[ CAS No. 617-35-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 617-35-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 617-35-6 ]

SDS Specification

Alternatived Products of [ 617-35-6 ]

Product Details of [ 617-35-6 ]

CAS No. :	617-35-6	MDL No. :	MFCD00009123
Formula :	C₅H₈O₃	Boiling Point :	-
Linear Structure Formula :	CH₃COCOOC₂H₅	InChI Key :	XXRCUYVCPSWGCC-UHFFFAOYSA-N
M.W :	116.12	Pubchem ID :	12041
Synonyms :		Chemical Name :	Ethyl 2-oxopropanoate

Calculated chemistry of [ 617-35-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.6
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	27.63
TPSA :	43.37 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.75 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.37
Log Po/w (XLOGP3) :	0.36
Log Po/w (WLOGP) :	0.14
Log Po/w (MLOGP) :	-0.09
Log Po/w (SILICOS-IT) :	0.34
Consensus Log Po/w :	0.42

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.59
Solubility :	29.9 mg/ml ; 0.258 mol/l
Class :	Very soluble
Log S (Ali) :	-0.84
Solubility :	17.0 mg/ml ; 0.146 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.64
Solubility :	26.4 mg/ml ; 0.228 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.04

Safety of [ 617-35-6 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P501-P210-P233-P370+P378-P303+P361+P353-P403+P235	UN#:	3272
Hazard Statements:	H225	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 617-35-6 ]

* 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 [ 617-35-6 ]
Downstream synthetic route of [ 617-35-6 ]

[ 617-35-6 ] Synthesis Path-Upstream 1~1

1
[ 617-35-6 ]
[ 100-48-1 ]
[ 97316-50-2 ]
[ 97316-54-6 ]
[ 97316-52-4 ]
[ 97316-53-5 ]

Reference： [1] Angewandte Chemie, 1985, vol. 97, # 8, p. 694 - 695
[2] Heterocycles, 1987, vol. 26, # 3, p. 731 - 744
[3] Angewandte Chemie, 1985, vol. 97, # 8, p. 694 - 695
[4] Angewandte Chemie, 1985, vol. 97, # 8, p. 694 - 695
[5] Heterocycles, 1987, vol. 26, # 3, p. 731 - 744
[6] Heterocycles, 1987, vol. 26, # 3, p. 731 - 744

[ 617-35-6 ] Synthesis Path-Downstream 1~10

1
[ 617-35-6 ]
[ 20265-35-4 ]
[ 112777-38-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 901 - 905

2
[ 617-35-6 ]
[ 16313-65-8 ]
2-Methyl-6-nitro-4-oxo-1,2,3,4-tetrahydrochinazolin-2-carbonsaeureethylester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1994,vol. 327,p. 571 - 579

3
[ 617-35-6 ]
[ 6972-82-3 ]
[ 2625-22-1 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 13511 - 13522

4
[ 617-35-6 ]
[ 1520-70-3 ]
[ 500801-00-3 ]

Reference： [1]Chemical Communications,2002,p. 2214 - 2215

5
[ 617-35-6 ]
[ 16732-66-4 ]
[ 16732-69-7 ]

Yield	Reaction Conditions	Operation in experiment
47%	toluene-4-sulfonic acid; In toluene; for 16h;Reflux; Water separator;	EXAMPLE XIX Ethyl 7-bromo-1H-indole-2-carboxylate 11.0 g <strong>[16732-66-4]2-bromophenylhydrazine</strong> and 550 mg p-toluenesulphonic acid monohydrate are dissolved in 200 ml of toluene, combined with 6.74 ml ethyl pyruvate and refluxed for 2 hours using the water separator. The mixture is allowed to cool to 40 C. and combined with a solution that is obtained by dissolving 44.75 g p-toluenesulphonic acid monohydrate in 300 ml of toluene and refluxing for two hours using the water separator. Then the mixture is refluxed for 12 hours using the water separator. After cooling to ambient temperature the solvents are eliminated in vacuo, the residue is taken up in ethyl acetate and washed successively with water and saturated aqueous sodium hydrogen carbonate solution. After drying with magnesium sulphate the mixture is combined with activated charcoal, stirred for 15 minutes and filtered through kieselguhr. The process of adding activated charcoal, stirring and filtering is repeated twice more. The solvents are eliminated in vacuo and the residue is taken up in petroleum ether/dichloromethane 7:3. 30 g of silica gel are added, the mixture is stirred for 10 minutes and then suction filtered through kieselguhr. The suction filtered silica gel is washed with petroleum ether/dichloromethane 7:3. The solvents are eliminated in vacuo. Yield: 7.37 g (47% of theory) HPLC (method 1): retention time=3.82 min. Mass spectrum (ESI+): m/z=268 [M+H]+

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 2978 - 2987
[2]Patent: US2011/269737,2011,A1 .Location in patent: Page/Page column 49

6
[ 617-35-6 ]
[ 17288-32-3 ]

Reference： [1]Synthesis,2005,p. 2571 - 2577

7
[ 617-35-6 ]
[ 6298-19-7 ]
[ 17288-32-3 ]

