Int. J. Mol. Sci. 2017, 18, 2292
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m.p. = 170–173 C). H NMR (300 MHz, DMSO)
δ
8.57 (1H, s, H2), 8.33 (1H, s, H50), 7.62 (2H, d,
J = 8.1 Hz, Ph00), 7.54 (1H, d, J = 3.7 Hz, H6), 7.23 (2H, d, J = 8.1 Hz, Ph00), 6.60 (1H, d, J = 3.6 Hz, H5),
4.92–4.86 (2H, m, CH2), 4.84–4.78 (2H, m,CH2), 2.61–2.54 (2H, m, CH200), 1.58 (2H, dt, J = 14.5, 7.1 Hz,
CH200), 1.35–1.24 (4H, m, CH200), 0.86 (3H, t, J = 6.8 Hz, CH300). 13C NMR (151 MHz, DMSO)
δ 150.9,
150.7, 150.4, 146.6, 142.3, 131.4, 128.9, 128.1, 125.2, 121.4, 116.9, 99.0, 49.2, 44.8, 35.0, 31.0, 30.7, 22.1, 14.1.
Anal. calcd. for C21H23ClN6: C, 63.87; H, 5.87; N, 21.28. Found: C, 63.82; H, 6.00; N, 20.96.
4-Chloro-7-(2-(4-(4-(pentyloxy)phenyl)-1H-1,2,3-triazol-1-yl)ethyl)-7H-pyrrolo[2,3-d]pyrimidine
Compound 4h was prepared using the above-mentioned procedure using compound
0.14 mmol) and 1-ethynyl-4-(pentyloxy)benzene to obtain 4h as white powder (49.7 mg, 86%,
(
4h).
3
(30 mg,
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m.p. = 166–168 C). H NMR (300 MHz, DMSO)
δ
8.57 (1H, s, H2), 8.26 (1H, s, H50), 7.62 (2H, d,
J = 8.7 Hz, Ph00), 7.55 (1H, d, J = 3.6 Hz, H6), 6.96 (2H, d, J = 8.8 Hz, Ph00), 060.60 (1H, d, J = 3.6 Hz, H050),
4.91–4.85 (2H, m, CH2), 4.83–4.77 (2H, m, CH2), 3.98 (2H, t, J = 6.5 Hz, CH2 ), 1.78–1.65 (2H, m, CH2 ),
1.46–1.28 (4H, m, CH200), 0.90 (3H, t, J = 7.0 Hz, CH200). 13C NMR (75 MHz, DMSO)
δ 158.5, 150.8,
150.6, 150.3, 146.3, 131.3, 126.5, 123.0, 120.7, 116.8, 114.8, 98.8, 67.5, 49.1, 44.7, 28.4, 27.7, 21.9, 14.0. Anal.
calcd. for C21H23ClN6O: C, 61.38; H, 5.64; N, 20.45. Found: C, 61.42; H, 5.55; N, 20.64.
N-((1-(2-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-4-methylbenzenesulf
onamide (4i). Compound 4i was prepared using the above-mentioned procedure using compound
3
(20 mg, 0.1 mmol) and 4-methyl-N-(prop-2-ynyl)benzenesulfonamide (24.07 mg, 0.12 mmol) to obtain
4i as white powder (30.3 mg, 73%, m.p. = 190–192 ◦C). 1H NMR (600 MHz, DMSO)
δ 8.59 (1H, s, H2),
7.98 (1H, t, J = 5.6 Hz, NH00), 7.78 (1H, s, H500), 7.65 (2H, d, J = 8.2 Hz, Ph00), 7.46 (1H, d, J = 3.6 Hz,
H6), 7.37 (2H, d, J = 8.1 Hz, Ph00), 6.59 (1H, d, J = 3.6 Hz, H5), 4.79 (2H, t, J = 5.8 Hz, CH2), 4.71 (2H, t,
J = 5.7 Hz, CH2), 3.92 (2H, d, J = 5.5 Hz, CH200), 2.38 (3H, s, CH300). 13C NMR (151 MHz, DMSO)
δ
150.7, 150.5, 150.3, 143.6, 142.6, 137.4, 131.1, 129.5, 126.6, 123.5, 116.7, 98.7, 48.7, 44.5, 38.0, 20.9. Anal.
calcd. for C18H18ClN7O2S: C, 50.06; H, 4.20; N, 22.70. Found: C, 49.91; H, 4.52; N, 22.33.
