85160-83-4|2,2-Dimethyl-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one| Ambeed

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Quality Control of [ 85160-83-4 ] Purity: 95% SDS Specification

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Product Details of [ 85160-83-4 ]

CAS No. :	85160-83-4
Formula :	C₁₀H₁₀N₂O₄
M.W :	222.20
SMILES Code :	O=C1NC2=CC=C([N+]([O-])=O)C=C2OC1(C)C
MDL No. :	MFCD11048438
InChI Key :	KGWYDVZSGRHPFK-UHFFFAOYSA-N
Pubchem ID :	12793543

Safety of [ 85160-83-4 ]

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

Computational Chemistry of [ 85160-83-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	6
Fraction Csp3	0.3
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	61.73
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	84.15 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.53
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	1.29
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.13
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.	0.12
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	-0.22
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.77

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.24
Solubility	1.27 mg/ml ; 0.00573 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.	-2.66
Solubility	0.49 mg/ml ; 0.0022 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	-2.78
Solubility	0.368 mg/ml ; 0.00166 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.74 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)	2.43

Application In Synthesis of [ 85160-83-4 ]

* 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 [ 85160-83-4 ]

[ 85160-83-4 ] Synthesis Path-Downstream 1~31

1
[ 114254-56-7 ]
[ 85160-83-4 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 4239,4242.

2
[ 85160-83-4 ]
[ 105807-83-8 ]

Yield	Reaction Conditions	Operation in experiment
73.4%	With iron; ammonium chloride; In ethanol; water; at 90℃;	30 mM 2,2-dimethyl-7-nitro-2H-1,4-benzoxazol-3 (4H) -one was added100 mL of solvent (EtOH: H20 = 3: 1)Under stirring at room temperature, 10 mM ammonium chloride and 30 mM iron powder were further added, and the mixture was heated to 90 C. and refluxed for 1-2 hours.After the TLC detection of the reaction is over, the excess iron powder is filtered while hot, after the reaction solution is cooled and the solvent is distilled off under reduced pressure,The residual solid was adjusted to pH 10 with an aqueous solution of potassium carbonate, precipitated with a solid, filtered,The filter cake was washed with cooling water and dried in vacuo to give pure intermediate product as 4.23 g of a yellow powder,Yield 73.4%. This intermediate was used directly in the next reaction without further purification
66%	With 20% palladium hydroxide-activated charcoal; hydrogen; In methanol; at 40℃; under 750.075 Torr; for 4h;	(2) Preparation of 7-amino-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one A mixture of the compound (wet material: 384.6 g) obtained in the above step (1), methanol (2880 mL), and 20% palladium hydroxide carbon (13.8 g) was stirred under hydrogen pressure (0.1 MPa) at 40C until hydrogen absorption terminated (about 4 hours). The reaction mixture was filtered, and the unfiltered residue was washed with methanol (300 mL). The filtrate and the washings were combined, then concentrated under reduced pressure at 50C or lower, to the residue were added methanol (288 mL) and water (1440 mL), and the mixture was stirred at 50C for about 1 hour. The mixture was cooled to 25C, then stirred for 30 minutes, the precipitated crystals were collected by filtration, washed with water (1440 mL), and then dried to obtain the title compound (163.94 g) as red-brown crystals (yield: 66%, purity: 100%). MS: ESI-MS m/Z: 193 [M+H]+ 1 H-NMR (CDCl3): delta 1.51 (6H, s), 3.56 (2H, brs), 6.29 (1H, dd), 6.32, 6.33 (1H, m), 6.59 (1H, d), 8.34 (1H, brs)
	With hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; methanol; at 20℃;	To a solution of the compound obtained in Reference Example 1(1) (500 mg) in tetrahydrofuran (7 mL)-methanol (5 mL) was added 10% palladium-carbon (100 mg, water content: ca. 50%), and the mixture was stirred overnight at room temperature <n="76"/>under atmospheric pressure of hydrogen. The insolubles were removed by filtration, and the filtrate was concentrated in vacuo to give 7-amino-2,2-dimethyl~2H-l,4- benzoxazin- 3(4H)-one (429 mg) as a pale pink solid. MS(APCI) m/z: 193 [M+H]+

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 262 - 267.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1263 - 1267.
[3]Patent: CN107459494,2017,A .Location in patent: Paragraph 0138; 0143-0145.
[4]Molecular Diversity,2017,vol. 21,p. 125 - 136.
[5]Patent: EP2883870,2015,A1 .Location in patent: Paragraph 0075; 0076.
[6]Patent: WO2007/89034,2007,A1 .Location in patent: Page/Page column 74-75.

