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Chemical Structure| 53090-43-0 Chemical Structure| 53090-43-0

Structure of 53090-43-0

Chemical Structure| 53090-43-0

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Product Details of [ 53090-43-0 ]

CAS No. :53090-43-0
Formula : C11H10Cl2O3
M.W : 261.10
SMILES Code : CCOC(=O)CC(=O)C1=CC(Cl)=C(Cl)C=C1
MDL No. :MFCD03424830
InChI Key :SIWICBKMMHBCSU-UHFFFAOYSA-N
Pubchem ID :2758176

Safety of [ 53090-43-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 53090-43-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 6
Fraction Csp3 0.27
Num. rotatable bonds 5
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 62.36
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.54
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.25
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.13
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.7
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.62
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.05

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.45
Solubility 0.0918 mg/ml ; 0.000352 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.83
Solubility 0.0382 mg/ml ; 0.000146 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.47
Solubility 0.00891 mg/ml ; 0.0000341 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.59 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<0.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.77

Application In Synthesis of [ 53090-43-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 53090-43-0 ]

[ 53090-43-0 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 1071-46-1 ]
  • [ 3024-72-4 ]
  • [ 53090-43-0 ]
  • 2
  • [ 113-00-8 ]
  • [ 53090-43-0 ]
  • [ 98305-86-3 ]
  • 3
  • [ 6148-64-7 ]
  • [ 3024-72-4 ]
  • [ 53090-43-0 ]
  • 5
  • [ 122-51-0 ]
  • [ 53090-43-0 ]
  • [ 1027729-45-8 ]
  • 6
  • [ 53090-43-0 ]
  • [ 191673-26-4 ]
  • 7
  • [ 53090-43-0 ]
  • 3-(3,4-dichloro-phenyl)-3,3-diethoxy-propan-1-ol [ No CAS ]
  • 8
  • [ 53090-43-0 ]
  • [ 191673-28-6 ]
  • 9
  • [ 53090-43-0 ]
  • [ 76519-33-0 ]
  • 10
  • [ 53090-43-0 ]
  • [ 76519-18-1 ]
  • 11
  • [ 53090-43-0 ]
  • [ 76519-19-2 ]
  • 12
  • [ 122-51-0 ]
  • [ 53090-43-0 ]
  • [ 191673-26-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; sodium chloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; 3-(3,4-Dichlorophenyl)-3-oxo-1-propanol In 2.4 liters of ethanol, 119 g (0.46 mole) of <strong>[53090-43-0]ethyl 3-(3,4-dichlorophenyl)-3-oxopropionate</strong> were dissolved. To the resulting solution, 115 ml (0.68 mole) of ethyl orthoformate and 4.4 g (2.28 mmol) of p-toluenesulfonic acid were added, followed by heating under reflux for 8 hours. The reaction mixture was poured into 1 liter of a saturated aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate (700 ml, three times). The organic layers were combined, washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was dissolved in 800 ml of tetrahydrofuran. The resulting solution was added dropwise to a suspension of 25.9 g (0.68 mole) of lithium aluminum hydride in 4 liters of tetrahydrofuran over 1 hour under ice-cooling. After stirring at 0 C. for 2 hours, 250 ml of water and 125 ml of a 10% aqueous solution of sodium hydroxide