N-((1-(2-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-4-fluorobenzenesulf
onamide (4j). Compound 4j was prepared using the above-mentioned procedure using compound
3
(20 mg, 0.1 mmol) and 4-fluoro-N-(prop-2-ynyl)benzenesulfonamide (26.60 mg, 0.12 mmol) to obtain
4j as white powder (10.1 mg, 24%, m.p. = 178–179 ◦C). 1H NMR (600 MHz, DMSO)
δ 8.58 (1H, s, H2),
8.13 (1H, s, NH00), 7.85–7.79 (3H, m, J = 9.5, 6.2 Hz, H50, Ph00), 7.47 (1H, d, J = 3.5 Hz, H6), 7.40 (2H, t,
J = 8.8 Hz, Ph00), 6.59 (1H, d, J = 3.5 Hz, H5), 4.79 (2H, t, J = 5.7 Hz, CH2), 4.72 (2H, t, J = 5.8 Hz, CH2),
3.96 (2H, s, CH200). 13C NMR (151 MHz, DMSO)
δ 164.9; 163.2 (JCF = 251.0 Hz), 150.7, 150.6, 150.2,
143.4, 136.8; 136.7 (JCF = 3.4 Hz), 131.1, 129.6, 129.5 (JCF = 9.5 Hz), 123.6, 116.7, 116.3; 116.1 (JCF = 22.7
Hz), 98.7, 48.7, 44.5, 37.9. Anal. calcd. for C17H15ClFN7O2S: C, 46.85; H, 3.47; N, 22.49. Found: C, 46.87;
H, 3.19; N, 22.62.
N-((1-(2-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-4-chlorobenzenesulf
onamide (4k). Compound 4k was prepared using the above-mentioned procedure using compound
3
(25 mg, 0.11 mmol), and 4-chloro-N-(prop-2-ynyl)benzenesulfonamide (28.83 mg, 0.13 mmol) to obtain
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4k as white powder (35.3 mg, 71%, m.p. = 195–197 C). 1H NMR (300 MHz, DMSO)
δ 8.59 (1H, s, H2),
8.20 (1H, bs, NH00), 7.80 (1H, s, H50), 7.76 (2H, d, J = 8.7 Hz, Ph00), 7.64 (2H, d, J = 8.7 Hz, Ph00), 7.47
(1H, d, J = 3.6 Hz, H6), 6.60 (1H, d, J = 3.6 Hz, H5), 4.86–4.74 (2H, m, CH2), 4.74–4.63 (2H, m, CH2), 3.97
(2H, s, CH200). 13C NMR (75 MHz, DMSO)
δ 150.8, 150.7, 150.3, 143.4, 139.3, 137.3, 131.2, 129.3, 128.6,
123.7, 116.8, 98.8, 48.9, 44.6, 37.9. Anal. calcd. for C17H15Cl2N7O2S: C, 45.14; H, 3.34; N, 21.68. Found:
C, 44.89; H, 3.46; N, 21.60.
4-Chloro-7-((1-(2-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-7H-pyrrolo
[2,3-d]pyrimidine (5a). Compound 5a was prepared using the above-mentioned procedure using
compound
0.22 mmol) to obtain 5a as white powder (57.2 mg, 77%, m.p. = 202–204 C). H NMR (600 MHz,
DMSO)
8.64 (1H, s, H200), 8.41 (1H, s, H2), 7.82 (1H, s, H50), 7.61 (1H, d, J = 3.6 Hz, H600), 7.47 (1H, d,
3 (40 mg, 0.18 mmol) and 4-chloro-7-(prop-2-yn-1-yl)-7H-pyrrolo[2,3-d]pyrimidine (38.6 mg,
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δ