(S)-N-(7-ethoxy-4-((1-(3-fluorobenzyl)-1H-indazol-5-
yl)amino)quinazolin-6-yl)-2-oxooxazolidine-4-carboxamide (9g).
1H), 8.21-8.19 (m, 1H), 8.12 (dd, J = 6.5, 2.5 Hz, 1H), 7.80-7.77
(m, 1H), 7.43 (t, J = 9.0 Hz, 1H), 7.20 (s, 1H), 5.14 (m, 1H), 4.68
(m, 1H), 4.62 (t, J = 9.0 Hz, 1H), 4.36 (dd, J = 8.5, 3.5 Hz, 1H),
2.84-2.82 (m, 2H), 2.41 (m, 2H), 2.31 (s, 3H), 2.04-1.95 (m, 1H);
HRMS (ESI): m/z calcd for (C23H22ClFN6O4+H)+: 501.1453;
found: 501.1437.
o
Light yellow solid, yield: 70%. m.p. >250 C; 1H NMR (500
MHz, DMSO) δ 9.84 (s, 1H), 9.69 (s, 1H), 8.85 (s, 1H), 8.43 (s,
1H), 8.20 (s, 1H), 8.13 (d, J = 11.0 Hz, 2H), 7.72 (d, J = 9.0 Hz,
1H), 7.66 (dd, J = 9.0, 1.5 Hz, 1H), 7.39-7.35 (m, 1H), 7.26 (s,
1H), 7.13-7.09 (m, 1H), 7.06 (d, J = 7.5 Hz, 2H), 5.70 (s, 2H),
4.68 (dd, J = 9.0, 3.5 Hz, 1H), 4.62 (t, J = 9.0 Hz, 1H), 4.35 (dd,
J = 8.5, 3.5 Hz, 1H), 4.29 (q, J = 7.0 Hz, 2H), 1.45 (t, J = 7.0 Hz,
3H); HRMS (ESI): m/z calcd for (C28H24FN7O4+H)+: 542.1952;
found: 542.1939.
(S)-N-(4-((3-chloro-2,
methylpiperidin-4-yl)
4-difluorophenyl)
methoxy)
amino)-7-((1-
quinazolin-6-yl)-2-
oxooxazolidine-4-carboxamide (9m).
o
Yellow solid, yield: 70%. m.p.:204-205 C; 1 H NMR (500
MHz, DMSO) δ 9.93 (s, 1H), 9.61 (s, 1H), 8.79 (s, 1H), 8.41 (s,
1H), 7.54-7.49 (m, 1H), 7.38 (t, J = 8.0 Hz, 1H), 7.32-7.30 (m,
1H), 4.689-4.67 (m, 1H), 4.62 (t, J = 9.0 Hz, 1H), 4.49-4.42 (m,
1H), 4.33 (dd, J = 8.5, 4.0 Hz, 1H), 4.10 (t, J = 6.5 Hz, 1H), 3.10
(m, 2H), 2.46 (s, 3H), 1.98-1.91 (m, 4H), 1.54-1.50 (m, 2H);
HRMS (ESI): m/z calcd for (C25H25ClF2N6O4+H)+: 547.1672;
found: 547.1710.
(S)-N-(4-((3-chloro-4-((6-methylpyridin-3-yl)
oxy)
phenyl)
amino)-7-ethoxyquinazolin-6-yl)-2-oxooxazolidine-4-
carboxamide (9h).
o
Light yellow solid, yield: 70%. m.p. >250 C; 1H NMR (500
MHz, DMSO) δ 9.88 (s, 1H), 9.67 (s, 1H), 8.86 (s, 1H), 8.55 (s,
1H), 8.22 (t, J = 2.0 Hz, 1H), 8.18-8.17 (m, 2H), 7.95 (s, 1H),
7.82 (dd, J = 9.0, 3.0 Hz, 1H), 7.30 (s, 1H), 7.27-7.26 (m, 2H),
7.20 (d, J = 9.0 Hz, 1H), 4.68 (dd, J = 9.0, 4.0 Hz, 1H), 4.61 (t, J
= 8.5 Hz, 1H), 4.36-4.33 (m, 1H), 4.30 (q, J = 7.0 Hz, 2H), 2.45
(s, 3H), 1.47 (t, J = 7.0 Hz, 3H); HRMS (ESI): m/z calcd for
(C26H23ClN6O5+H)+: 535.1496; found: 542.1938.
