N-(2-Hydroxyethyl)maleimide | Alcohols

CAS No. :	1585-90-6
Formula :	C₆H₇NO₃
M.W :	141.12
SMILES Code :	O=C(C=C1)N(CCO)C1=O
MDL No. :	MFCD00465266
InChI Key :	AXTADRUCVAUCRS-UHFFFAOYSA-N
Pubchem ID :	458487

Safety of [ 1585-90-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P264-P270-P280-P301+P312+P330-P305+P351+P338-P337+P313-P501

Computational Chemistry of [ 1585-90-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	0
Fraction Csp3	0.33
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	36.74
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	57.61 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.79
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	-0.08
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-1.48
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.	-0.65
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	-0.23
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.33

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.53
Solubility	41.4 mg/ml ; 0.293 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.	-0.68
Solubility	29.6 mg/ml ; 0.21 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	0.16
Solubility	203.0 mg/ml ; 1.44 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	No
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.	-7.22 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)	2.17

Application In Synthesis of [ 1585-90-6 ]

* 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.

Downstream synthetic route of [ 1585-90-6 ]

[ 1585-90-6 ] Synthesis Path-Downstream 1~54

1
[ 1585-90-6 ]
[ 358-23-6 ]
[ 155863-37-9 ]

References: [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 457 - 480.
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 2609 - 2618.

2
[ 1585-90-6 ]
[ 7143-01-3 ]
[ 155863-36-8 ]

Yield	Reaction Conditions	Operation in experiment
43%	at 105℃; for 3.5h;Inert atmosphere;	To a flame dried round bottom flask 0.5 g (3.6 mmol) of l-(2-hydroxyethyl)-lW- pyrrole-2,5-dione and 0.7 g (4.0 mmol) of methanesulfonic anhydride was added. The flask was evacuated and refilled with nitrogen. The flask was heated to 105C and stirred for 3.5 hr. The reaction was cooled to room temperature and dissolved in ethyl acetate (5 mL). The solution was taken up into a separatory funnel and washed four times with a saturated solution of sodium carbonate (40 mL). The aqueous layers were collected and washed with ethyl acetate (50 mL). The organic layers were combined and dried with MgS04 and concentrated in vacuo. The product was recrystallized from t-butyl methyl ether to yield 43 % (0.347 g, 1.58 mmol) of 2-(2,5-dioxo-2,5-dihydro-lH-pyrrol- l-yl)ethyl methanesulfonate.XH NMR (400 MHz, CD3CI) 6.78 (s, 2H), 4.41 (t, J = 5.23, 2H), 3.90 (t, J = 5.23, 2H), 3.04 (s, 3H)

References: [1]Patent: WO2012/12612,2012,A2 .Location in patent: Page/Page column 37.
[2]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 457 - 480.

3
[ 1585-90-6 ]
[ 32315-10-9 ]
2-maleimidoethyl chloroformiate [ No CAS ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 91 - 102.

4
[ 15519-86-5 ]
[ 1585-90-6 ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 91 - 102.

5
[ 1585-90-6 ]
[ 98-59-9 ]
[ 34321-85-2 ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 91 - 102.

6
[ 1585-90-6 ]
[ 1821-12-1 ]
4-Phenyl-butyric acid 2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl ester [ No CAS ]

References: [1]Archiv der Pharmazie,1998,vol. 331,p. 47 - 53.

7
[ 1585-90-6 ]
[ 305-03-3 ]
4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid 2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2701 - 2708.

9
[ 108-31-6 ]
[ 141-43-5 ]
[ 1585-90-6 ]

Yield	Reaction Conditions	Operation in experiment
30%		Maleic anhydride 0.6mmol weighed into three neck round bottom flask, dissolve with 5ml of acetone, 0.66mmol ethanolamine with 5ml of acetone was dissolved by constant pressure funnel was slowly added dropwise three-necked flask, with magnetic stirring. After the reaction at room temperature for 1h , the acetone solvent was removed by rotary evaporation, use 5ml of toluene as a solvent, 0.012g of anhydrous sodium acetate were added to the reaction system, 0.2ml of triethylamine, 0.018 g of hydroquinone, 115 deg.] C was slowly warmed to reflux for 2.5h, tracing the reaction by thin layer chromatography on silica plates.After the reaction was cooled to room temperature, the solvent was removed by rotary evaporation, to obtain a concentrate, the concentrate was subjected to silica gel column chromatography (eluent: VPetroleum ether: VEthyl acetate= 12: 1), and collecting the target fluid, the rotation solvent in vacuo to give the desired product.Yield 30percent.

