53911-68-5|4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione| Ambeed

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Quality Control of [ 53911-68-5 ] Purity: 96% SDS Specification

COA

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NMR

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Product Details of [ 53911-68-5 ]

CAS No. :	53911-68-5
Formula :	C₁₁H₉ClO₃
M.W :	224.64
SMILES Code :	O=C1CC(C2=CC=C(Cl)C=C2)CC(O1)=O
MDL No. :	MFCD00190250
InChI Key :	OCZRLOJECISNAO-UHFFFAOYSA-N
Pubchem ID :	104639

Safety of [ 53911-68-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P305+P351+P338

Computational Chemistry of [ 53911-68-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.27
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	55.02
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	43.37 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.66
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	1.91
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.29
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.	2.58
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	3.0
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.29

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.67
Solubility	0.485 mg/ml ; 0.00216 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.	-2.44
Solubility	0.808 mg/ml ; 0.0036 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	-3.7
Solubility	0.0452 mg/ml ; 0.000201 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	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	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.	-6.31 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	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	2.0 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)	1.6

Application In Synthesis of [ 53911-68-5 ]

* 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 [ 53911-68-5 ]

[ 53911-68-5 ] Synthesis Path-Downstream 1~42

1
[ 53911-68-5 ]
[ 151-10-0 ]
[ 108369-65-9 ]

References: [1]Patent: US2792418,1954, .

2
[ 35271-74-0 ]
[ 53911-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	With acetyl chloride; for 2h;Heating; Reflux;	The suspension of commercial 3-(4- chlorophenyl)glutaric acid (15 g) in acetyl chloride (20 ml) was heated to reflux for 2 h. Then precipitation of the product is completed by addition of petrol ether (50 ml) and cooling to rt. The precipitate is isolated by suction filtration, washed with petrol ether, and dried in vacuo to give 3-(4-chlorophenyl)gluta?c anhydride (13.3 g) as colourless crystals.
	With acetyl chloride; for 2h;Reflux;	3-(4-Chlorophenyl)glutaric anhydride : The suspension of commercial 3-(4-chlorophenyl)glutaric acid (15 g) in acetyl chloride (20 ml) was heated to reflux for 2 h. Then precipitation of the product is completed by addition of petrol ether (50 ml) and cooling to rt. The precipitate is isolated by suction filtration, washed with petrol ether, and dried in vacuo to give 3-(4-chlorophenyl)glutaric anhydride (13.3 g) as colourless crystals

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6714 - 6723.
[2]Journal of Medicinal Chemistry,2001,vol. 44,p. 1938 - 1950.
[3]Patent: US2792418,1954, .
[4]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.
[5]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849.
[6]Patent: WO2010/43711,2010,A1 .Location in patent: Page/Page column 52.
[7]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2211 - 2217.
[8]Patent: US2012/46307,2012,A1 .Location in patent: Page/Page column 25.
[9]MedChemComm,2015,vol. 6,p. 671 - 676.

3
[ 67-56-1 ]
[ 53911-68-5 ]
[ 5045-65-8 ]

References: [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.
[2]Recueil des Travaux Chimiques des Pays-Bas,1965,vol. 84,p. 1183 - 1199.

4
[ 53911-68-5 ]
[ 120-20-7 ]
[ 94760-33-5 ]

References: [1]Arzneimittel-Forschung/Drug Research,1967,vol. 17,p. 1145 - 1149.

5
[ 53911-68-5 ]
[ 35661-51-9 ]
[ 348110-33-8 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1938 - 1950.

6
[ 64-17-5 ]
[ 53911-68-5 ]
[ 860011-99-0 ]

References: [1]Tetrahedron,2005,vol. 61,p. 6064 - 6072.
[2]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.
[3]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849.

7
[ 64-17-5 ]
[ 53911-68-5 ]
[ 860012-01-7 ]
[ 183504-76-9 ]

References: [1]Tetrahedron,2005,vol. 61,p. 6064 - 6072.
[2]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.
[3]Tetrahedron Asymmetry,2006,vol. 17,p. 961 - 966.

