Paper
NJC
+
327.38 [M ꢀ H]+. HRMS: calcd for C17H20N4NaO3 , [M + Na]+,
3-[2-(p-Fluoro)phenylethynyl]-1-[(2-hydroxyethoxy)methyl]-
1,2,4-triazole-5-carboxamide (1i). White solid. 1H NMR (400 MHz,
351.1428; found, 351.1428.
3-[2-(p-Butyl)phenylethynyl]-1-[(2-hydroxyethoxy)methyl]-1,2,4- DMSO-d6) d 8.46 (br, 1H), 8.12 (br, 1H), 7.70–7.73 (m, 2H), 7.33
triazole-5-carboxamide (1d). White solid. 1H NMR (400 MHz, (t, 2H, J = 8.8Hz), 5.94 (s, 2H), 4.68 (t, 1H, J = 6.4 Hz), 3.58 (t, 2H,
DMSO-d6) d 8.46 (br, 1H), 8.11 (br, 1H), 7.53 (d, 2H, J = 7.6 Hz), J = 4.8 Hz), 3.45–3.49 (m, 2H). 13C NMR (100 MHz, DMSO-d6) d
7.30 (d, 2H, J = 8.0 Hz), 5.93 (s, 2H), 4.68 (t, 1H, J = 5.6 Hz), 3.58 163.17 (d, J = 248.0 Hz), 158.29, 148.26, 145.48, 134.75 (d, J =
(t, 2H, J = 4.8 Hz), 3.45–3.48 (m, 2H), 2.63 (t, 2H, J = 7.6 Hz), 8.8 Hz), 117.24 (d, J = 3.3 Hz), 116.78 (d, J = 22.2 Hz), 88.78, 80.17,
1.53–1.60 (m, 2H), 1.28–1.33 (m, 2H), 0.90 (t, 3H, J = 7.2 Hz). 79.27, 71.88, 60.24. IR: 2230.56 cmꢀ1 (–CRC–). MS (ESI, m/z): 303
+
13C NMR (100 MHz, DMSO-d6) d 158.33, 148.14, 145.67, [M ꢀ H]ꢀ. HRMS: calcd for C14H14FN4O3 , [M + H]+, 305.1044;
145.26, 132.14, 129.41, 117.89, 90.11, 79.80, 79.21, 71.82, found, 305.1041.
60.20, 35.17, 33.21, 22.13, 14.18. IR: 2225 cmꢀ1 (–CRC–). MS
3-[2-(o-fluoro)phenylethynyl]-1-[(2-hydroxyethoxy)methyl]-
(ESI, m/z): 707.61 [2M + Na]+, 365.42 [M + Na]+, 341.37 [M ꢀ H]+. 1,2,4-triazole-5-carboxamide (1j). White solid. 1H NMR (400 MHz,
+
HRMS: calcd for C18H22N4NaO3 , [M + Na]+, 365.1584; found, DMSO-d6) d 8.50 (br, 1H), 8.13 (br, 1H), 7.72 (td, 1H, J1 = 7.6 Hz,
365.1584.
J2 = 1.6 Hz), 7.55–7.61 (m, 1H), 7.40 (t, 1H, J = 8.8 Hz), 7.32 (t, 1H,
3-[2-(p-Pentyl)phenylethynyl]-1-[(2-hydroxyethoxy)methyl]-1,2,4- J = 7.6 Hz), 5.95 (s, 2H), 4.69 (t, 1H, J = 5.2 Hz), 3.59 (t, 2H, J =
triazole-5-carboxamide (1e). White solid. 1H NMR (400 MHz, 4.8 Hz), 3.45–3.49 (m, 2H). 13C NMR (100 MHz, DMSO-d6) d 162.30
DMSO-d6) d 8.49 (br, 1H), 8.12 (br, 1H), 7.54 (d, 2H, J = 8.0 Hz), (d, J = 249.5 Hz), 157.82, 147.93, 144.79, 133.80, 132.44 (d, J =
7.30 (d, 2H, J = 8.0 Hz), 5.93 (s, 2H), 4.70 (t, 1H, J = 5.6 Hz), 3.58 (t, 8.1 Hz), 125.12 (d, J = 3.3 Hz), 116.00 (d, J = 20.1 Hz), 108.81
2H, J = 5.2 Hz), 3.44–3.48 (m, 2H), 2.62 (t, 2H, J = 7.6 Hz), 1.54–1.60 (d, J = 15.2 Hz), 84.72, 82.77, 78.92, 71.47, 59.81. IR: 2236 cmꢀ1
(m, 2H), 1.25–1.34 (m, 4H), 0.86 (t, 3H, J = 6.8 Hz). 13C NMR (–CRC–). MS (ESI, m/z): 305.35 [M + H]+. HRMS: calcd for
+
(100 MHz, DMSO-d6) d 158.32, 148.18, 145.68, 145.25, 132.15, C14H13FN4NaO3 , [M + Na]+, 327.0864; found, 327.0866.
