10.1002/cmdc.202000458
ChemMedChem
FULL PAPER
1-(2-(3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-
1-(2-(3-(2,4-difluorophenyl)-5-(p-tolyl)-4,5-dihydro-1H-
pyrazol-1-yl)-2-oxoethyl)pyrrolidine-2,5-dione (S3) Yield 1.3 g
yl)-2-oxoethyl)pyrrolidine-2,5-dione (S8) Yield 0.8g (40 %);
M.P. 184.6°C; White crystalline solid; IR (cm-1) 2821, 1699, 1672,
(65%); M.P. 181.6°C; White crystalline solid; IR (cm-1) 2921, 1707, 1602, 1151; H NMR (400 MHz, DMSO-d6, δ ppm) 2.70(s, 4H),
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1676, 1599, 1168; 1H NMR (400 MHz, DMSO-d6, δ ppm) 2.27(s,
3H), 2.71(s, 4H), 3.16-3.17(dd, J = 18.4 Hz, 1H), 3.90-3.97(m, 1H), = 17.4 Hz, 2H), 5.52-5.57(dd, J = 11.8 Hz, 1H), 7.19-7.91(m, 9H);
3.16-3.22 (dd, J = 18.2 Hz, 1H), 3.87-3.95(m, 1H), 4.54-4.67(q, J
4.52-4.64(q, J = 16.4 Hz, 2H), 5.46-5.50(dd, J = 11.8 Hz, 1H),
7.08-7.16 (m, 4H), 7.18-7.20(m, 1H), 7.27-7.32(m, 1H), 7.80-
7.97(m, 1H); 13C NMR (400 MHz, DMSO-d6) 20.58, 27.95, 43.93-
43.98, 59.58, 104.66-138.39, 151.7-151.27, 176.89, 162.87,
162.12; UV Spectrum (10ppm) λmax 287.1 nm; Theoretical mass
411.1, LC-MS (m/z, I %), 412.1 [(M+H)+, 100%]; HPLC Purity %
Area 96.81 %, RT 8.04 mins.
13C NMR (400 MHz, DMSO-d6) 27.97, 42.07, 60.17, 115.57-
141.58, 155.06, 177.12, 162.20, 162.84, 164.68; UV Spectrum
(10ppm) λmax 289.2 nm; Theoretical mass 379.1, LC-MS (m/z, I %),
380.1 [(M+H)+, 100%]; HPLC Purity % Area 97.76 %, RT 5.27
mins.
1-(2-oxo-2-(3-phenyl-5-(thiophen-2-yl)-4,5-dihydro-1H-
pyrazol-1-yl)ethyl)pyrrolidine-2,5-dione (S9) Yield 1.0g (50 %);
M.P. 189.9°C; White crystalline solid; IR (cm-1) 2966, 1703, 1676,
1-(2-(3-(2,4-difluorophenyl)-5-(furan-2-yl)-4,5-dihydro-1H-
pyrazol-1-yl)-2-oxoethyl)pyrrolidine-2,5-dione (S4) Yield 1.15
g (57.5%); M.P. 149.8°C; White crystalline solid; IR (cm-1) 2929,
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1602; H NMR (400 MHz, DMSO-d6, δ ppm) 2.73(s, 4H), 3.37-
3.39(m, 1H), 3.87-3.94(m, 1H), 4.49-4.60 (m, 2H), 5.84-5.88(dd,
J = 11.2 Hz, 1H), 6.94-6.96(t, J= 4.4 Hz, 1H), 7.03-7.04(d, J= 3.2
Hz, 1H), 7.41-7.42(m, 1H), 7.41-7.51(m, 3H), 7.84-7.86(m, 2H);
13C NMR (400 MHz, DMSO-d6) 28, 41.62, 55.57, 124.89-143.91,
156.10, 177.11, 162.8; UV Spectrum (10ppm) λmax 289.1 nm;
Theoretical mass 367.1, LC-MS (m/z, I %), 368.1 [(M+H)+, 100%];
HPLC Purity- % Area 98.88 %, RT 4.36 mins.
