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L. ZARE ET AL.
3234, 3172, 2925, 2212, 1580, 1554, 1087. 1H NMR (DMSO, 500 MHz): 2.4 (s, 3H),
7.59 (d, J ¼ 8.5 Hz, 2H), 7.81 (d, J ¼ 8.5 Hz, 2H), 8.82 (s, br, 2H). Anal. calcd. for
C14H10ClN5: C, 59.27; H, 3.55; N, 24.68. Found: C, 59.55; H, 3.59; N, 24.73.
6-Amino-4-(4-bromophenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-
carbonitrile 4e. Off-white solid; mp 278–280 ꢀC; FT-IR (KBr, cmꢁ1): 3600, 3100,
1
2900, 2200, 1600, 1590, 1460, 1100. H NMR (DMSO, 500 MHz): 2.45 (s, 3H),
8.04 (d, J ¼ 7.78 Hz, 2H), 8.37 (d, J ¼ 7.78 Hz, 2H), 8.92 (s, br, 2H). Anal. calcd.
for C14H10BrN5: C, 51.24; H, 3.07; N, 21.34. Found: C, 51.55; H, 3.24; N, 21.53.
4,4’-((Butane-1,4-diylbis(oxy))bis(2,1-phenylene))bis(6-amino-3-methyl-
1H-pyrazolo[3,4-b]pyridine-5-carbonitrile) 4f. Yellow solid; mp 210–212 ꢀC;
FT-IR (KBr, cmꢁ1): 3458, 3037, 2946, 2219, 1589, 1483, 1452, 1255. 1H NMR
(DMSO, 500 MHz): 2.0 (s, br, 4H), 2.43 (s, br, 6H), 4.22 (s, br, 4H), 7.07 (s, br,
2H), 7.24 (s, br, 2H), 7.67 (s, br, 2H), 7.98 (s, br, 2H), 8.4 (s, br, 2H). Anal. calcd.
for C32H28N10O2: C, 65.74; H, 4.83; N, 23.96. Found: C, 65.54; H, 4.64; N, 23.59.
4,4’-((Pentane-1,5-diylbis(oxy))bis(2,1-phenylene))bis(6-amino-3-methyl-
1H-pyrazolo[3,4-b]pyridine-5-carbonitrile) 4g. Light brown solid; mp 204–
1
206 ꢀC; FT-IR (KBr, cmꢁ1): 3434, 3230, 2937, 2194, 1639, 1602, 1242. H NMR
(DMSO, 500 MHz): 1.4 (s, br, 2H), 2.0 (s, br, 4H), 2.5 (s, 3H), 4.20 (s, br, 4H),
7.14 (s, br, 2H), 7.23 (d, J ¼ 7.5 Hz, 2H), 7.66 (s, br, 3H),7.97 (d, J ¼ 6.30 Hz, 2H),
8.41(s, br, 1H). Anal. calcd. for C33H30N10O2: C, 66.21; H, 5.05; N, 23.40. Found:
C, 66.24; H, 5.33; N, 23.48.
4,4’-((Hexane-1,6-diylbis(oxy))bis(2,1-phenylene))bis(6-amino-3-methyl-
1H-pyrazolo[3,4-b]pyridine-5-carbonitrile) 4h. Yellow solid; mp 166–168 ꢀC;
FT-IR (KBr, cmꢁ1): 3471, 3458, 3035, 2945, 2219, 1591, 1573, 1454, 1257. 1H
NMR (DMSO, 500 MHz): 1.5 (s, br, 2H), 2.0 (s, br, 2H), 2.5 (s, 3H), 4.14 (s, br,
2H), 7.06 (s, br, 1H), 7.13 (s, br, 1H), 7.66 (s, br, 1H), 7.98 (s, br, 1H), 8.43 (s, br,
1H). Anal. calcd. for C34H32N10O2: C, 66.65; H, 5.26; N, 22.86. Found: C, 66.10;
H, 5.91; N, 22.74.
4,4’-((Butane-1,4-diylbis(oxy))bis(4,1-phenylene))bis(6-amino-3-methyl-
1H-pyrazolo[3,4-b]pyridine-5-carbonitrile) 4i. Yellow solid; mp 200–202 ꢀC;
1
FT-IR (KBr, cmꢁ1): 3473, 3039, 2943, 2200, 1589, 1452, 1253. H NMR (DMSO,
500 MHz): 1.9 (s, br, 2H), 2.45 (s, 3H), 4.2 (s, br, 2H), 7.18 (d, J ¼ 8.04 Hz, 2H),
7.96 (d, J ¼ 8.04 Hz, 2H), 8.38 (s, 1H). Anal. calcd. for C32H28N10O2: C, 65.74; H,
4.83; N, 23.96. Found: C, 65.36; H, 4.95; N, 23.69.
4,4’-(((1,4-Phenylenebis(methylene))bis(oxy))bis(2,1-phenylene))bis(6-
amino-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile) 4j. Yellow solid;
mp 230–232 ꢀC; FT-IR (KBr, cmꢁ1): 3446, 3029, 2936, 2225, 1593, 1483, 1456,
1299, 1244. 1H NMR (DMSO, 500 MHz): 2.5 (s, 3H), 5.3 (s, 2H), 7.17
(t, J ¼ 7.56 Hz, 1H), 7.31 (d, J ¼ 8.5 Hz, 1H), 7.57 (s, 2H), 7.66 (t, J ¼ 7.81 Hz,
1H), 8.01 (d, J ¼ 7.78 Hz, 1H), 8.5 (s, 1H). Anal. calcd. for C36H28N10O2: C,
68.34; H, 4.46; N, 22.14. Found: C, 68.62; H, 4.55; N, 22.07.