172732-52-4|2-(1,3,2-Dioxaborinan-2-yl)benzonitrile| Ambeed

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Quality Control of [ 172732-52-4 ] Purity: 98% SDS Specification

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Product Details of [ 172732-52-4 ]

CAS No. :	172732-52-4
Formula :	C₁₀H₁₀BNO₂
M.W :	187.00
SMILES Code :	N#CC1=CC=CC=C1B2OCCCO2
MDL No. :	MFCD04039012
InChI Key :	REQZFVYFYAZUMG-UHFFFAOYSA-N
Pubchem ID :	3529602

Safety of [ 172732-52-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 172732-52-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.3
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	53.14
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	42.25 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
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	1.75
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.69
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.	0.2
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	1.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.74

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.35
Solubility	0.829 mg/ml ; 0.00444 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.	-2.25
Solubility	1.04 mg/ml ; 0.00557 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	-2.84
Solubility	0.273 mg/ml ; 0.00146 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	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.	-6.2 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)	2.65

Application In Synthesis of [ 172732-52-4 ]

* 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 [ 172732-52-4 ]

[ 172732-52-4 ] Synthesis Path-Downstream 1~35

1
[ 578-57-4 ]
[ 172732-52-4 ]
2'-methoxy-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

References: [1]Journal of Organometallic Chemistry,2002,vol. 653,p. 269 - 278.

2
[ 106-38-7 ]
[ 172732-52-4 ]
[ 114772-53-1 ]

References: [1]Journal of Organometallic Chemistry,2002,vol. 653,p. 269 - 278.

3
[ 624-31-7 ]
[ 172732-52-4 ]
[ 114772-53-1 ]

References: [1]Journal of Organometallic Chemistry,2002,vol. 653,p. 269 - 278.
[2]Organic Letters,2013,vol. 15,p. 2742 - 2745.

4
[ 576-22-7 ]
[ 172732-52-4 ]
2',6'-dimethyl-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

References: [1]Journal of Organometallic Chemistry,2002,vol. 653,p. 269 - 278.

5
[ 29540-83-8 ]
[ 172732-52-4 ]
[ 114772-53-1 ]

References: [1]Journal of Organometallic Chemistry,2002,vol. 653,p. 269 - 278.

6
[ 25245-34-5 ]
[ 172732-52-4 ]
[ 75860-41-2 ]

References: [1]Journal of Organometallic Chemistry,2002,vol. 653,p. 269 - 278.

7
[ 172732-52-4 ]
[ 172732-49-9 ]
1-{3-(2-cyanophenyl)-4-chloro-5-[1-(R)-fluoropropyl]phenyl piperazine [ No CAS ]

References: [1]Journal of Organometallic Chemistry,2002,vol. 653,p. 269 - 278.
[2]Organic Process Research and Development,2003,vol. 7,p. 191 - 195.

8
[ 98-88-4 ]
[ 172732-52-4 ]
[ 37774-78-0 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 271 - 273.

9
[ 35660-94-7 ]
[ 172732-52-4 ]
2-[(E)-2-methylbut-2-enoyl]benzonitrile [ No CAS ]

References: [1]Synthesis,2003,p. 2882 - 2885.

10
[ 51-17-2 ]
[ 172732-52-4 ]
[ 611-20-1 ]
[ 100-47-0 ]
[ 25699-93-8 ]

References: [1]Advanced Synthesis and Catalysis,2004,vol. 346,p. 1679 - 1684.

11
[ 905300-60-9 ]
[ 172732-52-4 ]
2-(6-(2-(isopropylamino)thiazol-5-yl)-2-(2-methoxyethylamino)pyrimidin-4-yl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 110℃; for 2h;	Step 4: EXAMPLE 148; The title compound was prepared from Preparation 24 utilizing a similar procedure as described in step 6 of Example 1 by substituting 2-fluorophenyl boronic acid with <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong> and by substituting potassium carbonate with potassium phosphate as the base. Orange solid (30percent yield). HPLC Ret. time: 2.81 min. LCMS MH+ (m/z) 395.27. 1H NMR: (d6-DMSO, 500 MHz) delta 8.11 (d, 1H), 8.04 (br s, 1H), 7.96 (d, 1H), 7.81 (dd, 1H), 7.67 (dd, 1H), 7.35 (s, 1H), 7.15 (s, 1H), 3.83 (m, 1H), 3.53 (m, 2H), 3.49 (m, sH), 3.25 (s, 3H), 1.18 (d, 3H).

References: [1]Patent: US2006/178388,2006,A1 .Location in patent: Page/Page column 95.