(S)-N-(4-((3-chloro-4-fluorophenyl)
amino)-7-(2,
2,
2-
trifluoroethoxy)
quinazolin-6-yl)-2-oxooxazolidine-4-
carboxamide (9n).
o
Light yellow solid, yield: 75%. m.p. > 250 C; 1H NMR (500
MHz, DMSO) δ 9.94 (s, 1H), 9.84 (s, 1H), 8.73 (s, 1H), 8.59 (s,
1H), 8.17 (s, 1H), 8.14 (dd, J = 7.0, 2.5 Hz, 1H), 7.95 (s, 1H),
7.81-7.78 (m, 1H), 7.51 (s, 1H), 7.45 (t, J = 9.0 Hz, 1H), 5.06 (q,
J = 8.5 Hz, 2H), 4.63-4.62 (m, 2H), 4.31-4.30 (m, 1H); HRMS
(ESI): m/z calcd for (C20H14ClF4N5O4+H)+: 500.0748;
found:500.0729.
(S)-N-(4-((3-chloro-4-(cyclopropylmethoxy) phenyl) amino)-7-
ethoxyquinazolin-6-yl)-2-oxooxazolidine-4-carboxamide (9i).
o
1
Light yellow solid, yield: 70%. m.p. >250 C; H NMR (500
MHz, DMSO) δ 9.70 (s, 1H), 9.65 (s, 1H), 8.81 (s, 1H), 8.48 (s,
1H), 8.17 (s, 1H), 7.91 (d, J = 2.0 Hz, 1H), 7.65 (dd, J = 8.5, 2.0
Hz, 1H), 7.26 (s, 1H), 7.14 (d, J = 9.0 Hz, 1H), 4.68-4.66 (m,
1H), 4.62-4.59 (m, 1H), 4.35-4.34 (m, 1H), 4.29 (q, J = 7.0 Hz,
2H), 3.92 (d, J = 7.0 Hz, 2H), 1.45 (t, J = 7.0 Hz, 3H) , 0.60-0.59
(m, 2H), 0.36-0.35 (m, 2H); HRMS (ESI): m/z calcd for
(C24H24ClN5O5+H)+: 498.1544; found: 498.1549.
(S)-N-(4-((3-chloro-4-fluorophenyl)
amino)-7-(((R)-4-
methylmorpholin-3-yl)
methoxy)
quinazolin-6-yl)-2-
oxooxazolidine-4-carboxamide (9o).
o
Light yellow solid, yield: 55%. m.p. > 250 C; 1H NMR (500
MHz, DMSO) δ 9.89 (s, 1H), 9.67 (s, 1H), 8.76 (s, 1H), 8.56 (s,
1H), 8.22 (s, 1H), 8.14 (dd, J = 5.0, 2.5 Hz, 1H), 7.81-7.78 (m,
1H), 7.44 (t, J = 9.0 Hz, 1H), 7.37 (s, 1H), 4.64-4.610 (m, 2H),
4.40-4.35 (m, 2H), 4.16-4.13 (m, 1H), 3.96-3.94 (m, 1H), 3.74-
3.72 (m, 1H), 3.57 ((t, J = 10.0 Hz, 1H), 3.44 (t, J = 10.0 Hz,
1H), 2.59 (m, 1H), 2.33 (s, 3H), 2.28 (m, 1H); HRMS (ESI): m/z
calcd for (C24H24ClFN6O5+H)+: 531.1559; found: 531.1552.
