475216-25-2|4-Fluoro-N-methyl-3-nitrobenzamide| Ambeed

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Quality Control of [ 475216-25-2 ] Purity: 95% SDS Specification

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Product Details of [ 475216-25-2 ]

CAS No. :	475216-25-2
Formula :	C₈H₇FN₂O₃
M.W :	198.15
SMILES Code :	O=C(NC)C1=CC=C(F)C([N+]([O-])=O)=C1
MDL No. :	MFCD11855197
InChI Key :	LTGYDUQSOZFFEM-UHFFFAOYSA-N
Pubchem ID :	21884186

Safety of [ 475216-25-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H320-H335
Precautionary Statements:	P264-P270-P301+P312-P330

Computational Chemistry of [ 475216-25-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	48.22
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	74.92 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.13
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	1.04
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.51
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.	0.86
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	-0.32
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.84

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.84
Solubility	2.85 mg/ml ; 0.0144 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.	-2.2
Solubility	1.24 mg/ml ; 0.00626 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	-2.45
Solubility	0.703 mg/ml ; 0.00355 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.	-6.77 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	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)	1.75

Application In Synthesis of [ 475216-25-2 ]

* 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 [ 475216-25-2 ]

[ 475216-25-2 ] Synthesis Path-Downstream 1~35

1
[ 453-71-4 ]
[ 74-89-5 ]
[ 475216-25-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; at 20℃; for 2h;	[4-FLUORO-3-NITROBENZOIC] acid (3.00 g, 16.2 mmoles) was dissolved in dichloromethane (100 mL) and cooled in an ice bath to [0-5 C. EDC] (3.73 g, 19.5 mmoles) was added followed by dropwise addition of methylamine solution (8.1 mL, 16.2 mmoles, 2.0 M solution in THF). The mixture was allowed to slowly warm to room temperature and stirred for 2 h. The mixture was then diluted with ethyl acetate and washed successively with [1] M HC1, saturated aqueous [NAHCO3] and brine. The organic extracts were dried over [MGS04,] filtered and concentrated in vacuo to leave [4-FLUORO-3-NITRO-N-] methylbenzamide as a yellow solid (2.94 g, [91%)] which was used directly in the next step.
		PREPARATION 14-fluoro-/V-methyl-3-nitrobenzamideOxalyl chloride (7.09 mL, 81 mmol,) was dissolved in dichloromethane (DCM) (100 mL) under nitrogen and cooled in an ice/brine bath. A/JV-dimethylformamide (DMF) (0.42 mL, 5.4 mmol) was added dropwise and the mixture was stirred cooled for 10 minutes. Then 4-fluoro-3-nitrobenzoic acid (10.0 g, 54.0 mmol) was added slowly and reaction mixture was stirred cooled for 30 minutes. Methyl amine solution (135 mL, 270 mmol, 2M in THF) was added and reaction mixture was stirred at room temperature overnight. Reaction was diluted with satd. NaHC03 and more DCM, layers were separated and organics were dried over sodium sulfate. Organics were concentrated to give a solid which was triturated in diethyl ether, filtered and dried to give the title compound as a bright orange/yellow solid (9.72 g, 82%, >90% pure). 1H NMR (400 MHz, CHLOROFORM-d) delta 8.48 (dd, J = 2.27, 7.07 Hz, 1 H), 8.15 (m, 1 H), 7.41 (dd, J = 8.72, 10.23 Hz, 1 H), 6.34 (br. s., 1 H), 3.07 (d, J = 3.79 Hz, 3H); MS (m/z) 198.9 M+.

References: [1]Patent: WO2004/14905,2004,A1 .Location in patent: Page 161-162.
[2]Patent: WO2011/123609,2011,A1 .Location in patent: Page/Page column 42-43.

2
[ 475216-25-2 ]
[ 5332-73-0 ]
[ 658700-24-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	A solution of [4-FLUORO-3-NITRO-N-METHYLBENZAMIDE] (1.00 g, 5.05 mmoles) in 15 mL dichloromethane was prepared and added dropwise to a stirred solution of 3- methoxypropylamine (0.78 mL, 7.57 mmoles) and N, N-diisopropylethylamine (2.6 mL, 15.1 mmoles) in 10 mL dichloromethane. After stirring at room temperature overnight, TLC (EtOAc) revealed complete conversion to a lower Rf product. The mixture was diluted with ethyl acetate and washed successively with [1] M [HCI,] saturated aqueous [NAHCO3] and brine. The organic extracts were dried over [MGS04,] filtered and concentrated in vacuo to leave an orange solid residue. The crude product was dissolved in dichloromethane, adsorbed onto silica gel and then purified by flash column chromatography on silica gel. Elution with ethyl acetate provided pure fractions which were combined and concentrated to yield [4- (3-METHOXYPROPYLAMINO)-3-NITROPHENYL-N-] methylbenzamide as an orange solid product (1.34 g, [99%). IH] NMR [(CDC13)] was consistent with the desired product.

References: [1]Patent: WO2004/14905,2004,A1 .Location in patent: Page 162.

3
[ 475216-25-2 ]
[ 109-85-3 ]
[ 1338346-13-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-ethyl-N,N-diisopropylamine; In ethanol; at 150℃; for 0.25h;Microwave irradiation;	PREPARATION 2N-methyl-4-[2-(methyloxy)ethyl]amino}-3-nitrobenzamideThe <strong>[475216-25-2]4-fluoro-N-methyl-3-nitrobenzamide</strong> (2.63 g, 13.3 mmol) was partially dissolved in ethanol (7 ml.) in a microwave vial and /V,/V-diisopropylethylamine (DIEA) (2.3 ml_, 13.3 mmol) and [2-(methyloxy)ethyl]amine (1.16 ml_, 13.3 mmol) were added. The vial was capped and heated in the microwave at 150C for 15 minutes. Reaction was repeated two times on same scale and all crude reactions were combined. Mixture was cooled to room temperature and left to sit for 2 hours. A solid formed and it was filtered, rinsed with diethyl ether and dried to give the title compound as an orange solid (9.19 g, 86%, >95% purity). Product was taken on without further purification. 1H NMR (400 MHz, DMSO-d6) delta 8.63 (d, J = 2.27 Hz, 1 H), 8.48 (d, J = 4.55 Hz, 1 H), 8.36 - 8.44 (m, 1 H), 7.99 (dd, J = 2.02, 9.09 Hz, 1 H), 7.16 (d, J = 9.09 Hz, 1 H), 3.51 - 3.69 (m, 4H), 3.32 (s, 3H), 2.77 (d, J = 4.55 Hz, 3H); MS (m/z) 254.0 (M+H)+.

References: [1]Patent: WO2011/123609,2011,A1 .Location in patent: Page/Page column 43.

4
[ 475216-25-2 ]
2-(2',4'-dimethyl-[1,1'-biphenyl]-2-yl)-1-ethyl-N-methyl-1H-benzo[d]imidazole-5-carboxamid [ No CAS ]

References: [1]ACS Combinatorial Science,2015,vol. 17,p. 722 - 731.

5
[ 475216-25-2 ]
C₁₀H₁₅N₃O [ No CAS ]

References: [1]ACS Combinatorial Science,2015,vol. 17,p. 722 - 731.

6
[ 475216-25-2 ]
[ 75-04-7 ]
C₁₀H₁₃N₃O₃ [ No CAS ]

References: [1]ACS Combinatorial Science,2015,vol. 17,p. 722 - 731.

7
[ 453-71-4 ]
[ 593-51-1 ]
[ 475216-25-2 ]