Yield	Reaction Conditions	Operation in experiment
100%		Preparative Example 2 Synthesis of 2-(1,3,2-dioxaborinan-2-yl)benzonitrile STR10 543 mg (3.7 mmol) of 2-cyanophenylboric acid was added to a solution of 280 mg (3.7 mmol) of 1,3-propanediol in 5.4 ml of methylene chloride. The obtained mixture was stirred at room temperature for 1.5 hours, followed by the removal of formed water. The obtained mixture was distilled to remove the solvent under reduced pressure to give 0.7 g of the title compound (yield: 100percent). m.p.; 45°-48° C. 1 H-NMR(400 MHz, CDCl3); delta(ppm) 2.11(2H, m), 4.23(4H, d, J=5.5 Hz), 7.48(1H, dd, J=7.6, 7.6 Hz), 7.54(1H, dd, J=7.6, 7.6 Hz), 7.68(1H, d, J=7.6 Hz), 7.87(1H, dd, J=7.6 Hz). MS m/z: 188[MH]+.

13
potassium phosphate [ No CAS ]
[ 172732-42-2 ]
[ 172732-52-4 ]
[ 172732-18-2 ]

Yield	Reaction Conditions	Operation in experiment
83.9%	With hydrogenchloride;tetrakis(triphenylphosphine)palladium (0); In ethanol; water; N,N-dimethyl-formamide;	Example 241 Synthesis of 1-(2-hydroxyethyl)-4-[3-(2-cyanophenyl)-4-chloro-5-(1-fluoropropyl)]phenylpiperazine hydrochloride STR251 1-(2-Trimethylsilyloxyethyl)-4-[3-bromo-4-chloro-5-(1-fluoropropyl)]phenylpiperazine was dissolved in 4 ml of DMF, followed by the addition of 334 mg (1.58 mmol) of potassium phosphate and 61 mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium (0). A solution of 236 mg (1.26 mmol) of <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong> in 3 ml of DMF was dropwise added to the resulting mixture at 100° C. in 30 minutes. The obtained mixture was stirred as such at 100° C. for 30 minutes and cooled, followed by the addition of water. The resulting mixture was extracted with ethyl acetate. The organic phase was washed with water and a saturated brine, dried and distilled to remove the solvent, giving 0.52 g of a residue. This residue was dissolved in 1 ml of ethanol, followed by the dropwise addition of 0.57 g of a 10percent solution of hydrochloric acid in ethanol under cooling with ice. The obtained mixture was stirred at 4° C. for 20 hours to give a precipitate. The precipitate was recovered by filtration and dried to give 0.39 g of the title compound (yield: 83.9percent).

References: [1]Patent: US5849912,1998,A .

14
potassium phosphate [ No CAS ]
[ 172732-52-4 ]
[ 172732-49-9 ]
1-{3-(2-cyanophenyl)-4-chloro-5-[1-(R)-fluoropropyl]phenyl piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	tetrakis(triphenylphosphine) palladium(0); In water; ethyl acetate; N,N-dimethyl-formamide;	Example 246 Synthesis of 1-{3-(2-cyanophenyl)-4-chloro-5-[1-(R)-fluoropropyl]phenylpiperazine STR255 14.0 g (41.7 mmol) of 1-{3-bromo-4-chloro-5-[1-(R)-fluoropropyl]phenylpiperazine, 2.4 g (2.08 mmol) of tetrakis(triphenylphosphine)palladium and 13.3 g (62.6 mmol) of anhydrous tripotassium phosphate were suspended in 28 ml of DMF, followed by the dropwise addition of a solution of 9.5 g (50.0 mmol) of <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong> in 19 ml of DMF at 100° C. The obtained mixture was stirred as such for 3 hours and then cooled to room temperature. Water and ethyl acetate were added to the resulting mixture to conduct-partition. The organic phase was washed with a brine and distilled to remove the solvent. The obtained residue was purified by silica gel chromatography to give 10.6 g of the title compound (yield: 71percent).

References: [1]Patent: US5849912,1998,A .

15
[ 381248-06-2 ]
[ 172732-52-4 ]
[ 380917-97-5 ]

