Page 5 of 15
RSC Advances
DOI: 10.1039/C6RA15948F
yl)sulfamoyl)phenyl)amino)-1,3,5-triazin-2-yl)amino)-N-
1719 (C=O str), 1624 (C=C str), 1612 (C=N str), ), 1349 and
60 1162 (asymmetric and symetric SO2 str), 1254 (CF3 str), 1141
phenylacetamide (8a)
Yield: 74%; MP: 221ꢀ223oC; MW: 567.64; Rf: 0.63; FTꢀIR (νmax
;
(aromatic CꢀCstr), 984 (CꢀN str ), cm ꢀ1; HꢀNMR (400MHz,
1
cmꢀ1 KBr): 3387 (NꢀH), 3078 (Ar CꢀH str), 2987 (ali CꢀH str),
1714 (C=O str), 1628 (C=C str), 1608 (C=N str), ), 1341 and
DMSO, TMS) δ ppm: 8.09 (d, 2H, J = 7.8 Hz, ArH), 7.94 (d, 2H,
J = 7.6 Hz, ArꢀH), 7.56 (d, 2H, J = 5.3 Hz, ArꢀH), 7.21 (d, 2H, J
= 5.1 Hz, ArH), 7.25 (s, 1H, Sec. Amide), 7.23 (s, 1H, Thiazole),
5
1165 (asymmetric and symetric SO2 str), 1138 (aromatic CꢀCstr),
1
989 (CꢀN str ), 781 cm ꢀ1; HꢀNMR (400MHz, DMSO, TMS) δ 65 6.97 (s, 1H, Thiazole), 3.97 (s, 3H, Aromatic CꢀNH), 3.74 (s, 2H,
ppm: 8.12 (d, 2H, J = 7.9 Hz, ArH), 7.95 (d, 2H, J = 7.8 Hz, Arꢀ
H), 7.47 (d, 2H, J = 4.7 Hz, ArꢀH), 7.27 (d, 2H, J = 4.6 Hz, ArH),
10 7.26 (s, 1H, Thiazole), 7.23 (s, 1H, Sec. Amide,), 7.06 (s, 1H, J =
Methylene), 3.69ꢀ3.49 (m, 8H, Morpholine); 13CꢀNMR (100MHz,
CDCl3) δ,ppm:176.3, 171.8, 168.5, 165.8, 142.2, 141.9, 137.2,
132.4, 130.2, 129.8, 125.4, 124.2, 118.9, 113.9, 112.1, 66.4, 55.2,
48.7; Mass :636.65 (M+1); Elemental analysis for
1.2 Hz, ArꢀH), 6.97 (s, 1H, Thiazole), 3.96 (s, 3H, Aromatic Cꢀ
NH), 3.76 (s, 2H, Methylene), 3.67ꢀ3.54 (m, 8H, Morpholine) ; 70 C25H24F3N9O4S2: Calculated: C, 47.24; H, 3.81; N, 19.83; Found:
13CꢀNMR (100MHz, CDCl3) δ,ppm:176.2, 171.8, 168.5, 165.7,
142.2, 138.5, 137.1, 130.2, 129.8, 128.8, 128.1, 121.7, 113.9,
15 112.2, 66.4, 55.3, 48.7; Mass :568.62 (M+1); Elemental analysis
for C24H25N9O4S2: Calculated: C, 50.78; H, 4.44; N, 22.21;
Found: C, 50.79; H, 4.44; N, 22.23.
N-(4-chlorophenyl)-2-((4-morpholino-6-((4-(N-(thiazol-2-
yl)sulfamoyl)phenyl)amino)-1,3,5-triazin-2-yl)amino)acetamide
20 (8b)
C, 47.25; H, 3.82; N, 19.81.