(S)-N-(7-methoxy-4-((4-methoxyphenyl)amino)quinazolin-6-yl)-
2-oxooxazolidine-4-carboxamide (9j).
o
Light yellow solid, yield: 87%. m.p. >250 C; 1H NMR (500
MHz, DMSO) δ 9.81 (s, 1H), 9.67 (s, 1H), 8.85 (s, 1H), 8.42 (s,
1H), 8.14 (s, 1H), 7.61 (d, J = 8.5 Hz, 2H), 7.26 (s, 1H), 6.98-
6.93 (m, 2H), 4.69 (dd, J = 9.5, 4.0 Hz, 1H), 4.58 (t, J = 9.0 Hz,
1H), 4.33 (dd, J = 9.5, 4.0 Hz, 1H), 4.01 (s, 3H), 3.77 (s, 3H);
HRMS (ESI): m/z calcd for (C20H19N5O5+H)+: 410.1464; found:
410.1435.
(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-(2-
methoxyethoxy)quinazolin-6-yl)-2-oxooxazolidine-4-
carboxamide (9p).
o
(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-(((S)-
tetrahydrofuran-3-yl)oxy) quina zolin-6-yl)-2-oxooxazolidine-4-
carboxamide (9k).
Light yellow solid, yield: 89%. m.p. > 250 C; 1H NMR (500
MHz, DMSO) δ 9.89 (s, 1H), 9.71 (s, 1H), 8.81 (s, 1H), 8.54 (s,
1H), 8.18 (s, 1H), 8.13 (dd, J = 7.0, 3.0 Hz, 1H), 7.81-7.80 (m,
1H), 7.43 (t, J = 9.0 Hz, 1H), 7.34 (s, 1H), 4.65-4.62 (m, 2H),
4.37-4.36 (m, 3H), 3.79-3.78 (m, 2H), 3.35 (s, 3H); HRMS (ESI):
m/z calcd for (C21H19ClFN5O5+H)+: 476.1137; found: 476.1174.
1
Light yellow solid, yield:75%. m.p.:223-225 oC; H NMR
(500 MHz, DMSO) δ 9.88 (s, 1H), 9.59 (s, 1H), 8.84 (s, 1H),
8.54 (s, 1H), 8.19 (s, 1H), 8.12 (dd, J = 7.0, 2.5 Hz, 1H), 7.80-
7.77 (m, 1H), 7.43 (t, J = 9.0 Hz, 1H), 7.27 (s, 1H), 5.32-5.30 (m,
1H), 4.67 (dd, J = 9.0, 3.5 Hz, 1H), 4.61 (t, J = 9.0 Hz, 1H), 4.35
(dd, J = 9.0, 3.5 Hz, 1H), 4.03-4.00 (m, 1H), 3.97-3.91 (m, 2H),
3.82-3.78 (m, 1H), 2.37-2.33 (m, 1H), 2.13-2.10 (m, 1H); HRMS
(ESI): m/z calcd for (C22H19ClFN5O5+H)+: 488.1137; found:
488.1124.
(S)-N-(4-((3-chloro-4-fluorophenyl) amino)-7-(2-(piperidin-1-yl)
ethoxy) quinazolin-6-yl)-2-oxooxazolidine-4-carboxamide (9q).
o
1
Yellow solid, yield: 89%. m.p.:203-205 C; H NMR (500
MHz, DMSO) δ 9.86 (s, 1H), 9.64 (s, 1H), 8.81 (s, 1H), 8.54 (s,
1H), 8.18 (s, 1H), 8.12 (dd, J = 6.5, 2.5 Hz, 1H), 7.80-7.77 (m,
1H), 7.42 (t, J = 9.0 Hz, 1H), 7.34 (s, 1H), 4.63-4.60 (m, 2H),
4.37-4.36 (m, 1H), 4.33 (t, J = 6.0 Hz, 2H), 2.79 (m, 2H), 1.52-
1.50 (m, 5H), 1.40-1.39 (m, 3H), 1.18 (t, J = 7.0 Hz, 1H); HRMS
(ESI): m/z calcd for (C25H26ClFN5O4+H)+: 529.1766; found:
529.1760.
(S)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-(((S)-1-
methylpyrrolidin-3-yl) oxy) quinazolin-6-yl)-2-oxooxazolidine-
4-carboxamide (9l).
o
1
Yellow solid, yield: 70%. m.p.:213-215 C; H NMR (500
MHz, DMSO) δ 9.88 (s, 1H), 9.66 (s, 1H), 8.84 (s, 1H), 8.53 (s,