65370-42-5|4-Chloro-2-nitropyridine| Ambeed

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Quality Control of [ 65370-42-5 ] Purity: 97% SDS Specification

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Product Details of [ 65370-42-5 ]

CAS No. :	65370-42-5
Formula :	C₅H₃ClN₂O₂
M.W :	158.54
SMILES Code :	ClC1=CC(=NC=C1)[N+](=O)[O-]
MDL No. :	MFCD04114167
InChI Key :	YPKBJRKFGYVURL-UHFFFAOYSA-N
Pubchem ID :	2762847

Safety of [ 65370-42-5 ]

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

Computational Chemistry of [ 65370-42-5 ] 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	0.0
Molar Refractivity	38.07
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	58.71 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.11
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	1.34
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.64
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.	0.68
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	-0.09
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.94

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.05
Solubility	1.43 mg/ml ; 0.00901 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.	-2.17
Solubility	1.06 mg/ml ; 0.00669 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	-2.01
Solubility	1.55 mg/ml ; 0.00979 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.	-6.32 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)	2.02

Application In Synthesis of [ 65370-42-5 ]

* 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 [ 65370-42-5 ]

[ 65370-42-5 ] Synthesis Path-Downstream 1~35

2
[ 65370-42-5 ]
[ 1265355-07-4 ]
[ 1265361-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Step 1: Ethyl 2-(6-(4-chloropyridin-2-yloxy)- 1 -hydroxy-4-methyl- 1 ,3- dihydrobenzo[c] [1,2] oxaborol-3-yl) acetate[0523] To a mixture of ethyl 2-(l ,6-dihydroxy-4-methyl-l ,3- dihydrobenzo[c][l,2]oxaborol-3-yl)acetate (2 g, 8 mmol, 1 eq.) and 4-chloro-2- nitropyridine (2.53 g, 16 mmol, 2 eq.) in 50 ml DMF was added cesium carbonate (7.8 g, 24 mmol, 3 eq.). The reaction was stirred at room temperature overnight. It was then quenched by water, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude was purified by column chromatography on silica gel (DCM/methanol = 19:1 to 4:1) to give desired product as light yellow oil. MS (ESI) m/z = 721 [2M-H]+.

References: [1]Patent: WO2011/17125,2011,A1 .Location in patent: Page/Page column 189.

3
[ 65370-42-5 ]
[ 1265355-07-4 ]
[ 1265356-77-1 ]

References: [1]Patent: WO2011/17125,2011,A1 .

4
[ 65370-42-5 ]
9-methyl-9H-pyrrolo[2,3-b:4,5-c’]dipyridin-2-amine [ No CAS ]
C₁₆H₁₂N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 120℃; for 4h;Inert atmosphere;	1 ,4-Dioxane (20 mL) was degassed for 10 minutes with argon. Then palladium(ll)-acetate (0.017 g, 0.076 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.131 g, 0.227 mmol) were added. The suspension was then heated at 110C for 2 minutes. Then the title compound from Preparative Example 21 (0.150 g, 0.757 mmol), <strong>[65370-42-5]4-chloro-2-nitropyridine</strong> (0.168 g, 1.059 mmol) and cesium carbonate (0.740 g, 2.270 mmol) were added and the stirring was continued at 120C for 4 hours. Water was added and the solid was filtered. The solid was washed with water and dried to afford the title compound (0.246 g, quant.).MS (ESI); m/z = 320.81 [M+H]+
100%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 120℃; for 4h;Inert atmosphere;	(1027) Step A (1028) 1,4-Dioxane (20 mL) was degassed for 10 minutes with argon. Then palladium(II)-acetate (0.017 g, 0.076 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.131 g, 0.227 mmol) were added. The suspension was then heated at 110 C. for 2 minutes. Then the title compound from Preparative Example 21 (0.150 g, 0.757 mmol), <strong>[65370-42-5]4-chloro-2-nitropyridine</strong> (0.168 g, 1.059 mmol) and cesium carbonate (0.740 g, 2.270 mmol) were added and the stirring was continued at 120 C. for 4 hours. Water was added and the solid was filtered. The solid was washed with water and dried to afford the title compound (0.246 g, quant.). (1029) MS (ESI); m/z=320.81 [M+H]+.