8
[ 67-56-1 ]
[ 53911-68-5 ]
[ 137310-16-8 ]
[ 865366-99-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-((1R,2R)-2-(dimethylamino)-1-(4-nitrophenyl)-3-(trityloxy)propyl)-3,5-bis-(trifluoromethyl)benzamide; In tert-butyl methyl ether; at 20℃; for 72h;Inert atmosphere;	General procedure: An alcohol (5 mmol) was added dropwise at room temperature under nitrogen to astirred solution of an anhydride 8 (0.5 mmol) and 7i (36.1 mg, 0.05 mmol) in MTBE(20 mL). The reaction was monitored by using thin-layer chromatography. Onceanhydride consumption was complete, the solvent was evaporated under reducedpressure and the residue was dissolved in CH2Cl2 (10 mL). The solution was washedwith saturated Na2CO3 (2 × 5 mL) and the combined aqueous phase were acidifiedwith excess 2 N HCl, followed by extraction with EtOAc (3 × 10 mL). The combinedorganic phases were dried over Na2SO4 and concentrated to afford the correspondingmonoester, without further purification by flash chromatography

References: [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.
[2]Tetrahedron Letters,2009,vol. 50,p. 6166 - 6168.
[3]Tetrahedron Letters,2009,vol. 50,p. 6166 - 6168.
[4]ChemCatChem,2016,vol. 8,p. 2249 - 2253.
[5]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 309 - 317.

9
[ 53911-68-5 ]
[ 107-18-6 ]
(R)-3-(4-chlorophenyl)-glutaric acid monoallyl ester [ No CAS ]
[ 865367-02-8 ]

References: [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.

10
[ 53911-68-5 ]
[ 100-51-6 ]
3-(4-chlorophenyl)-glutaric acid monobenzyl ester [ No CAS ]

References: [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.

11
[ 53911-68-5 ]
[ 100-51-6 ]
(R)-3-(4-chloro-phenyl)pentanedioic acid monobenzyl ester [ No CAS ]
[ 865367-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	With quinindine; In toluene; at -35℃; for 168h;Inert atmosphere;	General procedure: To the cold 0.1 M toluene solution of anhydride (10 mmol), alkaloid (1.1 equiv) and alcohol (1.5 equiv) were added. The reaction mixture was stirred until >90% conversion was reached (see Table 3) and the reaction was stopped by the addition of 5% HCl. The organic layer was washed once more with 5% HCl and evaporated. Oily residue was dissolved in 2% K2CO3 and washed successively with EtOAc. Aqueous solution was acidified with HCl to pH 2 and extracted with EtOAc. The organic extracts were dried over Na2SO4 and evaporated in vacuo.
	With quinine; In toluene; at -35℃; for 168h;Inert atmosphere;	General procedure: To the cold 0.1 M toluene solution of anhydride (10 mmol), alkaloid (1.1 equiv) and alcohol (1.5 equiv) were added. The reaction mixture was stirred until >90% conversion was reached (see Table 3) and the reaction was stopped by the addition of 5% HCl. The organic layer was washed once more with 5% HCl and evaporated. Oily residue was dissolved in 2% K2CO3 and washed successively with EtOAc. Aqueous solution was acidified with HCl to pH 2 and extracted with EtOAc. The organic extracts were dried over Na2SO4 and evaporated in vacuo.

References: [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.
[2]Tetrahedron,2012,vol. 68,p. 8311 - 8317.
[3]Tetrahedron,2012,vol. 68,p. 8311 - 8317.

12
[ 53911-68-5 ]
[ 71-36-3 ]
(R)-3-(4-chlorophenyl)-glutaric acid monobutyl ester [ No CAS ]
[ 865367-00-6 ]

References: [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.

13
[ 53911-68-5 ]
[ 71-36-3 ]
3-(4-chlorophenyl)-glutaric acid monobutyl ester [ No CAS ]

References: [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.

