73841-32-4|3-Iodopicolinic acid| Ambeed

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Quality Control of [ 73841-32-4 ] Purity: 98% SDS Specification

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Product Details of [ 73841-32-4 ]

CAS No. :	73841-32-4
Formula :	C₆H₄INO₂
M.W :	249.01
SMILES Code :	O=C(O)C1=NC=CC=C1I
MDL No. :	MFCD01928487
InChI Key :	NBPSOUHMLHTKID-UHFFFAOYSA-N
Pubchem ID :	11253692

Safety of [ 73841-32-4 ]

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

Computational Chemistry of [ 73841-32-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	43.91
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.	0.99
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	1.36
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.38
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.	-0.18
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	1.71
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.05

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.62
Solubility	0.599 mg/ml ; 0.00241 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.	-2.02
Solubility	2.4 mg/ml ; 0.00963 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	-2.35
Solubility	1.1 mg/ml ; 0.00443 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.	-6.85 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)	1.73

Application In Synthesis of [ 73841-32-4 ]

* 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 [ 73841-32-4 ]

[ 73841-32-4 ] Synthesis Path-Downstream 1~23

1
[ 1462-86-8 ]
[ 73841-32-4 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1937,vol. <2> 148,p. 13,16.

2
[ 73841-32-4 ]
[ 74-88-4 ]
[ 73841-41-5 ]

References: [1]Synthetic Communications,1997,vol. 27,p. 1075 - 1086.

3
[ 57841-90-4 ]
[ 73841-32-4 ]

References: [1]Synthetic Communications,1997,vol. 27,p. 1075 - 1086.

4
lithium 3-iodo-pyridine-2-carboxylate [ No CAS ]
[ 73841-32-4 ]

References: [1]Tetrahedron,2002,vol. 58,p. 6723 - 6728.

5
[ 98-98-6 ]
[ 73841-32-4 ]

Yield	Reaction Conditions	Operation in experiment
66%		A solution of 2,2,6,6-tetramethylpiperidine (8.48 g, 60 mmol) in tetrahydrofuran (100 mL)Cooling to -78 deg C, N-butyllithium (2.5 mol / L, 16 mL, 40 mmol) was added dropwise, Slowly warmed to room temperature for 30 minutes. Cooling to -78 deg C, This was added dropwise to a suspension of pyridine-2-carboxylic acid (2.46 g, 20 mmol) in tetrahydrofuran, After completion of the dropwise addition, the reaction was allowed to proceed at room temperature for 30 minutes, Cooling to -30 deg C, A solution of iodine (15.23 g, 60 mmol) in tetrahydrofuran was added dropwise to the reaction flask, The mixture was stirred at room temperature for 1 hour, add water, Standing overnight Precipitation of solids, The target compound was filtered (3.3 g, yield 66percent).
41%		Description 1; 3-Iodo-2-pyridinecarboxylic acid (D1); To a stirred solution of 2,2,6,6-tetramethylpiperidine (20 ml, 0.122 mol) in dry THF (100 ml) at -78° C., under argon was added n-butyllithium (52 ml, 0.163 mol, 2.5M solution in hexanes) dropwise, followed 15 min later by a solution of 2-pyridinecarboxylic acid (5.0 g, 0.0407 mol) in dry THF (30 ml). After 10 min at -78° C., the reaction mixture was warmed to 0° C. for 30 min. and then transferred to a solution of iodine (30.9 g, 0.243 mol) in dry THF (70 ml) at 0° C., under argon. After 15 min at 0° C. the reaction mixture was warmed to 25° C. and stirred for 1 h. After this period water (80 ml) was added and the reaction mixture concentrated in vacuo. The residue was re-dissolved in water (100 ml) and washed with EtOAc (100 ml). The aqueous layer was separated, concentrated in vacuo and the resulting residue triturated with diethyl ether. The solid material was filtered and dried in vacuo before being re-dissolved in MeOH (200 ml). To this solution was added Amberlyte IR-120 ion-exchange resin (100 g) and the reaction mixture stirred at 25° C. for 2 h. After this period the resin was filtered off and the solvents concentrated in vacuo to afford the title compound (4.15 g, 41percent). deltaH (DMSO-d6, 250 MHz) 6.79 (1H, bs) 7.28 (1H, dd), 8.37 (1H, dd), 8.58 (1H, dd). MS (ES): C6H41NO2 requires 249. found (M-H+) 248.
41%		Description 1; 3-lodo-2-pyridinecarboxylic acid (D1);To a stirred solution of 2,2,6,6-tetramethylpiperidine (20ml, 0.122mol) in dry THF (100ml) at -78 °C, under argon was added /7-butyllithium (52ml, 0.163mol, 2.5M EPO <DP n="40"/>solution in hexanes) dropwise, followed 15min later by a solution of 2- pyridinecarboxylic acid (5.Og, 0.0407mol) in dry THF (30ml). After 10min at -78 0C, the reaction mixture was warmed to 00C for 30 min. and then transferred to a solution of iodine (30.9g, 0.243mol) in dry THF (70ml) at 00C, under argon. After 15min at O0C the reaction mixture was warmed to 25°C and stirred for 1h. After this period water (80ml) was added and the reaction mixture concentrated in vacuo. The residue was re-dissolved in water (100ml) and washed with EtOAc (100ml). The aqueous layer was separated, concentrated in vacuo and the resulting residue triturated with diethyl ether. The solid material was filtered and dried in vacuo before being re- dissolved in MeOH (200ml). To this solution was added Amberlyte IR-120 ion- exchange resin (100g) and the reaction mixture stirred at 25°C for 2h. After this period the resin was filtered off and the solvents concentrated in vacuo to afford the title compound (4.15g, 41percent). deltaH (DMSO-d6, 250MHz) 6.79 (1H, bs) 7.28 (1H, dd), 8.37 (1 H, dd), 8.58 (1H, dd). MS (ES): C6H4INO2 requires 249; found (M-H+) 248.