Yield	Reaction Conditions	Operation in experiment
		To the reactor containing the whole amount of the crude product of 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one obtained as the residue after concentration in Production Example 2 were added <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong> (214.9 g), palladium acetate (3.44 g), triphenylphosphine (16.07 g), cuprous iodide (7.29 g), 1,2-dimethoxyethane (3.1 L) and potassium carbonate (158.8 g). Stirring at heating was carried out at 70 °C (external temperature) under a nitrogen atmosphere for 30 minutes and, then, at heating under reflux for 4 hours. Subsequently, ethyl acetate (2.5 L) was added to the reaction mixture at 70 °C (external temperature) and the mixture was stirred for 10 minutes. The reaction mixture was filtrated and the filtrated residue was washed with ethyl acetate (2.5 L). This whole filtrate was transferred to a reactor, to which 12.5percent aqueous ammonia (5 L) was further added. Stirring was carried out at 60 °C (external temperature) for 53 minutes. The lower layer (aqueous layer) in the reaction mixture was separated. 5percent Brine (2.5 L) and 25percent aqueous ammonia (2.5 L) were added to the remaining organic layer. After stirring, the lower (aqueous layer) was separated. 5percent Brine (5 L) was further added to the remaining organic layer. After stirring, the lower (aqueous layer) was separated. The remaining organic layer was concentrated under reduced pressure, and then, acetone (4 L) was added, followed by concentration under reduced pressure. Acetone (7.2 L) and water (0.8 L) were added to this residue, and it was dissolved by stirring at 60 °C (external temperature) for 1 hour and 10 minutes. Next, cooling was carried out at 38 °C (external temperature) for 18 minutes while stirring. To the reaction mixture was added 1 g of seed crystals, crystals of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one hydrate. Stirring was carried out at 35 °C (external temperature) for 30 minutes. Subsequently, the reaction mixture was stirred at an external temperature being lowered by 5 °C every 30 minutes, and stirred at an external temperature of 10 °C for 17 hours. Water (2.29 L) was added dropwise to the reaction mixture at stirring over a period of 3 hours and 10 minutes. After the addition, stirring continued for additional 1 hour and 20 minutes. The reaction mixture was filtrated and the filtrated residue was washed with 2 L of 50percent acetone-water to give 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one (526.28 g) as a wet cake, which corresponded to 168.3 g as dry weight.Conversion of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one in the wet cake to dried weight The obtained wet cake (4.378 g) was weighed out and dried under reduced pressure at 50 °C for 4 hours to give 1.4005 g of a dried powder. Converted value as dried weight = (1.4005/4.378) x 526.28 = 168.3 gDetermination of acetone and water weight contents in the wet cake of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one Gas chromatographic analysis of the obtained wet cake under the conditions described below ascertained that the wet cake obtained in Production Example 3 contained 168 mL of acetone and 186 mL of water.Gas chromatographic analysis conditions: Column: DB-WAX (30m x 0.53mm, 1mum); detector: TCD; oven temp.: 60 °C (8min), 60-180 °C (70 °C/min), 180 °C (5min); detector temp.: 210 °C; inlet temp.: 150 °C; column flow: 5.0 mL/min; split ratio:(1:4); injection vol.: 2 muL
	With potassium carbonate;palladium diacetate; copper(l) iodide; triphenylphosphine; In 1,2-dimethoxyethane; at 70℃; for 4.5h;Heating / reflux;	To the reactor containing the whole amount of the crude product of 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one obtained as the residue after concentration in Production Example 2 were added <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong> (214.9 g), palladium acetate (3.44 g), triphenylphosphine (16.07 g), cuprous iodide (7.29 g), 1,2-dimethoxyethane (3.1 L) and potassium carbonate (158.8 g). Stirring at heating was carried out at 70° C. (external temperature) under a nitrogen atmosphere for 30 minutes and, then, at heating under reflux for 4 hours.Subsequently, ethyl acetate (2.5 L) was added to the reaction mixture at 70° C. (external temperature) and the mixture was stirred for 10 minutes. The reaction mixture was filtrated and the filtrated residue was washed with ethyl acetate (2.5 L). This whole filtrate was transferred to a reactor, to which 12.5percent aqueous ammonia (5 L) was further added. Stirring was carried out at 60° C. (external temperature) for 53 minutes. The lower layer (aqueous layer) in the reaction mixture was separated. 5percent Brine (2.5 L) and 25percent aqueous ammonia (2.5 L) were added to the remaining organic layer. After stirring, the lower (aqueous layer) was separated. 5percent Brine (5 L) was further added to the remaining organic layer. After stirring, the lower (aqueous layer) was separated. The remaining organic layer was concentrated under reduced pressure, and then, acetone (4 L) was added, followed by concentration under reduced pressure.Acetone (7.2 L) and water (0.8 L) were added to this residue, and it was dissolved by stirring at 60° C. (external temperature) for 1 hour and 10 minutes. Next, cooling was carried out at 38° C. (external temperature) for 18 minutes while stirring. To the reaction mixture was added 1 g of seed crystals, crystals of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one hydrate. Stirring was carried out at 35° C. (external temperature) for 30 minutes. Subsequently, the reaction mixture was stirred at an external temperature being lowered by 5° C. every 30 minutes, and stirred at an external temperature of 10° C. for 17 hours.Water (2.29 L) was added dropwise to the reaction mixture at stirring over a period of 3 hours and 10 minutes. After the addition, stirring continued for additional 1 hour and 20 minutes. The reaction mixture was filtrated and the filtrated residue was washed with 2 L of 50percent acetone-water to give 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one (526.28 g) as a wet cake, which corresponded to 168.3 g as dry weight.
	With copper(l) iodide; potassium carbonate;palladium diacetate; triphenylphosphine; In 1,2-dimethoxyethane; at 70℃; for 4.5h;Heating / reflux;	(Production Example 3) Synthesis of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one [Show Image] To the reactor containing the whole amount of the crude product of 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one obtained as the residue after concentration in Production Example 2 were added <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong> (214.9 g), palladium acetate (3.44 g), triphenylphosphine (16.07 g), cuprous iodide (7.29 g), 1,2-dimethoxyethane (3.1 L) and potassium carbonate (158.8 g). Stirring at heating was carried out at 70 °C (external temperature) under a nitrogen atmosphere for 30 minutes and, then, at heating under reflux for 4 hours. Subsequently, ethyl acetate (2.5 L) was added to the reaction mixture at 70 °C (external temperature) and the mixture was stirred for 10 minutes. The reaction mixture was filtrated and the filtrated residue was washed with ethyl acetate (2.5 L). This whole filtrate was transferred to a reactor, to which 12.5percent aqueous ammonia (5 L) was further added. Stirring was carried out at 60 °C (external temperature) for 53 minutes. The lower layer (aqueous layer) in the reaction mixture was separated. 5percent Brine (2.5 L) and 25percent aqueous ammonia (2.5 L) were added to the remaining organic layer. After stirring, the lower (aqueous layer) was separated. 5percent Brine (5 L) was further added to the remaining organic layer. After stirring, the lower (aqueous layer) was separated. The remaining organic layer was concentrated under reduced pressure, and then, acetone (4 L) was added, followed by concentration under reduced pressure. Acetone (7.2 L) and water (0.8 L) were added to this residue, and it was dissolved by stirring at 60 °C (external temperature) for 1 hour and 10 minutes. Next, cooling was carried out at 38 °C (external temperature) for 18 minutes while stirring. To the reaction mixture was added 1 g of seed crystals, crystals of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one hydrate. Stirring was carried out at 35 °C (external temperature) for 30 minutes. Subsequently, the reaction mixture was stirred at an external temperature being lowered by 5 °C every 30 minutes, and stirred at an external temperature of 10 °C for 17 hours. Water (2.29 L) was added dropwise to the reaction mixture at stirring over a period of 3 hours and 10 minutes. After the addition, stirring continued for additional 1 hour and 20 minutes. The reaction mixture was filtrated and the filtrated residue was washed with 2 L of 50percent acetone-water to give 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one (526.28 g) as a wet cake, which corresponded to 168.3 g as dry weight.