were added and the mixture was stirred at room temperature for a further 1 hour. The reaction mixture was filtered through Celite. The filtrate was poured into 1 liter of a saturated aqueous solution of sodium chloride, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. A residue was dissolved in 500 ml of chloroform. Under ice-cooling, 500 ml of 50% trifluoroacetic acid were added dropwise to the resulting solution over 30 minutes and the mixture was stirred for 30 minutes. The reaction mixture was diluted with 300 ml of methylene chloride. The organic layer was washed with water and a saturated aqueous solution of sodium bicarbonate and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (eluding solvent: n-hexane: ethyl acetate=9:1), whereby 46 g of the title compound were obtained as white crystals. Nuclear magnetic resonance spectrum (270 MHz, CDCl3) delta ppm: 8.05 (1H, d, J=2.0 Hz), 7.79 (1H, dd, J=2.0, 8.1 Hz), 7.57 (1H, d, J=8.1 Hz), 4.04 (2H, m), 3.19 (2H, t, J=5.3 Hz), 2.44 (1H, t, J=6.6 Hz, D2O disappeared).
  • 13
  • [ 122-51-0 ]
  • [ 76-05-1 ]
  • [ 53090-43-0 ]
  • [ 191673-26-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; sodium chloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; ethyl acetate; 7(a) 3-(3,4-Dichlorophenyl)-3-oxo-1-propanol 119 g (0.46 mole) of <strong>[53090-43-0]ethyl 3-(3,4-dichlorophenyl)-3-oxopropionate</strong> were dissolved in 2.4 liters of ethanol, and 115 ml (0.68 mole) of ethyl orthoformate and 4.4 g (22.8 mmole) of p-toluenesulfonic acid were added thereto. The mixture was then heated under reflux for 8 hours. At the end of this time, the reaction solution was poured into 1 liter of a saturated aqueous solution of sodium hydrogen-carbonate and extracted three times, each time with 700 ml of ethyl acetate. The organic extracts were combined, washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was dissolved in 800 ml of tetrahydrofuran and then added dropwise to 4 liters of a suspension of 25.9 g (0.68 mole) of lithium aluminum hydride in tetrahydrofuran over a period of 1 hour, whilst ice-cooling. The mixture was stirred at 0 C. for 2 hours, and then 250 ml of water and 125 ml of a 10% w/v aqueous solution of sodium hydroxide were added thereto, and the mixture was stirred for a further 1 hour at room temperature. It was then filtered through a Celite (trade mark) filter aid, and the filtrate was poured into 1 liter of a saturated aqueous solution of sodium chloride and then extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was dissolved in 500 ml of chloroform. 500 ml of 50% v/v aqueous trifluoroacetic acid were added to the resulting solution over a period of 30 minutes, whilst ice-cooling, and the mixture was stirred for a further 30 minutes at the same temperature. At the end of this time, the reaction solution was diluted with 300 ml of methylene chloride, and the organic layer was washed with water and then with a saturated aqueous solution of sodium hydrogencarbonate, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a 9:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 46 g of the title compound as white crystals. Nuclear Magnetic Resonance Spectrum (270 MHz, CDCl3) delta ppm:
  • 14
  • [ 96-31-1 ]
  • [ 53090-43-0 ]