References: [1]Archiv der Pharmazie,2016,vol. 349,p. 466 - 474.
[2]Patent: CN107162950,2017,A .Location in patent: Paragraph 0091-0093.
[3]Il Farmaco,2002,vol. 57,p. 421 - 426.

10
[ 1585-90-6 ]
[ 20769-85-1 ]
[ 653599-62-3 ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 16768 - 16771.
[2]Macromolecules,2004,vol. 37,p. 18 - 26.

11
[ 1585-79-1 ]
[ 1585-90-6 ]

References: [1]Macromolecules,2004,vol. 37,p. 18 - 26.

12
[ 110-00-9 ]
[ 1585-90-6 ]
[ 847757-03-3 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1181 - 1184.

13
[ 55750-48-6 ]
[ 141-43-5 ]
[ 1585-90-6 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1181 - 1184.
[2]Chemistry Letters,2012,vol. 41,p. 313 - 315.

14
(3aS,4aS,8aR,9aR)-5,6,7,8-Tetrachloro-2-(2-hydroxy-ethyl)-3a,4,4a,8a,9,9a-hexahydro-benzo[f]isoindole-1,3-dione [ No CAS ]
[ 1585-90-6 ]
C₂₀H₂₀Cl₄N₂O₆ [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 825 - 827.

15
[ 1585-90-6 ]
endo-3,4,5,6-Tetrachlorobicyclo<4.4.0>deca-2,4-diene-8,9-dicarboxylic acid N-phenylimide [ No CAS ]
C₂₄H₂₀Cl₄N₂O₅ [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 825 - 827.

16
[ 1585-90-6 ]
[ 847757-14-6 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1181 - 1184.

17
[ 1585-90-6 ]
[ 847757-12-4 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1181 - 1184.

18
[ 1585-90-6 ]
[ 847757-10-2 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1181 - 1184.

19
[ 1585-90-6 ]
[ 158745-41-6 ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2609 - 2618.

20
[ 1585-90-6 ]
2-maleimidoethoxy glycinate trifluoroacetic salt [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2609 - 2618.

21
[ 1585-90-6 ]
1-<2-(2,5-dioxo-1H-pyrrol-1-yl)ethyl>-4-<5-(4-methoxyphenyl)-2-oxazolyl>pyridinium methanesulfonate hemihydrate [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 457 - 480.

22
[ 1585-90-6 ]
1-<2-(2,5-dioxo-1H-pyrrol-1-yl)ethyl>-4-<5-(4-methoxyphenyl)-2-oxazolyl>pyridinium trifluoromethanesulfonate [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 457 - 480.

23
[ 1585-90-6 ]
1-<2-<3-propylthio-1-(2,5-dioxopyrrolidinyl)>ethyl>-4-<5-(4-methoxyphenyl)-2-oxazolyl>pyridinium methanesulfonate [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 457 - 480.

24
[ 1585-90-6 ]
1-<2-(2,5-dioxo-1H-pyrrol-1-yl)ethyl>-4-<2-<6-(3,4-dihydro-2H-1-benzopyranyl)>-5-oxazolyl>pyridinium trifluoromethanesulfonate [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 457 - 480.

25
[ 1585-90-6 ]
1-<2-<3-propylthio-1-(2,5-dioxpyrrolidinyl)>ethyl>-4-<5-(4-methoxyphenyl)-2-oxazolyl>pyridinium trifluoromethanesulfonate [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 457 - 480.

26
[ 1585-90-6 ]
1-<2-<3-propylthio-1-(2,5-dioxpyrrolidinyl)>ethyl>-4-<2-<6-(3,4-dihydro-2H-1-benzopyranyl)>-5-oxazolyl>pyridinium trifluoromethanesulfonate [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 457 - 480.