With tetrakis(triphenylphosphine) palladium(0); triethylamine; In dichloromethane; at 25 - 30℃; for 12h;

In a 1 L round bottom flask, equipped with a mechanical stirrer, thermometer and an addition funnel, a suspension of 188 g 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one, 161.2 g <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong>, 3.0 g tetrakis(triphenylphosphine)-palladium(0), 10 mL triethylamine (10 mL) in 300 mL methylene dichloride were stirred at 25-30° C. for 12 hours. To the reaction mixture was added 5 mL conc. aqueous ammonia, 10 mL water and 40 mL ethyl acetate. The separated organic layer was washed with water and saturated saline solution and dried over magnesium sulfate. The solvent was removed under vacuum. Ethyl acetate was added to the residue and heated obtain clear solution. n-hexane was added to this solution and cooled to 25-30° C. The obtained solid was filtered and washed with ethyl acetate and dried to obtain perampanel.

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10584 - 10600.
[2]Patent: EP1764361,2007,A1 .Location in patent: Page/Page column 10-11.
[3]Patent: US2009/88574,2009,A1 .Location in patent: Page/Page column 4.
[4]Patent: EP1970370,2008,A1 .Location in patent: Page/Page column 5-6.
[5]Patent: US2016/39759,2016,A1 .Location in patent: Paragraph 0061.

16
[ 138642-62-3 ]
[ 504-63-2 ]
[ 172732-52-4 ]

Yield	Reaction Conditions	Operation in experiment
82.4%	at 20℃; for 1h;	3.69 g (48.5 mmol) of 1,3-propanediol was added to the organic phase obtained in Example 1, and the mixture was stirred at room temperature for 1 hour. After separation of the separated aqueous phase, the solvent was distilled off with an evaporator. 2 ml of toluene and 120 ml of heptane were added to the remaining oily matter to precipitate crystals. The obtained crystals were washed with 30 ml of heptane and then dried, 7.44 g (yield: 82.4percent) of 1,3-propanediol ester (2- (1,3,2-dioxaborinan-2-yl) benzonitrile) of 2-cyanophenylboronic acid was obtained. The crystal contained 0.40percent of 1-phenyl-1- (2,2,6,6-tetramethylpiperidin-1-yl) methylimine
57.2%	In dichloromethane;	Step 1: Synthesis of 2-(1,3,2-dioxaborinan-2-yl)benzonitrile 49.0 g (334 mmol) 2-cyanobenzeneboronic acid and 25.9 g (340 mmol) 1,3-propanediol were dissolved in 1 L CH2Cl2 with stirring in a 2 L round bottom flask for 20 h. The solution was then poured over a filter with suction to remove gummy solids. The filtrate was then dried with anhydrous MgSO4 to remove residual water, filtered and evaporated of solvent to give light-colored oil. The oil was then dissolved in CH2Cl2 and purified on a silica gel plug using CH2Cl2 as eluent. The product fractions were evaporated down to give the product as clear oil (35.7 g, 57.2percent yield).
57.2%	In dichloromethane; for 20h;	Step 1: Synthesis of 2-(1,3,2-dioxaborinan-2-yl)benzonitrile 49.0 g (334 mmol) 2-cyanobenzeneboronic acid and 25.9 g (340 mmol) 1,3-propanediol were dissolved in 1 L CH2Cl2 with stirring in a 2 L round bottom flask for 20 h. The solution was then poured over a filter with suction to remove gummy solids. The filtrate was then dried with anhydrous MgSO4 to remove residual water, filtered and evaporated of solvent to give light-colored oil. The oil was then dissolved in CH2Cl2 and purified on a silica gel plug using CH2Cl2 as eluent. The product fractions were evaporated down to give the product as clear oil (35.7 g, 57.2percent yield).