  • 6-(3,4-dichlorophenyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 4 6-(3,4-Dichlorophenyl)-1,3-dimethyl-2,4(1H,3H)pyrimidinedione (5.27 g) was obtained according to substantially the same manner as that of Example 2 from <strong>[53090-43-0]ethyl 2-(3,4-dichlorobenzoyl)acetate</strong> (10.0 g) and N,N'-dimethylurea (3.71 g). mp: 172-175 C. IR (Nujol): 1695, 1660, 1620 cm-1 NMR (DMSO-d6, delta): 7.83 (1H, d, J=2 Hz), 7.80 (1H, d, J=8 Hz), 7.50 (1H, dd, J=2 Hz, 8 Hz), 5.68 (1H, s), 3.23 (3H, s), 3.10 (3H, s).
  • 15
  • [ 318469-73-7 ]
  • [ 53090-43-0 ]
  • [ 1399840-67-5 ]
  • 16
  • [ 53090-43-0 ]
  • [ 1399840-90-4 ]
  • 17
  • [ 53090-43-0 ]
  • ethyl 5-(3,4-dichlorophenyl)-7-oxo-6-oxabicyclo[3.2.0]heptane-4-carboxylate [ No CAS ]
  • [ 1399841-07-6 ]
  • 18
  • [ 53090-43-0 ]
  • ethyl 5-(3,4-dichlorophenyl)-7-oxo-6-oxabicyclo[3.2.0]heptane-4-carboxylate [ No CAS ]
  • 19
  • [ 53090-43-0 ]
  • [ 1184849-00-0 ]
  • 20
  • [ 53090-43-0 ]
  • [ 1184850-57-4 ]
  • 21
  • [ 57297-29-7 ]
  • [ 53090-43-0 ]
  • [ 1184850-56-3 ]
YieldReaction ConditionsOperation in experiment
49% Step A: 2-Cvclopropyl-6-(3.4-dichloro-phenyl)-pyrimidin-4-ol. To a solution consisting of <strong>[53090-43-0]3-(3,4-dichlorophenyl)-3-oxo-propionic acid ethyl ester</strong> (252 mg, <n="100"/>0.967 mmol) and MeOH were added cyclopropylcarbamidine hydrochloride (140 mg, 1.16 mmol) and potassium tert-butoxide (266 mg, 2.37 mmol). The reaction mixture was stirred at rt overnight, then concentrated. Water and CH2Cl2 were added, and the mixture was adjusted to pH 7 with glacial acetic acid. The layers were separated, and the aqueous phase was extracted with EtOAc. The organics were combined, dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give the title compound as a white solid (133 mg, 49percent).
  • 22
  • 2-diazo-3-(3,4-dichloro-phenyl)-3-hydroxy-propionic acid ethyl ester [ No CAS ]
  • [ 53090-43-0 ]
  • 23
  • [ 1159942-71-8 ]
  • [ 53090-43-0 ]
  • [ 1607023-54-0 ]
YieldReaction ConditionsOperation in experiment
65% With toluene-4-sulfonic acid; In butan-1-ol; for 2h;Reflux; To a solution of 4-(4-methylthiazol-2-yl)-lH-pyrazol-5-amine (50 mg, 0.27 mmol) in n-BuOH (1.0 mL) was added p-TsOH (4.7 mg, 0.03 mmol) and ethyl 3-(3,4- dichlorophenyl)-3-oxopropanoate (108 mg, 0.41 mmol). The reaction was stirred for 2 h at reflux, then cooled to room temperature and diluted with methanol (1 mL). The solids were collected by filtration and washed with MeOH (3 x 1 mL) to afford 5-(3,4-dichlorophenyl)-3-(4-methylthiazol-2-yl)pyrazolo[l ,5-a]pyrimidin- 7(4H)-one as a white solid (68.9 mg 65%). LCMS (ES, m/z): [M+l] +: 377.0 *H NMR (300 MHz, CD3OD): delta 8.46 (s, 1H), 8.43 (d, / = 2.1 Hz, 1H), 8.11 (dd, J 1= 2.1 Hz, J = 8.4 Hz, 1H), 7.62 (d, / = 8.4 Hz, 1H), 6.97 (s, 1H), 6.38 (s, 1H), 2.45 (s, 3H)
  • 24
  • [ 51-44-5 ]
  • [ 6148-64-7 ]
  • [ 53090-43-0 ]
YieldReaction ConditionsOperation in experiment
