[ CAS No. 848952-83-0 ] {[proInfo.proName]}

Name: 848952-83-0|5-Chloropyrazine-2-carboxylic acid hydrazide|98%
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SKU: A276788
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Quality Control of [ 848952-83-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 848952-83-0 ]

SDS Specification

Alternatived Products of [ 848952-83-0 ]

Product Details of [ 848952-83-0 ]

CAS No. :	848952-83-0	MDL No. :	MFCD12964049
Formula :	C₅H₅ClN₄O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IBDISQAOUDHXSW-UHFFFAOYSA-N
M.W :	172.57	Pubchem ID :	45789797
Synonyms :

Calculated chemistry of [ 848952-83-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	37.94
TPSA :	80.9 Å²

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) :	-7.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.01
Log Po/w (XLOGP3) :	-0.85
Log Po/w (WLOGP) :	-0.27
Log Po/w (MLOGP) :	-1.03
Log Po/w (SILICOS-IT) :	-0.02
Consensus Log Po/w :	-0.23

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.65
Solubility :	39.0 mg/ml ; 0.226 mol/l
Class :	Very soluble
Log S (Ali) :	-0.37
Solubility :	73.9 mg/ml ; 0.428 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.91
Solubility :	2.15 mg/ml ; 0.0124 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.1

Safety of [ 848952-83-0 ]

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 [ 848952-83-0 ]

* 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.

Upstream synthesis route of [ 848952-83-0 ]
Downstream synthetic route of [ 848952-83-0 ]

[ 848952-83-0 ] Synthesis Path-Upstream 1~3

1
[ 33332-25-1 ]
[ 848952-83-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With hydrazine In methanol for 48 h; Heating / reflux	Preparation 1; 5-ChloroDvrazine-2-carboxvlic acid hvdrazide; δ-chloropyrazine^-carboxylic acid methyl ester (10.02g, 58.25mmol) and hydrazine monohydrate (12.5ml_, 250mmol) were dissolved in methanol (40OmL) and the reaction mixture heated to reflux for 48 hours. The reaction mixture was then filtered and the precipitate collected dried in vacuo to yield the title product, 5.01 g (50percent). ¹H NMR(CDCI₃, 400MHz) δ: 4.09(d, 2H), 8.52(s, 1 H), 8.66(bs, 1 H), 9.14(s, 1 H). Microanalysis: C₅H₅CIN₄O requires: C 34.80; H 2.92; N 32.47; found C 34.89; H 2.91 , N 32.32. MS APCI+ m/z 173 [MH]⁺
50%	With hydrazine In methanol for 48 h; Heating / reflux	δ-chloro-pyrazine^-carboxylic acid methyl ester (10.02g, 58.25mmol) and hydrazine monohydrate(12.5mL, 250mmol) were dissolved in methanol (40OmL) and the reaction mixture heated to reflux for 48 hours. The reaction mixture was then filtered and the precipitate collected dried in vacuo to yield the title compound, 5.01 g (50percent).¹H NMR(CDCI₃, 400MHz) δ: 4.09(d, 2H), 8.52(s, 1 H), 8.66(bs, 1 H), 9.14(s, 1 H). Microanalysis:C₅H₅CIN₄O requires: C 34.80; H^" 2.92; N 32.47; found C 34.89; H 2.91 , N 32.32. MS APCI+ m/z 173[MH]⁺

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 13, p. 5344 - 5354
[2] Patent: WO2007/17752, 2007, A1, . Location in patent: Page/Page column 33
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 10, p. 2634 - 2636
[4] Patent: WO2006/100557, 2006, A1, . Location in patent: Page/Page column 24

2
[ 1254073-53-4 ]
[ 848952-83-0 ]

Reference： [1] Patent: WO2010/125102, 2010, A1, . Location in patent: Page/Page column 85

3
[ 36070-80-1 ]
[ 848952-83-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 13, p. 5344 - 5354

[ 848952-83-0 ] Synthesis Path-Downstream 1~24

2
[ 848952-83-0 ]
[ 75-36-5 ]
[ 848952-87-4 ]

Yield	Reaction Conditions	Operation in experiment
64%	With 4-methyl-morpholine; In dichloromethane; at 20.0℃; for 5.0h;	Preparation 2; S-Chloropyrazine^-carboxylic acid N'-acetyl-hvdrazide; The product of preparation 1 (2.Og, 29.2mmol) and N-methylmorpholine (1.8mL, 35mmol) were dissolved in dichloromethane (10OmL) and the solution treated with acetyl chloride (1.04mL, 11.4mmol). The reaction mixture was stirred at room temperature for 5 hours and then washed with water and in vacuo to afford 4.Og, (64%). MS APCI+ m/z 215 [MH]+
64%	With 4-methyl-morpholine; In dichloromethane; at 20.0℃; for 5.0h;	The product of preparation 4 (2.Og, 29.2mmol) and N-methylmorpholine (1.8mL, 35mmol) were dissolved in dichloromethane (10OmL) and the solution treated with acetyl chloride (1.04mL, 11.4mmol). The reaction mixture was stirred at room temperature for 5 hours and then washed with water and concentrated in vacuo to yield the title compound 4.Og, (64%). MS APCI+ m/z 215 [MH]+

