) m/z 297 (M+), 298 (MÀH+). Anal.