22227-59-4|2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid| Ambeed

Structure of 22227-59-4

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Quality Control of [ 22227-59-4 ] Purity: 97% SDS Specification

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Product Details of [ 22227-59-4 ]

CAS No. :	22227-59-4
Formula :	C₈H₃ClF₃NO₄
M.W :	269.56
SMILES Code :	O=C(O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1Cl
MDL No. :	MFCD11847295
InChI Key :	PSRPKTROFCUEOD-UHFFFAOYSA-N
Pubchem ID :	10084457

Safety of [ 22227-59-4 ]

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

Computational Chemistry of [ 22227-59-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	3
Num. H-bond acceptors	7.0
Num. H-bond donors	1.0
Molar Refractivity	52.24
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	83.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.06
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	2.79
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.12
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.	2.14
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	0.87
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.33
Solubility	0.125 mg/ml ; 0.000465 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.	-4.19
Solubility	0.0173 mg/ml ; 0.0000643 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-2.65
Solubility	0.597 mg/ml ; 0.00221 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.	-5.96 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.	0.56

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<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)	2.12

Application In Synthesis of [ 22227-59-4 ]

* 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 [ 22227-59-4 ]

[ 22227-59-4 ] Synthesis Path-Downstream 1~36

1
[ 657-06-7 ]
[ 22227-59-4 ]

Yield	Reaction Conditions	Operation in experiment
94.7%	With sulfuric acid; nitric acid; at 90℃; for 1.18333h;	Preparation of 2-chloro-3-nitro-5-trifluoromethylbenzoic acid [Show Image]2-Chloro-5-trifluoromethylbenzoic acid (6.5044 g, 28.965 mmol) was added to a solution of sulfuric acid (23 mL) and fuming nitric acid (3.2 mL), with an overhead stirring. The mixture was warmed to 90C over 26 min then a further 10 mL of sulfuric acid was added to the thick mixture and stirring was continued. After 45 min at 90C the mixture was cooled to ambient temperature and poured into crushed ice (150 g), rinsing forward with icy water (50 mL). The product was isolated by vacuum filtration, washed with cold water, and dried in vacuo to give 7.3752 g (94.7 %). LCMS: Rt = 5.74 min, 100 A% (at) 254 nm, [M-H]- = 268.0. Co- injection of the product and starting material revealed the compounds were baseline separated.
94.7%	With sulfuric acid; nitric acid; at 90℃; for 1.18333h;	2-Chloro-5-trifluoromethylbenzoic acid (6.5044 g, 28.965 mmol) was added to a solution of sulfuric acid (23 mL) and fuming nitric acid (3.2 mL), with an overhead stirring. The mixture was warmed to 90C over 26 min then a further 10 mL of sulfuric acid was added to the thick mixture and stirring was continued. After 45 min at 90C the mixture was cooled to ambient temperature and poured into crushed ice (150 g), rinsing forward with icy water (50 mL). The product was isolated by vacuum filtration, washed with cold water, and dried in vacuo to give 7.3752 g (94.7 %). LCMS: Rt = 5.74 min, 100 A% (at) 254 nm, [M-H]- = 268.0. Co-injection of the product and starting material revealed the compounds were baseline separated.
94.7%	With sulfuric acid; nitric acid; at 90℃; for 1.18333h;	2-Chloro-5-trifluoromethylbenzoic acid (6.5044 g, 28.965 mmol) was added to a solution of sulfuric acid (23 mL) and fuming nitric acid (3.2 mL) , with an overhead stirring. The mixture was warmed to 90 C over 26 min, then a further 10 mL of sulfuric acid was added to the thick . mixture and stirring was continued. After 45 min at 90 C the mixture was cooled to ambient temperature and poured into crushed ice (150 g) , rinsing forward with icy water (50 mL) . The product was isolated by vacuum filtration, washed with cold water, and dried in vacuo to give 7.3752 g (94.7 %) . LCMS: Rt = 5.74 min, 100 A% (at) 254 nm, [M-H] " = 268.0. Co- injection of the product and starting material revealed the compounds were baseline separated.