27
[ 32620-90-9 ]
[ 1585-90-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 1,4-dimethoxybezene; In xylene; at 130℃; for 3.25h;Heating / reflux;	A 0.19 mol (4Og) sample of the HEMI-A from above was mixed with 227g of xylene and 0.005g methyl hydroquinone (MEHQ), an antioxidant. After heating under reflux and nitrogen sparging for 3 hours 15 minutes at 1300C, the conversion of HEMI-A to HEMI reached 98.7% and the reaction yield was determined to be approximately 98.7%. The reactor was cooled to room temperature, and the cooled reaction product was filtered at room temperature, and the filtered solids were washed with 15g of xylenes. The washed solids were dried under vacuum, and 25. Ig of HEMI, a 93% yield based on the HEMI-A, was obtained. The purity of the HEMI was determined to be greater than 99% by H-NMR. It was EPO <DP n="13"/>also determined that the mother liquor and wash liquid was combined and determined to weigh 230.2g and contain 1.17g of HEMI, which could be recovered as described above, or recycled.
81%	In toluene; for 7h;Reflux;	The synthesis of 1-(2-Hydroxyethyl)-1H-pyrrole-2,5-dione (5) was carried out following methods reported in a previous publication [43]. In a 50mL round-bottom flask adapted with a flux condenser and magnetic stirring, the intermediate 4 (2.30g, 10.99mmol) was combined with toluene (30mL). The reaction was refluxed for 7h. The resulting mixture was immediately filtered, and the product crystallised from toluene in 81% yield (1.25g, 8.87mmol). 1H-NMR (400MHz, DMSO-d6) delta 7.01 (s, 2H), 4.78 (br, 1H), 3.46 (br, 4H); 13C-NMR (100MHz, DMSO-d6) delta 171.1, 134.5, 57.9, 39.9.
	In toluene; for 12h;Reflux; Inert atmosphere;	General procedure: N-(2-hydroxyethyl)maleimide (Mal-OH) was prepared according to a previously reported method [3, 34]. Firstly, 30.0 g maleic anhydride (306mmol)was dissolved in toluene and 22.4 ml furan (309mmol) was slowly injected into the solution via syringe. After the mixture stirred for 24 h at room temperature, the reaction was stopped and the white crystals were precipitated from the mixture, collected and washed with toluene. The white powder was dried in a vacuum oven to prepare furan-protected maleic anhydride. Secondly, the furan-protected maleic anhydride(4.98 g, 30mmol) was suspended in methanol and stirred at 0 C. Then1.8 ml of ethanolamine (30mmol) was added dropwise to the solution,stirred and refluxed at 80 C for 24 h. Then the reaction mixture was cooled to 0 C, the product was crystallized from the mixture and collected to obtain furan-protected N-(2-hydroxyethyl)-maleimide. Finally,furan-protected N-(2-hydroxyethyl)-maleimide (2.1 g, 10mmol) in 10 ml toluene was stirred and refluxed under nitrogen for 12 h. The reaction mixture was hot filtered, and the filtrate was stored at 4 C overnight.The product crystallized from the mixture, then collected, dried under vacuum for 24 h to obtain N-(2-hydroxyethyl)-maleimide (Mal-OH)

References: [1]Patent: WO2007/44169,2007,A1 .Location in patent: Page/Page column 10.
[2]Chemical Communications,2019,vol. 55,p. 12263 - 12266.
[3]Dyes and Pigments,2017,vol. 145,p. 518 - 527.
[4]Organic Letters,2011,vol. 13,p. 4364 - 4367.
[5]Advanced Functional Materials,2014,vol. 24,p. 5261 - 5268,8.
[6]Journal of Controlled Release,2018,vol. 285,p. 187 - 199.

28
2β-Carbomethoxy-3β-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane [ No CAS ]
[ 1585-90-6 ]
2β-carbomethoxy-3β-(4-fluorophenyl)-8-(2-maleimidoethyl)-8-azabicyclo[3.2.1]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		N-(2-Hydroxyethyl)maleimide (282 mg, 2 mmol) was dissolved in dichloromethane (50 mL) and cooled to 5° C. To this solution was added successively, by syringe, triethylamine (360 muL, 2.6 mmol) and trifluoromethanesulfonic anhydride (360 muL, 2.1 mmol). The solution was allowed to achieve room temperature and then stirred overnight. Dichloromethane (50 mL) was added and the resulting solution washed with water (4.x.50 mL), dried (sodium sulfate), filtered and concentrated. The viscous oil (400 mg, 73percent [Note: this compound is not stable, even at low temperature under nitrogen and should only be prepared immediately before use]) was taken up in dichloromethane (1 mL) and added to a solution of 11 (131 mg, 0.48 mmol) in dichloromethane (2 mL). DMF (2 drops) and triethylamine (67 muL, 0.48 mmol) were then added and the solution stirred overnight at room temperature. Dichloromethane (20 mL) and a saturated solution of sodium bicarbonate (20 mL) were then added to the solution and the phases separated. The aqueous phase was extracted further with dichloromethane (3.x.10 mL) and then all organic phases combined and dried (sodium sulfate). The solids were filtered and the filtrate concentrated and chromatographed on a silica gel column (200 g SiO2, eluent 2percent triethylamine in a 50:50 mixture of ethyl acetate and hexanes, fractions 1-11, 7 mL volume each and fractions 12-30, 13 mL volume each). The product containing fractions (14-19) were combined and concentrated and the white solid washed with ether and dried in a vacuum oven overnight to give 143 mg, 77percent of the title compound. Mp. 121-122° C.; Rf0.5 (2percent triethylamine in ether/hexanes 1:1); 1H NMR delta 7.18 (m, 2H), 6.93 (m, 2H), 6.68 (s, 2H), 3.68 (m, 1H), 3.30-3.60 (m, 3H), 3.40 (s, 3H), 2.93 (dt, 1 H, J=12.6, 5.2), 2.83 (t, 1H, J=3.8), 2.27-2.53 (m, 3H), 1.90-2.14 (m, 2H), 1.56-1.80 (m, 3H); 13C NMR 171.3, 170.9, 161.0 (d, J=243), 138.6 (bs), 134.0, 123.7 (d, J=7.5), 114.6 (d, J=20.8), 64.6, 59.5, 52.8, 50.92, 50.86, 36.7, 33.7, 33.5, 26.6, 25.3. Anal, (C21H23FN2O4)C,H,N.