14
[ 53911-68-5 ]
4-chlorocarbonyl-3-(4-chloro-phenyl)-butyric acid ethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849.

15
[ 53911-68-5 ]
[ 722549-40-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849.

16
[ 53911-68-5 ]
3-(4-chloro-phenyl)-5-oxo-6-trimethylsilanyl-hexanoic acid ethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849.

17
[ 53911-68-5 ]
3-(4-chloro-phenyl)-4-{2-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-thiazol-4-yl}-butyric acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849.

18
[ 53911-68-5 ]
[ 761401-08-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849.

19
[ 104-88-1 ]
[ 53911-68-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849.
[2]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.
[3]Patent: US2792418,1954, .
[4]MedChemComm,2015,vol. 6,p. 671 - 676.

20
[ 53911-68-5 ]
(4R)-4-(4-chlorophenyl)tetrahydro-2H-pyran-2-one [ No CAS ]

References: [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.
[2]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.
[3]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.
[4]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.
[5]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.

21
[ 53911-68-5 ]
3-(4-chloro-phenyl)-5-hydroxy-pentanoic acid [ No CAS ]

References: [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.

22
[ 53911-68-5 ]
(R)-3-(4-Chloro-phenyl)-5-hydroxy-pentanoic acid [ No CAS ]

23
[ 53911-68-5 ]
[ 5666-78-4 ]

References: [1]Tetrahedron Asymmetry,2005,vol. 16,p. 2475 - 2485.

24
[ 53911-68-5 ]
(S)-4-[((R)-1-Benzylcarbamoyl-3-methyl-butyl)-butyl-carbamoyl]-3-(4-chloro-phenyl)-butyric acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 6064 - 6072.

25
[ 101104-10-3 ]
[ 53911-68-5 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1938 - 1950.

26
[ 104-88-1 ]
resin-bound p-methylphenylboronic acid [ No CAS ]
[ 53911-68-5 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1938 - 1950.

27
N-[5-(4-amino-phenyl)-4-methyl-thiazol-2-yl]-guanidine hydrochloride [ No CAS ]
[ 53911-68-5 ]
rac-3-(4-chloro-phenyl)-4-[3-(2-guanidino-4-methyl-rhiazol-5-yl)-phenyl-carbamoyl]-butyric acid [ No CAS ]

References: [1]Patent: US6344562,2002,B1 .Location in patent: Page column 69.

28
[ 463-51-4 ]
[ 1158997-06-8 ]
[ 53911-68-5 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 2334 - 2336.

29
[ 463-51-4 ]
[ 104-88-1 ]
[ 53911-68-5 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 2334 - 2336.

30
[ 35271-74-0 ]
[ 108-24-7 ]
[ 53911-68-5 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 6166 - 6168.

31
[ 169105-70-8 ]
[ 53911-68-5 ]
C₂₁H₂₀ClNO₅ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 747 - 760.

32
[ 169105-70-8 ]
[ 53911-68-5 ]
[ 74-88-4 ]
(+)-(3aR,9bS)-methyl 3'-(4''-chlorophenyl)-5'-oxo-5'-(3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazol-1-yl)pentanoate [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 747 - 760.

33
[ 53911-68-5 ]
[ 169105-65-1 ]
C₂₁H₂₀ClNO₅ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 747 - 760.

34
[ 53911-68-5 ]
[ 169105-65-1 ]
[ 74-88-4 ]
(-)-(3aS,9bR)-methyl 3'-(4''-chlorophenyl)-5'-oxo-5'-(3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazol-1-yl)pentanoate [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 747 - 760.