81.1%	With fuming sulphuric acid; sulfuric acid; nitric acid; at 0 - 60℃; for 1.5h;	2-chloro-5-trifluoromethylbenzoic acid (8.98 g, 40 mmol) was dissolved in 14.4 mL of concentrated sulfuric acid. Stir until completely dissolved,to the reaction solution, fuming sulfuric acid (50%) 9.6 mL was added. cool in ice bath to 0 C, Slowly add 7.0 mL of fuming nitric acid to the reaction system. Keeping the temperature of the reaction system below 60 C during the dropwise addition, After 30 minutes, After stirring for 1 hour, Add ice water 150mL, Precipitated in white, Filtration, washing with water and drying to give the intermediate 2-chloro-3-nitro-5-(trifluoromethyl)benzoic acid 1a. The white solid was 8.73 g, yield 81.1%.
	With sulfuric acid; sulfur trioxide; nitric acid; at 20 - 60℃; for 0.5h;	Example 1: N-(3,4-Dichlorophenyl)-3-nitro-2-piperid-1-yl-5- triflupsilonoromethylbenzamide.Step a): 2-Chloro-3-nitro-5-trifluoromethylbenzoic acid.After dissolving at room temperature 2-chloro-5-trifluoromethylbenzoic acid (2.25 g; 10 mmol) in fuming sulfuric acid comprising 20% oleum (6 ml), fuming nitric acid (1.7 ml) is added dropwise over 30 minutes, so as to maintain the temperature of the reaction medium below 600C. After cooling, ice is added and the precipitate is separated out, washed with water and dried. After recrystallisation from water, 2.15 g of solid corresponding to 2-chloro-3-nitro-5-trifluoromethylbenzoic acid are obtained (m.p. = 173C).1H NMR (300 MHz, CDCI3) delta ppm: 8.41 (d, 1H), 8.71 (d, 1 H), 14.30 (s, 1H)

References: [1]Patent: EP2468746,2012,A1 .Location in patent: Page/Page column 6-7.
[2]Patent: WO2012/85654,2012,A1 .Location in patent: Page/Page column 7.
[3]Patent: WO2013/38259,2013,A1 .Location in patent: Page/Page column 12.
[4]Patent: CN104211708,2018,B .Location in patent: Paragraph 0113-0116.
[5]Patent: WO2006/97169,2006,A1 .Location in patent: Page/Page column 19.

2
[ 22227-59-4 ]
[ 87033-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In toluene; for 2h;Heating / reflux;	Step b): 2-Chloro-3-nitro-5-trifluoromethylbenzoyl chloride.To a solution of <strong>[22227-59-4]2-chloro-3-nitro-5-trifluoromethylbenzoic acid</strong> (1.35 g) in toluene (15 ml) are added 1.2 ml of SOCI2. After refluxing for 2 hours, the end of the reaction is confirmed by monitoring by infrared (new band at 1788 cm"1). The reaction medium is evaporated to dryness and the resulting yellow oil, 2-chloro-3-nitro-5- trifluoromethylbenzoyl chloride, is used without further purification in the following step.
	With thionyl chloride;N,N-dimethyl-formamide; In chloroform; for 3h;Inert atmosphere; Reflux;	Preparation of 2-chloro-3-nitro-5-(trifluoromethyl)benzaroide [Show Image] A mixture of <strong>[22227-59-4]2-chloro-3-nitro-5-trifluoromethylbenzoic acid</strong> (1.0015g, 3.7 mmol), chloroform (5 mL), DMF (375 muL) and thionyl chloride (630 muL, 8.6 mmol) was refluxed under N2 for 3 hr. The mixture was cooled to ambient temperature and evaporated to dryness (<30C) . The residue was slurried in acetonitrile (2 mL) and ice cold ammonium hydroxide solution (12 mL) was added (vigorous reaction.). The mixture was stirred for 30 min at 0C then the precipitate was isolated by vacuum filtration, and washed with cold water. The product was dried overnight in vacuo to give the desired product as a white solid 0.8206 g (82.1 %). LCMS: Rt = 5.60 min, 100 A% (at) 254 nm, [M+H]+ = 269.0, [M+H]+ = 269.0. 1H NMR (400 MHz, CDCl3) delta: 8.03 (dq, 1H, J = 0.6, 2.2), 7.88 (dq, 1H, J = 0.7, 2.2), 7.84 (br s, 1H) , 7.29 (br s, 1H).
	With thionyl chloride;N,N-dimethyl-formamide; In chloroform; for 3h;Reflux; Inert atmosphere;	A mixture of <strong>[22227-59-4]2-chloro-3-nitro-5-trifluoromethylbenzoic acid</strong> (1.0015g, 3.7 mmol), chloroform (5 mL), DMF (375 mu) and thionyl chloride (630 mu, 8.6 mmol) was refluxed under isb for 3 hr. The mixture was cooled to ambient temperature and evaporated to dryness (<30C). The residue was slurried in acetonitrile (2 mL) and ice cold ammonium hydroxide solution (12 mL) was added (vigorous reaction.). The mixture was stirred for 30 min at 0C then the precipitate was isolated by vacuum filtration, and washed with cold water. The product was dried overnight in vacuo to give the desired product as a white solid 0.8206 g (82.1 %). LCMS: Rt = 5.60 min, 100 A% (at) 254 nm, [M+H]+ = 269.0, [M+H]+ = 269.0. 1H NMR (400 MHz, CDCI3) delta: 8.03 (dq, 1 H, J= 0.6, 2.2), 7.88 (dq, 1 H, J= 0.7, 2.2), 7.84 (br s, 1 H), 7.29 (br s. 1 H).

