26215-14-5|7-Amino-2H-1,4-benzoxazin-3[4H]one| Ambeed

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Quality Control of [ 26215-14-5 ] Purity: 96% SDS Specification

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Product Details of [ 26215-14-5 ]

CAS No. :	26215-14-5
Formula :	C₈H₈N₂O₂
M.W :	164.16
SMILES Code :	O=C1COC2=CC(N)=CC=C2N1
MDL No. :	MFCD03425794
InChI Key :	RUZXDTHZHJTTRO-UHFFFAOYSA-N
Pubchem ID :	2764182

Safety of [ 26215-14-5 ]

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

Computational Chemistry of [ 26215-14-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	47.67
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	64.35 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.12
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	0.19
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.04
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.	-0.06
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	0.79
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.41

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.35
Solubility	7.38 mg/ml ; 0.0449 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.1
Solubility	13.0 mg/ml ; 0.0795 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-2.26
Solubility	0.9 mg/ml ; 0.00548 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	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.	-7.17 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)	1.98

Application In Synthesis of [ 26215-14-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 26215-14-5 ]

[ 26215-14-5 ] Synthesis Path-Downstream 1~35

1
[ 621-59-0 ]
[ 26215-14-5 ]
7-[1-(3-Hydroxy-4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

2
[ 26215-14-5 ]
[ 463-71-8 ]
[ 105808-00-2 ]

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

3
[ 26215-14-5 ]
[ 38870-89-2 ]
[ 106659-44-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1259 - 1262.

4
[ 26215-14-5 ]
[ 108-24-7 ]
[ 90814-93-0 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1259 - 1262.

5
[ 26215-14-5 ]
[ 104-87-0 ]
7-[1-p-Tolyl-meth-(E)-ylidene]-amino}-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

6
[ 26215-14-5 ]
[ 104-88-1 ]
7-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

7
[ 26215-14-5 ]
[ 555-16-8 ]
7-[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-amino}-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

8
[ 26215-14-5 ]
[ 5464-11-9 ]
[ 120711-66-2 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 1627 - 1630.

9
[ 26215-14-5 ]
[ 100-52-7 ]
7-[1-Phenyl-meth-(E)-ylidene]-amino}-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.
[2]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

10
[ 26215-14-5 ]
[ 123-11-5 ]
7-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

11
[ 26215-14-5 ]
[ 103-72-0 ]
[ 130137-41-6 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 697 - 699.

12
[ 26215-14-5 ]
[ 2131-55-7 ]
[ 130137-42-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 697 - 699.

13
[ 26215-14-5 ]
[ 79-22-1 ]
[ 81912-91-6 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 130 - 133.

14
[ 26215-14-5 ]
[ 6287-38-3 ]
7-[1-(3,4-Dichloro-phenyl)-meth-(E)-ylidene]-amino}-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

15
[ 26215-14-5 ]
[ 1985-12-2 ]
[ 130137-43-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 697 - 699.

16
[ 26215-14-5 ]
[ 105202-20-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1293 - 1294.

17
[ 81721-86-0 ]
[ 26215-14-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogen;palladium on activated charcoal; In tetrahydrofuran; at 20℃;	Synthesis of 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one A 1000 mL round-bottom flask was purged, flushed and maintained with a hydrogen atmosphere, then, was added a solution of 7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (16.5 g, 85.05 mmol, 1.00 equiv) in THF (500 mL). To the mixture was added Pd/C (10%, 4 g). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (PE/EtOAc=1:1). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 13.5 g (97%) of 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one as a red solid.
91%	With hydrogen;palladium 10% on activated carbon; In methanol; ethyl acetate; for 2h;	INTERMEDIATE 11; 7-Amino-4H-benzori,41oxazin-3-one; 7-Nitro-4i/-benzo[l,4]oxazin-3-one (0.65 g, 3.3 mmol) and 10% palladium on carbon (0.13 g) were combined in EtOAc (15 mL) and MeOH (15 mL) and hydrogenated for 2 h at atmospheric pressure. The catalyst was removed by filtration through celite and the filtrate reduced in vacuo to yield the title compound as a colourless oil (0.50 g, 91%). δH (DMSO-d6) 4.42 (2H, s), 4.89 (2H, br s), 6.13-6.20 (2H, m), 6.56 (IH, d, J 8.1 Hz),10.27 (IH, br s).
68%	With hydrogen;palladium 10% on activated carbon; In N,N-dimethyl-formamide; at 20℃; for 16h;	The suspension of 7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (61.9 mmol) and 10% palladium on carbon (5 g) in N,N-dimethylformamide (150 mL) was maintained under an atmosphere of hydrogen gas at rt for 16 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was diluted water and the precipitated solids were collected by filtration, washed with hexane, and dried to provide 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one in 68% yield as a yellow solid.

