10.1002/cmdc.201900216
ChemMedChem
FULL PAPER
1-(4-chlorophenyl)-3-(2-(2-fluorophenyl)benzo[d]oxazol-5-yl)urea
(5h)
White solid; 90% yield, Mp 260.5-262.5 oC; IR (KBr): νmax= 3334.65,
3263.96, 1648.34, 1564.59, 1555.74, 1474.30, 1426.04, 1330.31,
White solid; 94% yield, Mp 289.6-291.3 oC; IR (KBr): νmax= 3294.41,
1631.89, 1550.34, 1548.24, 1484.89, 1297.46, 1225.66, 1094.76, 819.11,
756.22, 669.21 cm‒1; 1H NMR (500 MHz, DMSO-d6) δ= 8.90 (d, J = 17.3
Hz, 2H, NH), 8.22 (td, J = 7.7, 1.9 Hz, 1H, ArH ), 8.03 (d, J = 2.1 Hz, 1H,
ArH), 7.79-7.63 (m, 2H, ArH), 7.57-7.39 (m, 5H, ArH), 7.39-7.30 (m, 2H,
ArH) ppm; 13C NMR (126 MHz, DMSO-d6) δ= 161.27, 159.70, 159.22,
152.99, 145.96, 141.83, 139.06, 137.26, 134.30, 130.77, 128.97, 125.75,
125.54, 120.16, 117.84, 117.64, 117.48, 115.06, 111.16, 109.50 ppm;
HRMS (TOF ESI): m/z calcd. for C20H12N3O2FCl [(M‒H)‒], 380.0607;
found, 380.0611. Purity by HPLC: 98.87%.
1223.79, 1174.91, 1109.36, 1030.19, 862.86, 735.11, 645.02 cm‒1 1H
;
NMR (500 MHz, DMSO-d6) δ= 8.88 (s, 1H, NH), 8.67 (s, 1H, NH), 8.16-
8.03 (m, 2H, ArH), 7.89 (dd, J = 8.0, 1.2 Hz, 1H, ArH), 7.73 (d, J = 8.8 Hz,
1H, ArH), 7.66-7.42 (m, 3H, ArH), 7.38-7.13 (m, 3H, ArH), 6.88-6.74 (m,
1H, ArH) ppm; 13C NMR (126 MHz, DMSO-d6) δ= 161.75, 153.10, 145.95,
141.77, 139.95, 138.30, 137.48, 134.77, 133.19, 132.53, 128.98, 128.47,
128.15, 122.99, 121.40, 119.20, 117.83, 115.88, 111.20, 109.51 ppm;
HRMS (TOF ESI): m/z calcd. for C21H11N3O2F3Cl2 [(M‒H)‒], 464.0185,
found, 464.0183. Purity by HPLC: 99.42%.
1-(2-(2-chlorophenyl)benzo[d]oxazol-5-yl)-3-(4-(trifluoromethoxy)-
phenyl)urea (5n)
1-(2-(2-chlorophenyl)benzo[d]oxazol-5-yl)-3-(m-tolyl)urea (5i)
White solid; 89% yield, Mp 227.4-229.3 oC; IR (KBr): νmax= 3266.96,
3033.97, 1633.17, 1566.41, 1561.32, 1475.46, 1301.02, 1226.47,
White solid; 89% yield, Mp 288.9-290.3 oC; IR (KBr): νmax= 3364.38,
3254.17, 1689.31, 1562.78, 1534.79, 1475.32, 1376.14, 1331.28,
1091.58, 1033.54, 871.20, 775.33, 684.11 cm‒1
;
1H NMR (500 MHz,
1223.10, 1144.38, 1124.12, 1037.48, 762.36, 735.78, 676.29 cm‒1 1H
;
DMSO-d6) δ= 8.88 (s, 1H, NH), 8.67 (s, 1H, NH), 8.16 (dd, J = 7.7, 1.8
Hz, 1H, ArH), 8.07 (d, J = 2.1 Hz, 1H, ArH), 7.79-7.54 (m, 4H, ArH), 7.45
(dd, J = 8.8, 2.1 Hz, 1H, ArH), 7.34 (s, 1H, ArH), 7.31-7.25 (m, 1H, ArH),
7.19 (t, J = 7.8 Hz, 1H, ArH), 6.86-6.77 (m, 1H, ArH), 2.30 (s, 3H, CH3)
ppm; 13C NMR (126 MHz, DMSO-d6) δ= 161.06, 153.09, 145.90, 141.81,
139.94, 138.31, 137.49, 133.15, 132.44, 132.22, 131.62, 128.99, 128.08,
125.93, 122.99, 119.18, 117.86, 115.87, 111.20, 109.45, 21.60 ppm;