	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 2h;	General procedure: Oxalyl Chloride (12.5 mmol) and catalytic amount of N,N-Dimethylformamide (DMF) were added successively to the suspension of 2a-b (5 mmol) in dichloromethane (15 mL). The reaction was stirred at room temperature for 2 h and evaporated in vacuo. The residue was dissolved in dichloromethane (20 mL) and added to ammonium thiocyanate (10 mmol) dropwise under stirring. A catalytic amount of PEG-400 was added to the suspension, it was then stirred at room temperature for 1.5 h. After consumption of the starting material, the appropriate amines 6a-i (5 mmol) were added. It was then stirred for another 1~2 hours at room temperature. The reaction mixture was then diluted with water (30 mL) and extracted with dichloromethane. The organic extracts were dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography to afford the title compounds 1 and 7a-8o.
	With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 2h;	To <strong>[22227-59-4]2-chloro-3-nitro-5-trifluoromethylbenzoic acid</strong> (12 mmol) was added 20 mL of dichloromethane.Oxalyl chloride (30.5 mmol) and 0.05 mL of DMF were slowly added dropwise under stirring at room temperature for two hours.After the reaction was completed, the reaction solution was spoked, dissolved in 15 mL of dichloromethane, and slowly added dropwise with ammonium thiocyanate (36 mmol).Further, PEG-400 (0.2 g) was added, and the mixture was stirred at room temperature for 1.5 hours. After filtration, the filtrate was added dropwise to a solution of 4-(2-fluorophenoxy)piperidine in dichloromethane, and stirred at room temperature for 40 minutes.After the reaction is completed, the reaction solution is spun dry.Column chromatography gave a yellow solid 1a, yield 52%.

References: [1]Patent: WO2006/97169,2006,A1 .Location in patent: Page/Page column 19.
[2]Patent: EP2468746,2012,A1 .Location in patent: Page/Page column 7.
[3]Patent: WO2012/85654,2012,A1 .Location in patent: Page/Page column 8.
[4]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4919 - 4922.
[5]RSC Advances,2018,vol. 8,p. 11163 - 11176.
[6]Patent: CN108456204,2018,A .Location in patent: Paragraph 0097; 0100.

Yield	Reaction Conditions	Operation in experiment
		(a) Preparation of 3-carboxy-4-chloro-5-nitrobenzotrifluoride. Concentrated nitric acid (15.5 ml) was added cautiously in portions to 4-chloro-3-cyanobenzotrifluoride (50 g) in concentrated sulphuric acid (150 ml). The solution was warmed to 75 C. when the reaction became exothermic; the solution was then heated to 95 for 1.5 hours, cooled, and poured into ice. The solid was collected, dried and recrystallized from chloroform to give the carboxylic acid with a melting point of 175-178.

4
[ 22227-59-4 ]
6-trifluoromethyl-1H-benzoimidazole-4-carboxylic acid [3-(1H-tetrazol-5-yl)phenyl]amide trifluoroacetate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2163 - 2172.

5
[ 22227-59-4 ]
6-trifluoromethyl-benzimidazole-4-carboxylic acid hydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2163 - 2172.

6
[ 22227-59-4 ]
[ 22227-60-7 ]

Yield	Reaction Conditions	Operation in experiment
80 mg	With ammonium hydroxide; at 120℃; for 1h;Sealed tube; Microwave irradiation;	Commercially available 2- chloro-3-nitro-5-trifluoromethylbenzoic acid (0.10 g, 0.37 mmol) and aqueous ammonium hydroxide (2 mL) were heated in a sealed tube in a CEM microwave at 120 C for an hour. After cooling, the pH was adjusted to 2 with IN HCI. The precipitate was filtered and dried to obtain 2-amino 3-nitro-5-trifluoromethylbenzoic acid as a yellow solid (80 mg). This material was used in the next step without further purification. NMR (DMSO-dis) delta 8.49 (s, 1 H), 8.32 (s, 1 H).
80 mg	With ammonium hydroxide; In water; at 120℃; for 1h;Sealed tube; Microwave irradiation;	2-amino 3-nitro-5-trifluoromethylbenzoic acid (25) Commercially available <strong>[22227-59-4]2-chloro-3-nitro-5-trifluoromethylbenzoic acid</strong> (0.10 g, 0.37 mmol) and aqueous ammonium hydroxide (2 mL) were heated in a sealed tube in a CEM microwave at 120 C. for an hour. After cooling, the pH was adjusted to 2 with 1N HCl. The precipitate was filtered and dried to obtain 2-amino 3-nitro-5-trifluoromethylbenzoic acid as a yellow solid (80 mg). This material was used in the next step without further purification. 1H NMR (DMSO-d6) delta 8.49 (s, 1H), 8.32 (s, 1H).

