[ CAS No. 65370-42-5 ] {[proInfo.proName]}

Name: 65370-42-5|4-Chloro-2-nitropyridine|97%
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SKU: A325381
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Quality Control of [ 65370-42-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 65370-42-5 ]

SDS Specification

Alternatived Products of [ 65370-42-5 ]

Product Details of [ 65370-42-5 ]

CAS No. :	65370-42-5	MDL No. :	MFCD04114167
Formula :	C₅H₃ClN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YPKBJRKFGYVURL-UHFFFAOYSA-N
M.W :	158.54	Pubchem ID :	2762847
Synonyms :

Calculated chemistry of [ 65370-42-5 ]

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 :	58.71 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.11
Log Po/w (XLOGP3) :	1.34
Log Po/w (WLOGP) :	1.64
Log Po/w (MLOGP) :	0.68
Log Po/w (SILICOS-IT) :	-0.09
Consensus Log Po/w :	0.94

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.05
Solubility :	1.43 mg/ml ; 0.00901 mol/l
Class :	Soluble
Log S (Ali) :	-2.17
Solubility :	1.06 mg/ml ; 0.00669 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.01
Solubility :	1.55 mg/ml ; 0.00979 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.02

Safety of [ 65370-42-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

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 1~44

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]+.

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

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

Reference： [1]Patent: WO2011/17125,2011,A1

4
[ 65370-42-5 ]
C₁₁H₁₀N₄ [ No CAS ]
C₁₆H₁₂N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 120℃; for 4.0h;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(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 120℃; for 4.0h;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]+.

Reference： [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 ]

Reference： [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 ]

Reference： [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℃;	<strong>[65370-42-5]4-chloro-2-nitro-pyridine</strong> (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.

Reference： [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 ]

Reference： [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 ]

Reference： [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, <strong>[65370-42-5]2-nitro-4-chloropyridine</strong> (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%,

Reference： [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 24.0h;	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%.

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

12
[ 65370-42-5 ]
C₁₃H₁₂N₄O₄ [ No CAS ]

Reference： [1]Patent: CN109942576,2019,A

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

Reference： [1]Patent: CN109942576,2019,A

14
[ 65370-42-5 ]
C₂₁H₁₅N₇O₃ [ No CAS ]

Reference： [1]Patent: CN109942576,2019,A

15
[ 65370-42-5 ]
C₂₁H₁₇N₇O [ No CAS ]

Reference： [1]Patent: CN109942576,2019,A

16
[ 65370-42-5 ]
4-([1,2,4]triazolo[1,5-α]pyridin-7-yloxy)-3-methylaniline [ No CAS ]

Reference： [1]Patent: CN109942576,2019,A

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

Reference： [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 17.0h;	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.

Reference： [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 ]

Reference： [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(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-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

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

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