HRMS (TOF ESI): m/z calcd. for C21H15N3O2Cl [(M‒H)‒], 376.0858; found,
376.0859. Purity by HPLC: 95.20%.
NMR (500 MHz, DMSO-d6) δ= 8.89 (s, 1H, NH), 8.71 (s, 1H, NH),
8.18(dd, J = 7.7, 1.6 Hz, 1H, ArH), 8.09 (d, J = 2.1 Hz, 1H, ArH), 7.74-
7.66 (m, 4H, ArH), 7.42 (dd, J = 8.8, 2.1 Hz, 1H, ArH), 7.24 (s, 1H, ArH),
7.31-7.22 (m, 1H, ArH), 7.17 (t, J = 7.8 Hz, 1H, ArH), 6.86-6.77 (m, 1H,
ArH) ppm; 13C NMR (126 MHz, DMSO-d6) δ= 163.08, 157.03, 145.78,
140.98, 139.74, 138.21, 137.39, 133.13, 132.43, 132.20, 131.61, 128.94,
128.18, 125.79, 122.86, 119.09, 117.79, 115.76, 111.17 109.43 ppm;
HRMS (TOF ESI): m/z calcd. for C21H12N3O3F3Cl [(M‒H)‒], 446.0524,
found, 446.0521. Purity by HPLC: 99.41%. Purity by HPLC: 99.66%.
1-(3-chlorophenyl)-3-(2-(2-chlorophenyl)benzo[d]oxazol-5-yl)urea
(5j)
1-(2-(2-chlorophenyl)benzo[d]oxazol-5-yl)-3-(2,5-dichlorophenyl)-
urea (5o)
White solid; 88% yield, Mp 249.1-249.8 oC; IR (KBr): νmax= 3277.71,
2315.96, 1635.58, 1563.76, 1473.59, 1422.45, 1226.38, 1089.63, 776.65,
White solid; 85% yield, Mp 267.8-268.7 oC; IR (KBr): νmax= 3317.23,
1656.24, 1540.45, 1470.60, 1411.64, 1212.81, 1086.62, 1030.05, 802.28,
732.72, 686.82 cm‒1; 1H NMR (500 MHz, DMSO-d6) δ= 9.71 (s, 1H, NH),
8.49 (s, 1H, NH), 8.36 (d, J = 2.5 Hz, 1H, ArH), 8.20-8.00 (m, 2H, ArH),
7.84-7.35 (m, 6H, ArH), 7.16-7.01 (m, 1H, ArH) ppm; 13C NMR (126 MHz,
DMSO) δ= 161.18, 152.43, 146.20, 141.84, 137.57, 136.76, 133.16,
132.45, 132.22, 131.61, 130.81, 128.05, 125.85, 122.97, 120.42, 120.34,
117.90, 111.36, 109.72 ppm; HRMS (TOF ESI): m/z calcd. for
C20H11N3O2Cl3 [(M‒H)‒], 429.9922, found, 429.9920. Purity by HPLC:
99.06%.
668.82 cm‒1 1H NMR (500 MHz, DMSO-d6) δ= 8.98 (d, J = 3.4 Hz, 2H,
;
NH), 8.16 (dd, J = 7.7, 1.7 Hz, 1H, ArH), 8.06 (d, J = 2.1 Hz, 1H, ArH),
7.79-7.70 (m, 2H, ArH), 7.62 (dtd, J = 29.2, 7.5, 1.5 Hz, 2H, ArH), 7.47
(dd, J = 8.8, 2.1 Hz, 2H, ArH), 7.38-7.29 (m, 2H, ArH), 7.08-6.99 (m, 1H,
ArH) ppm; 13C NMR (126 MHz, DMSO-d6) δ =161.11, 152.96, 146.08,
141.79, 141.62, 137.13, 133.56, 133.17, 132.45, 132.23, 131.62, 130.74,
128.08, 125.89, 121.84, 118.08, 117.08, 111.24, 109.80 ppm; HRMS
(TOF ESI): m/z calcd. for C20H12N3O2Cl2 [(M‒H)‒], 396.0312 found,
396.0313. Purity by HPLC: 99.42%.
1-(2-(2-bromophenyl)benzo[d]oxazol-5-yl)-3-(m-tolyl)urea (5p)
White solid; 87% yield, Mp 253.1-256.4 oC; IR (KBr): 3277.20, 1631.08,
1562.21, 1477.64, 1300.18, 1227.00, 1086.70, 1026.69, 870.36, 771.67,
;
681.34 cm‒1 1H NMR (500 MHz, DMSO-d6) δ= 8.95 (d, J = 3.8 Hz, 2H,
NH), 8.22 (tt, J = 7.7, 1.4 Hz, 1H, ArH ), 8.03 (s, 1H, ArH), 7.79-7.59 (m,
3H, ArH), 7.55-7.39 (m, 3H, ArH), 7.38-7.26 (m, 2H, ArH), 7.04 (dtt, J =
6.5, 3.3, 2.0 Hz, 1H, ArH); 13C NMR (126 MHz, DMSO-d6) δ= 161.28,
159.73, 159.24, 152.94, 146.04, 141.84, 141.63, 137.13, 134.29, 133.57,
130.77, 130.72, 125.51, 121.82, 118.02, 117.92, 117.63, 117.47, 117.07,
114.98, 111.15, 109.64; HRMS (TOF ESI): m/z calcd. for
C21H15N3O2Br[(M‒H)‒], 420.0353, found, 420.0357.
