1035229-32-3|8-Acetyl-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one| Ambeed

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Quality Control of [ 1035229-32-3 ] Purity: 95% SDS Specification

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Product Details of [ 1035229-32-3 ]

CAS No. :	1035229-32-3
Formula :	C₁₇H₁₅NO₄
M.W :	297.31
SMILES Code :	O=C1NC2=C(OCC3=CC=CC=C3)C=CC(C(C)=O)=C2OC1
MDL No. :	MFCD21607217
InChI Key :	DKSBVRUAVDKXSO-UHFFFAOYSA-N
Pubchem ID :	57988970

Safety of [ 1035229-32-3 ]

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

Computational Chemistry of [ 1035229-32-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	22
Num. arom. heavy atoms	12
Fraction Csp3	0.18
Num. rotatable bonds	4
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	84.43
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	64.63 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.25
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	2.02
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.08
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.	1.26
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	3.29
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.18

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.1
Solubility	0.239 mg/ml ; 0.000803 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.	-3.0
Solubility	0.294 mg/ml ; 0.00099 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	-5.62
Solubility	0.000716 mg/ml ; 0.00000241 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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	Yes
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.68 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	0.0 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<0.0
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)	2.72

Application In Synthesis of [ 1035229-32-3 ]

* 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 [ 1035229-32-3 ]

[ 1035229-32-3 ] Synthesis Path-Downstream 1~35

1
[ 871101-87-0 ]
[ 79-04-9 ]
[ 1035229-32-3 ]

Yield	Reaction Conditions	Operation in experiment
95%		2-Chloroacetyl chloride (1.77 mL) was added dropwise to a stirred mixture of 1-(3-amino-4-(benzyloxy)-2-hydroxyphenypethanone (5.20 g, 20.2 mmol) and sodium hydrogen carbonate (3.74 g, 44.5 mmol) in DMF (30 mL) and then stirred for a further two hours. Cesium carbonate (7.90 g, 24.2 mmol) was added and the mixture was heated at 100 C. for 20 hours. The mixture was cooled to room temperature, quenched with water (500 mL), extracted with ethyl acetate (2×200 mL), and the combined organic layers washed with water (3×300 mL) and brine. The organic layer was then dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The solid residue was treated with ether, filtered and the eluent dried to afford the title compound (5.70 g, 19.2 mmol, 95% yield) as a beige solid. MS (ESI+) 298 [M+H]+.
86%		Intermediate 148-Acetyl-5-benzyloxy-4Af-benzo[1 ,4]oxazin-3-one; Chloroacetyl chloride (1.25 mL, 15.5 mmol) was added to a stirred mixture of 1-(3-amino-4-benzyloxy-2-hydroxy-phenyl)-ethanone (US2005/0277632) (3.63 g, 14.1 mmol) and NaHCO3 (2.69 g, 32.0 mmol) in dry DMF (20 mL). The reaction mixture was stirred at RT for 2 h. Caesium carbonate (5.53 g, 17.0 mmol) was added and the mixture was heated at 100 0C, protected from moisture, for 2.5 h. The reaction mixture was cooled to RT and poured into water (-300 mL) to afford a turbid, milky solution from which a solid precipitated. The solid was removed by vacuum filtration and taken up in EtOAc by sonication and the aqueous layer was extracted with EtOAc. The combined organic layers were further washed with water, brine, dried (MgSO4), and concentrated in vacuo Xo afford a dark brown solid. Yield: 3.60 g (86%). LC-MS (Method 3): Rt 3.24 min, m/z 298 [M+H]+.
		Step iv) 8-Acetyl-5-(benzyloxy)-2H-benzo[b][l,4]oxazin-3(4H)-one2-Chloroacetyl chloride (1.771 mL) was added dropwise to a stirred mixture of l-(3- amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone (5.2 g) [Step iii] and sodium hydrogen carbonate (3.74 g) in DMF (30 mL) and then stirred for a further 2 h. Cesium carbonate (7.90 g) was added and heated at 1000C for 20 h. The mixture was cooled to ambient temperature, quenched with water (500 mL), extracted with ethyl acetate (2 x 200 mL), washed with water (3 x 300 mL) and brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The solid residue was treated with ether, filtered and dried to afford the subtitled compound as a beige solid (5.7 g).1E NMR (399.826 MHz, DMSO) delta 10.33 (s, IH), 7.55 (m, 2H), 7.39 (m, 2H), 7.34 (d, J = 8.8 Hz, IH), 7.33 (m, IH), 6.89 (d, J = 9.2 Hz, IH), 5.27 (s, 2H), 4.67 (s, 2H), 3.32 (s 3H).