57.2%	In dichloromethane; for 20h;	Step 1: synthesis of 2-(1,3,2-dioxaborainan-2-yl)benzonitrile 49.0 g (334 mmol) 2-cyano-benzeneboronic acid and 25.9 g (340 mmol) 1,3-propanediol and stirred while 2 ? 1 ? round bottom flask in CH2Cl2 20 hours dongan was dissolved. Then, the solution was poured into a suction filter to remove the solids on the gum. Then, the filtrate was dried over anhydrous MgSO4 and removal of the residue, filtered, to give a lighter colored oil by evaporation of the solvent. Thereafter, the oil was dissolved in CH2Cl2, was purified using CH2Cl2 as eluent on a silica gel plug. Distilling the product fractions to obtain the product (35.7 g, 57.2percent yield) as a clear oil
20%	In toluene; for 24h;Reflux;	2-cyano phenyl boronic acid and 1,3 propanediol was solubilized in anhydrous toluene. The reaction mixture was refluxed in a flask equipped with a Dean-Stark apparatus. After 24 h, the reaction was concentrated under reduced pressure to give colorless oil. The crude product was purified on silica gel (DCM) to give 2-[1-3]dioxaborinan-2-yl-benzonitrile; yield: 20percent; 1H NMR (300 MHz, CDCl3) delta ppm 2.08 (t, J = 5.4 Hz, 2H), 4.21 (q, J = 5.4 Hz, 4H), 5.31 (ls, 2H), 7.45 (td, J1 = 7.5 Hz, J2 = 1.5 Hz, 1H), 7.53 (td, J1 = 7.5 Hz, J2 = 1.5 Hz, 1H), 7.65 (d, J = 7.5 Hz, 1H), 7.85 (d, J = 7.5 Hz, 1H). The 2-[1-3]dioxaborinan-2-yl-benzonitrile was readily solubilized in toluene (0.2 M). To this solution, compound 3e (1eq), PdCl2(dppf) (2percent) and K3PO4 (2 eq) were added. The mixture was refluxed during 2 h, then was concentrated under reduced pressure. The obtained crude product was dissolved in ethyl acetate and washed by HCl 1N. The organic layer was concentrated under reduced pressure and purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (70/30) to give 9 as a yellow powder; purity 99percent; yield: 83percent; mp: 169-170 °C; 1H NMR (300 MHz, CDCl3) delta ppm 1.29 (t, J = 6.9 Hz, 3H), 2.10 (s, 3H), 4.23 (q, J = 6.9 Hz, 2H), 7.61 (td, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H), 7.69 (dd, J1 = 7.8 Hz, J2 = 0.9 Hz, 1H), 7.75 (d, J = 8.7 Hz, 2H), 7.82 (td, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H), 7.82 (dd, J1 = 7.8 Hz, J2 = 0.9 Hz, 1H), 7.82 (d, J = 8.7 Hz, 2H), 9.13 (s, 1H), 9.95 (sl, 1H); 13C NMR (75 MHz, CDCl3) delta ppm 15.0, 23.9, 60.8, 110.2, 110.9, 119.3, 119.5, 129.3, 130.1, 130.2, 132.7, 134.5, 134.8, 137.1, 139.6, 144.2, 148.4, 162.7, 169.6; LCMS (EI (+)) m/z = 389 [M + H] +. HRMS (EI) calcd for C21H18N4O2 [M + H]+ 375.14517. Found 375.14454.
	In tetrahydrofuran; hexane; at 20℃; for 2h;Product distribution / selectivity;	Example 3; The organic phase obtained in Example 2 was charged with 77 ml of 1,3-propanediol, and the resulting solution was stirred at room temperature for 2 hours. The free aqueous layer was separated, and then the solvent was removed by distillation using an evaporator. The residual oily substance was dissolved in 700 ml of dichloromethane, and the resulting solution was washed with 153 ml of water. The obtained organic phase was then dried with anhydrous magnesium sulfate, and turned into a solid by drying under reduced pressure using an evaporator. While stirring with a magnetic stirrer, 450 ml of hexane was slowly added dropwise to the oily residue under ice cooling to cause crystals to precipitate. The obtained crystals were washed with 500 of chilled hexane, and dried for 12 hours under reduced pressure at room temperature to obtain 184 g of the 1,3-propanediol ester of 2-cyanophenylboronic acid (2-(1,3,2-dioxaborinan-2-yl)benzonitrile). The purity was 99.4percent, and these crystals contained 0.45 mol percent of 1-phenyl-1-(2,2,6,6-tetramethylpiperidin-1-yl)methyl imine.
