Organic & Biomolecular Chemistry
Paper
(1-(4-Methoxybenzyl)-1H-1,2,3-triazol-4-yl)(2-((3,4,5-trimethoxy- (dd, J = 8.0, 4.7 Hz, 1H), 5.58 (s, 2H), 3.88 (s, 6H), 3.84 (s, 3H);
13C NMR (75 MHz, CDCl3): δ 185.66, 158.35, 156.47, 156.22,
phenyl)amino)pyridin-3-yl)methanone (6k). Compound 6k was
prepared according to the above explained general method by
employing 1-(2-((3,4,5-trimethoxyphenyl)amino)pyridin-3-yl)-
prop-2-yn-1-one (14c, 150 mg, 0.48 mmol) and 1-(azido-
methyl)-4-methoxybenzene (17a, 78 mg, 0.48 mmol) to afford
6k as a yellow solid. 166 mg; 73% yield; Mp: 99–100 °C; 1H
NMR (500 MHz, CDCl3): δ 11.04 (s, 1H), 9.42 (dd, J = 8.0, 1.9
Hz, 1H), 8.42 (dd, J = 4.6, 1.9 Hz, 1H), 8.10 (s, 1H), 7.32–7.29
(m, 2H), 7.01 (s, 2H), 6.95–6.92 (m, 2H), 6.83 (dd, J = 8.0, 4.7
Hz, 1H), 5.55 (s, 2H), 3.88 (s, 6H), 3.83 (s, 3H), 3.83 (s, 3H);
13C NMR (75 MHz, CDCl3): δ 185.77, 160.32, 156.48, 154.07,
153.24, 149.01, 144.03, 135.44, 134.23, 130.05, 128.18, 125.50,
114.76, 113.28, 113.19, 99.45, 60.97, 56.12, 55.40, 54.12;
MS (ESI): m/z 476 [M + H]+; HRMS calcd for C25H26O5N5
[M + H]+476.19285, found 476.19111.
154.16, 153.21, 149.12, 144.03, 135.42, 135.38, 134.11, 130.75,
129.98, 128.43, 124.04, 122.66, 119.41, 118.87, 118.23, 113.30,
113.12, 99.38, 60.97, 56.09, 54.17; MS (ESI): m/z 538 [M + H]+;
HRMS calcd for C30H28O5N5 [M
538.20727.
(1-(4-Fluorobenzyl)-1H-1,2,3-triazol-4-yl)(2-((3,4,5-trimethoxy-
phenyl)amino)pyridin-3-yl)methanone (6o). Compound 6o was
prepared according to the above explained general method by
employing 1-(2-((3,4,5-trimethoxyphenyl)amino)pyridin-3-yl)-
prop-2-yn-1-one (14c, 150 mg, 0.48 mmol) and 1-(azido-
methyl)-3-phenoxybenzene (17e, 66 mg, 0.48 mmol) to afford
6o as a yellow solid; 175 mg; 79% yield; Mp: 68–70 °C; 1H
NMR (500 MHz, CDCl3): δ 11.04 (s, 1H), 9.44–9.38 (m, 1H),
8.43 (dd, J = 4.6, 1.9 Hz, 1H), 8.14 (s, 1H), 7.35 (dd, J = 8.5, 5.2
+
H]+538.20850, found
(1-(3,4-Dimethoxybenzyl)-1H-1,2,3-triazol-4-yl)(2-((3,4,5-trimethoxy- Hz, 2H), 7.12 (t, J = 8.6 Hz, 2H), 7.01 (s, 2H), 6.83 (dd, J = 8.0,
4.7 Hz, 1H), 5.60 (s, 2H), 3.88 (s, 7H), 3.84 (s, 3H); 13C NMR
phenyl)amino)pyridin-3-yl)methanone (6l). Compound 6l was
prepared according to the above explained general method by
employing 1-(2-((3,4,5-trimethoxyphenyl)amino)pyridin-3-yl)-
prop-2-yn-1-one (14c, 150 mg, 0.48 mmol) and 4-(azido-
methyl)-1,2-dimethoxybenzene (17b, 92 mg, 0.48 mmol) to
afford 6l as a yellow solid. 184 mg; 76% yield; Mp: 108–110 °C;
1H NMR (300 MHz, CDCl3): δ 11.04 (s, 1H), 9.42 (d, J = 7.8 Hz,
1H), 8.43 (d, J = 3.0 Hz, 1H), 8.12 (s, 1H), 7.01 (s, 2H),
6.98–6.79 (m, 4H), 5.54 (s, 2H), 3.89 (d, J = 7.3 Hz, 12H), 3.83
(s, 3H); 13C NMR (75 MHz, CDCl3): δ 185.73, 156.47, 154.11,
153.23, 149.87, 149.67, 149.03, 144.00, 135.42, 134.20, 128.25,
125.85, 121.35, 113.29, 113.17, 111.48, 99.43, 60.97, 56.12,
56.03, 54.49; MS (ESI): m/z 506 [M + H]+; HRMS calcd for
C26H28O6N5 [M + H]+506.20341, found 506.20305.
(75 MHz, CDCl3): δ 185.64, 156.49, 154.22, 153.23, 149.21,
144.02, 135.36, 130.43, 130.32, 129.51, 128.27, 116.61, 116.32,
113.31, 113.09, 99.44, 60.99, 56.11, 53.80; MS (ESI): m/z 464 [M
+ H]+; HRMS calcd for C24H23O4N5F [M + H]+464.17286, found
464.17094.