Step iv) 8-Acetyl-5-(benzyloxy)-2H-benzo[b][l,4]oxazin-3(4H)-one 2-Chloroacetyl chloride (1.77 mL) was added dropwise to a stirred mixture of l-(3-amino- 4-(benzyloxy)-2-hydroxyphenyl)ethanone (5.2 g) and sodium hydrogen carbonate (3.74 g) in DMF (30 mL) and then stirred for a further 2 h. Cesium carbonate (7.90 g) was added and heated at 1000C for 20 h. The mixture was cooled to ambient temperature, quenched with water (500 mL), extracted with ethyl acetate (2 x 200 mL), washed with water (3 x 300 mL) and brine, dried over anhydrous sodium sulfate, filtered and evaporated under vacuum. The solid residue was treated with ether, filtered and dried to afford the subtitled compound as a beige solid (5.7 g). <n="34"/>1H NMR (400 MHz, DMSO-d6) delta 10.33 (s, IH), 7.55 (m, 2H), 7.39 (m, 2H), 7.34 (d, J = 8.8 Hz, IH), 7.33 (m, IH), 6.89 (d, J = 9.2 Hz, IH), 5.27 (s, 2H), 4.67 (s, 2H), 3.32 (s, 3H).

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.
[2]Patent: US2016/31838,2016,A1 .Location in patent: Paragraph 0116.
[3]Patent: WO2010/15792,2010,A1 .Location in patent: Page/Page column 49.
[4]Patent: WO2008/75025,2008,A1 .Location in patent: Page/Page column 85.
[5]Patent: WO2009/154557,2009,A1 .Location in patent: Page/Page column 32-33.

2
[ 1035229-32-3 ]
[ 1035229-33-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N,N,N-trimethylbenzenemethanaminium dichloroiodate; acetic acid; In dichloromethane; water; at 65℃; for 20h;	Benzyltrimethylammonium dichloroiodate (14.2 g, 40.8 mmol) was added to a stirred solution of <strong>[1035229-32-3]8-acetyl-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one</strong> (5.50 g, 18.5 mmol) in a mixture of dichloromethane (100 mL), acetic acid (33 mL) and water (5.5 mL). The reaction mixture was stirred at 65 C. for 20 hours. The reaction was then cooled to room temperature, treated with aqueous sodium bisulphate (5.78 g, in 100 mL), and stirred for another 30 minutes. The mixture was diluted with ether (200 mL) and the resulting solid was filtered off, washed with water, then ether, and dried under vacuum at 40 C. to afford the title compound (5.60 g, 17.4 mmol, yield 94% yield) as a yellow solid. MS (ESI+) 332 [M+1-1]+.
89%	With N,N,N-trimethylbenzenemethanaminium dichloroiodate; acetic acid; In dichloromethane; water; at 65℃; for 18h;Darkness;	Intermediate 15 5-Benzyioxy-8-(2-chloro-acetyl)-4f/-benzo[1 ,4]oxazin-3-one; Benzyltrimethylammonium dichloroiodate (9.27 g, 26.6 mmol) was added to a stirred solution of 8-acetyl-5-benzyloxy-4/-/-benzo[1 ,4]oxazin-3-one (3.60 g, 12.1 mmol) in a mixture of DCM (65 ml_), acetic acid (22 ml_), and water (3.6 mL) that was heated at 65 0C and protected from light, for 18 h. The reaction mixture was cooled to RT and a solution of sodium bisulphite (3.78 g) in water (65 mL) was added and mixed vigorously to form a suspension. After stirring for 0.5 h diethyl ether (150 mL) was added and the solids collected by filtration, washed with water, then ether and dried at 40 0C in vacuo to afford a light brown crystalline solid. Yield: 3.56 g (89%). LC-MS (Method 3): Rt 3.50 min, m/z 332 [M+H]+.
89%	With N,N,N-trimethylbenzenemethanaminium dichloroiodate; acetic acid; In dichloromethane; water; at 65℃; for 18h;	intermediate 61; <n="105"/>5-Benzyloxy-8-(2-chloro-acetyl)-4H-benzo[1,4]oxazin-3-one; Benzyltrimethylammonium dichloroiodate (9.27 g, 26.6 mmol) was added to a stirred solution of 8-acetyl-5-benzyloxy-4/-/-benzo[1 ,4]oxazin-3-one (3.60 g, 12.1 mmol) in a mixture of DCM (65 ml_), acetic acid (22 ml_), and water (3.6 ml_), which was heated at 65 0C, protected from light, for 18 h. The reaction mixture was cooled to RT and a solution of sodium bisulphite (3.78 g) in water (65 ml_) was added and mixed vigorously to form a suspension. After stirring for 0.5 h diethyl ether (150 ml_) was added and the solids collected by filtration, washed with water, then ether and dried at 40 0C in vacuo to afford a light brown crystalline solid. Yield: 3.56 g (89%).LC-MS (Method 4): Rt 3.50 min, m/z 332 [M+H]+.