68%	With hydrogen;palladium on activated charcoal; In N,N-dimethyl-formamide; at 20℃;	Synthesis of 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one Into a 500 mL 3-necked round-bottom flask was added a solution of 7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (12 g, 61.86 mmol) in DMF (150 mL). To the mixture was added Pd/C (5 g) followed by hydrogen. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (PE/EA=1:1). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The product was precipitated by the addition of H2O. A filtration was performed. The filter cake was washed 3 times with 300 mL of hexane. This resulted in 7.3 g (68%) of 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one as a yellow solid.
68%	With hydrogen;palladium 10% on activated carbon; In N,N-dimethyl-formamide; at 20℃; for 16h;	Intermediate 23: Synthesis of 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chloride; 1. Synthesis of 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one; The suspension of 7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (61.9 mmol) and 10% palladium on carbon (5 g) in N,N-dimethylformamide (150 mL) was maintained under an atmosphere of hydrogen gas at rt for 16 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was diluted water and the precipitated solids were collected by filtration, washed with hexane, and dried to provide 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one in 68% yield as a yellow solid.
68%	With hydrogen;palladium 10% on activated carbon; In N,N-dimethyl-formamide; at 20℃; for 16h;	Intermediate 29: Synthesis of 3-oxo-3,4-dihydro-2H-benzo[b][l,4]oxazine-7-sulfonyl chloride.1. Synthesis of 7-amino-2H-benzo[bl[ 1 ,4]oxazin-3(4H)-one.The suspension of 7-nitro-2//-benzo[b][l,4]oxazin-3(4H)-one (61.9 mmol) and 10% palladium on carbon (5 g) in N,N-dimethylformamide (150 mL) was maintained under an atmosphere of hydrogen gas at rt for 16 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was diluted water and the precipitated solids were collected by filtration, washed with hexane, and dried to provide 7-amino-2H- benzo[b][l,4]oxazin-3(4H)-one in 68% yield as a yellow solid.
68%	With hydrogen;palladium 10% on activated carbon; In N,N-dimethyl-formamide; at 20℃; for 16h;	The suspension of 7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (61.9 mmol) and 10% palladium on carbon (5 g) in N,N-dimethylformamide (150 mL) was maintained under an atmosphere of hydrogen gas at rt for 16 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was diluted water and the precipitated solids were collected by filtration, washed with hexane, and dried to provide 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one in 68% yield as a yellow solid.
68%	With hydrogen;palladium 10% on activated carbon; In N,N-dimethyl-formamide; at 20℃; for 16h;	Intermediate 29: Synthesis of 3-oxo-3,4-dihydro-2/7-benzo[b][l,4]oxazine-7-sulfonyl chloride. 1. Synthesis of 7-amino-2H-benzo[b][L4]oxazin-3(4H)-one.The suspension of 7-nitro-2H-benzo[b][l,4]oxazin-3(4H)-one (61.9 mmol) and 10% palladium on carbon (5 g) in N,7V-dimethylforrnamide (150 mL) was maintained under an atmosphere of hydrogen gas at rt for 16 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was diluted water and the precipitated solids were collected by filtration, washed with hexane, and dried to provide 7-amino-2H- benzo[b][l,4]oxazin-3(4H)-one in 68% yield as a yellow solid.
68%	With hydrogen;palladium 10% on activated carbon; In N,N-dimethyl-formamide; at 20℃; for 16h;	The suspension of 7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (61.9 mmol) and 10% palladium on carbon (5 g) in N,N-dimethylformamide (150 mL) was maintained under an atmosphere of hydrogen gas at rt for 16 h. The insoluble solids were removed by filtration and the filtrate was concentrated. The residue was diluted water and the precipitated solids were collected by filtration, washed with hexane, and dried to provide 7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one in 68% yield as a yellow solid.
68%	With hydrogen;palladium over charcoal; In N,N-dimethyl-formamide; at 20℃;	Into 500 mL 3-necked round bottom flask was added a solution of 7-nitro-2H- benzo[b][l,4]oxazin-3(4H)-one (12 g, 61.86 mmol) in DMF (150 mL). To the mixture was added Pd/C (5 g) followed by addition of hydrogen gas. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether = 1:1). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The product was precipitated by the addition of H2O. A filtration was performed. The filter cake was washed 3 times <n="144"/>with 300 mL of hexane. This resulted in 7.3 g (68%) of 7-amino-2H-benzo[b][l,4]oxazin-3(4H)-one as a yellow solid.
1.63 g (81%)	palladium; In methanol;	7-Amino-2H-1,4-benzoxazine-3-one (2c) A suspension of 10% palladium on carbon (0.24 g) and 2b (2.39 g, 12.3 mmol) in methanol (65 ml) was shaken under 25 lbs H2 in a Parr hydrogenation apparatus. After 3 h, the catalyst was filtered and the filtrate evaporated to afford 1.63 g (81%) of compound 2c. An analytical sample was recrystallization from MeOH/hexane. Mp 216-7 C.
	In methanol;	EXAMPLE 2 7-amino-3-oxo-3,4-dihydro-(2H)-1,4-benzoxazine Under argon, 10% palladium on carbon (350 mg, 5% w/w) was added to a suspension of 7-nitro-3-oxo-3,4-dihydro-(2H)-1,4-benzoxazine (7 g, 39.3 mmol) in 50 ml of MeOH. The reaction mixture was hydrogenated at 40 psi for 16 hours. The reaction mixture was then diluted with THF (-200 mls) and the reaction was filtered through celite. The solvent was evaporated, leaving a brown solid as the residue. Product was recrystallized from THF/Hexane (1:5). Collected 4.2 g (72%) of a tan solid: m.p. 213-215, 'H NMR (300 M Hz, DMSO) δ 4.410 (S, 2H), 4.869 (S, 2H) 6.141 (d, 1H, J=2.44) 6.176 (dd, 1H, J=2.25, 4.69), 6.563 (d, 1H, J=8.19), 9.535 (brs, 1H); 13 C NMR (300 MHz, DMSO) δ 66.9496, 102.2081, 108.1369, 116.5779; 116.8982, 144.5502, 145.4287, 164.389; Mass spectrum M+ at m/z 164
	With hydrogen;palladium 10% on activated carbon; In methanol; for 2h;	E. To a solution of 5-nitro-4H benzo[1,4]oxazin-3-one (0.314 g, 1.62 mmol) in 7 mL of MeOH was added 10% palladium on charcoal (0.172 g, 0.162 mmol). The reaction mixture was hydrogenated under balloon pressure of H2 gas for 2 hours. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to provide 7-amino-4H-benzo[1,4]oxazin-3-one as light brown solid.
13.5 g	With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20℃;	A 1000 mL round-bottom flask was purged, flushed and maintained with a hydrogen atmosphere, then was added a solution of compound 3 (R = H; 16.5 g, 85.05 mmol, 1.00 equiv) in THE (500 mL). To the mixture was added Pd/C (lOpercent, 4 g). The resulting solution was allowed to react, with stirring, overnightwhile the temperature was maintained at room temperature. The reaction progress was monitored by TLC (PE/EtOAc=1 :1). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 13.5 g (97%) of compound 4 a red solid. Compounds with R= OH and Cl were obtained by the same procedure.

