[ CAS No. 53090-43-0 ]

Name: 53090-43-0|Ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate|97%
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Quality Control of [ 53090-43-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 53090-43-0 ]

Product Details of [ 53090-43-0 ]

CAS No. :	53090-43-0	MDL No. :	MFCD03424830
Formula :	C₁₁H₁₀Cl₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SIWICBKMMHBCSU-UHFFFAOYSA-N
M.W :	261.10 g/mol	Pubchem ID :	2758176
Synonyms :

Calculated chemistry of [ 53090-43-0 ]

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 :	43.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.54
Log Po/w (XLOGP3) :	3.25
Log Po/w (WLOGP) :	3.13
Log Po/w (MLOGP) :	2.7
Log Po/w (SILICOS-IT) :	3.62
Consensus Log Po/w :	3.05

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.45
Solubility :	0.0918 mg/ml ; 0.000352 mol/l
Class :	Soluble
Log S (Ali) :	-3.83
Solubility :	0.0382 mg/ml ; 0.000146 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.47
Solubility :	0.00891 mg/ml ; 0.0000341 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.77

Safety of [ 53090-43-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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.

Upstream synthesis route of [ 53090-43-0 ]
Downstream synthetic route of [ 53090-43-0 ]

[ 53090-43-0 ] Synthesis Path-Upstream 1~4

1
[ 51-44-5 ]
[ 6148-64-7 ]
[ 53090-43-0 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: With 1,1'-carbonyldiimidazole In tetrahydrofuran at 25℃; for 4 h; Stage #2: With triethylamine; magnesium chloride In tetrahydrofuran; acetonitrile at 20℃; for 2 h;	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 25°C. 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 (73percent) of ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate as a colorless oil

Reference： [1] Patent: WO2014/66795, 2014, A1, . Location in patent: Paragraph 0175

2
[ 6148-64-7 ]
[ 3024-72-4 ]
[ 53090-43-0 ]

Reference： [1] Synlett, 2003, # 3, p. 353 - 356
[2] Synthesis, 1993, # 3, p. 290 - 292

3
[ 141-78-6 ]
[ 3024-72-4 ]
[ 53090-43-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9184 - 9204

4
[ 1071-46-1 ]
[ 3024-72-4 ]
[ 53090-43-0 ]

Reference： [1] Journal of Organic Chemistry, 1979, vol. 44, # 2, p. 310 - 311

[ 53090-43-0 ] Synthesis Path-Downstream 1~58

1
[ 1071-46-1 ]
[ 3024-72-4 ]
[ 53090-43-0 ]

Reference： [1]Journal of Organic Chemistry,1979,vol. 44,p. 310 - 311

2
[ 113-00-8 ]
[ 53090-43-0 ]
[ 98305-86-3 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1864 - 1869

3
[ 6148-64-7 ]
[ 3024-72-4 ]
[ 53090-43-0 ]

Reference： [1]Synlett,2003,p. 353 - 356
[2]Synthesis,1993,p. 290 - 292

5
[ 122-51-0 ]
[ 53090-43-0 ]
[ 1027729-45-8 ]

Reference： [1]Synlett,2003,p. 353 - 356

6
[ 53090-43-0 ]
[ 191673-26-4 ]

Reference： [1]Synlett,2003,p. 353 - 356

7
[ 53090-43-0 ]
3-(3,4-dichloro-phenyl)-3,3-diethoxy-propan-1-ol [ No CAS ]

Reference： [1]Synlett,2003,p. 353 - 356

8
[ 53090-43-0 ]
[ 191673-28-6 ]

Reference： [1]Synlett,2003,p. 353 - 356

9
[ 53090-43-0 ]
[ 76519-33-0 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1864 - 1869

10
[ 53090-43-0 ]
[ 76519-18-1 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1864 - 1869

11
[ 53090-43-0 ]
[ 76519-19-2 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1864 - 1869

12
[ 122-51-0 ]
[ 53090-43-0 ]
[ 191673-26-4 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Patent: US6362179,2002,B1

13
[ 122-51-0 ]
[ 76-05-1 ]
[ 53090-43-0 ]
[ 191673-26-4 ]

Yield	Reaction Conditions	Operation 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:

Reference： [1]Patent: US6159967,2000,A

14
[ 96-31-1 ]
[ 53090-43-0 ]
6-(3,4-dichlorophenyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione [ No CAS ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Patent: US4612376,1986,A

15
[ 318469-73-7 ]
[ 53090-43-0 ]
[ 1399840-67-5 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 7309 - 7313

16
[ 53090-43-0 ]
[ 1399840-90-4 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 7309 - 7313

17
[ 53090-43-0 ]
ethyl 5-(3,4-dichlorophenyl)-7-oxo-6-oxabicyclo[3.2.0]heptane-4-carboxylate [ No CAS ]
[ 1399841-07-6 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 7309 - 7313