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354
[2]Patent: WO2007/17752,2007,A1 .Location in patent: Page/Page column 33-34
[3]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2634 - 2636
[4]Patent: WO2006/100557,2006,A1 .Location in patent: Page/Page column 24

3
[ 33332-25-1 ]
[ 848952-83-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With hydrazine; In methanol; for 48.0h;Heating / reflux;	Preparation 1; 5-ChloroDvrazine-2-carboxvlic acid hvdrazide; delta-chloropyrazine^-carboxylic acid methyl ester (10.02g, 58.25mmol) and hydrazine monohydrate (12.5ml_, 250mmol) were dissolved in methanol (40OmL) and the reaction mixture heated to reflux for 48 hours. The reaction mixture was then filtered and the precipitate collected dried in vacuo to yield the title product, 5.01 g (50%). 1H NMR(CDCI3, 400MHz) delta: 4.09(d, 2H), 8.52(s, 1 H), 8.66(bs, 1 H), 9.14(s, 1 H). Microanalysis: C5H5CIN4O requires: C 34.80; H 2.92; N 32.47; found C 34.89; H 2.91 , N 32.32. MS APCI+ m/z 173 [MH]+
50%	With hydrazine; In methanol; for 48.0h;Heating / reflux;	delta-chloro-pyrazine^-carboxylic acid methyl ester (10.02g, 58.25mmol) and hydrazine monohydrate(12.5mL, 250mmol) were dissolved in methanol (40OmL) and the reaction mixture heated to reflux for 48 hours. The reaction mixture was then filtered and the precipitate collected dried in vacuo to yield the title compound, 5.01 g (50%).1H NMR(CDCI3, 400MHz) delta: 4.09(d, 2H), 8.52(s, 1 H), 8.66(bs, 1 H), 9.14(s, 1 H). Microanalysis:C5H5CIN4O requires: C 34.80; H" 2.92; N 32.47; found C 34.89; H 2.91 , N 32.32. MS APCI+ m/z 173[MH]+

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354
[2]Patent: WO2007/17752,2007,A1 .Location in patent: Page/Page column 33
[3]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2634 - 2636
[4]Patent: WO2006/100557,2006,A1 .Location in patent: Page/Page column 24

4
[ 1254073-53-4 ]
[ 848952-83-0 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 1 ,1-dimethylethyl 2-[(5-chloro-2-pyrazinyl)carbonyl]hydrazine carboxylate (I48) (2.182 g, 8 mmol) in 1 ,4-dioxane (20 ml.) was added 4M HCI in 1 ,4- dioxane (20.00 ml_, 80 mmol). The solution was then stirred under argon for 4 hours. Analysis by LCMS showed some sign of starting material still present thus 4M HCI in 1 ,4-dioxane (8.00 ml_, 32.0 mmol) was added. The solvent was then evaporated in vacuo and the remaining solid was loaded onto an SCX cartridge (2 x 10 g). The solid was then washed with methanol (2 x 30 ml.) before being eluted from the cartridge by 2M NH3/MeOH. TLC confirmed product location and the solvent from the combined fractions was evaporated in vacuo. The solid was triturated with diethyl ether, filtered, and washed with diethyl ether to afford product in 1.02 g. 1H NMR (400 MHz; CDCI3) delta 9.14 (1 H, s), 8.68 (1 H, broad s), 8.53 (1 H, s), 4.11 (2H, s)

Reference： [1]Patent: WO2010/125102,2010,A1 .Location in patent: Page/Page column 85

5
[ 848952-83-0 ]
[ 848952-92-1 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354
[2]Patent: WO2006/100557,2006,A1

6
[ 848952-83-0 ]
6-(5-(5-methyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yloxy)benzo[c][1,2]oxaborol-1(3H)-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354

7
[ 36070-80-1 ]
[ 848952-83-0 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5344 - 5354

8
[ 848952-83-0 ]
2-(2-chloro-4-fluorophenyl)-5-[4-(6-methoxypyridin-3-yl)-5-methyl-4H-[1,2,4]triazol-3-yl]pyrazine [ No CAS ]

Reference： [1]Patent: WO2006/100557,2006,A1

9
[ 848952-83-0 ]
[ 848953-06-0 ]

Reference： [1]Patent: WO2006/100557,2006,A1

10
[ 54013-04-6 ]
[ 848952-83-0 ]