73% CDI (41.5 g, 290.32 mmol, 3.70 equiv) was added to a solution of 3,4- dichlorobenzoic acid (15 g, 78.53 mmol, 1.00 equiv) in tetrahydrofuran (200 mL), The resulting solution was stirred for 4 h at 25C. Separately, to a solution of potassium 3-ethoxy-3-oxopropanoate (37.7 g, 235 mmol, 3.00 equiv) in CH3CN (400 mL) was added MgCl2 (33.5 g, 353 mmol, 4.5 equiv) and triethylamine (23.8 g, 235 mmol, 3.00 equiv). The two solutions were combined and stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was diluted with 200 mL of water. The pH of the solution was adjusted to pH 5 with HC1 (1M). The resulting solution was extracted with 4x50 mL of ethyl acetate and the organic layers were combined and dried over magnesium sulfate. The organics were concentrated in vacuo and purified by silica gel column chromatography with petroleum ether/ethyl acetate (50: 1). This resulted in 15 g (73%) of ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate as a colorless oil
  • 25
  • [ 1607024-46-3 ]
  • [ 53090-43-0 ]
  • [ 1607023-10-8 ]
YieldReaction ConditionsOperation in experiment
43% With toluene-4-sulfonic acid; In butan-1-ol; for 1h;Reflux; To a solution of 4-(benzo[d]isoxazol-3-yl)-lH-pyrazol-5-amine (50 mg, 0.25 mmol) in n-BuOH (0.2 mL) was added ethyl 3-(3,4-dichlorophenyl)-3- oxopropanoate (100 mg, 0.37 mmol) and p-TsOH (5 mg) at room temperature.After refluxing 1 hour, the solids were collected by filtration and washed with methanol (3 x 2 mL) to afford 3-(benzo[d]isoxazol-3-yl)-5-(3,4- dichlorophenyl)pyrazolo[l,5-a]pyrimidin-7(4H)-one as a yellow solid (42.5 mg, 43%). LCMS (ES, m/z): [M+H]+ 396.9 *H NMR (400 MHz, DMSO+NH3 (saturated D20 solution)) delta 12.3 (brs, IH), 8.72 (s, IH), 8.30-8.28 (m, IH), 8.11 (s, IH), 7.88-7.74 (m, 4H), 7.53-7.49 (m, IH), 6.34 (s, IH)
  • 26
  • [ 1607024-50-9 ]
  • [ 53090-43-0 ]
  • [ 1607023-51-7 ]
YieldReaction ConditionsOperation in experiment
37% With toluene-4-sulfonic acid; In butan-1-ol; for 2h;Reflux; To a solution of 2-methyl-l'H,2H-3,4'-bipyrazol-5'-amine (50 mg, 0.30 mmol) in n- BuOH (0.2 mL) was added <strong>[53090-43-0]ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate</strong> (120 mg, 0.45 mmol) and p-TsOH (5 mg) at room temperature. After refluxing 2 hours, the solids were collected by filtration and washed with methanol (3 x 2 mL) to afford 5- (3,4-dichlorophenyl)-3-(l-methyl-lH-pyrazol-5-yl)pyrazolo[l,5-a]pyrimidin- 7(4H)-one as an off-white solid (39.5 mg, 37 %). LCMS (ES, m/z): [M+H]+ 360.0 'H-NMR (300 MHz, DMSO) delta 12.46(brs, 1H), 8.10-8.08(m,2H), 7.80(s,2H), 7.51(d, / = 1.8 Hz, 1H), 6.48(s, 1H), 6.18 (s, 1H), 3.80 (s, 3H)
  • 27
  • [ 1607024-52-1 ]
  • [ 53090-43-0 ]
  • [ 1607023-20-0 ]
YieldReaction ConditionsOperation in experiment
80% With toluene-4-sulfonic acid; In butan-1-ol; for 1h;Reflux; To a solution of l'H,2H-3,4'-bipyrazol-5'-amine (50 mg, 0.33 mmol) in n-BuOH (0.2 mL) was added <strong>[53090-43-0]ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate</strong> (130 mg, 0.50 mmol) and p-TsOH (5 mg) at room temperature. After refluxing 1 hour, the solids were collected by filtration and washed with methanol (3 x 2 mL) to afford 5-(3,4- dichlorophenyl)-3-(lH-pyrazol-3-yl)pyrazolo[l,5-a]pyrimidin-7(4H)-one as a white solid (93 mg, 80%). LCMS (ES, m/z): [M+H]+ 345.9 *H NMR (300 MHz, DMSO) delta 8.32-8.28 (d, / =11.7Hz, 1H), 8.17 (s, 1H), 7.88- 7.80 (m, 3H), 6.71-6.70 (d, / = 2.1 Hz, 1H), 6.21 (s, 1H)
  • 28
  • [ 1607024-59-8 ]
  • [ 53090-43-0 ]
  • [ 1607023-48-2 ]
YieldReaction ConditionsOperation in experiment