129.39, 117.97, 90.06, 79.88, 79.22, 71.86, 60.23, 35.47, 31.27,
3-[2-(m-Fluoro)phenylethynyl]-1-[(2-hydroxyethoxy)methyl]-
30.76, 22.38, 14.35. IR: 2224 cmꢀ1 (–CRC–). MS (ESI, m/z): 1,2,4-triazole-5-carboxamide (1k). White solid. 1H NMR (400 MHz,
735.62 [2M + Na]+, 379.49 [M + Na]+, 355.37 [M ꢀ H]+. HRMS: DMSO-d6) d 8.48 (br, 1H), 8.14 (br, 1H), 7.48–7.56 (m, 3H), 7.36–
+
calcd for C19H25N4O3 , [M + H]+, 357.1921; found, 357.1911.
7.41 (m, 1H), 5.94 (s, 2H), 4.70 (t, 1H, J = 5.2 Hz), 3.58 (t, 2H,
3-[2-(p-Heptyl)phenylethynyl]-1-[(2-hydroxyethoxy)methyl]- J = 5.2 Hz), 3.45–3.49 (m, 2H). 13C NMR (100 MHz, DMSO-d6)
1,2,4-triazole-5-carboxamide (1f). White solid. 1H NMR (400 MHz, d 162.28 (d, J = 243.8 Hz), 158.25, 148.32, 145.23, 131.66
DMSO-d6) d 8.46 (br, 1H), 8.11 (br, 1H), 7.53 (d, 2H, J = 8.0 Hz), (d, J = 8.7 Hz), 128.70 (d, J = 2.7 Hz), 122.65 (d, J = 9.5 Hz),
7.29 (d, 2H, J = 7.6 Hz), 5.94 (s, 2H), 4.68 (br, 1H), 3.59 (t, 2H, J = 118.83 (d, J = 23.1 Hz), 117.88 (d, J = 20.9 Hz), 88.35, 81.12,
4.8 Hz), 3.47–3.48 (m, 2H), 2.62 (t, 2H, J = 7.6 Hz), 1.57 (t, 2H, 79.33, 71.90, 60.23. IR: 2236 cmꢀ1 (–CRC–). MS (ESI, m/z):
J = 6.4 Hz), 1.25–1.28 (m, 8H), 0.85 (t, 3H, J = 6.0 Hz). 13C NMR 305.35 [M + H]+. HRMS: calcd for C14H13FN4NaO3 , [M + Na]+,
+
(100 MHz, DMSO-d6) d 158.31, 148.19, 145.69, 145.22, 132.13, 327.0864; found, 327.0865.
129.36, 117.98, 90.04, 79.88, 79.22, 71.86, 60.24, 35.50, 31.65,
3-[2-(p-Cyano)phenylethynyl]-1-[(2-hydroxyethoxy)methyl]-
31.05, 29.01, 28.92, 22.50, 14.36. IR: 2225 cmꢀ1 (–CRC–). MS 1,2,4-triazole-5-carboxamide (1l). White solid. 1H NMR (400 MHz,
(ESI, m/z): 791.7 [2M + Na]+. HRMS: calcd for C21H28N4NaO3 , DMSO-d6) d 8.52 (br, 1H), 8.17 (br, 1H), 7.97 (d, 2H, J = 8.4 Hz), 7.84
+
[M + Na]+, 407.2054; found, 407.2057.
