Shi et al.
FULL PAPER
(15h) 110.6 mg; 90% yield; white solid; m.p. 57-
58 ℃; H NMR (600 MHz, CDCl3) δ: 8.58 (s, 1H),
3.77 (s, 2H), 3.64 (s, 4H), 3.56 (s, 2H), 3.50 (s, 2H),
3.44 (s, 4H), 3.36 (s, 2H), 1.26 (s, 9H); 19F NMR (565
MHz, CDCl3) δ: 70.67 (s); 13C NMR (151 MHz,
CDCl3) δ: 157.20, 155.09, 154.05, 148.40, 147.61,
147.25, 136.28, 125.84, 122.27, 120.23 (q, J=291.27
Hz), 109.42, 107.66, 103.47, 79.58 (m), 70.73 (3C),
70.57 (2C), 70.22, 69.75, 68.94, 66.44, 65.56, 56.01,
1
8.16 (s, 1H), 7.53 (s, 2H), 7.41 (s, 1H), 7.12 (s, 3H),
4.16 (s, 2H), 4.00 (s, 6H), 3.86 (s, 3H), 3.81 (s, 2H),
3.66 (s, 4H), 3.56 (s, 2H), 3.51 (s, 2H), 3.45 (s, 4H),
3.36 (s, 2H), 2.29 (s, 3H); 19F NMR (565 MHz, CDCl3)
δ: 70.67 (s); 13C NMR (151 MHz, CDCl3) δ: 157.33,
154.95, 154.03, 148.31, 147.50, 136.30, 134.12, 129.51,
122.91, 120.22 (q, J=290.44 Hz), 109.37, 107.56,
103.29, 79.56 (m), 70.69 (3C), 70.53 (2C), 70.20, 69.72,
68.78, 66.37, 65.47, 56.02, 46.26, 20.88; HRMS (ESI)
46.29, 34.43, 31.37; HRMS (ESI) found m/z 1272.2713,
[M+H]+ calcd for C44H45F27N3O9 1272.2719.
+
N-(4-Fluorophenyl)-7-methoxy-6-((18,18,18-triflu-
oro-14,14-bis(((1,1,1,3,3,3-hexafluoro-2-(trifluorome-
thyl)propan-2-yl)oxy)methyl)-17,17-bis(trifluorome-
thyl)-3,6,9,12,16-pentaoxaoctadecyl)oxy)quinazolin-
4-amine (15l) 107.3 mg; 87% yield; white solid; m.p.
43-45 ℃; 1H NMR (400 MHz, CDCl3) δ: 8.55 (s, 1H),
8.41 (s, 1H), 7.62 (s, 2H), 7.42 (s, 1H), 7.06 (s, 1H),
6.99 (s, 2H), 4.07 (s, 2H), 3.99 (s, 6H), 3.78 (s, 5H),
3.63 (s, 4H), 3.54 (s, 2H), 3.49 (s, 2H), 3.43 (s, 4H),
3.35 (s, 2H); 19F NMR (376 MHz, CDCl3) δ: 70.73 (s),
118.49 (s); 13C NMR (101 MHz, CDCl3) δ: 159.59 (d,
J=241.30 Hz), 157.22, 155.17, 153.81, 148.47, 147.54,
135.06, 124.50 (d, J=7.71 Hz), 120.23 (q, J=290.72
Hz), 115.58 (d, J=22.52 Hz), 109.26, 107.50, 103.41,
79.58 (m), 70.70 (3C), 70.54 (2C), 70.22, 69.75, 68.89,
found m/z 1230.2250, [M+H]+ calcd for C41H39F27-
+
N3O9 1230.2250.
7-Methoxy-N-(4-methoxyphenyl)-6-((18,18,18-tri-
fluoro-14,14-bis(((1,1,1,3,3,3-hexafluoro-2-(trifluoro-
methyl)propan-2-yl)oxy)methyl)-17,17-bis(trifluoro-
methyl)-3,6,9,12,16-pentaoxaoctadecyl)oxy)quinazo-
lin-4-amine (15i) 105.8 mg; 85% yield; white solid;
m.p. 105-107 ℃; 1H NMR (400 MHz, CDCl3) δ: 8.56
(s, 1H), 8.06 (s, 1H), 7.53 (d, J=8.5 Hz, 2H), 7.39 (s,
1H), 7.12 (s, 1H), 6.86 (d, J=8.5 Hz, 2H), 4.15 (s, 2H),
4.01 (s, 6H), 3.86 (s, 3H), 3.81 (s, 2H), 3.76 (s, 3H),
3.66 (d, J=3.1 Hz, 4H), 3.56 (d, J=4.1 Hz, 2H), 3.51
(s, 2H), 3.46 (s, 4H), 3.37 (s, 2H); 19F NMR (376 MHz,
CDCl3) δ: 70.57 (s); 13C NMR (101 MHz, CDCl3) δ:
157.47, 156.84, 155.11, 154.15, 148.39, 147.57, 131.83,
124.77, 120.26 (q, J=290.98 Hz), 114.31, 109.22,
107.75, 103.47, 79.62 (m), 70.77, 70.75, 70.61, 70.56,
70.27, 69.81, 69.04, 66.49, 65.61, 56.08, 55.51, 46.31;
66.44, 65.53, 55.98, 46.28; HRMS (ESI) found m/z
+
1234.2002, [M + H] + calcd for C40H36F28N3O9
1234.1999.
