66176-17-8|8-Methyl-1H-benzo[d][1,3]oxazine-2,4-dione| Ambeed

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Quality Control of [ 66176-17-8 ] Purity: 98% SDS Specification

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Product Details of [ 66176-17-8 ]

CAS No. :	66176-17-8
Formula :	C₉H₇NO₃
M.W :	177.16
SMILES Code :	O=C(NC1=C(C)C=CC=C12)OC2=O
MDL No. :	MFCD03426399
InChI Key :	CHKUQVBJPDLANA-UHFFFAOYSA-N
Pubchem ID :	2759870

Safety of [ 66176-17-8 ]

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

Computational Chemistry of [ 66176-17-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	10
Fraction Csp3	0.11
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	48.07
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	63.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.33
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	1.38
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.79
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.	1.33
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	2.52
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.47

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.38
Solubility	0.744 mg/ml ; 0.0042 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.	-2.31
Solubility	0.872 mg/ml ; 0.00492 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	-3.53
Solubility	0.0522 mg/ml ; 0.000294 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.	-6.4 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	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<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)	2.63

Application In Synthesis of [ 66176-17-8 ]

* 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 [ 66176-17-8 ]

[ 66176-17-8 ] Synthesis Path-Downstream 1~35

1
[ 96-50-4 ]
[ 66176-17-8 ]
[ 33373-90-9 ]

References: [1]Journal of Pharmaceutical Sciences,1971,vol. 60,p. 1251 - 1253.

2
[ 75-44-5 ]
[ 4389-45-1 ]
[ 66176-17-8 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 735 - 742.
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3753 - 3757.
[3]Journal of Medicinal Chemistry,1978,vol. 21,p. 485 - 489.
[4]Journal of the American Chemical Society,1987,vol. 109,p. 6493 - 6502.

3
[ 66176-17-8 ]
[ 75-03-6 ]
[ 66176-18-9 ]

References: [1]Journal of Medicinal Chemistry,1978,vol. 21,p. 485 - 489.

4
[ 1127-59-9 ]
[ 66176-17-8 ]

References: [1]Angewandte Chemie,1980,vol. 92,p. 196 - 197.

5
[ 66176-17-8 ]
[ 76746-16-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate; In ethanol; at 20℃; for 2h;	General procedure: To a solution of different substituted 2-aminobenzoic acid (3 mmol) in 15 mL of THF was added triphosgene (0.30 g, 1 mmol). The mixture was stirred at room temperature and monitored with TLC. After more than 4 h, the solvent was evaporated and the residue was dissolved in 15 mL of EtOH. The hydrazine hydrate (80 %) (0.94 g, 15 mmol) was added to this mixture dropwise. After 2 h, the reaction was completed, 30 mL of ethyl acetate was added. The solution was washed with 1 mol/L hydrochloric acid solution, saturated sodium bicarbonate solution, and brine. The ethyl acetate solution was dried and evaporated, and the residue was applied to a flash column chromatography by eluting with ethyl acetate to give the compounds 1a-f.

References: [1]Organic Letters,2017,vol. 19,p. 3033 - 3036.
[2]Journal of Medicinal Chemistry,1981,vol. 24,p. 735 - 742.
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2295 - 2299.
[4]Chemical Biology and Drug Design,2018,vol. 92,p. 1914 - 1919.

6
[ 66176-17-8 ]
[ 147-85-3 ]
[ 110419-73-3 ]

References: [1]Journal of the American Chemical Society,1987,vol. 109,p. 6493 - 6502.

7
[ 32315-10-9 ]
[ 4389-45-1 ]
[ 66176-17-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;	a 8-Methyl-1H-benzo[d][1,3]oxazine-2,4-dione To a solution of 2-amino-3-methylbenzoic acid (9.07 g, 60 mmol) in THF (60 mL) was added simultaneously diisopropylethylamine (20.9 mL) and a solution of triphosgene (5.94 g, 20 mmol) in dichloromethane (60 mL) over 30 minutes period. After the addition was completed, the mixture stirred at ambient temperature for 16 hours. Solid was filtered and washed with ether (2100 mL) and H2O (350 mL), and dried in high vacuum to afford the title compound (10.02 g, 94% yield) as a white solid. 1H NMR (DMSO) delta 11.02 (s, 1H), 7.76 (d, 1H, J=7.7 Hz), 7.57 (d, 1H, J=7.5 Hz), 7.17-7.13 (m, 1H), 2.32 (s, 3H).
94%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;	a) 8-Methyl-1H-benzo[d][1,3]oxazine-2,4-dione To a solution of 2-amino-3-methylbenzoic acid (9.07 g, 60 mmol) in THF (60 mL) was added simultaneously diisopropylethylamine (20.9 mL) and a solution of triphosgene (5.94 g, 20 mmol) in dichloromethane (60 mL) over 30 minutes period. After the addition was completed, the mixture stirred at ambient temperature for 16 hours. Solid was filtered and washed with ether (2100 mL) and H2O (350 mL), and dried in high vacuum to afford the title compound (10.02 g, 94% yield) as a white solid. 1H NMR (DMSO): delta 11.02 (s, 1H), 7.76 (d, 1H, J=7.7 Hz), 7.57 (d, 1H, J=7.5 Hz), 7.17-7.13 (m, 1H), 2.32 (s, 3H).
86.4%	In tetrahydrofuran; at 20℃; for 0.25h;	Example 2268-Methyl- 1 -(3 -(4-(pyrimidin-2-yl)piperazine- 1 -carbonyl)benzyl)quinazoline-2,4( lH,3H)-dione a) 8-Methyl- lH-benzo[<i][l,3]oxazine-2,4-dione: To a solution of 2-amino-3-methylbenzoic acid (5.03 g, 33.3 mmol) in THF (50 mL) was added triphosgene (9.92 g, 33.4 mmol). The mixture was stirred at room temperature for 15 min and then filtered. The precipitate was washed by THF and water, dried to give the title compound (5.10 g, 86.4% yield) as white solid. MS: m/z 178.1 [M+H]+.