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2163 - 2172.
[2]Patent: WO2013/103760,2013,A1 .Location in patent: Page/Page column 39.
[3]Patent: US9556131,2017,B2 .Location in patent: Page/Page column 30.

7
[ 98-56-6 ]
[ 22227-59-4 ]

References: [1]Patent: EP2468746,2012,A1 .
[2]Patent: WO2012/85654,2012,A1 .
[3]Patent: WO2013/38259,2013,A1 .

8
[ 22227-59-4 ]
[ 22227-47-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With di-tert-butyl dicarbonate; ammonium bicarbonate; In 1,4-dioxane; pyridine; at 20℃;	To a strirred solution of 2chloro3nitro5(trifluoromethyl)benzoic acid (2.7 g, 10 mmol, 1.0 equiv.), pyridine (0.50 ml,6.2 mmol, 0.62 equiv.), and Boc2O(2.8 g, 13.0 mmol, 1.3 equiv.)in 1,4-dioxane (10 ml) at room temperature was added ammonium bicarbonate (1.00 g, 12.6 mmol, 1.26 equiv.). The reaction was stirred overnight at room temperature and then partitioned between EtOAc (50 ml) and H2O (50 ml). The organic layer was separated, washed consecutively with water 50 ml) and 0.6 N aqueous HCl (50 ml), dried (Mg2SO4), and filtered. The filtrate was concentrated under reduced pressureto provide 2 as a white solid [yield 2.42 g, 90%; m.p. 190-193 C; literature (Welch et al., 1969) 195-197 C]. 1H NMR and MS data are consistent with previously reported spectra(Cooper et al., 2013).
82.1%		A mixture of <strong>[22227-59-4]2-chloro-3-nitro-5-trifluoromethylbenzoic acid</strong>(1.0015g, 3.7 mmol), chloroform (5 mL) , DMF (375 iL) and thionyl chloride (630 i , 8.6 mmol) was refluxed under N2 for 3 hr . The mixture was cooled to ambient temperature and evaporated to dryness ({vigorous reaction. ) . The mixture was stirred for 30 min at 0C then the precipitate was isolated by vacuum filtration, and washed with cold water. The product was dried overnight in vacuo to give the desired product as a white solid 0.8206"g (82.1 %) . LCMS: Rt = 5.60 min, 100 A% (at) 254 nm, [M+H] + = 269.0. XH NMR (400 MHz, CDC13) ?: 8.03 (dq, 1H, J" = 0.6, 2.2), 7.88 (dq, 1H, J" = 0.7, 2.2), 7.84 (br s, lH) , 7.29 (br s, 1H) .

References: [1]Acta Crystallographica Section C: Structural Chemistry,2019,vol. 75,p. 1031 - 1035.
[2]Patent: WO2013/38259,2013,A1 .Location in patent: Page/Page column 12-13.
[3]RSC Advances,2017,vol. 7,p. 1480 - 1483.
[4]Patent: EP2468746,2012,A1 .
[5]Patent: WO2012/85654,2012,A1 .

9
[ 22227-59-4 ]
[ 1344087-73-5 ]

References: [1]Patent: EP2468746,2012,A1 .
[2]Patent: WO2012/85654,2012,A1 .
[3]Patent: WO2013/38259,2013,A1 .
[4]RSC Advances,2017,vol. 7,p. 1480 - 1483.

10
[ 22227-59-4 ]
[ 1383531-32-5 ]

References: [1]Patent: EP2468746,2012,A1 .
[2]Patent: WO2012/85654,2012,A1 .

11
[ 22227-59-4 ]
[ 1396842-98-0 ]

References: [1]Patent: WO2013/38259,2013,A1 .

12
[ 22227-59-4 ]
[ 1427469-45-1 ]

References: [1]Patent: WO2013/38259,2013,A1 .

13
[ 22227-59-4 ]
[ 1427469-48-4 ]

References: [1]Patent: WO2013/38259,2013,A1 .

14
[ 22227-59-4 ]
2-(2-methyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-8-nitro-6-(trifluoromethyl)-4H-benzo[e][1,3]thiazin-4-one [ No CAS ]