7-Methoxy-6-((18,18,18-trifluoro-14,14-bis(((1,1,1,
3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl)oxy)-
methyl) 17,17-bis(trifluoromethyl)-3,6,9,12,16-pen-
taoxaoctadecyl)oxy)-N-(4-(trifluoromethyl)phenyl)-
quinazolin-4-amine (15m) 83.4 mg; 65% yield; white
HRMS (ESI) found m/z 1246.2197, [M+H]+ calcd for
+
C41H39F27N3O10 1246.2199.
Methyl-4-((7-methoxy-6-((18,18,18-trifluoro-14,
14-bis(((1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-
propan-2-yl)oxy)methyl)-17,17-bis(trifluoromethyl)-
3,6,9,12,16-pentaoxaoctadecyl)-oxy)quinazolin-4-yl)-
amino)benzoate (15j) 114.6 mg; 90% yield; white
1
solid; m.p. 44-46 ℃; H NMR (600 MHz, CDCl3) δ:
8.62 (s, 2H), 7.92 (d, J=7.4 Hz, 2H), 7.57 (d, J=7.6
Hz, 2H), 7.48 (s, 1H), 7.04 (s, 1H), 4.16 (s, 2H), 3.98 (s,
6H), 3.82 (s, 2H), 3.75 (s, 3H), 3.67 (s, 2H), 3.65 (s, 2H),
3.55 (s, 2H), 3.48 (s, 2H), 3.39 (s, 4H), 3.32 (s, 2H); 19F
NMR (565 MHz, CDCl3) δ: 62.32 (s), 70.73 (s); 13C
NMR (151 MHz, CDCl3) δ: 156.62, 155.21, 153.46,
148.63, 147.75, 142.66, 126.01, 125.35 (q, J=32.38
Hz), 124.38 (q, J=269.55 Hz), 121.51, 120.22 (q, J=
291.14 Hz), 109.53, 107.42, 103.14, 79.53 (m), 70.65,
70.64, 70.62, 70.50, 70.16, 69.84, 68.89, 66.30, 65.39,
1
solid; m.p. 60-62 ℃; H NMR (400 MHz, CDCl3) δ:
8.67 (s, 1H), 8.28 (s, 1H), 8.04 (s, 1H), 8.02 (s, 1H),
7.90 (s, 1H), 7.88 (s, 1H), 7.49 (s, 1H), 7.14 (s, 1H),
4.30-4.26 (m, 2H), 4.00 (s, 6H), 3.89 (s, 3H), 3.87 (s,
4H), 3.71 (d, J=4.5 Hz, 2H), 3.67 (d, J=4.7 Hz, 2H),
3.57 (d, J=4.1 Hz, 2H), 3.51 (d, J=4.3 Hz, 2H), 3.43
(s, 4H), 3.35 (s, 2H), 2.45 (s, 1H); 19F NMR (376 MHz,
CDCl3) δ: -70.51 (s); 13C NMR (101 MHz, CDCl3) δ:
166.96, 156.37, 155.45, 153.60, 148.86, 148.06, 143.85,
130.76, 124.86, 120.55, 120.26 (q, J=290.86 Hz),
109.68, 107.86, 103.27, 79.62 (m), 70.77, 70.75, 70.63,
70.50, 70.27, 69.98, 69.28, 66.50, 65.61, 56.19, 52.07,
56.02, 46.27; HRMS (ESI) found m/z 1284.1964 [M+
H]+ calcd for C41H36F30N3O9 1284.1967.
+
N-(4-Bromo-2-fluorophenyl)-7-methoxy-6-((18,18,
18-trifluoro-14,14-bis(((1,1,1,3,3,3-hexafluoro-2-(tri-
fluoromethyl)propan-2-yl)oxy)methyl)-17,17-bis(tri-
fluoromethyl)-3,6,9,12,16-pentaoxaoctadecyl)oxy)-
quinazolin-4-amine (15n) 119.3 mg; 91% yield;
46.32; HRMS (ESI) found m/z 1274.2148, [M+H]+
+
calcd for C42H39F27N3O11 1274.2148.
1
N-(4-(tert-Butyl)phenyl)-7-methoxy-6-((18,18,18-
trifluoro-14,14-bis(((1,1,1,3,3,3-hexafluoro-2-(trifluo-
romethyl)propan-2-yl)oxy)methyl)-17,17-bis(trifluo-
romethyl)-3,6,9,12,16-pentaoxaoctadecyl)oxy)quina-
zolin-4-amine (15k) 106.8 mg; 84% yield; white solid;
m.p. 150-151 ℃; 1H NMR (600 MHz, CDCl3) δ: 8.59
(s, 1H), 8.28 (s, 1H), 7.59 (s, 2H), 7.42 (s, 1H), 7.33 (s,
2H), 7.10 (s, 1H), 4.10 (s, 2H), 4.00 (s, 6H), 3.82 (s, 3H),
white solid; m.p. 74-76 ℃; H NMR (400 MHz,
CDCl3) δ: 8.63 (s, 1H), 8.17 (s, 1H), 7.90 (s, 1H), 7.30
(d, J=10.1 Hz, 3H), 7.17 (s, 1H), 4.24 (s, 2H), 4.06 (s,
6H), 3.92 (s, 5H), 3.73 (s, 2H), 3.68 (s, 2H), 3.60 (s, 2H),
3.52 (s, 6H), 3.44 (s, 2H); 19F NMR (376 MHz, CDCl3)
δ: 70.73 (s), 124.20 (s); 13C NMR (101 MHz, CDCl3)
δ: 156.32, 155.43, 154.38 (d, J=247.69 Hz), 153.47,
149.00, 147.69, 127.65 (d, J=3.24 Hz), 126.57 (d, J=
6
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2017, XX, 1—8