Yield	Reaction Conditions	Operation in experiment
190 mg		3-Amino-2-chloro-pyridine 4f (150 mg, 1.17 mmol), ethyl pyruvate 8 (0.25 ml, 2.00 mmol), pyridinium p-toluenesulfonate, (73 mg, 0.29 mmol) and tetraethoxy-silane (0.26 ml, 1.18 mmol) were suspended in 0.4 ml pyridine and stirred for 24 h at 20 °C. Afterwards Pd[P(C6H6)3]4 (70 mg, 0.06 mmol) and N,N-dicyclohexylmethylamine (0.35 ml, 2.06 mmol) were added and the reaction mixture was heated in a microwave oven to 160 °C for 20 min. The reaction mixture is diluted with 100 ml dichloromethan and extracted two times with 50 ml of a half saturated aqueous sodium hydrogencarbonat solution. The organic layer was dried with sodium sulfate, the solvent was evaporated under reduced pressure and the crude product was purified using chromatography method P3, yielding 190 mg (1.00 mmol) of 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester. The ester was dissolved in 17 ml ethanol and 5 ml water. To this solution lithium hydroxide (120 mg, 5.00 mmol) was added. After 16 h the pH value of the reaction mixture was adjusted to pH 4 and the solvent is evaporated in vacuum. The crude product was purified using an acid ion exchanger (Strata-X-C, Phenomenex), yielding of 155 mg (82percent) of the title compound. Purity by method A1: >95percent; MS (ESI) m/z 163 (M + H)+; 1H NMR (DMSO) delta (ppm) 13.34 (br, 1H), 8.77 (d, J = 5.3 Hz, 1H), 8.53 (d, J = 8.3 Hz, 1H), 7.73 (dd, J = 5.4 Hz, J = 8.3 Hz, 1H), 7.33 (br, 1H); 13C NMR (500 MHz, DMSO) delta (ppm) 161.4 (s), 138.0 (s), 136.1 (s), 135.8 (s), 132.7 (s), 128.6 (s), 119.6 (s), 101.2 (s).

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11859 - 11862
Angew. Chem.,2016,vol. 128,p. 12038 - 12041,4
[2]European Journal of Medicinal Chemistry,2012,vol. 54,p. 660 - 668

8
[ 617-35-6 ]
[ 7579-20-6 ]
ethyl 5-chloroisoquinoline-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In neat (no solvent); at 20 - 100℃; for 1.25h;	3-Aminoisonicotinic acid (10 g, 72.4 mmol) and ethyl pyruvate (40 ml, 360 mmol) were combined neat and stirred at room temperature for 15 min. POCl3(200 ml, 2146 mmol) was added and the mixture was heated to 100 . After 1 h the mixture was cooled to room temperature and concentrated in vacuo. The resulting dark oil was taken up in ice cold water. This solution was added to saturated aqueous NaHCO3slowly until reaching a final pH 8. The resulting slurry was extracted with EtOAc (3x) . The combined organic extracts were filtered through a pad of silica gel and concentrated. The crude product was subjected to silica gel chromatography (Silicycle-330 g, 40EtOAc/hexanes) to give a solid.

Reference： [1]Patent: WO2016/29454,2016,A1 .Location in patent: Page/Page column 45

9
[ 617-35-6 ]
[ 106-49-0 ]
[ 16382-15-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With oxygen; palladium diacetate; acetic acid; In dimethyl sulfoxide; at 70℃; for 18h;Schlenk technique; Molecular sieve;	Take a 25mL Schlenk reaction tube, add p-methylaniline 43mg, palladium acetate 9mg and molecular sieve 80mg,93 mg of ethyl 2-oxopropionate, 96 mg of acetic acid and 2 mL of dimethyl sulfoxide were injected, followed by a 200 mL oxygen balloon, and stirred at 70 ° C for 18 hours.After the reaction was completed, 15 mL of ethyl acetate was added to dilute the reaction solution, and the filtrate was washed twice with 10 mL of saline.The organic phase was separated and the aqueous phase was extracted with ethyl acetate.Column chromatography was carried out to obtain 63 mg of the objective product as a pure product, yield 78percent.

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 14472 - 14488
[2]Patent: CN109748840,2019,A .Location in patent: Paragraph 0055-0058

10
[ 617-35-6 ]
[ 5369-19-7 ]
[ 261712-28-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With oxygen; palladium diacetate; acetic acid; In dimethyl sulfoxide; at 70℃; for 12h;Schlenk technique; Molecular sieve;	Take a 25mL Schlenk reaction tube, add 60 mg of <strong>[5369-19-7]3-tert-butylaniline</strong>, 9 mg of palladium acetate and 80 mg of molecular sieve.93 mg of ethyl 2-oxopropionate, 96 mg of acetic acid and 2 mL of dimethyl sulfoxide were injected, followed by a 200 mL oxygen balloon, and stirred at 70 ° C for 12 hours.After the reaction was completed, 15 mL of ethyl acetate was added to dilute the reaction solution, and the filtrate was washed twice with 10 mL of saline.The organic phase was separated, and the aqueous phase was extracted with ethyl acetate.Column chromatography to give pure desired product 80mg, 82percent yield.

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 14472 - 14488
[2]Patent: CN109748840,2019,A .Location in patent: Paragraph 0151-0154

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[ CAS No. 617-35-6 ] {[proInfo.proName]}

Quality Control of [ 617-35-6 ]

Related Doc. of [ 617-35-6 ]

Product Details of [ 617-35-6 ]

Calculated chemistry of [ 617-35-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 617-35-6 ]

Application In Synthesis of [ 617-35-6 ]

[ 617-35-6 ] Synthesis Path-Upstream 1~1

[ 617-35-6 ] Synthesis Path-Downstream 1~10

Similar Product of [ 617-35-6 ]

Related Functional Groups of [ 617-35-6 ]

Aliphatic Chain Hydrocarbons

Esters

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Similar Product of
[ 617-35-6 ]

Related Functional Groups of
[ 617-35-6 ]