[ CAS No. 58483-95-7 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 58483-95-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 58483-95-7 ]

SDS Specification

Alternatived Products of [ 58483-95-7 ]

Product Details of [ 58483-95-7 ]

CAS No. :	58483-95-7	MDL No. :	MFCD06659499
Formula :	C₆H₅ClN₂O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	WCZUTMZMEAPPIX-UHFFFAOYSA-N
M.W :	172.57	Pubchem ID :	22736791
Synonyms :

Calculated chemistry of [ 58483-95-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.61
TPSA :	76.21 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.89
Log Po/w (XLOGP3) :	1.21
Log Po/w (WLOGP) :	1.02
Log Po/w (MLOGP) :	-1.1
Log Po/w (SILICOS-IT) :	0.68
Consensus Log Po/w :	0.54

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.01
Solubility :	1.69 mg/ml ; 0.00978 mol/l
Class :	Soluble
Log S (Ali) :	-2.41
Solubility :	0.676 mg/ml ; 0.00392 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.65
Solubility :	3.85 mg/ml ; 0.0223 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 58483-95-7 ]

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

Application In Synthesis of [ 58483-95-7 ]

* 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 [ 58483-95-7 ]

[ 58483-95-7 ] Synthesis Path-Downstream 1~12

1
[ 77287-34-4 ]
[ 58483-95-7 ]
[ 171178-47-5 ]

Yield	Reaction Conditions	Operation in experiment
83.9%	at 140℃;Product distribution / selectivity;	Step (e): 6-CHLORO-3H-PYRIDO [3, 4-D] PYRIMIDIN-4-ONE A suspension of 5-amino-2-chloro-isonicotinic acid in formamide (240 mL) was heated at an internal temperature of 140°C overnight with stirring. The mixture was cooled to room temperature, diluted with water (600mL), and stirred for 1 hour. The resulting solid was collected by filtration, washed with water, and dried to give 17. 20g of 6-chloro-3H-pyrido [3, 4-d] PYRIMIDIN-4-ONE as a brown solid (83. 9percent yield). 1H NMR (400 MHz, DMSO-D6) d ppm 7.9 (s, 1H), 8.2 (s, 1H), 8.9 (s, 1H), 12.7 (bs, 1H) MS (APCI) M+1 = 182.0
	at 140℃; for 12h;	a) Method for synthesising P-1 a:; delta-amino^-chloro-isonicotinic acid (4 g, 23.18 mmol) is taken up in the form of the amide (50 ml.) and stirred for 12 h at 140 0C. The reaction mixture is cooled to RT and mixed with water. The precipitate formed is filtered off, washed with water and then dried at 60 0C for 24h in the vacuum drying cupboard.The intermediate product obtained, 6-chloro-3/-/-pyrido[3,4-c/]pyrimidin-4-one (745 mg, 4.1 mmol), is suspended in thionyl chloride (10 ml_), mixed with one drop of DMF and refluxed for 16 h. The excess thionyl chloride is distilled off. The residue is taken up in DCM, washed 1x with semisaturated NaHCC>;3 solution and saturated NaCI solution, dried on Na2SC>;4 and concentrated to dryness by rotary evaporation. The crude product P-1a is further used directly.

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 2221 - 2226
[2]Patent: WO2005/16926,2005,A1 .Location in patent: Page/Page column 116
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 3484 - 3493
[4]Patent: WO2010/94695,2010,A1 .Location in patent: Page/Page column 35