References: [1]Patent: US2008/318941,2008,A1 .Location in patent: Page/Page column 30.
[2]Patent: WO2008/44022,2008,A1 .Location in patent: Page/Page column 28.
[3]Journal of Medicinal Chemistry,2005,vol. 48,p. 71 - 90.
[4]European Journal of Medicinal Chemistry,2008,vol. 43,p. 1216 - 1221.
[5]Patent: WO2009/23844,2009,A2 .Location in patent: Page/Page column 119.
[6]Patent: US2008/200471,2008,A1 .Location in patent: Page/Page column 52; 53.
[7]Patent: US2010/16297,2010,A1 .Location in patent: Page/Page column 31.
[8]Patent: WO2010/21797,2010,A1 .Location in patent: Page/Page column 83-84.
[9]Patent: US2010/29629,2010,A1 .Location in patent: Page/Page column 58.
[10]Patent: WO2010/24980,2010,A1 .Location in patent: Page/Page column 102.
[11]Patent: US2010/22581,2010,A1 .Location in patent: Page/Page column 42.
[12]Patent: WO2007/98418,2007,A1 .Location in patent: Page/Page column 142-143.
[13]Journal of Medicinal Chemistry,1989,vol. 32,p. 1627 - 1630.
[14]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1263 - 1267.
[15]Patent: US5610158,1997,A .
[16]Patent: US5091528,1992,A .
[17]European Journal of Medicinal Chemistry,2009,vol. 44,p. 3027 - 3031.
[18]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4464 - 4467.
[19]Patent: US2006/116368,2006,A1 .Location in patent: Page/Page column 67; 68.
[20]Archiv der Pharmazie,2010,vol. 343,p. 657 - 663.
[21]Patent: WO2017/70719,2017,A2 .Location in patent: Paragraph 0135; 0138.

18
[ 26215-14-5 ]
[ 496056-40-7 ]
2-[4-(4-methyl-benzyl)-piperidin-1-yl]-2-oxo-N-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-acetamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3953 - 3956.

19
[ 26215-14-5 ]
[ 1208-65-7 ]
3-(4-tert-butyl-phenyl)-N-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-acrylamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 71 - 90.