2-((4-morpholino-6-((4-(N-(thiazol-2-
yl)sulfamoyl)phenyl)amino)-1,3,5-triazin-2-yl)amino)-N-(4-
nitrophenyl)acetamide (8e)
75 Yield: 77%; MP: 263ꢀ264oC; MW: 612.64; Rf: 0.72; FTꢀIR (νmax
;
cmꢀ1 KBr): 3392 (NꢀH), 3089 (Ar CꢀH str), 2984 (ali CꢀH str),
1723 (C=O str), 1627 (C=C str), 1614 (C=N str), 1524 (NO2 str),
1345 and 1165 (asymmetric and symetric SO2 str), 1146
Yield: 67%; MP: 243ꢀ245oC; MW: 602.09; Rf: 0.68; FTꢀIR (νmax
;
(aromatic CꢀCstr), 987 (CꢀN str ), cm ꢀ1; HꢀNMR (400MHz,
1
cmꢀ1 KBr): 3389 (NꢀH), 3076 (Ar CꢀH str), 2984 (ali CꢀH str), 80 DMSO, TMS) δ ppm: 8.22 (d, 2H, J = 7.9 Hz, ArH), 8.09 (d, 2H,
1716 (C=O str), 1629 (C=C str), 1612 (C=N str), ), 1345 and
1162 (asymmetric and symetric SO2 str), 1135 (aromatic CꢀCstr),
25 992 (CꢀN str ), 821 (CꢀCl str) cm ꢀ1; 1HꢀNMR (400MHz, DMSO,
TMS) δ ppm: 8.14 (d, 2H, J = 7.8 Hz, ArH), 7.93 (d, 2H, J = 7.7
J = 8.6 Hz, ArꢀH), 7.95 (d, 2H, J = 7.6 Hz, ArꢀH), 7.35 (d, 2H, J
= 8.4 Hz, ArH), 7.27 (s, 1H, Sec. Amide), 7.21 (s, 1H, Thiazole),
6.95 (s, 1H, Thiazole), 3.94 (s, 3H, Aromatic CꢀNH), 3.76 (s, 2H,
Methylene), 3.71ꢀ3.49 (m, 8H, Morpholine); 13CꢀNMR (100MHz,
Hz, ArꢀH), 7.74 (d, 2H, J = 5.4 Hz, ArꢀH), 7.42 (d, 2H, J = 5.3 85 CDCl3) δ,ppm:176.2, 171.8, 168.6, 165.7, 144.6, 143.7, 142.2,
Hz, ArH), 7.22 (s, 1H, Thiazole), 7.24 (s, 1H, Sec. Amide,), 6.98
(s, 1H, Thiazole), 3.98 (s, 3H, Aromatic CꢀNH), 3.74 (s, 2H,
30 Methylene), 3.69ꢀ3.52 (m, 8H, Morpholine); 13CꢀNMR (100MHz,
CDCl3) δ,ppm:176.4, 171.8, 168.6, 165.7, 142.2, 137.1, 136.8,
133.4, 130.2, 129.7, 129.1, 120.5, 113.9, 112.2, 66.4, 55.2, 48.7;
Mass :603.08 (M+1); Elemental analysis for C24H24ClN9O4S2:
Calculated: C, 47.88; H, 4.02; N, 20.94; Found: C, 47.89; H,
35 4.03; N, 20.94.
137.1, 130.2, 129.8, 124.2, 119.8, 113.7, 112.1, 66.3, 55.2, 48.7;
Mass :613.67 (M+1); Elemental analysis for C24H24N10O6S2:
Calculated: C, 47.05; H, 3.95; N, 22.86; Found: C, 47.06; H,
3.94; N, 22.86.