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1705, 1660, 1602, 1157; H NMR (400 MHz, DMSO-d6, δ ppm)
2.73(s, 4H), 3.80-3.87(m, 1H), 3.90-3.97(m, 2H), 5.61-5.65(dd, J
= 11.8 Hz, 1H), 6.33(d, J = 2.8, 1H), 6.39(d, J = 1.6, 1H), 7.21-
7.26 (m, 1H), 7.38-7.44(m, 1H), 7.57(s, 1H), 7.97-8.08(m, 1H); 13
C
NMR (400 MHz, DMSO-d6) 27.98, 40.05, 53.35, 104.87-142.64,
151.55-151.70, 177.15, 163.03; UV Spectrum (10ppm) λmax
285.5nm; Theoretical mass 387.1, LC-MS (m/z, I %), 388 [(M+H)+,
100%]; HPLC Purity % Area 98.44 %, RT 4.56 mins.
1-(2-(5-(furan-2-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-2-
oxoethyl)pyrrolidine-2,5-dione (S10) Yield 0.9g (45 %); M.P.
216.2°C; White crystalline solid; IR (cm-1) 2920, 1703, 1674, 1600,
1-(2-(5-(2-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-
yl)-2-oxoethyl)pyrrolidine-2,5-dione (S5) Yield 1.22 g (61 %);
M.P. 222.6 °C; White crystalline solid; IR (cm-1) 2820, 1703, 1676,
1601, 692; 1H NMR (400 MHz, DMSO-d6, δ ppm) 2.70(s, 4H),
3.10-3.16 (dd, J = 18 Hz, 1H), 3.97-4.05 (m, 1H), 4.56-4.60 (d, J
= 16.8 Hz, 1H), 4.69-4.73(d, J = 17.2 Hz, 1H), 5.75-5.79 (dd, J =
12 Hz, 1H), 7.11-7.83 (m, 9H); 13C NMR (400 MHz, DMSO-d6):
27.99, 42.92, 57.86, 129.59-130.85, 156.05, 177.11, 162.99,
129.69; UV Spectrum (10ppm) λmax 288.3 nm; Theoretical mass
395.1, LC-MS (m/z, I %), 396.1 [(M+H)+, 100%]; HPLC Purity %
Area 98.14 %, RT 7.20 mins.
1
1168; H NMR (400 MHz, DMSO-d6, δ ppm) 2.73(s, 4H), 3.38-
3.41(m, 1H), 3.70-3.82(m, 1H), 4.49-4.59(m, 2H), 5.63-5.69(dd, J
= 11.6 Hz, 1H), 6.33(m, 1H), 6.39(m, 1H), 7.50-7.59 (m, 4H), 7.83-
8.85(m, 1H); 13C NMR (400 MHz, DMSO-d6): 27.99, 38.16, 53.64,
107.44-142.59, 151.87, 177.15, 162.84; UV Spectrum (10ppm)
λmax 288.1 nm; Theoretical mass 351.1, LC-MS (m/z, I %), 352.1
[(M+H)+, 100%]; HPLC Purity- % Area 98.38 %, RT 3.73 mins.
1-(2-(3-(4-fluorophenyl)-5-(furan-2-yl)-4,5-dihydro-1H-
pyrazol-1-yl)-2-oxoethyl)pyrrolidine-2,5-dione (S11) Yield
1.11 g (55.5%); M.P. 175.4°C; White crystalline solid; IR (cm-1)
1
1-(2-(3,5-diphenyl-4,5-dihydro-1H-pyrazol-1-yl)-2-
2966, 1703, 1666, 1602, 1168; H NMR (400 MHz, DMSO-d6, δ
oxoethyl)pyrrolidine-2,5-dione (S6) Yield 0.9 g (45 %); M.P.