		Step v) 5-(Benzyloxy)-8-(2-chloroacetyl)-2H-benzo[b] [1 ,4]oxazin-3(4H)-oneBenzyltrimethylamnionium dichloroiodate (14.17 g) was added to a stirred solution of 8- acetyl-5-(benzyloxy)-2H-benzo[b][l,4]oxazin-3(4H)-one (5.5 g) [Step iv] in a mixture of dichloromethane (100 mL), AcOH (33 mL) and water (5.5 niL) and the reaction mixture stirred at 65 0C for 20 h. The reaction was cooled to ambient temperature, treated with aqueous sodium bisulphite (5.78 g in 100 mL) and stirred for a further 30 minutes. The mixture was diluted with diethylether (200 mL) and the resulting solid filtered off, washed with water and furtehr diethylether, and dried under vacuum at 40 0C to afford the subtitled compound as a light brown solid (5.6 g).1U NMR (299.947 MHz, DMSO) delta 10.41 (s, IH), 7.55 (m, 2H), 7.44 (d, J = 9.4 Hz, IH), 7.39 (m, 2H), 7.32 (m, IH), 6.95 (d, J = 9.4 Hz, IH), 5.30 (s, 2H), 4.96 (s, 2H), 4.69 (s, 2H).
	With N,N,N-trimethylbenzenemethanaminium dichloroiodate; In ethanol; for 1h;Reflux;Product distribution / selectivity;	Step v) 5-(Benzyloxy)-8-(2-chloroacetyl)-2H-benzo[b] [ 1 ,4]oxazin-3(4H)-one The solvent can be changed from dichloromethane, acetic acid and water to ethanol/water leading to the product precipitating directly rather then needing an extractive work-up. With this procedure there is no need to use an aqueous sodium bisulfite wash. For example:To the product from Preparation 2 Step iv) (23 g) and benzyltrimethylammonium dichloroiodate (53.85 g) was added ethanol (230 mL). The mixture was heated at reflux for 1 h then cooled to 500C and water (230 mL) added. The mixture was cooled to 200C and stirred for at least 1 h. The suspension was filtered, washed with water (46 mL) and then ethanol (69 mL). To the damp solid was added ethyl acetate (460 mL). The mixture was heated at reflux for 1 h then cooled to 200C and stirred for at least 1 h. The suspension was filtered and the residue was washed with ethyl acetate (115 mL) and dried under vacuum to yield the sub-titled compound (61.0 g).

