4
KOTHAYER ET AL.
N-(2-(4-chlorophenyl)-1-methyl-4-oxo-1,2-dihydroquinazolin-3[4H]-yl)
N-(1,2-dimethyl-4-oxo-1,2-dihydroquinazolin-3(4H)-yl)-2 phenylace-
tamide (4i): (74% yield). M.p. 165–167ꢀC. 1H NMR (CDCl3) δ 1.27 (3H,
d, J = 5.9, NCHCH3), 2.92 (3H, s, NCH3), 3.69 (2H, q, J = 15, CH2CO),
4.96 (1H, q, J = 5.7, NCHCH3), 6.65 (1H, d, J = 8.3, ph H), 6.84 (1H, t,
J = 7.4, ph H), 7.28–7.38 (6H, m, ph H), 7.89 (1H, d, J = 7.5, ph H),
9.28 (1H, s, NHCO, exch.). 13C NMR (CDCl3) δ 14.23 (NCHCH3),
35.56 (NCH3), 41.27 (CH2CO), 75.26 (NCHCH3), 112.87, 114.89,
118.16, 127.12, 128.73, 129.32, 134.34, 134.63, 146.78, 162.36,
170.00, 176.65. MS, m/z: 309 (M+), 310 (M++1). Analysis calcd. For
C18H19N3O2: C, 69.88; H, 6.19; N, 13.58. Found: C, 70.04; H,
6.29; N, 13.60.
benzamide (4d): (73% yield). M.p. 183–185ꢀC. 1H NMR (DMSO, d6) δ
2.81 (3H, s, NCH3), 5.96 (1H, s, NCHN), 6.76 (1H, d, J = 8.3, ph H), 6.88
(1H, t, J = 7.4, ph H), 7.35 (2H, d, J = 8.4, ph H), 7.42 (2H, d, J = 8.4, ph
H), 7.45–7.51 (3H, m, ph H), 7.59 (1H, t, J = 7.4, ph H), 7.81 (3H, t,
J = 6.5, ph H), 10.79 (1H, s, NHCO, exch.). 13C NMR (DMSO, d6) δ
35.54 (NCH3), 79.60 (NCHN), 113.04, 115.31, 118.57, 128.12, 128.52,
128.93, 128.97, 129.26, 132.46, 132.62, 134.13,135.15, 136.58,
147.30, 160.87, 165.94. MS, m/z: 391 (M+), 392 (M++1), 393 (M++2).
Analysis calcd. For C22H18ClN3O2: C, 67.43; H, 4.63; N, 10.72.
Found: C, 67.25; H, 4.83; N, 10.98.
N-(2-(4-fluorophenyl)-1-methyl-4-oxo-1,2-dihydroquinazolin-3[4H]-yl)