35
[ 53911-68-5 ]
[ 95-54-5 ]
[ 1221961-82-5 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; at 20℃; for 1h;	The solution of commercial 1,2-phenylenediamine (1.08g) and <strong>[53911-68-5]3-(4-chlorophenyl)glutaric anhydride</strong> (2.25 g) in 1,4-diotaoxane (7 ml) was stirred at rt for 10 min. A voluminous precipitate is formed which is kept at rt for further 50 min. The thick slurry is heated to reflux with methanol, cooled to rt, isolated by suction filtration, and washed with methanol. After drying in vacuo /V-(2-aminophenyl)-3-(4- chlorophenyl)glutaramic acid (2.1 g) is obtained as off-white solid.
	In 1,4-dioxane; at 20℃; for 1h;	The solution of commercial 1,2-phenylenediamine (1.08 g) and <strong>[53911-68-5]3-(4-chlorophenyl)glutaric anhydride</strong> (2.25 g) in 1,4-dioxane (7 ml) was stirred at rt for 10 min. A voluminous precipitate is formed which is kept at rt for further 50 min. The thick slurry is heated to reflux with methanol, cooled to rt, isolated by suction filtration, and washed with methanol. After drying in vacuo N-(2-aminophenyl)-3-(4-chlorophenyl)glutaramic acid (2.1 g) is obtained as off- white solid

References: [1]Patent: WO2010/43711,2010,A1 .Location in patent: Page/Page column 52.
[2]Patent: US2012/46307,2012,A1 .Location in patent: Page/Page column 25.

36
[ 53911-68-5 ]
[ 139-59-3 ]
[ 1221962-01-1 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of triethyl amine (1.5 ml) in 1,4-dioxane (5 ml) was added to a mixture of commercial 4- phenoxyaniline (1.85 g) and <strong>[53911-68-5]3-(4-chlorophenyl)glutaric anhydride</strong>. The resulting solution was stirred at rt for 0.5 h and at 400C for 2 h. Under cooling with ice cone. HCI (2 ml) and water (10 ml) was added. A gummy precipitate is formed from which the aqueous layer is removed by decantation. Crystallisation was induced by heating with methanol (5 ml). After cooling in the refrigerator the precipitate was isolated by filtration, washed with methanol and diethyl ether, and dried in vacuo to give colourless, powdery crystals (3 g) of /V-(4-phenoxyphenyl)-3-(4-chlorophenyl)- glutaramic acid.
		A solution of triethyl amine (1.5 ml) in 1,4-dioxane (5 ml) was added to a mixture of commercial 4-phenoxyaniline (1.85 g) and <strong>[53911-68-5]3-(4-chlorophenyl)glutaric anhydride</strong>. The resulting solution was stirred at rt for 0.5 h and at 40 C. for 2 h. Under cooling with ice conc. HCl (2 ml) and water (10 ml) was added. A gummy precipitate is formed from which the aqueous layer is removed by decantation. Crystallisation was induced by heating with methanol (5 ml). After cooling in the refrigerator the precipitate was isolated by filtration, washed with methanol and diethyl ether, and dried in vacuo to give colourless, powdery crystals (3 g) of N-(4-phenoxyphenyl)-3-(4-chlorophenyl)-glutaramic acid

References: [1]Patent: WO2010/43711,2010,A1 .Location in patent: Page/Page column 62.
[2]Patent: US2012/46307,2012,A1 .Location in patent: Page/Page column 30.

37
[ 53911-68-5 ]
[ 95-85-2 ]
[ 1221962-66-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	In dichloromethane;	Prepared by dissolving an equimolar mixture of <strong>[53911-68-5]3-(4-chlorophenyl)glutaric anhydride</strong> and commercial 5-chloro-2-hydroxyaniline in boiling dichloromethane. Upon cooling to rt product precipitates and yields after isolation 87% of /V-(2-hydroxy-5- chlorophenyl)-3-(4-chlorophenyl)glutaramic acid as colourless crystals.
87%	In dichloromethane;	Prepared by dissolving an equimolar mixture of <strong>[53911-68-5]3-(4-chlorophenyl)glutaric anhydride</strong> and commercial 5-chloro-2-hydroxyaniline in boiling dichloromethane. Upon cooling to rt product precipitates and yields after isolation 87% of N-(2-hydroxy-5-chlorophenyl)-3-(4-chlorophenyl)glutaramic acid as colourless crystals

References: [1]Patent: WO2010/43711,2010,A1 .Location in patent: Page/Page column 91-92.
[2]Patent: US2012/46307,2012,A1 .Location in patent: Page/Page column 44.