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.
[2]Patent: US2016/31838,2016,A1 .Location in patent: Paragraph 0117.
[3]Patent: WO2010/15792,2010,A1 .Location in patent: Page/Page column 49-50.
[4]Patent: WO2008/149110,2008,A1 .Location in patent: Page/Page column 103-104.
[5]Patent: WO2008/75025,2008,A1 .Location in patent: Page/Page column 86.
[6]Patent: WO2009/154557,2009,A1 .Location in patent: Page/Page column 37.

3
C₁₇H₁₆ClNO₄ [ No CAS ]
[ 1035229-32-3 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2.5h;	Intermediate 60; 8-Acetyl-5-benzyloxy-4W-benzo[1 ,4]oxazin-3-one; Chloroacetyl chloride (1.25 ml_, 15.5 mmol) was added to a stirred mixture of 1-(3-amino-4-benzyloxy-2-hydroxy-phenyl)-ethanone (3.63 g, 14.1 mmol) andNaHCO3 (2.69 g, 32.0 mmol) in dry DMF (20 ml_). The reaction mixture was stirred for 2 h at RT. Caesium carbonate (5.53 g, 17.0 mmol) was added and the mixture was heated at 100 0C, protected from moisture, for 2.5 h. The reaction mixture was cooled to RT and poured into water (-300 ml_) to afford a turbid, milky solution from which a solid precipitated. The solid was removed by vacuum filtration and taken up in EtOAc by sonication and the aqueous layer was extracted with EtOAc. The combined organic layers were further washed with water, brine, dried (MgSO4), and concentrated in vacuo to afford a dark brown, fine solid.Yield: 3.60 g (86%). LC-MS (Method 4): Rt 3.24 min, m/z 298 [M+H]+.

References: [1]Patent: WO2008/149110,2008,A1 .Location in patent: Page/Page column 103.

4
[ 601-89-8 ]
[ 1035229-32-3 ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.
[2]Patent: US2016/31838,2016,A1 .
[3]Patent: WO2009/154557,2009,A1 .

5
[ 89684-58-2 ]
[ 1035229-32-3 ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.
[2]Patent: US2016/31838,2016,A1 .
[3]Patent: WO2009/154557,2009,A1 .

6
[ 1035229-31-2 ]
[ 1035229-32-3 ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.
[2]Patent: US2016/31838,2016,A1 .
[3]Patent: WO2009/154557,2009,A1 .

7
[ 1035229-32-3 ]
[ 1035229-34-5 ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.
[2]Patent: US2016/31838,2016,A1 .
[3]Patent: WO2009/154557,2009,A1 .

8
[ 1035229-32-3 ]
[ 1035492-00-2 ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.
[2]Patent: US2016/31838,2016,A1 .

9
[ 1035229-32-3 ]
[ 1035229-43-6 ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.
[2]Patent: US2016/31838,2016,A1 .

10
[ 1035229-32-3 ]
N-cyclohexyl-3-((3,4-dichlorobenzyl)amino)-N-(2-((2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)amino)ethyl)-propanamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.
[2]Patent: US2016/31838,2016,A1 .

11
[ 1035229-32-3 ]
[ 1035227-29-2 ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.

12
[ 1035229-32-3 ]
N-cyclopentyl-N-(2-((2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)amino)ethyl)-3-(phenethylamino)propanamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.

13
[ 1035229-32-3 ]
N-cyclobutyl-N-(2-((2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo-[b][1,4]oxazin-8-yl)ethyl)amino)ethyl)-3-(phenethylamino)propanamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.

14
[ 1035229-32-3 ]
C₂₅H₃₅N₃O₆ [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.

15
[ 1035229-32-3 ]
C₂₄H₃₃N₃O₆ [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 695 - 700.

16
[ 871101-87-0 ]
[ 1035229-32-3 ]

References: [1]Patent: WO2008/149110,2008,A1 .

17
[ 1035229-32-3 ]
[ 1092407-74-3 ]

References: [1]Patent: WO2008/149110,2008,A1 .

18
[ 1035229-32-3 ]
[ 1092407-77-6 ]

References: [1]Patent: WO2008/149110,2008,A1 .

19
[ 1035229-32-3 ]
[ 1092407-75-4 ]

References: [1]Patent: WO2008/149110,2008,A1 .

20
[ 1035229-32-3 ]
[ 1092407-76-5 ]