Example 503-[4-Chloro-3-[[(2-tricyclo[3.3.1.13'7]dec-l-ylethyl)amino]carbonyl]phenyl]-2-pyridinecarboxylic acidCIa) 3-Iodo-2-pyridinecarboxylic acid, methyl esterButyllithium (32 mL, 2.5 M in hexanes) was added dropwise over 10 minutes to a solutionof 2,2,6,6-tetramethylpiperidine (10.2 mL) in tetrahydrofuran (100 mL) at-7 8 °C undernitrogen. The mixture was stirred at -78 °C for 15 minutes and then picolinic acid (2.4 g)was added portionwise over 10 minutes. After a further 10 minutes at -78 °C the mixturewas allowed to warm to 0 °C and stirred under nitrogen for 30 minutes. The reactionmixture was then added dropwise over 15 minutes to a solution of iodine (15 g) intetrahydrofuran (100 mL) at 0 °C. This was then allowed to warm to room temperature andstirred for 1 hour before water (20 mL) was added. The mixture was evaporated to drynessto leave a black oil. Dichloromethane (50 mL) was added and the mixture was cooled to 0°C. A^JV-Dimethylformamide (1 drop) and oxalyl chloride (4 mL) were added. The reactionwas allowed to warm to room temperature and stirred under nitrogen for 2 hours, thenevaporated to dryness. The residue was dissolved hi dichloromethane (20 mL) and thenmethanol (20 mL) was added. The mixture was then stirred for 10 minutes before beingevaporated to afford the sub-title compound as an oil (1.0 g) which was used in the nextstep without purification.MS: APCI(+ve) 264 (M+H4").

References: [1]Patent: CN106317027,2017,A .Location in patent: Paragraph 0246; 0247; 0248.
[2]Patent: US2008/312209,2008,A1 .Location in patent: Page/Page column 13.
[3]Patent: WO2007/7018,2007,A1 .Location in patent: Page/Page column 38-39.
[4]Tetrahedron,2002,vol. 58,p. 6723 - 6728.
[5]Patent: WO2006/25783,2006,A1 .Location in patent: Page/Page column 120-121.
[6]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4236 - 4238.

6
[ 10354-53-7 ]
[ 73841-32-4 ]

References: [1]Synthetic Communications,1997,vol. 27,p. 1075 - 1086.

7
[ 67-56-1 ]
[ 73841-32-4 ]
[ 73841-41-5 ]

