848952-83-0|5-Chloropyrazine-2-carboxylic acid hydrazide| Ambeed

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Quality Control of [ 848952-83-0 ] Purity: 98% SDS Specification

COA

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Product Details of [ 848952-83-0 ]

CAS No. :	848952-83-0
Formula :	C₅H₅ClN₄O
M.W :	172.57
SMILES Code :	ClC1=CN=C(C=N1)C(=O)NN
MDL No. :	MFCD12964049
InChI Key :	IBDISQAOUDHXSW-UHFFFAOYSA-N
Pubchem ID :	45789797

Safety of [ 848952-83-0 ]

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

Computational Chemistry of [ 848952-83-0 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	80.9 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.01
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	-0.85
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.27
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.	-1.03
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	-0.02
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.23

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.65
Solubility	39.0 mg/ml ; 0.226 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.37
Solubility	73.9 mg/ml ; 0.428 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-1.91
Solubility	2.15 mg/ml ; 0.0124 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	No
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.	-7.96 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)	2.1

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.

Downstream synthetic route of [ 848952-83-0 ]

[ 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]+

References: [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]+

References: [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)

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

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

References: [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 ]

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

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

References: [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 ]

References: [1]Patent: WO2006/100557,2006,A1 .

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

References: [1]Patent: WO2006/100557,2006,A1 .

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