4467-07-6|3-(Pyridin-2-yl)benzoic acid| Ambeed

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Quality Control of [ 4467-07-6 ] Purity: 98% SDS Specification

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Product Details of [ 4467-07-6 ]

CAS No. :	4467-07-6
Formula :	C₁₂H₉NO₂
M.W :	199.21
SMILES Code :	O=C(O)C1=CC=CC(C2=NC=CC=C2)=C1
MDL No. :	MFCD05864807
InChI Key :	IRXFQXMHMRTLIR-UHFFFAOYSA-N
Pubchem ID :	5152592

Safety of [ 4467-07-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 4467-07-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	56.63
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.	1.57
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	2.16
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.45
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.	1.61
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	2.37
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.03

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.9
Solubility	0.253 mg/ml ; 0.00127 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.	-2.85
Solubility	0.284 mg/ml ; 0.00142 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	-3.92
Solubility	0.0239 mg/ml ; 0.00012 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	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.	-5.98 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.	0.56

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	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)	1.95

Application In Synthesis of [ 4467-07-6 ]

* 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 [ 4467-07-6 ]

[ 4467-07-6 ] Synthesis Path-Downstream 1~31

2
[ 109-04-6 ]
[ 25487-66-5 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; at 100℃; for 24.0h;Inert atmosphere;	Example 161 A3-(pyridin-2-yl)benzoic acid; To a solution of 3-boronobenzoic acid (1.66 g, 10 mmol) and 2-bromopyridine (1.72 g, 11 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II)chloride (400 mg, 0.37 mmol) was added. The mixture was degassed and purged withed nitrogen. The mixture was stirred at 100 C. for 24 h. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.69 g of white solid of 3-(pyridin-2-yl)benzoic acid. Yield: 85%. LC-MS (ESI) m/z: 200 (M+1)+.

References: [1]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 75.

3
[ 4467-07-6 ]
3-(pyridin-2-yl)benzoyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;Reflux;	Example 161 Bmethyl 2-hydroxy-3-(3-(pyridin-2-yl)benzamido)benzoate; Thionyl chloride (10 mL) was added to <strong>[4467-07-6]3-(pyridin-2-yl)benzoic acid</strong> (1.69 g, 8.5 mmol) and the mixture was stirred under reflux overnight. The solvent was evaporated under reduced pressure and the residue was dried in vacuum to give 3-(pyridin-2-yl)benzoyl chloride. 1.66 g of crude product was obtained. To a solution of methyl 3-amino-2-hydroxybenzoate (0.84 g, 5 mmol) and pyridine (790 mg, 10 mmol) in toluene (50 mL) were added crude 3-(pyridin-2-yl)benzoyl chloride (1.6 g, 7.37 mmol) portion-wise at 0 C. and then stirred at 70 C. for 4 h. The resulting mixture was extracted with ethyl acetate (100 mL×4), the organic phase was washed with water and saturated sodium bicarbonate, dried with anhydrous sodium sulfate and evaporated under reduced pressure to obtain yellow solid of methyl 2-hydroxy-3-(3-(pyridin-2-yl)benzamido)benzoate (1.48 g, yield 85%). LC-MS (ESI) m/z: 349 (M+1)+.

References: [1]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 75.

4
ammonium hexafluorophosphate [ No CAS ]
[ 345911-20-8 ]
[ 7732-18-5 ]
[ 4467-07-6 ]
[Ru(2,2'-bipyridine)2(3-(2-pyridinyl)benzoic acid(-H))]PF₆*0.5water [ No CAS ]

References: [1]Inorganic Chemistry,2009,vol. 48,p. 9631 - 9643.