	In tetrahydrofuran; Isopropyl acetate; toluene; at 20 - 25℃; for 2h;	Example 2Synthesis of 2-(i ,3,2-dioxaborinane-2-yl)benzoni- trile?Effect of the Temperature in step a) on molaryield and chemical purity 10062] Into a previously dried flask, equipped with a thermometer, condenser and dropping thnnel, under nitrogen flow, 100.0 g (1.00 equiv.) of 2-bromobenzonitrile and 750 ml (7.5 V) of anhydrous Toluene are charged. The mixture is cooled at ?22/?18° C. and 519.0 g (1.30 equiv.) of Isopropylmagnesium chloride/lithium chloride complex 1.3 M (about 20percent wt/wt) in THF are added keeping the Tat ?22/?18° C., over about 1.5 h. The reaction is stirred at ?22/?18° C. for additional 4 hthen the conversion in checked by HPLC. When the reaction is complete, 125.6 g (2.20 equiv.) oftrimethylborate are added keeping the Tat ?22/?18° C. over about 0.5 h. Once the addition is complete, cooling is removed and the reaction is warmed to 20-25° C. and stirred for about 0.5 h. The conversion is checked by HPLC. When the reaction is complete, the mixture is cooled to 0-5°C. and a solution of 0.1 M hydrochloric acid, prepared by mixing 10 ml of 32percent hydrochloric acid (10.17 M) and 990 ml (9.9 V) of purified water, is added at 0-20° C. Afier stirring 0.25 h at 20-25° C. the pH is modified to 3-4 with appropriate amount of 32percent hydrochloric acid. The layers are then separated. The aqueous phase is extracted again with 500 ml (5 V) of Toluene. The organic phases are recombined and washed with 500 ml (5 V) of a saturated sodium chloride solution. The organic layer is extracted at 20-25° C. with 0.1 M sodium hydroxide solution, prepared by mixing 5 ml (0.05 V) of 30percent sodium hydroxide solution and 495 ml (4.95 V) of purified water (the product passes into the aqueous phase). Before performing layer separation the pH is modified to 10-11 with the appropriate amount of 30percent sodium hydroxide solution. Layers are separated and the organic layer is extracted twice with 0.1 M sodium hydroxide solution, prepared by mixing 5 ml (0.05 V) of 30percent sodium hydroxide solution and 495 ml (4.95 V) of purified water. The pH is corrected to 10-11 if needed before each layer separation. The aqueous phases are recombined and are washed with 2x300 ml (2x3 V) of Isopropyl acetate. The organic phase is discarded. The pH of the aqueous phase (containing the reaction product) is corrected with hydrochlonc acid to a final pH of 3-4. The aqueous phase is extracted with 2x500 ml (2x5 V) of Isopropyl acetate. The product passes into the organic phase. 46.0 g (1.1 equiv.) of 1,3- propanediol are then added to the organic solution and the mixture stirred at 20-25° C. for 2 h. The conversion in checked by TLC. When the reaction is complete, the aqueous phase is separated (water is generated during the reaction) and the organic layer is concentrated to residue at T bath 3 5-40° C. The residue is dissolved with 500 ml (5 V) of Dichloromethane and the organic phase is washed with 100 ml (1.0 V) of purified watet Layers are separated and the organic phase is concentrated to small volume in T bath 35-40°C. 100 ml (1.0 V) of n-Heptane are added keeping boiling under vacuum at T bath 35-40° C. and the mixture is concentrated to small volume. Then, 5 ml of Isopropanol and 300 ml (3.0 V) of n-Heptane are slowly added under vigorous stirring. The product crystallizes out. The slurry is stirred at 20-25° C. for 0.5 hand then at 0-5° C. for at least 2 h. The mixture is filtered and washed with 100 ml (1.0 V) of n-Heptane pre-cooled to 0-5° C. Afier vacuum drying at 20-25° C. for at least 8 h 75.1g of 2-(1,3,2-dioxaborinane-2-yl)benzonitrile equal to amolar yield from 2-bromo benzonitrile of 73percent. HPLC purity(AlA percent 99.9percent).