benzamide (4e): (79% yield). M.p. 179–181ꢀC. 1H NMR (DMSO, d6) δ
2.80 (3H, s, NCH3), 5.97 (1H, s, NCHN), 6.77 (1H, d, J = 8.3, ph H),
6.88 (1H, t, J = 7.2, ph H), 7.16–7.21 (2H, m, ph H), 7.37–7.40 (2H, m,
ph H), 7.45–7.51 (3H, m, ph H), 7.57–7.62 (1H, m, ph H), 7.81 (3H, d,
J = 7, ph H), 10.79 (1H, s, NHCO, exch.). 13C NMR (DMSO, d6) δ 35.50
(NCH3), 79.61 (NCHN), 113.00, 115.38, 115.89, 118.49, 128.13,
128.52, 128.90, 129.59 (d, J = 8.5), 132.55, 133.99, 134.02, 135.08,
147.41, 160.92, 161.70, 165.89. MS, m/z: 375 (M+), 376 (M++1),
377 (M++2). Analysis calcd. For C22H18FN3O2: C, 70.39; H, 4.83; N,
11.19. Found: C, 70.51; H, 5.10; N, 11.52.
N-(1-methyl-4-oxo-2-phenyl-1,2-dihydroquinazolin-3(4H)-yl)-2-phenyla-
cetamide (4j): (75% yield). M.p. 140–142ꢀC. 1H NMR (DMSO, d6) δ 2.76
(3H, s, NCH3), 3.48 (2H, s, CH2CO), 5.74 (2H, s, NCHN), 6.69 (1H, d,
J = 8.4, ph H), 6.84 (1H, t, J = 7.2, ph H), 7.20–7.45 (10H, m, ph H), 7.78
(1H, d, J = 7.6, ph H), 10.44 (1H, s, NHCO, exch.). 13C NMR (DMSO, d6)
δ 35.53 (NCH3), 40.73 (CH2CO), 80.02 (NCHN), 112.68, 114.44, 115.08,
118.25, 126.99, 127.09, 128.46, 128.70, 129.54, 135.04, 135.87,
137.55, 147.28, 150.68, 160.92, 169.47. MS, m/z: 371 (M+). Analysis
calcd. For C23H21N3O2: C, 74.37; H, 5.70; N, 11.31. Found: C, 74.07; H,
6.02; N, 11.22.
N-(2-(4-chlorophenyl)-1-methyl-4-oxo-1,2-dihydroquinazolin-3(4H)-
yl)-2-phenylacetamide (4k): (77% yield). M.p. 164–166ꢀC. 1H NMR
(CDCl3) δ 2.77 (3H, s, NCH3), 3.58 (2H, q, J = 14.6, CH2CO), 5.82 (1H,
s, NCHN), 6.62 (1H, d, J = 8.3, ph H), 6.88 (1H, t, J = 7.5, ph H), 6.96
(2H, d, J = 8.4, ph H), 7.13 (2H, d, J = 8.3, ph H), 7.26–7.33 (5H, m, ph
H), 7.43 (1H, t, J = 7.8, ph H), 7.75 (1H, d, J = 7.7, ph H), 8.86 (1H, s,
NHCO, exch.). 13C NMR (CDCl3) δ 35.62 (NCH3), 41.41(CH2CO),
79.46 (NCHN), 111.96, 113.79, 118.44, 127.16, 128.11, 128.70,
129.02, 129.08, 129.29, 134.34, 135.13, 135.24, 135.25, 147.09,
162.30, 169.59. MS, m/z: 405 (M+), 406 (M++1), 407 (M++2). Analysis
calcd. For C23H20ClN3O2: C, 68.06; H, 4.97; N, 10.35. Found: C,
68.17; H, 5.29; N, 10.64.
N-(2-(4-methoxyphenyl)-1-methyl-4-oxo-1,2-dihydroquinazolin-3(4H)-
yl)benzamide (4f): (83% yield). M.p. 162–164ꢀC. 1H NMR (DMSO, d6) δ
2.77 (3H, s, NCH3), 3.72 (3H, s, OCH3), 5.87 (1H, s, NCHN), 6.75 (1H,
d, J = 8.3, ph H), 6.85–6.90 (3H, m, ph H), 7.26 (2H, d, J = 8.7, ph H),
7.44–7.50 (3H, m, ph H), 7.58 (1H, t, J = 7.4, ph H), 7.79–7.83 (3H, m,
ph H), 10.77 (1H, s, NHCO, exch.). 13C NMR (DMSO, d6) δ 35.44
(NCH3), 55.56 (OCH3), 80.03 (NCHN), 112.87, 114.01, 114.24, 115.44,
118.27, 128.16, 128.48, 128.87, 129.67, 132.64, 134.97, 147.60,
160.21, 161.08, 165.87, 172.55. MS, m/z: 387 (M+), 388 (M++1). Analy-
sis calcd. For C23H21N3O3: C, 71.30; H, 5.46; N, 10.85. Found: C,
71.30; H, 5.46; N, 10.85.
N-(1-methyl-2-(4-nitrophenyl)-4-oxo-1,2-dihydroquinazolin-3(4H)-yl)
benzamide (4g): (88% yield). M.p. 177–179ꢀC. 1H NMR (DMSO, d6) δ
2.87 (3H, s, NCH3), 6.16 (1H, s, NCHN), 6.78 (1H, d, J = 8.3, ph H),
6.91 (1H, t, J = 7.4, ph H), 7.47–7.51 (3H, m, ph H), 7.57–7.64 (3H, m,
ph H), 7.82–7.84 (3H, m, ph H), 8.23 (2H, d, J = 8.7, ph H), 10.86 (1H,
s, NHCO, exch.). 13C NMR (DMSO, d6) δ 35.74 (NCH3), 79.27
(NCHN), 113.27, 115.44, 118.85, 124.18, 128.16, 128.63, 128.77,
128.95, 132.40, 132.65, 135.21, 144.81, 147.07, 148.37, 160.70,
165.98. MS, m/z: 402 (M+), 403 (M++1). Analysis calcd. For
C22H18N4O4: C, 65.66; H, 4.51; N, 13.92. Found: C, 65.52; H,
4.67; N, 14.08.