(2-((4-Fluorophenyl)amino)pyridin-3-yl)(1-(4-methoxybenzyl)-
1H-1,2,3-triazol-4-yl)methanone (6p). Compound 6p was pre-
pared according to the above explained general method by
employing 1-(2-((4-fluorophenyl)amino)pyridin-3-yl)prop-2-yn-
1-one (14d, 150 mg, 0.62 mmol) and 1-(azidomethyl)-4-meth-
oxybenzene (17a, 101 mg, 0.62 mmol) to afford 6p as a yellow
1
solid; 193 mg; 77% yield; Mp: 148–150 °C; H NMR (500 MHz,
CDCl3): δ 11.01 (s, 1H), 9.41 (dd, J = 8.0, 1.9 Hz, 1H), 8.39 (dd,
(1-(3,5-Dimethoxybenzyl)-1H-1,2,3-triazol-4-yl)(2-((3,4,5-tri- J = 4.6, 1.7 Hz, 1H), 8.09 (s, 1H), 7.66–7.61 (m, 2H), 7.32–7.28
methoxyphenyl)amino)pyridin-3-yl)methanone
(6m). Com-
(m, 2H), 7.07–7.01 (m, 2H), 6.96–6.91 (m, 2H), 6.82 (dd, J = 8.0,
4.7 Hz, 1H), 5.54 (s, 2H), 3.82 (s, 3H). 13C NMR (75 MHz,
CDCl3): δ 185.72, 160.56, 160.25, 157.35, 156.44, 154.00,
148.98, 143.98, 135.36, 135.33, 130.04, 128.19, 125.48, 123.44,
123.34, 115.59, 115.29, 114.72, 113.39, 113.07, 55.39, 54.09; MS
(ESI): m/z 404 [M + H]+; HRMS calcd for C22H19O2N5F [M +
H]+404.15173, found 404.15112.
pound 6m was prepared according to the above explained
general method by employing 1-(2-((3,4,5-trimethoxyphenyl)-
amino)pyridin-3-yl)prop-2-yn-1-one (14c, 150 mg, 0.48 mmol)
and 1-(azidomethyl)-3,5-dimethoxybenzene (17c, 92 mg,
0.48 mmol) to afford 6m as a yellow solid. 174 mg; 72% yield;
1
Mp: 101–103 °C; H NMR (300 MHz, CDCl3): δ 11.04 (s, 1H),
9.42 (dd, J = 8.0, 1.9 Hz, 1H), 8.43 (dd, J = 4.6, 1.9 Hz, 1H), 8.16
(s, 1H), 7.01 (s, 2H), 6.84 (dd, J = 8.0, 4.7 Hz, 1H), 6.46 (s, 3H),
5.53 (s, 2H); 13C NMR (75 MHz, CDCl3): δ 185.72, 161.51,
156.48, 154.15, 153.22, 149.09, 144.02, 135.56, 135.39, 128.43,
113.29, 113.15, 106.49, 100.66, 99.39, 60.97, 56.09, 55.47,
54.60; MS (ESI): m/z 506 [M + H]+; HRMS calcd for C26H28O6N5
[M + H]+506.20341, found 506.20205.
(1-(3,4-Dimethoxybenzyl)-1H-1,2,3-triazol-4-yl)(2-((4-fluoro-
phenyl)amino)pyridin-3-yl)methanone (6q). Compound 6q was
prepared according to the above explained general method by
employing 1-(2-((4-fluorophenyl)amino)pyridin-3-yl)prop-2-yn-
1-one (14d, 150 mg, 0.62 mmol) and 4-(azidomethyl)-1,2-
dimethoxybenzene (17b, 120 mg, 0.62 mmol) to afford 6q as a
yellow solid; 213 mg; 79% yield; Mp: 175–176 °C; 1H NMR
(1-(3-Phenoxybenzyl)-1H-1,2,3-triazol-4-yl)(2-((3,4,5-trimethoxy- (500 MHz, CDCl3): δ 11.01 (s, 1H), 9.41 (dd, J = 8.0, 1.9 Hz,
phenyl)amino)pyridin-3-yl)methanone (6n). Compound 6n was
prepared according to the above explained general method by
employing 1-(2-((3,4,5-trimethoxyphenyl)amino)pyridin-3-yl)-
prop-2-yn-1-one (14c, 150 mg, 0.48 mmol) and 1-(azido-
methyl)-3-phenoxybenzene (17d, 108 mg, 0.48 mmol) to afford
1H), 8.39 (dd, J = 4.6, 1.9 Hz, 1H), 8.12 (s, 1H), 7.66–7.61 (m,
2H), 7.07–7.02 (m, 2H), 6.94 (dd, J = 8.2, 2.0 Hz, 1H), 6.89 (d,
J = 8.2 Hz, 1H), 6.86 (d, J = 1.9 Hz, 1H), 6.83 (dd, J = 8.0,
4.7 Hz, 1H), 5.54 (s, 2H), 3.90 (s, 3H), 3.87 (s, 3H); 13C NMR
(75 MHz, CDCl3): δ 185.67, 160.54, 157.33, 156.43, 154.02,
149.79, 149.59, 143.94, 128.23, 125.82, 123.42, 123.32,
121.30, 115.58, 115.28, 113.38, 111.40, 111.34, 55.99, 54.46;
MS (ESI): m/z 434 [M + H]+; HRMS calcd for C23H21O3N5F
[M + H]+434.16052, found 434.16048.
1
6n as a yellow solid. 209 mg; 81% yield; Mp: 105–107 °C; H
NMR (500 MHz, CDCl3): δ 11.05 (s, 1H), 9.41 (dd, J = 8.0, 1.3
Hz, 1H), 8.43 (dd, J = 4.5, 1.6 Hz, 1H), 8.16 (s, 1H), 7.36 (td, J =
7.9, 2.3 Hz, 3H), 7.15 (t, J = 7.4 Hz, 1H), 7.06–6.97 (m, 7H), 6.84
This journal is © The Royal Society of Chemistry 2015
Org. Biomol. Chem.