38557-72-1|2-Chloro-3,5-dimethylpyrazine| Ambeed

Structure of 38557-72-1

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Quality Control of [ 38557-72-1 ] Purity: 97% SDS Specification

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Product Details of [ 38557-72-1 ]

CAS No. :	38557-72-1
Formula :	C₆H₇ClN₂
M.W :	142.59
SMILES Code :	CC1=CN=C(Cl)C(C)=N1
MDL No. :	MFCD00126945
InChI Key :	BTGGHNHGPURMEO-UHFFFAOYSA-N
Pubchem ID :	11672680

Safety of [ 38557-72-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P261-P280-P302+P352-P305+P351+P338

Computational Chemistry of [ 38557-72-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.33
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	36.97
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	25.78 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.81
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	1.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.75
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.	0.49
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	2.42
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.6

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.19
Solubility	0.926 mg/ml ; 0.00649 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.	-1.69
Solubility	2.91 mg/ml ; 0.0204 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	-3.02
Solubility	0.137 mg/ml ; 0.000959 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	Yes
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.	-6.08 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	0.0 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)	2.07

Application In Synthesis of [ 38557-72-1 ]

* 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 [ 38557-72-1 ]
Downstream synthetic route of [ 38557-72-1 ]

[ 38557-72-1 ] Synthesis Path-Upstream 1~2

1
[ 38557-72-1 ]
[ 60187-00-0 ]

References: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 311 - 320.

2
[ 38557-72-1 ]
[ 77164-93-3 ]

References: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 311 - 320.
[2] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 311 - 320.

[ 38557-72-1 ] Synthesis Path-Downstream 1~35

1
[ 38557-72-1 ]
[ 86725-70-4 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 311 - 320.

2
[ 38557-72-1 ]
[ 60187-00-0 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 311 - 320.

3
[ 930-61-0 ]
[ 67-66-3 ]
[ 14331-54-5 ]
[ 123-32-0 ]
[ 95-89-6 ]
[ 38557-72-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1431 - 1435.

4
[ 930-61-0 ]
[ 67-66-3 ]
[ 123-32-0 ]
[ 95-89-6 ]
[ 38557-72-1 ]
[ 75712-74-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1431 - 1435.

5
[ 930-62-1 ]
[ 67-66-3 ]
[ 4472-45-1 ]
[ 95-89-6 ]
[ 38557-72-1 ]
[ 75712-73-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1427 - 1430.

6
[ 31396-38-0 ]
[ 38557-72-1 ]

References: [1]European Journal of Organic Chemistry,2005,p. 4141 - 4153.

7
[ 108-50-9 ]
[ 38557-72-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	With sulfuryl dichloride; In N,N-dimethyl-formamide; at 60℃; for 2.5h;Cooling with ice;	Example 12 [00659] Preparation of Cpd 88 H2 N 150 C / 3 days N [00660] Part 1, Step A: To a cooled solution of 2,6-dimethylpyrazine (108 g, 1.0 mol) in DMF (260 mL) on an ice/H20 bath, while stirring vigorously, was added sulfuryl chloride (270 mL, 3.3 mol). The rate of addition was controlled to maintain the reaction temperature between 40-60 C for about 2 hours. After the addition, the cooling bath was removed and the mixture was stirred for an additional 0.5 hours. LC/MS analysis of an aliquot showed <5% starting material remained. The reaction mixture was then cooled in an ice/water bath and, while maintaining the temperature below 35 C, quenched carefully with 10 M NaOH (1 L), followed by the addition of Na2C03 (solid) to pH 6. After the addition of water (800 mL), the mixture was distilled. The distillate was collected and the organics were separated. The aqueous layer was extracted with ethyl ether (100 mL x 3) and the ether extracts were combined with the organics separated previously. The combined extracts were washed with water (30 mL x 3), then brine and dried over Na2S04. After the extracts were concentrated, the residue was distilled and the product was collected as a colorless liquid, approximate boiling point: 127 C at 154 mmHg (99.1 g, 69%). 1H NMR (500 MHz, CHLOROFORM- ) delta ppm 8.05 (1H, s), 2.61 (3H, d, J=0.63 Hz), 2.50 (3H, s).
36%		First, a synthesis method of an intermediate, 2-chloro-3,5-dimethylpyrazine is described. 7.12 g of 2,6-dimethylpyrazine and 6.5 mL of dimethylformamide (abbreviation : DMF) were put in a three-neck flask equiiped with a drop funnel and a thermometer, and the inside was refluxed under a nitrogen atmosphere. 6.7 mL of sulfuric chloride was put in a drop funnel and the reaction container was soaked in an ice bath. While the reaction solution was being stirred, the sulfuric chloride was dropped in such a way that the temperature of the solution be kept 45 C +/- 5 C. After that, water was added after it was confirmed that the temperature of the solution was 40 0C or lower. After it was confirmed again that the temperature of the solution was 40 0C or lower, an aqueous sodium hydroxide was added and the pH of the solution was adjusted to 7 to 8. This solution was subjected to steam distillation. The obtained <n="82"/>solution was subjected to extraction using dichloromethane to separate an organic layer. The organic layer obtained was dried with magnesium sulfate. After the drying, the solution was filtrated. After the solvent of this solution was distilled off, the obtained residue was distilled under reduced pressure, so that an objective intermediate was obtained (clear and colorless liquid, yield of 36 %).

References: [1]Patent: WO2013/112788,2013,A1 .Location in patent: Paragraph 00660.
[2]Patent: WO2008/149828,2008,A1 .Location in patent: Page/Page column 80-81; 82.
[3]European Journal of Organic Chemistry,2005,p. 4141 - 4153.

8
[ 38557-72-1 ]
[ 33837-26-2 ]