ACCEPTED MANUSCRIPT
4.1.14.6.1-methyl-8-(p-tolylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (13e). Yellow solid.
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Yield: 45%. H-NMR (CDCl3, 400 MHz) δ: 8.29 (s, 1H, -N=CH-), 7.65 (d, J = 7.8 Hz, 2H, HAr), 7.35 (d, J =7.8
Hz, 2H, HAr), 4.44 (s, 3H, -NCH3), 3.10 (t, J = 8.0 Hz, 2H, -N=CHCCH2CH2-), 3.00 (s, 3H, Ar-CH3), 2.88 (t, J =
8.0 Hz, 2H, -N=CHCCH2CH2-). 13C-NMR (DMSO-d6, 100 MHz): δ 163.9, 159.2, 158.2, 140.9, 140.7, 130.1,
128.9, 121.9, 119.7, 32.0, 25.0, 20.7; HRMS (ESI): calcd for C20H22N8O2, [(M+H)+], 407.1944, found 407.1939.
4.1.14.7.8-((4-(dimethylamino)phenyl)amino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamid
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e (13f). Yellow solid. Yield: 55%. H-NMR (CDCl3, 400 MHz) δ: 9.19 (s, 1H, Ar-NH-), 8.32 (s, 1H, -N=CH-),
7.45 (d, J = 7.6 Hz, 2H, HAr), 6.72 (d, J = 7.6 Hz, 2H, HAr), 4.32 (s, 3H, -NCH3), 3.02 (s, 6H, -N(CH3)2), 2.95 (t, J
= 8.0 Hz, 2H, -N=CHCCH2CH2-), 2.80 (t, J = 8.0 Hz, 2H, -N=CHCCH2CH2-). 13C-NMR (DMSO-d6, 100 MHz): δ
162.2, 159.6, 146.9, 138.0, 130.6, 126.2, 121.7, 117.8, 113.3, 66.8, 60.7, 24.5; HRMS (ESI): calcd for C19H21N7O,
[(M+H)+], 364.1886, found 364.1878.
4.1.14.8.1-methyl-8-((4-(piperazin-1-yl)phenyl)amino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide
(13g). Yellow solid. Yield: 63%. 1H-NMR (CDCl3, 400 MHz) δ: 9.30(s, 1H, Ar-NH-), 8.35 (s, 1H, -N=CH-), 7.55
(d, J = 7.8 Hz, 2H, HAr), 7.00 (d, J = 7.8 Hz, 2H, HAr), 4.32 (s, 3H, -NCH3), 3.00 (t, J = 8.0 Hz, 4H,
Ar-NCH2CH2N), 2.79 (t, J = 8.0 Hz, 2H, -N=CHCCH2CH2-), 2.89 (t, J = 8.0 Hz, 2H, -N=CHCCH2CH2-), 2.78 (t,
J = 8.0 Hz, 4H, Ar-NCH2CH2N). 13C-NMR (DMSO-d6, 100 MHz): δ 162.2, 159.6, 146.9, 138.0, 130.6, 126.2,
121.7, 117.8, 113.3, 66.8, 60.7, 24.5, 19.8; HRMS (ESI): calcd for C21H24N8O, [(M+H)+], 405.2151, found
405.2148.
4.1.14.9.
1-methyl-8-((4-morpholinophenyl)amino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide
(13h). Yellow solid. Yield: 43%. 1H-NMR (CDCl3, 400 MHz) δ: 9.29 (s, 1H, Ar-NH-), 8.35 (s, 1H, -N=CH-), 7.53
(d, J = 7.8 Hz, 2H, HAr), 6.90 (d, J = 7.8 Hz, 2H, HAr), 4.32 (s, 3H, -NCH3), 3.00 (t, J = 8.0 Hz, 4H,
Ar-NCH2CH2O), 2.87 (t, J = 8.0 Hz, 4H, Ar-NCH2CH2O), 2.99 (t, J = 8.0 Hz, 2H, -N=CHCCH2CH2-), 2.89 (t, J =
8.0 Hz, 2H, -N=CHCCH2CH2-). 13C-NMR (DMSO-d6, 100 MHz): δ 166.8, 162.7, 161.6, 159.1, 139.6, 138.6,
128.4, 125.3, 125.1, 118.4, 116.2, 113.6, 66.3, 53.3, 37.5, 28.3; HRMS (ESI): calcd for C21H23N7O2, [(M+H)+],
406.1992, found 406.1982.
4.1.14.10 . 8-((5-(dimethylamino)pyridin-2-yl)amino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-
1
carboxamide (13k). Yellow solid. Yield: 56%. H-NMR (CDCl3, 400 MHz) δ: 9.51 (s, 1H, Pyr-NH), 8.41 (s, 1H,
-N=CH-), 7.87 (s, 1H, Pyr-H), 7.28 (d, J = 7.6 Hz, 1H, Pyr-H), 7.25 (d, J = 7.6 Hz, 1H, Pyr-H), 4.36 (s, 3H,
-NCH3), 3.58 (s, 6H, -N(CH3)2), 2.98 (t, J = 8.0 Hz, 2H, -N=CHCCH2CH2-), 2.85 (t, J = 8.0 Hz, 2H,
-N=CHCCH2CH2-). 13C-NMR (DMSO-d6, 100 MHz): δ 162.2, 159.6, 146.9, 138.0, 130.6, 126.2, 121.7, 117.8,
113.3, 66.8, 60.6; HRMS (ESI): calcd for C18H20N8O, [(M+H)+], 365.1838, found 365.1830.
4.1.14.11.1-methyl-8-((5-(piperazin-1-yl)pyridin-2-yl)amino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carbo
xamide (13l). Yellow solid. Yield: 59%. 1H-NMR (CDCl3, 400 MHz) δ: 9.62 (s, 1H, Pyr-NH), 8.42 (s, 1H,
-N=CH-), 7.99 (s, 1H, Pyr-H), 7.97 (d, J = 7.6 Hz, 1H, Pyr-H), 7.41 (d, J = 7.6 Hz, 1H, Pyr-H), 4.36 (s, 3H,
-NCH3), 3.02 (t, J = 4.8 Hz, 4H, Pyr-NCH2CH2N), 2.96 (t, J = 8.0 Hz, 2H, -N=CHCCH2CH2-), 2.89 (t, J = 4.8 Hz,
2H, -N=CHCCH2CH2-), 2.84 (t, J = 4.8 Hz, 4H, Pyr-NCH2CH2N). 13C-NMR (DMSO-d6, 100 MHz): δ 157.6,
153.2, 151.8, 148.5, 141.2, 138.3, 133.9, 131.9, 121.9, 121.4, 114.7, 108.2, 56.2, 50.2, 44.9, 41.4, 35.8; HRMS
(ESI): calcd for C19H19N8O2, [(M+H)+], 406.2104, found 406.2100.
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