90
N-(4-hydroxyphenyl)-2-((4-morpholino-6-((4-(N-(thiazol-2-
yl)sulfamoyl)phenyl)amino)-1,3,5-triazin-2-yl)amino)acetamide
(8f)
N-(4-fluorophenyl)-2-((4-morpholino-6-((4-(N-(thiazol-2-
yl)sulfamoyl)phenyl)amino)-1,3,5-triazin-2-yl)amino)acetamide
(8c)
95 Yield: 64%; MP: 251ꢀ252oC; MW: 583.64; Rf: 0.68; FTꢀIR (νmax
;
cmꢀ1 KBr): 3596 (OH str) 3398 (NꢀH), 3082 (Ar CꢀH str), 2989
(ali CꢀH str), 1714 (C=O str), 1621 (C=C str), 1617 (C=N str),
1348 and 1161 (asymmetric and symetric SO2 str), 1149
Yield: 78%; MP: 234ꢀ235oC; MW: 585.63; Rf: 0.72; FTꢀIR (νmax
;
40 cmꢀ1 KBr): 3383 (NꢀH), 3078 (Ar CꢀH str), 2986 (ali CꢀH str),
1714 (C=O str), 1627 (C=C str), 1615 (C=N str), ), 1347 and
1
(aromatic CꢀCstr), 992 (CꢀN str ), cm ꢀ1; HꢀNMR (400MHz,
1163 (asymmetric and symetric SO2 str), 1157 (CꢀF str), 1138 100 DMSO, TMS) δ ppm: 8.14 (d, 2H, J = 7.8 Hz, ArH), 7.97 (d, 2H,
1
(aromatic CꢀCstr), 989 (CꢀN str ), cm ꢀ1; HꢀNMR (400MHz,
DMSO, TMS) δ ppm: 8.12 (d, 2H, J = 7.9 Hz, ArH), 7.92 (d, 2H,
45 J = 7.6 Hz, ArꢀH), 7.73 (d, 2H, J = 5.8 Hz, ArꢀH), 7.27 (s, 1H,
Sec. Amide), 7.24 (s, 1H, Thiazole), 7.08 (d, 2H, J = 5.2 Hz,
J = 7.5 Hz, ArꢀH), 7.31 (d, 2H, J = 5.4 Hz, ArꢀH), 7.28 (s, 1H,
Sec. Amide), 7.24 (s, 1H, Thiazole), 6.98 (s, 1H, Thiazole), 6.67
(d, 2H, J = 5.2 Hz, ArH), 5.34 (s, 1H, ArꢀOH), 3.97 (s, 3H,
Aromatic CꢀNH), 3.78 (s, 2H, Methylene), 3.74ꢀ3.52 (m, 8H,
ArH), 6.96 (s, 1H, Thiazole), 3.95 (s, 3H, Aromatic CꢀNH), 3.72 105 Morpholine); 13CꢀNMR (100MHz, CDCl3) δ,ppm:176.2, 171.8,
(s, 2H, Methylene), 3.67ꢀ3.51 (m, 8H, Morpholine); 13CꢀNMR
(100MHz, CDCl3) δ,ppm:176.4, 171.8, 168.6, 165.9, 162.8,
50 142.2, 137.3, 134.2, 130.4, 129.8, 120.8, 115.8, 113.9, 112.2,
66.4, 55.3, 48.7; Mass :586.64 (M+1); Elemental analysis for
168.5, 165.7, 154.2, 142.2, 137.1, 130.2, 129.8, 131.2, 123.1,
116.2, 113.9, 112.2, 66.4, 55.2, 48.7; Mass :584.65 (M+1);
Elemental analysis for C24H25N9O5S2: Calculated: C, 49.39; H,
4.32; N, 21.60; Found: C, 49.40; H, 4.31; N, 21.60.
C24H24FN9O4S2: Calculated: C, 49.22; H, 4.13; N, 21.53; Found: 110 2-((4-morpholino-6-((4-(N-(thiazol-2-
C, 49.23; H, 4.12; N, 21.53.
yl)sulfamoyl)phenyl)amino)-1,3,5-triazin-2-yl)amino)-N-(p-
2-((4-morpholino-6-((4-(N-(thiazol-2-
tolyl)acetamide (8g)
55 yl)sulfamoyl)phenyl)amino)-1,3,5-triazin-2-yl)amino)-N-(4-
(trifluoromethyl)phenyl)acetamide (8d)
Yield: 81%; MP: 248ꢀ249oC; MW: 581.67; Rf: 0.72; FTꢀIR (νmax
;
cmꢀ1 KBr): 3394 (NꢀH), 3082 (Ar CꢀH str), 2982 (ali CꢀH str),
115 2924 (CH3 str), 1721 (C=O str), 1623 (C=C str), 1612 (C=N str),
1343 and 1164 (asymmetric and symetric SO2 str), 1151
Yield: 72%; MP: 254ꢀ256oC; MW: 635.64; Rf: 0.62; FTꢀIR (νmax
;
cmꢀ1 KBr): 3387 (NꢀH), 3083 (Ar CꢀH str), 2989 (ali CꢀH str),
This journal is © The Royal Society of Chemistry [year]
Journal Name, [year], [vol], 00–00 | 5