18
[ 53090-43-0 ]
ethyl 5-(3,4-dichlorophenyl)-7-oxo-6-oxabicyclo[3.2.0]heptane-4-carboxylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 7309 - 7313

19
[ 53090-43-0 ]
[ 1184849-00-0 ]

Reference： [1]Patent: WO2009/105220,2009,A1

20
[ 53090-43-0 ]
[ 1184850-57-4 ]

Reference： [1]Patent: WO2009/105220,2009,A1

21
[ 57297-29-7 ]
[ 53090-43-0 ]
[ 1184850-56-3 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Patent: WO2009/105220,2009,A1 .Location in patent: Page/Page column 98-99

22
2-diazo-3-(3,4-dichloro-phenyl)-3-hydroxy-propionic acid ethyl ester [ No CAS ]
[ 53090-43-0 ]

Reference： [1]RSC Advances,2013,vol. 3,p. 12616 - 12620

23
[ 1159942-71-8 ]
[ 53090-43-0 ]
[ 1607023-54-0 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Patent: WO2014/66795,2014,A1 .Location in patent: Paragraph 0175

24
[ 51-44-5 ]
[ 6148-64-7 ]
[ 53090-43-0 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Patent: WO2014/66795,2014,A1 .Location in patent: Paragraph 0175

25
[ 1607024-46-3 ]
[ 53090-43-0 ]
[ 1607023-10-8 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Patent: WO2014/66795,2014,A1 .Location in patent: Paragraph 0175

26
[ 1607024-50-9 ]
[ 53090-43-0 ]
[ 1607023-51-7 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Patent: WO2014/66795,2014,A1 .Location in patent: Paragraph 0175

27
[ 1607024-52-1 ]
[ 53090-43-0 ]
[ 1607023-20-0 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Patent: WO2014/66795,2014,A1 .Location in patent: Paragraph 0175

28
[ 1607024-59-8 ]
[ 53090-43-0 ]
[ 1607023-48-2 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Patent: WO2014/66795,2014,A1 .Location in patent: Paragraph 0175

29
[ 53090-43-0 ]
[ 1607024-98-5 ]

Reference： [1]Patent: WO2014/66795,2014,A1

30
[ 53090-43-0 ]
[ 1607024-99-6 ]

Reference： [1]Patent: WO2014/66795,2014,A1

31
[ 53090-43-0 ]
[ 1607023-53-9 ]

Reference： [1]Patent: WO2014/66795,2014,A1

32
[ 1607025-41-1 ]
[ 53090-43-0 ]
[ 1607023-55-1 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Patent: WO2014/66795,2014,A1 .Location in patent: Paragraph 0175

33
[ 16617-46-2 ]
[ 53090-43-0 ]
[ 1607024-97-4 ]

Yield	Reaction Conditions	Operation 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)

Reference： [1]Patent: WO2014/66795,2014,A1 .Location in patent: Paragraph 0175

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 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 8036 - 8053

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 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 8036 - 8053

36
[ 108-00-9 ]
[ 53090-43-0 ]
ethyl 3-(3,4-dichlorophenyl)-3-[2-(dimethylamino)ethyl]amino}propanoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 8036 - 8053

37
[ 4414-88-4 ]
[ 53090-43-0 ]
3-(3,4-dichlorophenyl)-1-hydroxybenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1432 - 1448

38
tert-butyl 2-hydrazinylthiazole-4-carboxylate [ No CAS ]
[ 53090-43-0 ]
2-(3-(3,4-dichlorophenyl)-5-hydroxy-1H-pyrazol-1-yl)thiazole-4-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9184 - 9204

39
[ 141-78-6 ]
[ 3024-72-4 ]
[ 53090-43-0 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9184 - 9204

40
[ 130-15-4 ]
[ 53090-43-0 ]
ethyl 2-(3,4-dichlorophenyl)-5-hydroxynaphtho[1,2-b]furan-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With zinc(II) iodide; In dichloromethane; at 110℃; for 0.5h;Sealed tube;	General procedure: 1,4-naphthoquinone (1.5equiv.) ZnI2 (0.7equiv.) and b-keto esters5 a-n (1.0 equiv.) were dissolved in dry CH2Cl2(6 mL) in a 10mLreaction glass vial containing a tiny stirring magnet The vial wassealed tightly with an aluminium-Teflon crimp top and themixture was irradiated for 30 min at a pre-selected temperature of110 C, with an irradiation power of 60W. After the reaction, thevial was cooled to 50 C by gas jet cooling. The crude mixture wasportioned between CH2Cl2 and saturated solution of sodium chloride(6 mL) and the aqueous layer was extracted with methylenchloride (3 6 mL). The combined organic layer were dried onSodium sulfate anhydrous, filtered and the solvent was removedunder reduce pressure. Then, final crude compounds were purifiedby flash chromatography over silica gel.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 155,p. 946 - 960