References: [1]Patent: WO2015/110263,2015,A1 .Location in patent: Page/Page column 235.
[2]Patent: US2017/2005,2017,A1 .Location in patent: Paragraph 1026; 1027; 1028; 1029.

5
[ 65370-42-5 ]
2-aminopyridin-4-yl 3-deoxy-3-[4-(3,4,5-trifluorophenyl)-1H-1,2,3-triazol-1-yl]-1-thio-α-D-galactopyranoside [ No CAS ]

References: [1]Patent: WO2016/120403,2016,A1 .

6
[ 65370-42-5 ]
2-aminopyridin-4-yl 2,4,6-tri-O-acetyl-3-deoxy-3-[4-(3,4,5-trifluorophenyl)-1H-1,2,3-triazol-1-yl]-1-thio-α-D-galactopyranoside [ No CAS ]

References: [1]Patent: WO2016/120403,2016,A1 .

7
[ 65370-42-5 ]
4-thio-2-nitro-pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With sodium hydrogen sulfide; In N,N-dimethyl-formamide; at 50℃;	4-chloro-2-nitro-pyridine (5000 mg, 31.54 mmol) and NaHS (2122 mg, 37.84 mmol) were dissolvent in DMF (50 mL). Then it was stirred at 50C overnight. Aq NaOH (50 mL) was added to the mixture. The mixture was extracted with EtOAc (10 mL X 3). The aqueous was acidified with aq NaHS04 to PH ~ 4. Then it was extracted with EtOAc (15 mL X 3). The combined organic layers were washed with brine, dried over Na2S04 and concentrated in vacuo to afford crude product, which was purified by washed with EtOAc (10 mL) to afford 2-nitropyridine-4-thio 1(1700 mg, 35% yield). ESI-MS m/z calcd for [C5H4N202S]" [M-H]~: 156.0; found: 155.0.

References: [1]Patent: WO2016/120403,2016,A1 .Location in patent: Page/Page column 237; 238.

8
[ 65370-42-5 ]
2-nitropyridin-4-yl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-α-D-galactopyranoside [ No CAS ]

References: [1]Patent: WO2016/120403,2016,A1 .

9
[ 65370-42-5 ]
2-nitropyridin-4-yl 2,4,6-tri-O-acetyl-3-deoxy-3-[4-(3,4,5-trifluorophenyl)-1H-1,2,3-triazol-1-yl]-1-thio-α-D-galactopyranoside [ No CAS ]

References: [1]Patent: WO2016/120403,2016,A1 .

10
[ 65370-42-5 ]
[ 73183-34-3 ]
4-(4,4,5 ,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		Under nitrogen protection, 550 mL of dioxane, 2-nitro-4-chloropyridine (15.8 g, 0.10 mol) and pinacol borate (25.4 g, 0.10 mol) were sequentially added to the reaction flask. After stirring potassium acetate (14.7 g, 0.15 mol), Finally, the catalyst PdCl2dppf (0.74 g, 0.001 mol) was added, and the temperature was slowly raised to 80-90 C, and the reaction was stirred for 2-3 h. After the completion of the GC reaction, the reaction was stopped by cooling, and the reaction solution was filtered through celite to obtain a dark-black reaction solution. After charging at 1 atm of hydrogen, the mixture was reacted at room temperature overnight. After the reaction was completed, the activated carbon was decolorized, and the filtrate was distilled under reduced pressure until no liquid was poured. /Heptane mixed solvent is cooled and beaten for half an hour, filtered to obtain a light gray crude product, heated again with ethanol, and then cooled down, and the filter cake is rinsed with -20 C anhydrous ethanol, and dried to obtain 16.5 g of an off-white solid. 75%, HPLC purity 99.1%,

References: [1]Patent: CN108047258,2018,A .Location in patent: Paragraph 0005; 0020; 0021.