3
[ 600-00-0 ]
[ 121-88-0 ]
[ 85160-83-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 90℃; for 13.5h;Cooling with ice;	125 mM potassium carbonate was added to 100 mL of dry DMF (N, N-dimethylformamide)To this was added 50 mM 2-amino-5-nitrophenol and stirred at room temperature for 1 h until it was completely dissolved.Under ice bath conditions,50 mM 2-Bromo-2-methylpropionic acid ethyl ester in DMF was slowly added dropwise.After half an hour, the reaction solution was slowly warmed to room temperature and reacted at 90 C for 12 hours.After the reaction solution was cooled, part of the solvent was distilled off under reduced pressure,Slowly add ice water 300-500mL with a solid precipitation under stirring, stirring for half an hour under an ice bath,Filter, the filter cake was dried in vacuo to give pure intermediate product as brown powder 8.32g, 75.0% yield. This intermediate was used directly in the next reaction without further purification
348.6 g	With potassium carbonate; In dimethyl sulfoxide; at 26 - 30℃; for 24h;	(1) Preparation of 2,2-dimethyl-7-nitro-2H-1,4-benzoxazin-3(4H)-one To a solution of 2-amino-5-nitrophenol (200 g) in dimethylsulfoxide (1000 mL) was added anhydrous potassium carbonate (269 g) under stirring at 30C or lower, then to the mixture was added ethyl 2-bromo-2-methylpropionate (278.4 g) at 30C or lower, and the mixture was stirred at 26C for 24 hours. To the reaction mixture was added water (2000 mL) at 40C or lower, and then stirred at room temperature for 3 hours. The reaction product was collected by filtration, and successively washed with dimethylsulfoxide/water (2:1, 800 mL) and water (3200 mL) to obtain the title compound (348.6 g) as a yellow solid (wet material) (yield: 121%, purity: 96%). MS: ESI-MS m/Z: 223 [M+H]+ 1 H-NMR (CDCl3): delta 1.59 (6H, s), 6.95 (1H, d), 7.87 (1H, d), 7.92 (1H, dd), 9.38 (1H, brs)

References: [1]Patent: CN107459494,2017,A .Location in patent: Paragraph 0138; 0140-0142.
[2]Synthesis,1982,vol. No. 11,p. 986 - 987.
[3]Molecular Diversity,2017,vol. 21,p. 125 - 136.
[4]Patent: EP2883870,2015,A1 .Location in patent: Paragraph 0073; 0074.

4
[ 85160-83-4 ]
[ 144293-76-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; iodine; In tetrahydrofuran; for 16h;Reflux;	Anhydrous THF (10 mL) at C1 (1.33 g, 6.0 mmol) and NaBH4 (570 mg, 15.0 mmol) to a stirred solution in I2 (127 mg, 1mmol) was added. The mixture was refluxed for 16 hours. After cooling to room temperature, followed by saturated NH4Cl (10 mL) was added NaOH (2 M, 30 mL). The mixture was extracted with EtOAc (20 mL × 3). Wash the combined extracts with brine (50 mL), and dried over anhydrous Na2SO4, and concentrated under reduced pressure to produce a C2.

References: [1]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 103 - 114.
[2]Patent: KR101576386,2015,B1 .Location in patent: Paragraph 0116; 0119-0120.

5
[ 85160-83-4 ]
[ 174714-58-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 103 - 114.

6
[ 85160-83-4 ]
[ 105808-06-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1263 - 1267.

7
[ 85160-83-4 ]
[ 105808-23-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1263 - 1267.