(d, 2H, J = 8.4 Hz), 5.95 (s, 2H), 4.72 (t, 1H, J = 5.6 Hz), 3.58 (t, 2H,
3-[2-(p-Methoxyl)phenylethynyl]-1-[(2-hydroxyethoxy)methyl]- J = 4.8 Hz), 3.44–3.48 (m, 2H). 13C NMR (100 MHz, DMSO-d6)
1,2,4-triazole-5-carboxamide (1g). White solid. 1H NMR (400 MHz, d 158.19, 148.41, 144.97, 133.25, 133.02, 125.51, 118.66, 112.68,
DMSO-d6) d 8.48 (br, 1H), 8.12 (br, 1H), 7.58 (d, 2H, J = 8.8 Hz), 88.14, 83.74, 79.40, 71.91, 60.21. IR: 2235 cmꢀ1 (–CRC–), 2250
7.03 (d, 2H, J = 8.8 Hz), 5.92 (s, 2H), 4.71 (t, 1H, J = 5.6 Hz), 3.81 cmꢀ1 (–CRN). MS (ESI, m/z): 312.32 [M + H]+, 334.31 [M + Na]+.
+
(s, 3H), 3.57 (t, 2H, J = 5.2 Hz), 3.47 (t, 2H, J = 5.2 Hz). 13C NMR HRMS: calcd for C15H13N5NaO3 , [M + Na]+, 334.0911; found,
(100 MHz, DMSO-d6) d 160.85, 158.34, 148.11, 145.83, 133.93, 334.0911.
115.09, 112.52, 90.15, 79.17, 71.83, 60.21, 55.83. IR: 2224 cmꢀ1
3-[2-(p-Bromo)phenylethynyl]-1-[(2-hydroxyethoxy)methyl]-
(–CRC–). MS (ESI, m/z): 339.31 [M + Na]+, 317.32 [M + H]+, 1,2,4-triazole-5-carboxamide (1m). White solid. 1H NMR (400 MHz,
+
315.30 [M ꢀ H]+. HRMS: calcd for C15H17N4O4 , [M + H]+, DMSO-d6) d 8.49 (br, 1H), 8.14 (br, 1H), 7.69 (d, 2H, J = 8.4 Hz),
317.1244; found, 317.1236.
7.59 (d, 2H, J = 8.4 Hz), 5.93 (s, 2H), 4.71 (t, 1H, J = 5.6 Hz), 3.57
3-[2-(p-Trifluoromethyl)phenylethynyl]-1-[(2-hydroxyethoxy)- (t, 2H, J = 4.8 Hz), 3.44–3.48 (m, 2H). 13C NMR (100 MHz,
methyl]-1,2,4-triazole-5-carboxamide (1h). White solid. 1H NMR DMSO-d6) d 158.25, 148.29, 145.34, 134.12, 132.53, 124.10,
(400 MHz, DMSO-d6) d 8.48 (br, 1H), 8.14 (br, 1H), 7.83–7.88 (m, 119.95, 88.73, 81.42, 79.30, 71.88, 60.21; IR: 2228 cmꢀ1
3H), 5.95 (s, 2H), 4.69 (t, 1H, J = 5.6 Hz), 3.59 (t, 2H, J = 4.8 Hz), (–CRC–). MS (ESI, m/z): 365.25 [M + H]+, 387.24 [M + Na]+.
3.46–3.49 (m, 2H). 13C NMR (100 MHz, DMSO-d6) d 158.21, HRMS: calcd for C14H13BrN4NaO3+, [M + Na]+, 387.0063; found,
148.38, 145.08, 133.04, 130.19 (q, J = 32 Hz), 126.24 (q, J = 3.6 Hz), 387.0062.
125.04, 124.20 (q, J = 270.9 Hz), 88.16, 82.54, 79.38, 79.11, 60.23.
3-[2-(p-Nitryl)phenylethynyl]-1-[(2-hydroxyethoxy)methyl]-1,2,4-
IR: 2025 cmꢀ1 (–CRC–). MS (ESI, m/z): 377.3 [M + Na]+, 731.4 triazole-5-carboxamide (1n). Brown solid. 1H NMR (400 MHz,
[2M + Na]+, 353.3 [M ꢀ H]ꢀ. HRMS: calcd for C15H13F3N4NaO3 , DMSO-d6) d 8.50 (br, 1H), 8.30 (d, 2H, J = 8.4 Hz), 8.16 (br, 1H),
+
[M + Na]+, 377.0832; found, 377.0833.
7.92 (d, 2H, J = 8.4 Hz), 5.95 (s, 2H), 4.70 (t, 1H, J = 4.8 Hz),
New J. Chem.
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