Yield	Reaction Conditions	Operation in experiment
70%		Description 2; Methyl 3-iodo-2-pyridinecarboxylate (D2); A mixture of D1 (3.0 g, 0.012 mol) and c.H2SO4 (2 ml) in MeOH (100 ml) was heated at 65° C. for 18 h. After this period, solvents were evaporated in vacuo and the residue basified with solid NaHCO3. The residue was then extracted with EtOAc (3.x.100 ml). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to afford the title compound (2.2 g, 70percent). deltaH(CDCl3, 250 MHz) 4.01 (3H, s), 7.13 (1H, dd), 8.29 (1H, dd), 8.64 (1H, dd). MS (ES): C7H61NO2 requires 263. found 264 (MH+)
70%		Description 2; Methyl 3-iodo-2-pyridinecarboxylate (D2); A mixture of D1 (3.Og, 0.012mol) and CH2SO4 (2ml) in MeOH (100ml) was heated at65°C for 18 h. After this period, solvents were evaporated in vacuo and the residue basified with solid NaHCO3. The residue was then extracted with EtOAc (3x100ml). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to afford the title compound (2.2g, 70percent). deltaH (CDCI3, 250MHz) 4.01 (3H, s), 7.13 (1 H, dd), 8.29 (1H, dd), 8.64 (1H, dd). MS (ES): C7H6INO2 requires 263; found 264 (MH+)
		Example 503-[4-Chloro-3-[[(2-tricyclo[3.3.1.13'7]dec-l-ylethyl)amino]carbonyl]phenyl]-2-pyridinecarboxylic acidCIa) 3-Iodo-2-pyridinecarboxylic acid, methyl esterButyllithium (32 mL, 2.5 M in hexanes) was added dropwise over 10 minutes to a solutionof 2,2,6,6-tetramethylpiperidine (10.2 mL) in tetrahydrofuran (100 mL) at-7 8 °C undernitrogen. The mixture was stirred at -78 °C for 15 minutes and then picolinic acid (2.4 g)was added portionwise over 10 minutes. After a further 10 minutes at -78 °C the mixturewas allowed to warm to 0 °C and stirred under nitrogen for 30 minutes. The reactionmixture was then added dropwise over 15 minutes to a solution of iodine (15 g) intetrahydrofuran (100 mL) at 0 °C. This was then allowed to warm to room temperature andstirred for 1 hour before water (20 mL) was added. The mixture was evaporated to drynessto leave a black oil. Dichloromethane (50 mL) was added and the mixture was cooled to 0°C. A^JV-Dimethylformamide (1 drop) and oxalyl chloride (4 mL) were added. The reactionwas allowed to warm to room temperature and stirred under nitrogen for 2 hours, thenevaporated to dryness. The residue was dissolved hi dichloromethane (20 mL) and thenmethanol (20 mL) was added. The mixture was then stirred for 10 minutes before beingevaporated to afford the sub-title compound as an oil (1.0 g) which was used in the nextstep without purification.MS: APCI(+ve) 264 (M+H4").

References: [1]Patent: US2008/312209,2008,A1 .Location in patent: Page/Page column 13.
[2]Patent: WO2007/7018,2007,A1 .Location in patent: Page/Page column 39.
[3]Patent: WO2006/25783,2006,A1 .Location in patent: Page/Page column 120-121.

8
[ 73841-32-4 ]
[ 583-78-8 ]
tetrakis(acetonitrile)copper(I) hexa-fluorophosphate [ No CAS ]
2C₁₂H₆Cl₂NO₃^(1-)*Cu⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5.6%	With caesium carbonate; In toluene; at 110℃;	<strong>[73841-32-4]3-iodopyridine-2-carboxylic acid</strong> (3 g, 12 mmol) was suspended in toluene (100 mL) Cesium carbonate (11.7 g, 36 mmol) was added, 2,5-dichlorophenol (1.96 g, 12 mmol) and tetrafluoroacetonitrile hexafluoride (447 mg, 1.2 mmol) 110 ° C overnight. Vacuum concentration, Add water (100mL), Ethyl acetate extraction (200 mL x 2), Dried over anhydrous sodium sulfate, Concentrated in vacuo to give the title compound (215mg, 5.6percent yield).

References: [1]Patent: CN106317027,2017,A .Location in patent: Paragraph 0249; 0250; 0251.

9
[ 73841-32-4 ]
3-(2,5-dichlorophenoxy)pyrazine-2-carboxylic acid [ No CAS ]

References: [1]Patent: CN106317027,2017,A .

10
[ 73841-32-4 ]
3-(2,5-dichlorophenoxy)pyrazine-2-carboxylic acid chloride [ No CAS ]

References: [1]Patent: CN106317027,2017,A .

11
[ 73841-32-4 ]
(3-(2,5-dichlorophenoxy)pyrazin-2-yl)-(4-methyl-3,4-dihydroquinoxaline-1-(2H)-yl)methanone [ No CAS ]

References: [1]Patent: CN106317027,2017,A .

12
[ 73841-32-4 ]
C₁₉H₂₁IN₂O₄ [ No CAS ]

References: [1]RSC Advances,2018,vol. 8,p. 13879 - 13890.

13
[ 73841-32-4 ]
C₁₄H₁₃IN₂O₂ [ No CAS ]

References: [1]RSC Advances,2018,vol. 8,p. 13879 - 13890.

14
[ 73841-32-4 ]
C₆H₃ClINO [ No CAS ]

References: [1]RSC Advances,2018,vol. 8,p. 13879 - 13890.

15
[ 73841-32-4 ]
(S,E)-1-tert-butyl 3-methyl 4-(3-(3-(dimethylamino)prop-1-en-1-yl)picolinoyl)piperazine-1,3-dicarboxylate [ No CAS ]