8
[ 600-00-0 ]
[ 85160-83-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of potassium fluoride (4.71 g) in N,N-dimethylformamide (40 mL) was added 2-amino-5-nitrophenol (5.00 g), and the mixture was stirred at room temperature for 1 hour. To the suspension was added dropwise a solution of ethyl alpha- bromoisobutyrate (6.33 g) in N,N-dimethylforrnamide (10 mL) over a period of 20 minutes, and the mixture was stirred at 60 C for 20 hours. After cooling, to the reaction mixture was added cool, water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with an aqueous 10% HCl solution, water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was suspended in ethyl acetate, and the precipitates were collected by filtration and washed with ethyl acetate to give 2,2-dimethyl-7-nitro-2H-l,4-benzoxazin-3(4H)-one (2.80 g) as a pale brown powder. ESI-MS m/z: 221 [M-H]"

References: [1]Patent: WO2007/89034,2007,A1 .Location in patent: Page/Page column 73.

9
[ 85160-83-4 ]
[ 98-80-6 ]
[ 945968-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	With copper diacetate; triethylamine; In dichloromethane; at 20℃; for 20h;Molecular sieve;	To a suspension of the compound obtained in the above step (1) (600 mg) in dichloromethane (12 mL) were added phenylboronic acid (659 mg), copper(II) acetate (589 mg) and Molecular sieves-4A powder (600 mg), and thereto was added <n="75"/>triethylamine (753 muL). The mixture was vigorously stirred at room temperature for 20 hours. The reaction mixture was filtered and the residue was washed with chloroform. The filtrate and the washings were combined, concentrated in vacuo and purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate = 9/1) to give 2,2- dimethyl-7-nitro-4-phenyl-2H-l,4-benzoxazin-3(4H)-one (755 mg) as a pale yellow solid. MS(APCI) m/z: 316 [MfNH4]*

References: [1]Patent: WO2007/89034,2007,A1 .Location in patent: Page/Page column 73-74.

10
[ 85160-83-4 ]
N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-N-(methylsulfonyl)methanesulfonamide [ No CAS ]

References: [1]Patent: EP2883870,2015,A1 .
[2]Patent: EP2883870,2015,A1 .

11
[ 85160-83-4 ]
N-(4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)methanesulfonamide [ No CAS ]

References: [1]Patent: EP2883870,2015,A1 .
[2]Patent: EP2883870,2015,A1 .

Yield	Reaction Conditions	Operation in experiment
69%		General procedure: (Step 1) (0774) To a suspension of potassium fluoride (2.36 g, 40.55 mmol) in DMF (15.0 mL) was added methyl 2-bromobutyrate (2.06 mL, 17.84 mmol), and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added 2-amino-5-nitrophenol (2.5 g, 16.22 mmol), and the mixture was stirred at 50-60C for 6 hr, and then at room temperature for 14 hr. The same reaction was repeated, both of the reaction mixtures were combined, and ice (175 g) was added. The precipitate white solid was collected by filtration, and the obtained solid was washed successively with water and hexane, and dried under reduced pressure to give 2-ethyl-7-nitro-4H-benzo[1,4]oxazin-3-one (6.0 g, 83%) as a white solid. MS (API) :221 (M+H)

13
[ 85160-83-4 ]
N-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-4-methylbenzenesulfonamide [ No CAS ]

References: [1]Molecular Diversity,2017,vol. 21,p. 125 - 136.
[2]Patent: CN107459494,2017,A .
[3]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 262 - 267.

14
[ 85160-83-4 ]
N-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-4-nitrobenzenesulfonamide [ No CAS ]

References: [1]Molecular Diversity,2017,vol. 21,p. 125 - 136.

15
[ 85160-83-4 ]
N-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-4-methoxy-2-nitrobenzenesulfonamide [ No CAS ]

References: [1]Molecular Diversity,2017,vol. 21,p. 125 - 136.

16
[ 85160-83-4 ]
N-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-2-fluorobenzenesulfonamide [ No CAS ]

References: [1]Molecular Diversity,2017,vol. 21,p. 125 - 136.

17
[ 121-88-0 ]
[ 85160-83-4 ]