38
[ 53911-68-5 ]
[ 95-83-0 ]
C₁₇H₁₆Cl₂N₂O₃ [ No CAS ]
C₁₇H₁₆Cl₂N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; at 20℃; for 1h;	The solution of 4-chloro-l,2-phenylenediamine (2.85 g) and 3-(4-chlorophenyl)- glutaric anhydride (4.49 g) in 1,4-dioxane (7 ml) was stirred at rt for 1 h. The precipitate is collected by suction filtration, washed with 1,4-dioxane, and dried in vacuo to provide a mixture of regioisomeric amides (5.37 g) as beige coloured solid.

References: [1]Patent: WO2010/43711,2010,A1 .Location in patent: Page/Page column 54-55.
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 6714 - 6723.

39
[ 53911-68-5 ]
[ 2683-43-4 ]
C₁₆H₁₁Cl₃N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; at 20℃;Heating; Reflux;	The solution of commercial 2,4-dichloro-6-nitroaniline (621 mg) and 3-(4- chlorophenyl)glutaric anhydride (674 mg) in 1,4-dioxane (2 ml) was heated to reflux shortly and stirred at rt for Ih. The solvent was removed by distillation and the residue dried in vacuo. The oily residue was dissolved in acetic acid (6 ml) and heated to reflux. Iron powder (1.01 g) was added and the mixture stirred under reflux for 1 h. Then cone. HCI (6 ml) was added cautiously and the green-yellow solution was refluxed for additional 2 h. All volatiles were removed at the water aspirator and the residue precipitated from acetic acid/cone. HCI solution with water. The solid was collected by suction filtration and washed well with IM HCI and water. The crude was recrystallised from acetic acid to give 4-(5,7-dichloro-2- benzimidazolyl)-3-(4-chlorophenyl)butanoic acid HCI (325 mg) as colourless crystals.1H-NMR (500 MHz, DMSOd5): delta (ppm) = 2.70 (dd, J = 16.2, 8.9 Hz, IH), 2.79 (dd, J = 16.2, 5.9 Hz, IH), 3.35 (dd, J = 14.7, 8.3 Hz, IH), 3.43 (dd, J = 14.7, 7.6 Hz, IH), 3.83 (m, IH), 7.33 (q, J = 8.6 Hz, 4H), 7.59 (d, J = 1.6 Hz, IH), 7.73 (d, J = 1.6 Hz, IH).13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 33.39 (CH2), 39.39 (CH), 39.46 (CH2), 112.58 (CH), 119.26 (C), 123.64 (CH), 128.28 (2 CH), 128.63 (C), 129.14 (2 CH), 131,1 (br, C), 131,29 (C), 134.40 (C), 141.22 (C), 154.96 (C), 172.24 (CO). MS ( + ESI): m/z = 383 (M + H).

References: [1]Patent: WO2010/43711,2010,A1 .Location in patent: Page/Page column 67-68.

40
[ 5348-42-5 ]
[ 53911-68-5 ]
C₁₆H₁₃Cl₃N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In 1,4-dioxane; at 40℃;Cooling with ice;	The solution of commercial 4,5-dichloro-l,2-phenylenediamine (0.36 g) and triethyl amine (0.32 ml) in 1,4-dioxane (1.5 ml) was added to a solution of 3-(4- chlorophenyl)glutaric anhydride (0.45 g) in 1,4-dioxane (1 ml) with ice cooling. The resulting mixture was stirred at rt for 0.5 h and at 400C for 0.5 h. Again under ice cooling IM HCI (3 ml) was added dropwise. A gummy precipitate is formed. After 0.5 h of cooling the aqueous layer is removed by decantation and the residue is dissolved in methanol. The dark solution is decolourised with activated carbon, filtered, and the filtrate concentrated in vacuo. The amorphous solid is redissolved in ethanol (6 ml) and cone. HCI (2 ml) and stirred at reflux for 16 h. After cooling to rt the pH is adjusted to 8 by addition of first NaOH solution, then sat. sodium bicarbonate solution. The aqueous layer is extracted with dichloromethane (40 ml) and the organic layer is washed with sat. sodium chloride solution and dried (sodium sulfate). After concentration the crude (0.46 g) is purified by flash chromatography ((dichloromethane/2% methanol/1% triethyl amine) on silica gel to afford ethyl 4-(5,6-dichloro-2-benzimidazolyl)-3-(4-chlorophenyl)butanoate (0.33 g) as yellowish, amorphous solid.