41
[ 53090-43-0 ]
ethyl 3-amino-3-(3,4-dichlorophenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With ammonium acetate; acetic acid; In toluene; at 140℃; for 0.333333h;Molecular sieve; Sealed tube;	General procedure: b-keto esters 5 a-n (1.0 equiv.), Ammonium acetate (3.0 equiv.)and Acetic acid (drops) were dissolved in dry Toluol (6 mL) in a10 mL reaction glass vial containing a tiny stirring magnet andmolecular sieves. The vial was sealed tightly with an aluminium-Teflon crimp top and the mixture was irradiated for 20 min at apre-selected temperature of 140 C, with an irradiation power of60W. After the reaction, the vial was cooled to 50 C by gas jetcooling. The crude mixture was portioned between ethyl acetateand saturated solution of Sodium bicarbonate (15 mL of each) andthe aqueous layer was extracted with ethyl acetate (3 15 mL). Thecombined organic layer were dried on Sodium sulfate anhydrous,filtered and the solvent was removed under reduce pressure. Then,final crude compounds were purified by flash chromatography oversilica gel.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 155,p. 946 - 960

42
[ 53090-43-0 ]
ethyl 2-(3,4-dichlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 155,p. 946 - 960

43
[ 106-51-4 ]
[ 53090-43-0 ]
C₁₇H₁₂Cl₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With zinc(II) iodide; In dichloromethane; at 110℃; for 0.5h;Sealed tube; Microwave irradiation;	General procedure: 1,4-naphthoquinone (1.5equiv.) ZnI2 (0.7equiv.) and b-keto esters5 a-n (1.0 equiv.) were dissolved in dry CH2Cl2(6 mL) in a 10mLreaction glass vial containing a tiny stirring magnet The vial wassealed tightly with an aluminium-Teflon crimp top and themixture was irradiated for 30 min at a pre-selected temperature of110 C, with an irradiation power of 60W. After the reaction, thevial was cooled to 50 C by gas jet cooling. The crude mixture wasportioned between CH2Cl2 and saturated solution of sodium chloride(6 mL) and the aqueous layer was extracted with methylenchloride (3 6 mL). The combined organic layer were dried onSodium sulfate anhydrous, filtered and the solvent was removedunder reduce pressure. Then, final crude compounds were purifiedby flash chromatography over silica gel.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 155,p. 946 - 960

44
[ 53090-43-0 ]
(E)-ethyl 3-(3,4-dichlorophenyl)-5-(4-fluorophenyl)pent-2-enoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 18127 - 18135

45
[ 108-22-5 ]
[ 53090-43-0 ]
(Z)-ethyl 3-acetoxy-3-(3,4-dichlorophenyl)acrylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 18127 - 18135

46
[ 2642-63-9 ]
[ 105-58-8 ]
[ 53090-43-0 ]

Yield	Reaction Conditions	Operation in experiment
51%	With potassium tert-butylate; In tetrahydrofuran; at 20 - 60℃; for 6h;	To a mixture of 152-1 (5.00 g, 26.4 mmol) and t-BuOK (1.0 M in THF, 52.9 mL, 52.9 mmol) in THF (50.0 mL) was added diethyl carbonate (4.69 g, 39.7 mmol) at room temperature. The reaction was stirred at 60 C for 6 h. When the reaction was completed, the mixture was concentrated and purified by silica gel column chromatography (petrol ether/ethyl acetate = 50/1) to afford 152-2 (3.50 g, 51% yield) as yellow oil.

Reference： [1]Patent: WO2021/178488,2021,A1 .Location in patent: Paragraph 00398; 00434
[2]Organic Letters,2020,vol. 22,p. 8836 - 8841
[3]Organic and Biomolecular Chemistry,2021,vol. 19,p. 3173 - 3180

47
[ 53090-43-0 ]
ethyl 6-(3,4-dichlorophenyl)-2,2-dimethyl-4-oxo-3,4-dihydro-2H-thiopyran-5-carboxylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2021,vol. 19,p. 3173 - 3180

48
[ 53090-43-0 ]
ethyl 5-(3,4-dichlorophenyl)-1,2,3-thiadiazole-4-carboxylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2021,vol. 19,p. 3173 - 3180

49
[ 53090-43-0 ]
C₁₁H₈Cl₂N₂O₃ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2021,vol. 19,p. 3173 - 3180

50
[ 4637-24-5 ]
[ 3034-19-3 ]
[ 53090-43-0 ]
ethyl 5-(3,4-dichlorophenyl)-1-(2-nitrophenyl)-1H-pyrazole-4-carboxylate [ No CAS ]