2
[ 171178-46-4 ]
[ 58483-95-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With trifluoroacetic acid; In dichloromethane;	5-Amino-2-chloropyridine-4-carboxylic acid. A stirred suspension of <strong>[171178-46-4]5-[N-(tert-butoxycarbonyl)amino]-2-chloropyridine-4-carboxylic acid</strong> (1.91 g, 7 mmol) in CH2 Cl2 (200 mL) is treated slowly with trifluoroacetic acid until homogeneous (ca. 12 mL). The solution is stirred overnight and extracted with dilute NH4 OH, and the aqueous layer is then acidified with dilute HCl to gave a precipitate of 5-amino-2-chloropyridine-4-carboxylic acid (1.05 g, 87percent yield). 1 H NMR (DMSO) delta 9.01 (2H, m), 8.03 (1H, s), 7.48 (1H, s).
80 - 93.6%	With trifluoroacetic acid; In dichloromethane; at 20℃;	Step (d): 5-AMINO-2-CHLORO-ISONICOTINIC acid A suspension of <strong>[171178-46-4]5-tert-butoxycarbonylamino-2-chloro-isonicotinic acid</strong> in methylene chloride (600mL) was treated dropwise at room temperature with TFA until the solid had dissolved into solution (95 mL). The reaction mixture was stirred overnight under nitrogen at room temperature, evaporated to dryness, diluted with water, and the solid collected by filtration. The solid was washed with water, dried under low heat and house vacuum, to afford 19.55g of 5-amino- 2-chloro-isonicotinic acid as a yellow solid (93.6percent yield). 1H NMR (400 MHz, DMSO-D6) 8 ppm 7.5 (s, 2H), 8.0 (s, 2H) MS (APCI) M+1= 173.0; Step (d): 5-AMINO-2-CHLORO-ISONICOTINIC acid A 3 L round bottomed flask was charged with 5-tert- BUTOXYCARBONYLAMINO-2-CHLORO-ISONICOTINIC acid (138 g, 0.51 moles), 1 L of CH2C12, and 400 mL of TFA. The resulting orange solution was stirred overnight at room temperature. One liter of H20 was added to the reaction solution, which caused a solid to precipitate out. The solid was collected, washed once with H2O and dried overnight in the vacuum oven at 45°C. The reaction yielded 69.6 g (80percent total yield) of 5-amino-2-chloro-isonicotinic acid as a pale yellow solid, which was pure enough by NMR to use in the next reaction. ON (DMSO) 7.99 (1 H, d), 7.45 (1 H, d) MS [M+H] + 173
		Step 3: Preparation of 5-amino-2-chloroisonicotinic acid; A suspension of 5- tert-butoxycarbonylamino-2-chloro- isonicotinic acid (2.46 g) in aqueous 2N potassium hydroxide solution (45 mL) was stirred at 90°C for 5 hours, <n="407"/>After cooling to room temperature, the solution was acidified by slow addition of 6N hydrochloric acid. The formed precipitate was filtered off, washed with water, MTB-ether and hexane and dried in vacuum to afford 700 mg of the title compound of the formulaas beige solid .1H-NMR ( DMSO-D6) delta (ppm) : 7 . 47 ( IH , s ) , 8 . 02 ( IH, s ) .

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 2221 - 2226
[2]Patent: US5654307,1997,A
[3]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1401 - 1405
[4]Patent: WO2005/16926,2005,A1 .Location in patent: Page/Page column 115-116; 123
[5]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 256 - 261
[6]Patent: WO2008/130021,2008,A2 .Location in patent: Page/Page column 405-406

3
[ 3473-63-0 ]
[ 58483-95-7 ]
[ 171178-47-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	In 2-methoxy-ethanol; for 18h;Heating / reflux;Product distribution / selectivity;	Step (e) 6-Chloro-3H-pyrido [3,4-d] pyrimidin-4-one A 1 L round bottomed flask was charged with 5-amino-2-chloro- isonicotinic acid (69.5 g, 0.40 moles), formamidine acetate (84 g, 0.81 moles, 2 mole equivalents), and 600 mL of methoxyethanol. The resulting solution was heated at reflux for 18 hours. After cooling to 5°C, a precipitate was collected by filtration, washed twice with methoxyethanol, and dried overnight in the vacuum oven at 45°C. The reaction yielded 67 g (92percent total yield) of 6-chloro-3H- pyrido [3, 4-D] PYRIMIDIN-4-ONE as a tan solid that was sufficiently pure by NMR to use in the next reaction. 8H (DMSO) 12.70 (1 H, s), 8.86 (1 H, d), 8. 19 (1 H, s), 7.93 (1 H, d) MS [M+H3+ 182

Reference： [1]Patent: WO2005/16926,2005,A1 .Location in patent: Page/Page column 123-124
[2]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1401 - 1405

4
[ 5326-23-8 ]
[ 58483-95-7 ]