References: [1]Patent: WO2010/43711,2010,A1 .Location in patent: Page/Page column 67.

41
[ 5348-42-5 ]
[ 53911-68-5 ]
[ 1221962-08-8 ]

Yield	Reaction Conditions	Operation in experiment
		The solution of commercial 4,5-dichloro-l,2-phenylenediamine (0.38 g) and 3- phenylglutaric anhydride (0.4 g) in THF (1 ml) was heated shortly and kept at rt for 0.5 h. The solvent was removed in vacuo and the residue redissolved in acetic acid (3 ml). The dark solution was heated to reflux overnight. Then all volatiles were removed in vacuo and the residue was heated with ethanol (5 ml). After reccoling to rt the precipitate was collected by filtration, washed with ethanol, and dried to give a crude (0.39 g). The crude was decolourised in boiling acetone solution with activated carbon and filtered over Celite. Concentration of the filtrate and drying of the residue afforded 7,8-dichloro-3-phenyl-3,4-dihydropyrido[l,2-a]benzimidazol- l(2H)-one (0.13 g) as colourless crystals.

References: [1]Patent: WO2010/43711,2010,A1 .Location in patent: Page/Page column 65.

42
[ 53911-68-5 ]
[ 99-56-9 ]
C₁₇H₁₆ClN₃O₅ [ No CAS ]
C₁₇H₁₆ClN₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; for 0.75h;Reflux;	The solution of commercial 4-nitro-l,2-phenylenediamine (0.31 g) and 3-(4- chlorophenyl)glutaric anhydride (0.45 g) in 1,4-dioxane (3 ml) was stirred under reflux for 0.75 h. 4M HCI in 1,4-dioxane (3 ml) was added and the solution is further heated to reflux for 1 h. After cooling to rt the precipitate is collected by suction filtration and washed with 1,4-dioxane and diethyl ether. The crude is recrystallised from acetic acid to give 4-(5-benzoyl-2-benzimidazolyl)-3-(4- chlorophenyl)butanoic acid HCI (0.59 g) as beige coloured solid. 1H-NMR (500 MHz, DMSO-d6)): delta (ppm) = 2.72 (dd, J = 16.2, 8.7 Hz, IH), 2.84(dd, J = 16.2, 6.1 Hz, IH), 3.41 (dd, J = 14.9, 8.9 Hz, IH), 3.52 (dd, J = 14.9, 7.0 Hz, IH), 3.85 (m, IH), 7.30 (d, J = 8.5 Hz, 2H), 7.36 (d, J = 8.5 Hz, 2H), 7.85 (d, J = 9.0 Hz, IH), 8.23 (dd, J = 9.0, 2.2 Hz, IH), 8.51 (d, J = 2.1 Hz, IH). 13C-NMR and DEPT (125 MHz, DMSO-d6) : delta (ppm) = 33.46 (CH2), 39.28 (CH), 39.64 (CH2), 110.68 (CH), 114.50 (CH), 119.70 (CH), 128.31 (2 CH), 129.19 (2 CH), 131.36 (C), 132.76 (C), 136.93 (C), 140.97 (C), 144.01 (C), 156.90 (C), 172.23 (CO).

References: [1]Patent: WO2010/43711,2010,A1 .Location in patent: Page/Page column 60-61.

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Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • 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 • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • 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 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 • Wittig Reaction • Wolff-Kishner Reduction

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CAS No.: 53911-68-5

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CAS No.: 53911-68-5

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