References: [1]Patent: US2003/232827,2003,A1 .Location in patent: Page 19; Fig.2.

29
[ 6719-02-4 ]
[ 1585-90-6 ]
[ 1186033-58-8 ]
[ 1186033-59-9 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 7274 - 7282.
[2]Journal of Organic Chemistry,2009,vol. 74,p. 7274 - 7282.

30
[ 6719-02-4 ]
[ 67-56-1 ]
[ 1585-90-6 ]
[ 1186033-58-8 ]
[ 1186033-59-9 ]
[ 1186033-60-2 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 7274 - 7282.

31
[ 1585-90-6 ]
[ 31776-87-1 ]
[ 76-05-1 ]
1-(2-(6-(4-fluorophenyl)pyridin-3-yloxy)ethyl)pyrrole-2,5-dione trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		80 mg (0.42 mmol) of 6-(4-fluorophenyl)pyridin-3-ol, 61.2 mg (0.43 mmol) of <strong>[1585-90-6]1-(2-hydroxyethyl)pyrrole-2,5-dione</strong> and 155.3 mg (0.59 mmol) of triphenylphosphane were dissolved in 20 ml of THF. After cooling to 0°C, 136.2 mg (0.59 mmol) of azodicarboxylic acid di-tert-butyl ester in 3 ml THF were slowly added. The mixture was stirred at room temperature for 6 h, evaporated and treated with ethyl acetate and diluted hydrochloric acid. The aqueous layer was evaporated and purified by chromatography (RP18, acetonitrile/water containing 0.1 percent TFA). Yield: 17 mg. MS: M+H+ = 313.1.

References: [1]Patent: EP1741709,2007,A1 .Location in patent: Page/Page column 42.

32
[ 1585-90-6 ]
MHAT [ No CAS ]
polyurethane-1 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of Polyurethane-l (PU-I); [0035] The pre-polymer (150 g) was charged to a jacketed glass reactor fitted with an axial flow overhead stirrer, dry-air bubbler, and a thermocouple. An antioxidant, 4-methoxyphenol (MEHQ, 0.05 g) was added, dried air was bubbled subsurface, and the temperature was adjusted to 420C. Hydroxethylmaleimide (HEMI) (24 g) was charged at once to the reactor, which was then heated to 55-60°C for one hour. 2-[N-methyl-N-(2-hydroxyethyl)]ethylthioxanthone (MHAT) (8 g) was then dissolved in dry acetone (7.5 mL) and charged to the reactor. The reactor was stirred at 55-60°C for 30 minutes and then dibutyltindilaurate (0.07 g) was charged and the reactor was stirred at 60-650C for 3 hrs. The NCO content of the reaction mixture was verified and then the polymer was end-capped by addition of ethanol (1 mL) and stirring the reaction mixture continued for another hour at 60-65°C. MEHQ (0.06 g) was added and stirred at 60-650C for 30 minutes. The resulting oligomer's (PU-I) NCO content was zero, its viscosity <n="14"/>was 8400 cP at 60°C, its maleimide content was 8.3 wtpercent, and its thioxanthone content of 2.6 wtpercent.

References: [1]Patent: WO2007/92935,2007,A1 .Location in patent: Page/Page column 11-12.

33
[ 1585-90-6 ]
[ 77-76-9 ]
[ 118377-62-1 ]

References: [1]Pharmaceutical Research,2010,vol. 27,p. 683 - 698.

34
[ 1585-90-6 ]
[ 65967-52-4 ]
[ 118377-60-9 ]

References: [1]Pharmaceutical Research,2010,vol. 27,p. 683 - 698.

35
[ 1585-93-9 ]
[ 1585-90-6 ]

References: [1]Pharmaceutical Research,2010,vol. 27,p. 683 - 698.
[2]Organic Preparations and Procedures International,2013,vol. 45,p. 314 - 320.

36
[ 124-09-4 ]
[ 1585-90-6 ]
C₅₀H₆₈Cl₄N₁₀O₈ [ No CAS ]