20
[ 26215-14-5 ]
[ 575474-01-0 ]

Yield	Reaction Conditions	Operation in experiment
4%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 70℃; for 3h;	To asolution of 7-amino-4H-1,4-benzoxazin-3-one (300 mg, 1.83mmol) in THF (10 mL) was added LiA1H4 (2.0 M in THF, 4.6 mL,9.15 mmol), and the mixture stirred at 70 C for 3 h. The reaction was cooled to room temperature, H20 (50 mL) added and the product extracted with EtOAc (50 mL) . The organic phase was separated, washed with brine (50 mL), dried over anhydrous Na2504, filtered and the solvent evaporated underreduced pressure. The resultant residue was purified by silica gel flash-column chromatography, with DCM/EtOAc (6:4)as the eluent, to yield the title compound as a dark oil(120 mg, 44%) : ‘H NNR (400 MHz, DMSO-d6) 6 6.30 (d, J = 8.9Hz, 1H) , 6.03-5.94 (m, 2H) , 4.07-3.98 (m, 2H) , 3.21-3.07 (m, 2H) ; UPLC-MS: tR = 1.24 mm (polar method) ; MS (ESI)m/z calcd for C8H,,N20 (M+H): 151.1, found: 151.1.

References: [1]Patent: WO2018/167695,2018,A1 .Location in patent: Page/Page column 67; 68.
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 71 - 90.

21
[ 895635-25-3 ]
[ 26215-14-5 ]
[ 895637-99-7 ]

Yield	Reaction Conditions	Operation in experiment
	hydrogenchloride; In isopropyl alcohol; at 85℃;	Example 200 2,6-Difluoro-N-[3-(3-{2-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]benzamide; A mixture of N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide (which may be prepared according to a procedure similar to Example 27, Step C) and 7-amino-2H1,4-benzoxazin-3(4H-one are heated in isopropanol with catalytic conc. HCl at approximately 85 C. to afford the product. ES-LCMS m/z 590 (M+H).

References: [1]Patent: US2008/51395,2008,A1 .Location in patent: Page/Page column 130.

22
[ 26215-14-5 ]
[ 321436-06-0 ]

Yield	Reaction Conditions	Operation in experiment
9%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; for 3h;	INTERMEDIATE 12; 7-Bromo-4H-benzori,41oxazm-3-one; Intermediate 11 (0.5 g, 3.0 mmol), copper(II) bromide (0.67 g, 3.3 mmol) and tert- butyl nitrite (0.52 mL, 4.3 mmol) were combined in acetonitrile (30 mL) and stirred for 3 h. The mixture was partitioned between EtOAc (100 mL) and water (100 mL). The organics were dried (MgSO4), filtered and concentrated in vacuo to give a crude product which was purified by prep ηPLC to yield the title compound as a beige solid (65 mg, 9%). δη (DMSO-d6) 4.60 (2H, br s), 6.83 (IH, d, J 8.3 Hz), 7.10-7.20 (2H, m), 10.83 (IH, br s).

References: [1]Patent: WO2008/44022,2008,A1 .Location in patent: Page/Page column 28.

23
[ 26215-14-5 ]
3-(4-tert-butyl-phenyl)-N-(3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-acrylamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 71 - 90.

24
[ 121-88-0 ]
[ 26215-14-5 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 71 - 90.

25
[ 26215-14-5 ]
7-(4-Oxo-2-p-tolyl-thiazolidin-3-yl)-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

26
[ 26215-14-5 ]
7-[2-(4-Chloro-phenyl)-4-oxo-thiazolidin-3-yl]-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

27
[ 26215-14-5 ]
7-[2-(4-Methoxy-phenyl)-4-oxo-thiazolidin-3-yl]-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

28
[ 26215-14-5 ]
7-[2-(3,4-Dichloro-phenyl)-4-oxo-thiazolidin-3-yl]-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

29
[ 26215-14-5 ]
7-[2-(3-Hydroxy-4-methoxy-phenyl)-4-oxo-thiazolidin-3-yl]-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

30
[ 26215-14-5 ]
7-[2-(4-Nitro-phenyl)-4-oxo-thiazolidin-3-yl]-4H-benzo[1,4]oxazin-3-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1986,vol. 63,p. 223 - 225.

31
[ 26215-14-5 ]
[ 106659-52-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1259 - 1262.

32
[ 26215-14-5 ]
[ 105808-17-1 ]

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

33
[ 26215-14-5 ]
[ 106659-48-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1259 - 1262.

34
[ 26215-14-5 ]
[ 106659-49-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1259 - 1262.

35
[ 26215-14-5 ]
[ 106684-87-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1259 - 1262.

Historical Records

Technical Information

• Acyl Group Substitution • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P222	Do not allow contact with air.
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P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
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P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 26215-14-5

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CAS No.: 26215-14-5

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[ 26215-14-5 ] Synthesis Path-Downstream 1~35

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