201.1 °C; White crystalline solid; IR (cm-1) 2951, 1707, 1674,
1601; H NMR (400 MHz, DMSO-d6, δ ppm) 2.71(s, 4H), 3.16-
3.21 (dd, J = 18.2 Hz, 1H), 3.88-3.95(m, 1H), 4.54-4.68 (q, J =
18.1 Hz, 2H), 5.52-5.56(dd, J = 11.2 Hz, 1H), 7.19-7.84 (m, 10H);
13C NMR (400 MHz, DMSO-d6) 27.99, 42.92, 57.86, 129.59-
130.85, 156.05, 177.11, 162.99, 129.69; UV- Spectrum
(10ppm)λmax 290nm; Theoretical mass 361.1, LC-MS (m/z, I %),
362.1 [(M+H)+, 100%]; HPLC Purity % Area 98.59 %, RT 5.11
mins.
ppm) 2.73(s, 4H), 3.44-3.45 (m, 1H), 3.78-3.82 (m, 1H), 4.47-
4.57(m, 2H), 5.63-5.67(dd, J = 11.8 Hz, 1H), 6.32(d, J = 2.8, 1H),
6.39(d, J = 1.6, 1H), 7.32-7.36(t, J= 8.8 2H), 7.57(S, 1H), 7.90-
8.92 (m, 1H), 7.57(s, 2H); 13C NMR (400 MHz, DMSO-d6) 27.99,
38.24, 53.75, 107.46-142.59, 151.83, 162.24-162.84, 177.15,
162.84; UV Spectrum (10ppm) λmax 287.5nm; Theoretical mass
369.1, LC-MS (m/z, I %), 370.1 [(M+H)+, 100%]; HPLC Purity- %
Area 98.61 %, RT 3.83 mins.
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1-(2-(3-(2,4-difluorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-
dihydro-1H-pyrazol-1-yl)-2-oxo
ethyl)pyrrolidine-2,5-dione
1-(2-(5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-
yl)-2-oxoethyl)pyrrolidine-2,5-dione Yield 0.99g (49.5 %); M.P.
181.1°C; White crystalline solid; IR (cm-1) 2903, 1701, 1674,
(S12) Yield 1.25 g (62.5%); M.P. 116.3 °C; White crystalline
solid; IR (cm-1) 2913, 1703, 1674, 1602, 1166; 1H NMR (400 MHz,
DMSO-d6, δ ppm) 2.71(s, 4H), 3.13-3.20 (dd, J=18.4 Hz, 1H),
3.72-3.73 (s, 1H), 3.89-3.97(m, 1H), 4.50-4.54 (d, J= 16.8 Hz, 1H),
4.61-4.65 (d, J= 16.8 Hz, 1H), 5.45-5.49 (dd, J = 11.6 Hz, 1H),
6.70-6.73 (dd, J = 8.4 Hz, 1H), 6.78-6.79 (d, J = 1.8, 1H), 6.88-
6.90 (d, J = 8.4, 1H), 7.20-7.25 (m, 1H), 7.37-7.43 (m, 1H), 7.92-
8.03 (m, 1H); 13C NMR (400 MHz, DMSO-d6) 27.95, 44.03, 55.36-
55.50, 59.52, 104.82-148.77, 151.51, 148.77, 148.06, 177.13,
163.02; UV Spectrum (10ppm) λmax 286.2 nm; Theoretical mass
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1602; H NMR (400 MHz, DMSO-d6, δ ppm) 2.71(s, 4H), 3.18-
3.23(dd, J = 11.6 Hz, 1H), 3.90-3.95 (m, 1H), 4.53-4.66(q, J = 16.9
Hz, 2H), 5.53-5.58 (dd, J = 11.6 Hz, 1H), 7.13-7.84(m, 9H); 13C
NMR (400 MHz, DMSO-d6) 27.97, 41.87, 59.42, 125.54-141.58,
155.97, 177.12, 162.57, 162.91, 160.15; UV Spectrum (10ppm)
λmax 289.2 nm; Theoretical mass 379.1, LC-MS (m/z, I %), 380.1
[(M+H)+, 100%]; HPLC Purity % Area 97.52 %, RT 5.29 mins.
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