55750-49-7|Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate| Ambeed

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Quality Control of [ 55750-49-7 ] Purity: 97% SDS Specification

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Product Details of [ 55750-49-7 ]

CAS No. :	55750-49-7
Formula :	C₇H₇NO₄
M.W :	169.13
SMILES Code :	O=C(N1C(C=CC1=O)=O)OCC
MDL No. :	MFCD16619570
InChI Key :	XUXSQROIUORWRI-UHFFFAOYSA-N
Pubchem ID :	319934

Safety of [ 55750-49-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H317
Precautionary Statements:	P280

Computational Chemistry of [ 55750-49-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	0
Fraction Csp3	0.29
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	42.06
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	63.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.21
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.03
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.31
Log P_o/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.	-0.81
Log P_o/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	-0.19
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.01

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.71
Solubility	33.0 mg/ml ; 0.195 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.92
Solubility	20.4 mg/ml ; 0.12 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-0.11
Solubility	131.0 mg/ml ; 0.776 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	No
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.	-7.31 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	1.0
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<1.0
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)	2.52

Application In Synthesis of [ 55750-49-7 ]

* 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 [ 55750-49-7 ]

[ 55750-49-7 ] Synthesis Path-Downstream 1~35

1
[ 55750-49-7 ]
[ 106788-30-1 ]

References: [1]Helvetica chimica acta,1975,vol. 58,p. 531 - 541.

2
[ 55750-49-7 ]
[ 60-32-2 ]
6-((Z)-4-Ethoxycarbonylamino-4-oxo-but-2-enoylamino)-hexanoic acid [ No CAS ]

References: [1]Helvetica chimica acta,1975,vol. 58,p. 531 - 541.

3
[ 55750-49-7 ]
[ 76387-70-7 ]
(S)-2-tert-Butoxycarbonylamino-3-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-propionic acid [ No CAS ]

References: [1]Polish Journal of Chemistry,1993,vol. 67,p. 673 - 683.

4
[ 55750-49-7 ]
[ 133342-66-2 ]
[ 133342-67-3 ]

References: [1]Journal of Pharmacy and Pharmacology,1991,vol. 43,p. 27 - 31.

7
[ 55750-49-7 ]
[ 134272-63-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	In tetrahydrofuran; sodium hydrogencarbonate;	a) N-(tert.-butyloxycarbonyl)-2-(N-maleinimido)ethylamine 0.8 g (5 mmol) of the compound produced according to Example 1a is dissolved in 25 ml saturated sodium bicarbonate solution. The solution is filtered over a folded filter and cooled to 0 C. Subsequently 0.84 g (5 mmol) <strong>[55750-49-7]N-(ethoxycarbonyl)maleinimide</strong> (produced according to the method of O. Keller and J. Rudinger, Helv. Chim. Acta 58 (1975), 531-541) is added while stirring and it is left to stir for a further 15 min at room temperature. During this the <strong>[55750-49-7]N-(ethoxycarbonyl)maleinimide</strong> dissolves completely after a short time while the title compound precipitates during the course of the reaction. 40 ml THF is added and stirred for a further 45 min at room temperature. Afterwards it is adjusted to pH 6.0 with 1n HCl, extracted twice with 50 ml acetic ester and the extract is dried with 5 g Na2 SO4. After evaporation in a water-jet vacuum the title compound is obtained as a colourless, solid residue. Yield: 1.1 g (92% of the theoretical yield). TLC: silica gel, chloroform/acetic ester (66/33 v/v), spray with 0.1% KMnO4 solution; Rf =0.50.

References: [1]Patent: US5595741,1997,A .

8
[ 55750-49-7 ]
[ 192212-24-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	In tetrahydrofuran; sodium carbonate;	b) N-(tert.butyloxycarbonyl)-5-(N-maleinimido)pentylamine 13.1 g (50 mmol) of the compound prepared according to Example 1b is dissolved in 250 ml saturated sodium carbonate solution. The solution is filtered over a folded filter and cooled to 0 C. 8.4 g (50 mmol) N-(ethoxycarbonyl)-maleinimide is added while stirring and is left to stir for a further 15 min at room temperature, during which the N-(ethoxycarbonyl)-maleinimide dissolves completely after a short time. Subsequently 400 ml tetrahydrofuran is added together with 250 ml saturated sodium carbonate solution and it is allowed to react for a further 1 h. The solution is then extracted with 2*500 ml acetic ester, the extract is washed with 500 ml water and dried with 50 g Na2 SO4. After evaporation in a rotary evaporator the product is obtained as a viscous oil which is dried in a high vacuum. Yield: 9.6 g (corresponds to 68% of the theoretical yield). TLC: silica gel, n-butanol/glacial acetic acid/water 40/10/50 (v/v/v), spray with 0.1% KMnO4 solution; Rf =0.85.