5
ammonium hexafluorophosphate [ No CAS ]
[ 15746-57-3 ]
[ 4467-07-6 ]
[Ru(bpy)2(ppy)]PF₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%		To a flask containing 95 mg (0.48 mmol) of <strong>[4467-07-6]3-(pyridin-2-yl)benzoic acid</strong> and 20 mg (0.50 mmol) of NaOH was added 30 mL of degassed aqueous methanol solution (Fi20:MeOH 1 :5 v/v). The reagents were stirred until all components were dissolved and then transferred to a flask containing 188 mg (0.362 mmol) of Ru(bpy)2Cl2 and 180 mg (0.93 mmol) AgBF4. The reaction mixture was heated at reflux for 18 hrs, cooled, and then filtered through celite to afford a dark red/purple filtrate. The solvent was removed in vacuo and then passed through a silica column (MeCN:KN03(aq) 7: 1 v/v), followed by anion exchange with a saturated aqueous NH4PF methanolic solution to produce 52 mg of a red precipitate (yield = 19%). NMR (CD3CN): 6.61 (d, 1H, J = 8 Hz), 6.98 (dt, 1H, J = 7 Hz, 6 Hz, l = 1 Hz), 7.17-7.25 (m, 3H), 7.39, (dd, 1H, J = 8 Hz, l = 2 Hz), 7.42 (dt, 1H, J = 8 Hz, l = 1 Hz), 7.60 (d, 1H, J = 5 Hz), 7.69-7.75 (m, 3H), 7.78-7.87 (m, 4H), 7.95 (d, 1H, 3 J = 6 Hz), 7.99 (dt, 1H, J = 8 Hz, J = 2 Hz), 8.14 (d, 1H, J = 8 Hz), 8.31 (d, 1H, J = 7 Hz), 8.33 (d, 1H, J = 7 Hz), 8.38 (d, 1H, J = 8 Hz), 8.41 (d, 1H, l = 2 Hz), 8.46 (d, 1H, J = 8 Hz), 9.08 (vbr, 1H). ESI-MS: m/z, 612.1 (calcd for {M+} 612.1) Anal. Calcd. for C32H24F6N5O2PRU + 0.5 H20: C, 50.20; H, 3.29; N, 9.15. Found: C, 50.29; H, 3.49; N, 9.07.

References: [1]Patent: WO2011/32269,2011,A1 .Location in patent: Page/Page column 36.

6
[ 4467-07-6 ]
[ 141-43-5 ]
[ 1440513-09-6 ]

References: [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81.

7
[ 591-17-3 ]
[ 4467-07-6 ]

References: [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81.

8
[ 109-04-6 ]
[ 4467-07-6 ]

References: [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81.
[2]Patent: WO2014/100734,2014,A1 .
[3]Organic Letters,2015,vol. 17,p. 1513 - 1516.
[4]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166.

9
[ 4373-61-9 ]
[ 4467-07-6 ]

References: [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81.
[2]Organic Letters,2015,vol. 17,p. 1513 - 1516.

10
[ 4467-07-6 ]
[ 1440513-10-9 ]

References: [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81.

11
[ 4467-07-6 ]
[ 1440513-11-0 ]

References: [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81.

12
[ 4467-07-6 ]
[ 1440513-12-1 ]

References: [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81.

13
[ 98061-20-2 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With water; sodium hydroxide; In methanol; at 20℃; for 3.0h;	[00336] To a solution of methyl 3-(pyridin-2-yl)benzoate (400 mg, 1.88 mmol) in MeOH (3 mL) was added aqueous of NaOH (1 mL, 40 mol%). The reaction mixture was stirred at room temperature for 3 h and concentrated. The crude residue was dissolved in water and the pH was adjusted to 5-6 with 2N of HCl. The solution was extracted with ethyl acetate, brine, dried over sodium sulfate, filtered and concentrated. (350 mg, yield 93%) MS (ESI+) e/z: 200.1 [M+l]+.

References: [1]Patent: WO2014/100734,2014,A1 .Location in patent: Paragraph 00336.
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166.

14
[ 99769-19-4 ]
[ 4467-07-6 ]

References: [1]Patent: WO2014/100734,2014,A1 .
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166.

15
[ 933713-75-8 ]
[ 4467-07-6 ]
[ 1616059-37-0 ]

Yield	Reaction Conditions	Operation in experiment
27%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 25℃; for 16.0h;	[00337] To a solution of <strong>[4467-07-6]3-(pyridin-2-yl)benzoic acid</strong> (60 mg, 0.30 mmol) in DCM (8 mL) was added EDCI (86 mg, 0.45 mmol), HOBt (61 mg, 0.45 mmol), Et3N (61 mg, 0.6 mmol) and l-amino-3-(isoindolin-2-yl)propan-2-ol (86 mg, 0.45 mmol). The mixture was stirred at 25 C for 16 h, washed with water and extracted with DCM. The combined organic extracts were concentrated, and the residue was purified by preparative HPLC purification. (30 mg, 27%) MS (ESI+) e/z: 374.2 [M+l]+ 1H NMR (MeOD, 400 MHz), delta ppm: 8.65 (d, J=4.8 Hz, 1H), 8.15 (d, J=8.0 Hz, 1H), .96-1.92 (m, 3H), 7.62 (dd, J=7.2 Hz, 1H), 7.40-7.35 (m, 6H), 4.70 (s, 4H), 4.29 (br.s, 1H), 3.63-3.30 (m, 4H).

References: [1]Patent: WO2014/100734,2014,A1 .Location in patent: Paragraph 00337.

16
[ 17933-03-8 ]
[ 4467-07-6 ]