86.4%	In tetrahydrofuran; at 20℃; for 0.25h;	To a solution of 2-amino-3-methylbenzoic acid (5.03 g, 33.3 mmol) in THF (50 mL) was added triphosgene (9.92 g, 33.4 mmol). The mixture was stirred at room temperature for 15 min and then filtered. The precipitate was washed by THF and water, dried to give the title compound (5.10 g, 86.4% yield) as white solid. MS: m/z 178.1 [M+H]+.
78%	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 18h;	General procedure: Toa solution of amino-benzoic acid (2.90 mmol, 1 eq) in anhydrous THF (25 mL), triethylamine (2.90 mmol, 1 eq) was added and the mixture was cooled down to 0C. Then triphosgene (0.97 mmol, 1 eq) was added portion wise and the reaction allowed to reach room temperature and left stirring for 18 hours. 1mL of H2O was carefully added to the mixture and the solvent was removed under reduced pressure. The residue was precipitated from H2O, affording pure product.
	In tetrahydrofuran; at 20℃; for 4h;	General procedure: To a solution of different substituted 2-aminobenzoic acid (3 mmol) in 15 mL of THF was added triphosgene (0.30 g, 1 mmol). The mixture was stirred at room temperature and monitored with TLC. After more than 4 h, the solvent was evaporated and the residue was dissolved in 15 mL of EtOH. The hydrazine hydrate (80 %) (0.94 g, 15 mmol) was added to this mixture dropwise. After 2 h, the reaction was completed, 30 mL of ethyl acetate was added. The solution was washed with 1 mol/L hydrochloric acid solution, saturated sodium bicarbonate solution, and brine. The ethyl acetate solution was dried and evaporated, and the residue was applied to a flash column chromatography by eluting with ethyl acetate to give the compounds 1a-f.
		General procedure: Compound 12 was prepared according tothe procedure previously reported.36 A mixture of anthranilicacid 11 (50 mmol) and tetrahydrofuran (THF, 100 mL) wasstirred at -10 C for 30 min. Then, a solution of triphosgene(BTC, 50 mmol) in THF (30 mL) was added dropwise to themixture described above. After that, the mixture was stirred for1 h at -10 C, followed by 18-24 h at 20-25 C. The solventwas removed under reduced pressure, and anhydrous ether(150 mL) was added to the obtained residue while the mixturewas being vigorously stirred. The precipitate was collected byfiltration, washed with anhydrous ether, and dried to givecompound 12 in yields of 80-90%.
	In tetrahydrofuran; at 20℃;	(4) Add 5g of raw material 4 and tetrahydrofuran to a 100ml three-necked flask and stir at room temperature, and add 8.65g of triphosgene in portions.The reaction was followed by TLC until the raw materials disappeared, dissolved, and the solid was washed with n-hexane solution multiple times to obtain intermediate 5.

References: [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 10942 - 10951.
[2]Patent: US2004/9995,2004,A1 .
[3]Patent: US2005/4031,2005,A1 .
[4]Patent: WO2012/130166,2012,A1 .Location in patent: Page/Page column 84.
[5]Patent: US2014/23642,2014,A1 .Location in patent: Paragraph 0593.
[6]European Journal of Medicinal Chemistry,2015,vol. 95,p. 526 - 545.
[7]European Journal of Medicinal Chemistry,1994,vol. 29,p. 925 - 940.
[8]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2295 - 2299.
[9]Journal of Agricultural and Food Chemistry,2015,vol. 63,p. 6883 - 6889.
[10]Biochemistry,2017,vol. 56,p. 6491 - 6502.
[11]Chemical Biology and Drug Design,2018,vol. 92,p. 1914 - 1919.
[12]Chinese Chemical Letters,2020,vol. 31,p. 739 - 745.
[13]Patent: CN110526863,2019,A .Location in patent: Paragraph 0042-0043; 0047.