References: [1]Patent: US5595741,1997,A .

9
[ 541-59-3 ]
[ 541-41-3 ]
[ 55750-49-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	With 4-methyl-morpholine; In water; ethyl acetate;	1) Ethyl-2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate 9.7 g (0.1 mol) of maleimide are solubilized in 50 ml of ethyl acetate and 1.1 ml of N-methylmorpholine at 5 C. 1.1 ml of ethyl chloroformate are added dropwise. The mixture is stirred for 1/2 hour. The insoluble material is removed by filtration. The filtrate is washed with 50 ml of water. The organic phase is dried over MgSO4 and is then concentrated under vacuum. The oil obtained is purified on Merck Geduran silica gel (40-63 mum). Elution: CH2Cl2/ACOEt 66/34. 16.9 g are isolated with a yield of 50%. Mass spectrum: M/z=170.1 (ES+) theoretical M=169
41%	With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 4h;	Ethyl chloroformate (0.38 ml, 4 mmol) was added dropwise to a stirred solution maleimide (0.3 g, 3 mmol) and triethylamine (0.5 ml, 3.5 mmol) in dimethylformamide (2 ml) at 0-5 C. The reaction mixture was allowed to warm to room temperature and stand for 4 h. Methyl alcohol (1 ml) was added, diluted with chloroform (20 ml) and washed with water (3*10 ml). The chloroform solution was dried (Na2SO4) and concentrated in vacuum. The residue was purified in chloroform and hexane on a silica gel column to give N-ethoxycarbonyl-maleimide (yield 41%). 1H NMR (CDCl3) delta 1.34 (3H, t, CH3), 4.27 (2H, q, CH2), 6.21 (1H, d, CH=), 6.72 (1H, d, CH=).

References: [1]Organic Letters,2015,vol. 17,p. 5846 - 5849.
[2]Chemical Communications,2014,vol. 50,p. 859 - 861.
[3]Patent: US2010/297025,2010,A1 .
[4]Patent: US9273304,2016,B2 .Location in patent: Page/Page column 16.

10
[ 55750-49-7 ]
[ 57260-73-8 ]
[ 134272-63-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In water; at 0 - 20℃; for 1.5h;	(11) Synthesis of the following IL- Ira conjugate:JV-(ethoxycarbonyl) maleimide (0.53 g, 3.1 mmol) was added to N-(tert- butoxycarbonyl)-ethylenediamine (0.40 g, 2.5 mmol) in saturated aqueous bicarbonate solution (15 mL) at 00C. The reaction mixture was stirred for 30 min at 00C, and then stirred for an additional 1.0 hour at room temperature. The aqueous layer was extracted with methylene chloride (30 mL) three times. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under vacuum.

References: [1]Chemical Science,2017,vol. 8,p. 5454 - 5459.
[2]Patent: WO2011/9047,2011,A2 .Location in patent: Page/Page column 16-17.

11
[ 55750-49-7 ]
[ 56882-00-9 ]
(4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenyl maleimide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4067 - 4076.

12
[ 55750-49-7 ]
[ 929-06-6 ]
[ 34321-81-8 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4067 - 4076.

13
[ 55750-49-7 ]
[ 15430-52-1 ]
[ 209395-32-4 ]

Yield	Reaction Conditions	Operation in experiment
1.24 g	With sodium hydrogencarbonate; at 20℃;Cooling with ice;	A solution of 1.08 grams of propargylamine hydrochloride in 50 ml of saturated sodium bicarbonate was cooled with an ice water bath, and 2.0 grams of <strong>[55750-49-7]N-carboethoxymaleimide</strong> were added portionwise over a few minutes. The reaction was stirred in the cold for 30 min., then while warming to room temperature over 25 min. The reaction was then extracted with 3*25 ml of dichloromethane, which was dried over sodium sulfate, filtered and concentrated. The residue was taken up in 10 ml of ethyl acetate and heated at 50 C. for two hours to complete the cyclization. The reaction was concentrated and the residue was which was subjected to flash column chromatography on silica gel with 30% ethyl acetate in hexane. A second chromatography as before gave 1.24 g of the product as a very light yellow oil. NMR (CDCl3): delta 6.77 (s, 2H, CHC=O), 4.30 (d, 2H, NCH2, J=2.4 Hz), 2.22 (t, 1H, CCH, J=2.5 Hz).

References: [1]Patent: US2014/24776,2014,A1 .Location in patent: Paragraph 0422; 0423.

14
[ 55750-49-7 ]
[ 4097-89-6 ]
[ 139112-38-2 ]