1040681-74-0|2-Fluoro-4-(trifluoromethyl)nicotinic acid| Ambeed

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Quality Control of [ 1040681-74-0 ] Purity: 97% SDS Specification

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Product Details of [ 1040681-74-0 ]

CAS No. :	1040681-74-0
Formula :	C₇H₃F₄NO₂
M.W :	209.10
SMILES Code :	O=C(O)C1=C(F)N=CC=C1C(F)(F)F
MDL No. :	MFCD10687403
InChI Key :	ABXMDMDQUVWALB-UHFFFAOYSA-N
Pubchem ID :	28307766

Safety of [ 1040681-74-0 ]

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

Computational Chemistry of [ 1040681-74-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	7.0
Num. H-bond donors	1.0
Molar Refractivity	36.16
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	50.19 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.95
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	1.7
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.51
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.	0.41
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	2.23
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.76

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.39
Solubility	0.847 mg/ml ; 0.00405 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.	-2.37
Solubility	0.893 mg/ml ; 0.00427 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	-2.57
Solubility	0.561 mg/ml ; 0.00269 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	Yes
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.	-6.37 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	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)	1.79

Application In Synthesis of [ 1040681-74-0 ]

* 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 [ 1040681-74-0 ]

[ 1040681-74-0 ] Synthesis Path-Downstream 1~9

1
[ 1040681-74-0 ]
[ 1353678-52-0 ]

References: [1]Patent: US2011/319394,2011,A1 .

2
[ 1040681-74-0 ]
[ 1353678-53-1 ]

References: [1]Patent: US2011/319394,2011,A1 .

3
[ 1040681-74-0 ]
[ 1353678-54-2 ]

References: [1]Patent: US2011/319394,2011,A1 .

4
[ 1040681-74-0 ]
[ 1353678-55-3 ]

References: [1]Patent: US2011/319394,2011,A1 .

5
[ 1040681-74-0 ]
[ 1353678-56-4 ]

References: [1]Patent: US2011/319394,2011,A1 .

6
[ 1040681-74-0 ]
[ 1353678-57-5 ]

References: [1]Patent: US2011/319394,2011,A1 .

7
[ 1040681-74-0 ]
[ 74-88-4 ]
[ 1227516-48-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3.0h;	Example 130; 1-ethyl-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-7-(trifluoromethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 130a) methyl 2-fluoro-4-(trifluoromethyl)pyridine-3-carboxylate To a mixture of <strong>[1040681-74-0]2-fluoro-4-(trifluoromethyl)pyridine-3-carboxylic acid</strong> (1.06 g) and K2CO3 (0.701 g) in DMF (dry) (10 mL) was added MeI (0.317 mL). The mixture was stirred at room temperature for 3 h. The mixture was directly purified by column chromatography (silica gel, EtOAc/hexane) to give the title compound (1.13 g, containing EtOAc and hexane, ca. 75% purity).MS (API+): [M+H]+224.0

References: [1]Patent: US2011/319394,2011,A1 .Location in patent: Page/Page column 105.

8
[ 123652-95-9 ]
[ 1040681-74-0 ]
C₁₉H₁₈F₄N₂O₃ [ No CAS ]

References: [1]Patent: WO2014/160185,2014,A2 .

9
[ 123652-95-9 ]
[ 1040681-74-0 ]
C₁₅H₁₁F₅N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		2[00319] A solution of compound 8 (2.0 g, 9.6 mmol) in SOd2 was refluxed for 2h. Thenconcentrated and re-dissolved in dichloromethane (10 mL), which was added to another solution of the amine 2(1.2 g, 7.5 mmol) and TEA (0.96 g, 70 mmol) in dichloromethane (15 mL) at 0 C. After stirring overnight at room temperature, the reaction mixture was then poured into water and extracted with dichloromethane. The combined organic extracts were washed with brine, water and dried over Na2SO4, filtered and evaporated in vacuum. The resulting yellow solid was purified by flash colunm chromatography to provide the title compound 9 as a pale white solid(450 mg). ‘H NMR (400 MHz, CDC13): 3 8.45 (t, J = 2.8 Hz, 1H), 7.51 (d, J = 5.2 Hz, 1H), 7.10- 7.06 (m, 2H), 6.92 (dd, J1 = 11.2 Hz, J2 = 8.0 Hz, 1H), 4.58 (d, J = 5.6 Hz, 2H), 3.89 (s, 3H); mlz (ESI+) (M+H)+ = 347.05.

References: [1]Patent: WO2014/160185,2014,A2 .Location in patent: Paragraph 00319.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

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[ 1040681-74-0 ]

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CAS No.: 1040681-74-0

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