References: [1]Patent: JP2015/160823,2015,A .Location in patent: Paragraph 0056.
[2]Patent: EP2243785,2010,A1 .
[3]Patent: US9281483,2016,B2 .Location in patent: Page/Page column 93.
[4]Patent: KR2016/30582,2016,A .Location in patent: Paragraph 0258; 0259; 0260; 0261; 0262.
[5]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3867 - 3876.
[6]Patent: US2009/184289,2009,A1 .Location in patent: Page/Page column 4.
[7]Organic Letters,2013,vol. 15,p. 2742 - 2745.
[8]Patent: US2014/357886,2014,A1 .Location in patent: Paragraph 0061; 0062.

17
[ 51605-98-2 ]
[ 172732-52-4 ]
[ 946147-28-0 ]

Yield	Reaction Conditions	Operation in experiment
65.9%	With potassium carbonate;tetrakis(triphenylphosphine)palladium (0); In ethanol; toluene;	Step 1: Preparation of 2-(n-butyl)-6-aminophenanthridine 20.0 g (87.7 mmol) <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong>, 13.7 g (73.1 mmol) 2-bromo-4-butylaniline, 1.70 g (1.46 mmol) tetrakis(triphenylphosphine)palladium(0), and 27.2 g (198 mmol) potassium carbonate where refluxed in 400 mL toluene and 200 mL ethanol under N2 atmosphere for 20 h. HPLC and TLC revealed almost complete consumption of the aniline. An additional 1.8 g <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong> was added and refluxed continued for an additional 18 h. The reaction mixture was cooled and passed through a filter The solids were washed with ethyl acetate to remove organics from the collected base. The filtrate was then evaporated down and dried on silica. The sample was purified using silica gel chromatography with 100percent ethyl acetate as the eluent. The product fractions were then evaporated down to a minimal amount and the product recrystallized from EtOAc/hexanes to give 12.0 g of the title compound as light yellow solids (65.9percent yield, GC-MS confirmed).
65.9%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 38h;Reflux; Inert atmosphere;	Step 1: Preparation of 2-(n-butyl)-6-aminophenanthridine 20.0 g (87.7 mmol) <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong>, 13.7 g (73.1 mmol) 2-bromo-4-butylaniline, 1.70 g (1.46 mmol) tetrakis(triphenylphosphine)palladium(0), and 27.2 g (198 mmol) potassium carbonate where refluxed in 400 mL toluene and 200 mL ethanol under N2 atmosphere for 20 h. HPLC and TLC revealed almost complete consumption of the aniline. An additional 1.8 g <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong> was added and refluxed continued for an additional 18 h. The reaction mixture was cooled and passed through a filter. The solids were washed with ethyl acetate to remove organics from the collected base. The filtrate was then evaporated down and dried on silica. The sample was purified using silica gel chromatography with 100percent ethyl acetate as the eluent. The product fractions were then evaporated down to a minimal amount and the product recrystallized from EtOAc/hexanes to give 12.0 g of the title compound as light yellow solids (65.9percent yield, GC-MS confirmed).
65.9%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 38h;Reflux; Inert atmosphere;	Step 1: ) Preparation of 2-(n-butyl)-6-aminophenanthridine 20.0 g (87.7 mmol) 2- (1,3,2- I-dioxa barley-2-yl) benzonitrile, 13.7 g (73.1 mmol) 2-bromo-4-butylaniline, 1.70g (1.46 mmol) tetratetrakis(triphenylphosphine)palladium(0) and was refluxed for 20 hours under 27.2 g (198 mmol) of potassium carbonate a N2 atmosphere from 400 toluene and 200 ethanol. According to HPLC and TLC, it showed almost complete consumption of the aniline. Add 1.8 g 2- (1,3,2- I-dioxa barley-2-yl) benzonitrile was added in and allowed to continue to reflux for 18 h more. The reaction mixture was cooled, passed through a filter. The solid was washed with ethyl acetate to remove organics from the collected base. Then, the filtrate was evaporated and dried over silica. It was purified by silica gel chromatography using 100percent ethyl acetate as an eluent sample. Thereafter, the product fractions was evaporated to a minimum amount, the product was recrystallized from EtOAc / hexane to obtain 12.0 g of the title compound as a pale yellow solid (the yield: 65.9percent, GC-MS confirmed).

References: [1]Patent: EP2243785,2010,A1 .
[2]Patent: US9281483,2016,B2 .Location in patent: Page/Page column 98.
[3]Patent: KR2016/30582,2016,A .Location in patent: Paragraph 0295; 0296; 0297; 0298; 0299.