8
[ 56-17-7 ]
[ 66176-17-8 ]
Bis<2-(2-amino-3-methyl-benzoylamino)ethyl>disulfan [ No CAS ]

References: [1]Archiv der Pharmazie,1995,vol. 328,p. 277 - 281.

9
[ 66176-17-8 ]
[ 120538-52-5 ]
3'-(2-amino-3-methylbenzoylamino)quinuclidine [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 925 - 940.

10
[ 623-33-6 ]
[ 66176-17-8 ]
9-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5241 - 5253.

Yield	Reaction Conditions	Operation in experiment
85%	With cetyltrimethylammonim bromide; triphenylphosphine; In acetonitrile; at 60℃; under 760.051 Torr; for 24h;	General procedure: First of all, water of 0.5mL (In the case of Ex. No. 1) oran organic solvent ( In the case of Ex. Nos. 2 to 17) was charged into thereaction vessel, and orthoazide benzoate used in the reaction (81.6mg :0.0005mol), Orthoazide benzoic acid withan equivalent amount (0.0005mol) triphenylphosphine (131.2mg: 0.0005mol) and1.5 times equivalent amount(0.00075mol) CTMABr of orthoazide benzoic acid wereadded to this solvent and the mixture wasstirred for 5 minutes at 20 .Thereafter, water or pH7.6 potassium dihydrogen phosphate (KH2P04)/ sodium hydroxide (NaOH) buffer solution 4.5mL was added and the reactionsystem was made as an aqueous solvent, and reaction vessel was degassed, and after the reaction vessel was made as a carbondioxide atmosphere using a balloon inflated with carbon dioxide, it was allowed to react with stirring under the conditions of 20, 18 hours.
	With diphenyl diselenide; dihydrogen peroxide; In N,N-dimethyl-formamide; acetonitrile; at 25℃; for 24h;	General procedure: In a round bottom flask was added 1.47 g of isatin (10 mmol),0. 16 g diphenyl diselenide (0. 5 mmol).With stirring,The temperature of the mixing system was maintained at 25 C,And 25 ml of a DMF-acetonitrile mixed solution (DMF volume content: 10%) in which 20 mmol of 30% hydrogen peroxide was dissolved was slowly added dropwise.The mixture was stirred at a system temperature of 25 CShould be 24 hours.After completion of the reaction, 30 ml of a 5% aqueous solution of ferrous chloride was added, and the mixture was extracted with ethyl acetate (50 ml, 3 times)The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified by column chromatography to give 1.39 g of isatoic anhydride (yield 85%).

12
[ 66176-17-8 ]
[ 64-19-7 ]
[ 34637-44-0 ]
N-(8,3'-dimethyl-4,4'-dioxo-3',4'-dihydro-4H-[2,2']biquinazolinyl-3-yl)-acetamide [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2002,vol. 41,p. 1950 - 1952.

13
[ 66176-17-8 ]
[ 34637-44-0 ]
2-[N'-(2-amino-3-methylbenzoyl)hydrazinocarbonyl]-3-methylquinazolin-4(3H)-one [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2002,vol. 41,p. 1950 - 1952.

14
[ 66176-17-8 ]
[ 34535-42-7 ]
7-methyl-12H-5,6,11a-triaza-dibenzo[b,h]fluoren-11-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5757 - 5761.

15
[ 66176-17-8 ]
[ 22223-49-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3753 - 3757.

16
[ 362640-60-6 ]
[ 66176-17-8 ]
8-methyl-2-(2-phenyl-5-trifluoromethyl-2H-pyrazol-3-yl)-benzo[d][1,3]oxazin-4-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4898 - 4906.

17
2-(3-chloro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride [ No CAS ]
[ 66176-17-8 ]
2-[2-(3-chloro-phenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-8-methyl-benzo[d][1,3]oxazin-4-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4898 - 4906.

18
2-(4-chloro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride [ No CAS ]
[ 66176-17-8 ]
2-[2-(4-chloro-phenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-8-methyl-benzo[d][1,3]oxazin-4-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4898 - 4906.

19
[ 511533-50-9 ]
[ 66176-17-8 ]
[ 1064445-77-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4898 - 4906.

20
[ 66176-17-8 ]
[ 100-39-0 ]
C₆H₄C₂O₃NCH₃C₇H₆ [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7058 - 7061.

21
[ 66176-17-8 ]
1-benzyl-4-hydroxy-8-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7058 - 7061.

22
[ 66176-17-8 ]
methyl 3-methyl-2-(1H-pyrrol-1-yl)benzoate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3753 - 3757.

23
[ 66176-17-8 ]
[ 76746-28-6 ]