N-(2-(4-fluorophenyl)-1-methyl-4-oxo-1,2-dihydroquinazolin-3(4H)-yl)-
2-phenylacetamide (4l): (77% yield). M.p. 147–149ꢀC. 1H NMR (DMSO,
d6) δ 2.75 (3H, s, NCH3), 3.47 (2H, s, CH2CO), 5.78 (1H, s, NCHN), 6.71
(1H, d, J = 8.4, ph H), 6.85 (1H, t, J = 7.6, ph H), 7.14–7.32 (9H, m, ph
H), 7.44 (1H, t, J = 8.4, ph H), 7.78 (1H, d, J = 7.6, ph H), 10.43 (1H, s,
NHCO, exch.). 13C NMR (CDCl3) δ 35.61 (NCH3), 41.58 (CH2CO),
79.55 (NCHN), 111.88, 113.78, 115.69, 115.90, 118.30, 127.27,
128.60 (d, J = 8.4), 128.78, 129.19 (d, J = 19.0), 132.60, 134.13, 135.0,
147.14, 162.19, 164.42, 169.50. MS, m/z: 389 (M+), 390 (M++1),
407 (M++2). Analysis calcd. For C23H20FN3O2: C, 70.94; H, 5.18; N,
10.79. Found: C, 71.18; H, 5.29; N, 10.96.
N-(1-methyl-4-oxo-1,2-dihydroquinazolin-3(4H)-yl)-2-phenylaceta-
mide (4h): (87% yield). M.p. 157–159ꢀC. 1H NMR (DMSO, d6) δ 2.85
(3H, s, NCH3), 3.54 (2H, s, CH2CO), 4.62 (2H, s, NCH2N), 6.82–6.89
(2H, m, ph H), 7.25–7.33 (5H, m, ph H), 7.44 (1H, t, J = 7.2, ph H),
7.74 (1H, d, J = 7.6, ph H), 10.60 (1H, s, NHCO, exch.). 13C NMR
N-(2-(4-methoxyphenyl)-1-methyl-4-oxo-1,2-dihydroquinazolin-3(4H)-
yl)-2-phenylacetamide (4m): (81% yield). M.p. 136–138ꢀC. 1H NMR
(DMSO, d6) δ 2.73 (3H, s, NCH3), 3.48 (2H, s, CH2CO), 3.73 (3H, s,
OCH3), 5.69 (1H, s, NCHN), 6.78 (1H, d, J = 8.4, ph H), 6.82–6.89 (3H,
m, ph H), 7.14 (2H, d, J = 8.4, ph H), 7.24–7.34 (5H, m, ph H), 7.42 (1H,
t, J = 7.6, ph H), 7.78 (1H, d, J = 7.6, ph H), 10.41 (1H, s, NHCO, exch.).
13C NMR (DMSO, d6) δ 35.35 (NCH3), 40.62 (CH2CO), 55.60 (OCH3),
79.71 (NCHN), 112.47, 114.38, 115.03, 118.14, 126.97, 128.43,
128.48, 128.69, 129.53, 129.57, 134.98, 135.90, 147.33, 160.27,
160.98, 169.40. MS, m/z: 401 (M+), 402 (M++1). Analysis calcd. For
(DMSO, d6)
δ 35.75 (NCH3), 40.26 (CH2CO), 69.03 (NCH2N),
113.25, 116.22, 118.89, 127.05, 128.77, 128.80, 129.57, 134.54,
135.76, 150.08, 162.84, 170.00. MS, m/z: 295 (M+), 296 (M++1).
Analysis calcd. For C17H17N3O2: C, 69.14; H, 5.80; N, 14.23.
Found: C, 69.30; H, 5.97; N, 14.20.