18
[ 1335105-43-5 ]
[ 172732-52-4 ]
[ 1335105-44-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In water; toluene; for 1.5h;Reflux;	2-cyano-phenyl boronic acid (1.32 mmol) was dissolved in anhydrous toluene (6 mL) and 1,3-propane-diol (1.32 mmol).The reaction mixture was refluxed in a flask equipped with a Dean-Stark apparatus for 24 h. The aryle iodide 12 (0.66 mmol), PdCl2(P(C6H5)3)2 (0.066 mmol), K3PO4 (1.32 mmol) and 5 muL of water were then added. The mixture was refluxed 90 min and then concentrated under reduced pressure. The crude product was dissolved in ethyl acetate. The organic layer was washed once with HCl 1N, twice with aq.NaHCO3 5percent and once with brine. The organic layer was dried, concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel with cyclohexane and ethyle acetate (7/3) to give 5-[acetyl-(2'-cyano-biphenyl-4-yl)-amino]-1-butyl-1H-pyrazole-4-carboxylic acid ethyl ester as a colorless oil; purity 100percent; yield: 71percent; 1H NMR (300 MHz, CD2Cl2) delta ppm 0.86 (t, J = 7.5 Hz, 3H); 1.28 (m, 5H); 1.50 (qt, J = 7.2 Hz, 1H); 1.70 (qt, J = 7.2 Hz, 1H); 2.05 (sl, 3H); 3.90 (t, J = 7.5 Hz, 2H); 4.32 (q, J = 7.5 Hz, 2H); 7.36-7.60 (m, 6H); 7.64 (t, J = 7.5 Hz, 1H); 7.74 (d, J = 8.7 Hz, 1H); 8.03 (s, 1H).13C NMR (75 MHz, CD2Cl2) delta ppm 13.5, 14.3, 19.7, 22.9, 31.1, 48.6, 60.6, 110.5, 111.1, 118.4, 126.0, 127.9, 129.7, 130.0, 133.0, 133.8, 141.3, 144.1, 161.9, 170.3; LCMS (EI(+)) m/z = 431 [M + H]+. The cyano derivative (0.465 mmol) was dissolved in toluene (5 mL). To the solution were added SnO(nBu)2 (0.093 mmol) and trimethylsilylazide (4.65 mmol). The reaction mixture was refluxed for 60 h, concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel with toluene/propane-2-ol/acetic acid (95/5/0.2) to give 13 as a colorless oil; yield: 60percent; 1H NMR (300 MHz, DMSO-d6) delta ppm 0.76 (t, J = 7.5 Hz, 3H); 1.1 (m, 7H); 1.97 (sl, 3H); 3.92 (m, 2H); 4.32 (q, J = 7.5 Hz, 2H); 7.10-7.68 (m, 8H); 8.03 (ls, 1H); 13C NMR (75 MHz, DMSO-d6) delta ppm 13.8, 14.6, 19.5, 23.0, 30.9, 48.1, 60.4, 108.2, 110.5, 124.3, 125.9, 126.9, 128.6, 130.1, 131.1, 131.4, 137.9, 139.3, 141.1, 141.7, 155.7, 161.9, 170,4; LCMS (EI(+)) m/z = 474 [M + H]+.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3867 - 3876.

19
[ 1335105-20-8 ]
[ 172732-52-4 ]
[ 1335105-40-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium phosphate; PdCl2(dppf); In toluene; for 2h;Reflux;	2-cyano phenyl boronic acid and 1,3 propanediol was solubilized in anhydrous toluene. The reaction mixture was refluxed in a flask equipped with a Dean-Stark apparatus. After 24 h, the reaction was concentrated under reduced pressure to give colorless oil. The crude product was purified on silica gel (DCM) to give 2-[1-3]dioxaborinan-2-yl-benzonitrile; yield: 20percent; 1H NMR (300 MHz, CDCl3) delta ppm 2.08 (t, J = 5.4 Hz, 2H), 4.21 (q, J = 5.4 Hz, 4H), 5.31 (ls, 2H), 7.45 (td, J1 = 7.5 Hz, J2 = 1.5 Hz, 1H), 7.53 (td, J1 = 7.5 Hz, J2 = 1.5 Hz, 1H), 7.65 (d, J = 7.5 Hz, 1H), 7.85 (d, J = 7.5 Hz, 1H). The 2-[1-3]dioxaborinan-2-yl-benzonitrile was readily solubilized in toluene (0.2 M). To this solution, compound 3e (1eq), PdCl2(dppf) (2percent) and K3PO4 (2 eq) were added. The mixture was refluxed during 2 h, then was concentrated under reduced pressure. The obtained crude product was dissolved in ethyl acetate and washed by HCl 1N. The organic layer was concentrated under reduced pressure and purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (70/30) to give 9 as a yellow powder; purity 99percent; yield: 83percent; mp: 169-170 °C; 1H NMR (300 MHz, CDCl3) delta ppm 1.29 (t, J = 6.9 Hz, 3H), 2.10 (s, 3H), 4.23 (q, J = 6.9 Hz, 2H), 7.61 (td, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H), 7.69 (dd, J1 = 7.8 Hz, J2 = 0.9 Hz, 1H), 7.75 (d, J = 8.7 Hz, 2H), 7.82 (td, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H), 7.82 (dd, J1 = 7.8 Hz, J2 = 0.9 Hz, 1H), 7.82 (d, J = 8.7 Hz, 2H), 9.13 (s, 1H), 9.95 (sl, 1H); 13C NMR (75 MHz, CDCl3) delta ppm 15.0, 23.9, 60.8, 110.2, 110.9, 119.3, 119.5, 129.3, 130.1, 130.2, 132.7, 134.5, 134.8, 137.1, 139.6, 144.2, 148.4, 162.7, 169.6; LCMS (EI (+)) m/z = 389 [M + H] +. HRMS (EI) calcd for C21H18N4O2 [M + H]+ 375.14517. Found 375.14454.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3867 - 3876.

20
[ 172732-52-4 ]
[ 1335105-41-3 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3867 - 3876.

21
[ 172732-52-4 ]
[ 1335105-42-4 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3867 - 3876.

22
[ 172732-52-4 ]
[ 1335105-45-7 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3867 - 3876.

23
[ 172732-52-4 ]
[ 1335105-46-8 ]

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3867 - 3876.

24
[ 172732-52-4 ]
[ 380917-96-4 ]