65% With toluene-4-sulfonic acid; In butan-1-ol; for 2h;Reflux; To a solution of 2-ethyl-l'H,2H-3,4'-bipyrazol-5'-amine (50 mg, 0.28 mmol) in n- BuOH (0.2 mL) was added <strong>[53090-43-0]ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate</strong> (110 mg, 0.42 mmol) and p-TsOH (5 mg) at room temperature. After refluxing 2 hours, the solids were collected by filtration and washed with methanol (3 x 2 mL) to afford 5- (3,4-dichlorophenyl)-3-(l -ethyl- lH-pyrazol-5-yl)pyrazolo[l ,5-a]pyrimidin-7(4H)- one as off-white solid (68.5 mg, 65 ). LCMS (ES, m/z): [M+H]+ 374.0 'H-NMR (300 MHz, DMSO) delta 12.44 (brs, 1H), 8.03-8.01 (m, 2H), 7.79-7.70(m, 2H), 7.51(d, / = 1.8 Hz, 1H), 6.40(d, / = 1.8 Hz, 1H), 6.13(s, 1H), 4.02(q, / = 7.2 Hz, 2H), 2.23(s, 3H), l,24(t, / = 7.2 Hz, 3H)
  • 29
  • [ 53090-43-0 ]
  • [ 1607024-98-5 ]
  • 30
  • [ 53090-43-0 ]
  • [ 1607024-99-6 ]
  • 31
  • [ 53090-43-0 ]
  • [ 1607023-53-9 ]
  • 32
  • [ 1607025-41-1 ]
  • [ 53090-43-0 ]
  • [ 1607023-55-1 ]
YieldReaction ConditionsOperation in experiment
55% With toluene-4-sulfonic acid; In butan-1-ol; for 2h;Reflux; To a solution of 4-(5-methylthiazol-2-yl)-lH-pyrazol-5-amine (100 mg, 0.55 mmol) in n-BuOH (0.2 mL) was added <strong>[53090-43-0]ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate</strong> (220 mg, 0.83 mmol) and p-TsOH (10 mg) at room temperature. After refluxing for 2 hours, the solids were collected by filtration and washed with methanol (3 x 2 mL) to afford 5-(3,4-dichlorophenyl)-3-(5-methylthiazol-2-yl)pyrazolo[l ,5-a]pyrimidin- 7(4H)-one as a yellow solid (115.9 mg, 55 ). LCMS (ES, m/z): [M+H]+ 377.0 'H-NMR (300 MHz, DMSO) delta 8.41-8.39(m,2H), 8.14-8.10 (dd, / = 2.1 Hz, 8.4 Hz, 1H), 7.63(d, / = 8.4 Hz, 1H), 7.35(d, / = 1.2 Hz, 1H), 6.37(s, 1H), 2.54 (s, 3H)
  • 33
  • [ 16617-46-2 ]
  • [ 53090-43-0 ]
  • [ 1607024-97-4 ]
YieldReaction ConditionsOperation in experiment
71% With toluene-4-sulfonic acid; In butan-1-ol; at 130℃; for 1h; A mixture of <strong>[53090-43-0]ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate</strong> (1.2 g, 4.60 mmol, 1.20 equiv), 5-amino-lH-pyrazole-4-carbonitrile (400 mg, 3.70 mmol, 1.00 equiv), butan-l-ol (1 mL), and TsOH (10 mg, 0.06 mmol, 0.05 equiv) was stirred for 1 h at 130C. The reaction progress was monitored by LCMS. The solids were collected by filtration. The solid was washed with 3x1 mL of methanol. This resulted in 0.8 g (71%) of 5-(3,4-dichlorophenyl)-7-oxo-4H,7H-pyrazolo[l,5-a]pyrimidine-3- carbonitrile as a white solid. *H NMR (300 MHz, DMSO): delta 8.44 (s, 1H), 8.17 (s, 1H), 7.85 (s, 1H), 6.37 (s, 1H)
  • 34
  • [ 53090-43-0 ]
  • ethyl 3-(3,4-dichlorophenyl)-3-([2-(dimethylamino)ethyl][3-(4-fluoro-3-methylphenyl)-5-methoxyimidazo[1,2-a]pyridin-2-yl]carbonyl}amino)propanoate [ No CAS ]
  • 35
  • [ 53090-43-0 ]
  • N-[1-(3,4-dichlorophenyl)-3-hydroxypropyl]-N-[2-(dimethylamino)ethyl]-3-(4-fluoro-3-methylphenyl)-5-methoxyimidazo[1,2-a]pyridine-2-carboxamide [ No CAS ]
 

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Ester Cleavage • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

Related Functional Groups of
[ 53090-43-0 ]

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Esters

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Ketones

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Similarity: 0.96

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