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HETEROCYCLES, Vol. 65, No. 11, 2005
organic extracts were washed with water (3×25 mL) and brine (25 mL), dried (sodium sulfate) and
evaporated in vacuum yielded the reduction compound (4) as oil. The crude product was recrystallized
from ethyl acetate/petroleum ether (4:1) to give the solid compound.
4a: 90%; mp 112-113 °C; 1H NMR (DMSO-d6) δ 9.03 (s, 1H, NH), 7.53 (d, 1H, J=8.8, ArH), 6.87 (d, 1H,
J=8.4, ArH), 6.45 (s, 1H, ArH), 5.29 (s, 2H, NH2), 4.59 (q, 1H, J=7.3, CH), 1.76 (d, 3H, J=7.2, CH3).
Anal. Calcd for C9H10N2OCl2: C, 46.35; H, 4.29; N, 12.02. Found: C, 46.41; H, 4.20; N, 12.07.
4b: 93%; mp 69-100 °C; 1H NMR (DMSO-d6) δ 9.13 (s, 1H, NH), 7.28 (d, 1H, J=8.8, ArH), 6.77 (d, 1H,
J=8.4, ArH), 6.61 (s, 1H, ArH), 5.27 (s, 2H, NH2), 4.59 (q, 1H, J=3.3, CH), 1.76 (d, 3H, J=7.2, CH3).
Anal. Calcd for C9H10N2OBrCl: C, 38.93; H, 3.60; N, 10.09. Found: C, 39.01; H, 3.58; N, 10.00.
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4c: 90%; mp 107-108 °C; H NMR (DMSO-d6) δ 9.13 (s, 1H, NH), 7.68 (q, 1H, J=6.8, ArH), 6.66 (m,
1H, ArH), 6.25 (q, 1H, J=7.2, ArH), 5.23 (s, 2H, NH2), 4.57 (q, 1H, J=6.3, CH), 1.83 (d, 3H, J=8.4, CH3).
Anal. Calcd for C9H10N2OClF: C, 49.88; H, 4.62; N, 12.93. Found: C, 49.93; H, 4.74; N, 12.02.
4d: 92%; mp 155-156 °C; 1H NMR (DMSO-d6) δ 9.13 (s, 1H, NH), 7.28 (s, 1H, ArH), 6.18 (s, 1H, ArH),
5.27 (s, 2H, NH2), 4.59 (q, 1H, J=7.7, CH), 2.35 (s, 3H, CH3), 1.76 (d, 3H, J=8.0, CH3). Anal. Calcd for
C10H12N2OCl2: C, 48.58; H, 4.86; N, 11.34. Found: C, 48.66; H, 4.89; N, 11.27.
4e: 83%; mp 131-132 °C; 1H NMR (DMSO-d6) δ 9.09 (s, 1H, NH), 7.08 (q, 1H, J=5.4, ArH), 6.17 (q, 1H,
J=5.1, ArH), 5.27 (s, 2H, NH2), 4.59 (q, 1H, J=7.5, CH), 1.76 (d, 3H, J=9.6, CH3). Anal. Calcd for
C9H9N2OClF2: C, 46.06; H, 3.84; N, 11.94. Found: C, 46.13; H, 3.76; N, 11.92.
4f: 89%; mp 145-146 °C; 1H NMR (DMSO-d6) δ 9.19 (s, 1H, NH), 7.27 (d, 1H, J=8.4, ArH), 6.40 (q, 1H,
J=7.5, ArH), 6.24 (s, 1H, ArH), 5.26 (s, 2H, NH2), 4.54 (q, 1H, J=6.3, CH), 2.35 (s, 3H, CH3), 1.76 (d,
3H, J=8.8, CH3). Anal. Calcd for C10H13N2OCl: C, 56.47; H, 6.12; N, 13.18. Found: C, 56.55; H, 6.08; N,
13.27.
4g: 83%; mp 96-97 °C; 1H NMR (DMSO-d6) δ 9.35 (s, 1H, NH), 7.47 (d, 1H, J=1.2, ArH), 7.26 (s, 1H,
ArH), 6.87 (d, 1H, J=8.4, ArH), 5.41 (s, 2H, NH2), 4.58 (q, 1H, J=8.7, CH), 2.57 (t, 2H, J=6.5, CH2),
1.78 (d, 3H, J=9.2, CH3), 1.59 (m, 2H, CH2), 1.29 (m, 2H, CH2), 0.89 (t, 3H, J=5.3, CH3). Anal. Calcd for
C13H19N2OCl: C, 61.30; H, 7.47; N, 11.00. Found: C, 61.38; H, 7.40; N, 10.95.
4h: 85%; mp 137-138 °C; 1H NMR (DMSO-d6) δ 9.50 (s, 1H, NH), 7.28 (d, 1H, J=2.0, ArH), 6.71 (q, 1H,
J=5.1, ArH), 6.04 (d, 1H, J=8.8, ArH), 5.17 (s, 2H, NH2), 4.58 (q, 1H, J=7.7, CH), 3.75 (s, 3H, CH3),
1.75 (d, 3H, J=7.2, CH3). Anal. Calcd for C10H13N2O2Cl: C, 52.52; H, 5.69; N, 12.25. Found: C, 52.48; H,
5.76; N, 12.29.
4i: 90%; mp 164-165 °C; 1H NMR (DMSO-d6) δ 9.68 (s, 1H, NH), 7.29 (d, 1H, J=2.8, ArH), 7.06 (d, 1H,
J=3.6, ArH), 6.98 (q, 1H, J=7.1, ArH), 5.26 (s, 2H, NH2), 4.58 (q, 1H, J=6.3, CH), 4.04 (q, 2H, J=3.4,
CH2), 1.69 (d, 3H, J=7.2, CH3), 1.33 (t, 3H, J=8.9, CH3). Anal. Calcd for C11H15N2O2Cl: C, 54.43; H,
6.19; N, 11.55. Found: C, 54.38; H, 6.25; N, 11.64.