1-(4-chlorophenyl)-3-(2-(2-chlorophenyl)benzo[d]oxazol-5-yl)urea
(5k)
White solid; 83% yield, Mp 229.0-230.8 oC; IR (KBr): νmax= 3283.26,
1627.29, 1566.56, 1481.33, 1420.88, 1220.50, 1089.39, 1024.78, 653.84
cm‒1 1H NMR (500 MHz, DMSO-d6) δ= 8.92 (d, J = 16.2 Hz, 2H, NH),
;
8.16 (dd, J = 7.7, 1.9 Hz, 1H, ArH), 8.06 (d, J = 2.2 Hz, 1H, ArH), 7.73
(dd, J = 12.4, 8.4 Hz, 2H, ArH), 7.68-7.56 (m, 2H, ArH), 7.55-7.49 (m, 2H,
ArH), 7.45 (dd, J = 8.9, 2.2 Hz, 1H, ArH), 7.40-7.31 (m, 2H, ArH) ppm;
13C NMR (126 MHz, DMSO-d6) δ= 161.10, 153.01, 146.01, 141.80,
139.06, 137.27, 133.16, 132.45, 132.22, 131.63, 128.98, 128.08, 125.90,
125.76, 120.18, 118.00, 111.23, 109.67 ppm; HRMS (TOF ESI): m/z
calcd. for C20H12N3O2Cl2 [(M‒H)‒], 396.0312 found, 396.0308. Purity by
HPLC: 99.91%.
1-(2-(2-bromophenyl)benzo[d]oxazol-5-yl)-3-(3-chlorophenyl)urea
(5q)
White solid; 90% yield, Mp 228.0-230.6 oC; IR (KBr): νmax= 3287.52,
1632.34, 1560.67, 1475.36, 1418.20, 1296.76, 1226.20, 1082.52,
1-(3-chloro-4-methylphenyl)-3-(2-(2-chlorophenyl)benzo[d]oxazol-5-
yl)urea (5l)
1024.53, 914.68, 861.07, 785.41, 724.85, 654.63 cm‒1 1H NMR (500
;
White solid; 88% yield, Mp 245.0-247.1 oC; IR (KBr): νmax= 3268.60,
1630.66, 1562.54, 1484.23, 1297.86, 1230.41, 1041.81, 871.25, 804.47,
652.24 cm‒1; 1H NMR (500 MHz, DMSO-d6) δ= 8.92 (s, 1H, NH), 8.84 (s,
1H, NH), 8.15 (dd, J = 7.8, 1.8 Hz, 1H, ArH), 8.05 (d, J = 2.1 Hz, 1H,
ArH), 7.80-7.68 (m, 3H, ArH), 7.61 (dtd, J = 29.2, 7.5, 1.6 Hz, 2H, ArH),
7.45 (dd, J = 8.8, 2.2 Hz, 1H, ArH), 7.31-7.15 (m, 2H, ArH), 2.27 (s, 3H,
CH3) ppm; 13C NMR (126 MHz, DMSO-d6) δ= 161.08, 153.01, 146.01,
141.78, 139.23, 137.24, 133.47, 133.15, 132.44, 132.21, 131.62, 131.51,
128.63, 128.07, 125.89, 118.59, 118.02, 117.40, 111.20, 109.70, 19.17
ppm; HRMS (TOF ESI): m/z calcd. for C21H14N3O2Cl2 [(M‒H)‒], 410.0468,
found, 410.0464. Purity by HPLC: 99.64%.
MHz, DMSO-d6) δ= 9.75 (s, 1H, NH), 8.74-8.59 (m, 2H, ArH), 8.15 (dd, J
= 7.7, 1.8 Hz, 1H, ArH), 8.07 (d, J = 2.2 Hz, 1H, ArH), 7.80-7.68 (m, 3H,
ArH), 7.61 (dtd, J = 29.4, 7.5, 1.6 Hz, 2H, ArH), 7.41 (ddd, J = 39.2, 8.6,
2.2 Hz, 2H, ArH) ppm; 13C NMR (126 MHz, DMSO-d6) δ= 161.20, 152.57,
146.25, 141.85, 137.29, 136.68, 133.16, 132.46, 132.21, 131.62, 130.68,
128.05, 125.84, 125.69, 119.62, 117.98, 117.14, 111.36, 109.82 ppm;
HRMS (TOF ESI): m/z calcd. for C20H12N3O2ClBr[(M‒H)‒], 439.9806,
found, 439.9811. Purity by HPLC: 96.34%.
1-(2-(2-bromophenyl)benzo[d]oxazol-5-yl)-3-(4-chlorophenyl)urea
(5r)
White solid; 91% yield, Mp 294.5-296.8 oC; IR (KBr): νmax= 3285.98,
1629.22, 1556.96, 1461.79, 1414.87, 1214.65, 1088.47, 1020.16, 765.93,
1-(2-chloro-5-(trifluoromethyl)phenyl)-3-(2-(2-chlorophenyl)benzo-
[d]oxazol-5-yl)urea (5m)
652.27 cm‒1 1H NMR (500 MHz, DMSO-d6) δ= 9.01-8.81 (m, 2H, NH),
;
7
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