11
[ 99-53-6 ]
[ 65370-42-5 ]
[ 864244-98-4 ]

Yield	Reaction Conditions	Operation in experiment
50%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 150℃; for 24h;	Compound 8 (4g, 0.03mol) was added to a 100mL eggplant-shaped bottle, NMP 30mL was added, stirred, and added sequentially Diisopropylethylamine (10 g, 0.08 mol), compound 9 (4.8 g, 0.03 mol), then reacted at 150 C for 24 h, using thin layer chromatography(TLC) followed the reaction. After 24 h, TLC showed the end of the reaction. Part of the solvent was evaporated under reduced pressure. After suction filtration, drying and recrystallization, 3.20 g of a gray solid compound 10 was obtained in a yield of 50%.

References: [1]Patent: CN109942576,2019,A .Location in patent: Paragraph 0060; 0061; 00620086; 0087; 0088.

12
[ 65370-42-5 ]
N-hydroxy-N'-(4-(2-methyl-4-nitrophenoxy)pyridin-2-yl)formimidamide [ No CAS ]

References: [1]Patent: CN109942576,2019,A .

13
[ 65370-42-5 ]
[ 937263-44-0 ]

References: [1]Patent: CN109942576,2019,A .

14
[ 65370-42-5 ]
N-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-6-nitroquinazolin-4-amine [ No CAS ]

References: [1]Patent: CN109942576,2019,A .

15
[ 65370-42-5 ]
N⁴-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)quinazoline-4,6-diamine [ No CAS ]

References: [1]Patent: CN109942576,2019,A .

16
[ 65370-42-5 ]
[ 937263-71-3 ]

References: [1]Patent: CN109942576,2019,A .

17
[ 65370-42-5 ]
[ 937263-43-9 ]

References: [1]Patent: CN109942576,2019,A .

18
[ 65370-42-5 ]
[ 873-62-1 ]
C₁₂H₇N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1 g	With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 17h;	To a suspension of compound B5 (4.00 g, 25.2 mmol) and Cs2C03 (16.4 g, 50.5 mmol) in DMF (50 mL) was added 3-cyanophenol (3.16 g, 26.5 mmol), the mixture was stirred at 60C for 17 hours to give a brown suspension. Crude LCMS (RT: 1.384 min) showed the reaction was completed. The mixture was poured into water (400 mL), a lot of white solid appeared, filtered, the filter cake was washed with water (30 mL x 3) to give the crude product. The crude product was purified by Combi flash to give 1.00 g of compound B6 as a yellow powder.

References: [1]Patent: WO2019/197546,2019,A1 .Location in patent: Page/Page column 33; 40; 41.

19
[ 65370-42-5 ]
[ 873-62-1 ]
C₁₂H₁₃N₃O [ No CAS ]

References: [1]Patent: WO2019/197546,2019,A1 .

20
[ 65370-42-5 ]
5-amino-3-(5-chloro-2-fluorophenyl)-6-isopropylpyridin-2(1H)-one [ No CAS ]
3-(5-chloro-2-fluorophenyl)-6-isopropyl-5-((2-nitropyridin-4-yl)amino)pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.07%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 20 - 120℃;Inert atmosphere;	To a stirred solution of 5-amino-3-(5-chloro-2-fluorophenyl)-6- isopropylpyridin-2(lH)-one (0.580 g, 2.06 mmol, 1.0 eq) and <strong>[65370-42-5]4-chloro-2-nitropyridine</strong> (0.394 g, 2.479 mmol, 1.2 eq) in dioxane (20.0 mL) was added CS2CO3 (2.02 g, 6.198 mmol, 3.0 eq) at rt. The resulting mixture was purged with nitrogen for 10 min followed by addition of Pd2(dba)3 (0.227 g, 0.247 mmol, 0.12 eq) and xatphos (0.180 g, 0.309 mmol, 0.15 eq), again purged with nitrogen for 10 min. The reaction mixture was heated at l20C for overnight. The progress of reaction was monitored by LCMS. The reaction mixture was diluted with water (50 mL), extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with water (50 mL), with brine (50 mL), dried over Na2S04, concentrated and purified by combi flash chromatography [silica gel 100-200 mesh: elution 0-50 % EtOAc in Hexane] to afford the desired compound (400 mg, 48.07%) as brown solid. LCMS: (M+l)+ 403.1

References: [1]Patent: WO2020/12357,2020,A1 .Location in patent: Paragraph 000286; 000287.

21
[ 65370-42-5 ]
C₃₀H₃₅N₉O₄ [ No CAS ]