102645-33-0|2,5-Dichloroisonicotinaldehyde| Ambeed

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Quality Control of [ 102645-33-0 ] Purity: 97% SDS Specification

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Product Details of [ 102645-33-0 ]

CAS No. :	102645-33-0
Formula :	C₆H₃Cl₂NO
M.W :	176.00
SMILES Code :	O=CC1=C(Cl)C=NC(Cl)=C1
MDL No. :	MFCD06410679
InChI Key :	UIPSRNHDSBVXHY-UHFFFAOYSA-N
Pubchem ID :	2762993

Safety of [ 102645-33-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 102645-33-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	39.64
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.96 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.47
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	1.9
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.2
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.	1.0
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	2.79
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.87

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.51
Solubility	0.549 mg/ml ; 0.00312 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.	-2.15
Solubility	1.24 mg/ml ; 0.00705 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.2
Solubility	0.111 mg/ml ; 0.000628 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.	-6.02 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)	1.59

Application In Synthesis of [ 102645-33-0 ]

* 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 [ 102645-33-0 ]

[ 102645-33-0 ] Synthesis Path-Downstream 1~27

1
[ 102645-33-0 ]
[ 108-24-7 ]
[ 862170-49-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; at 20℃; for 20h;	Intermediate 9: (2. 5-Dichloro-4-pyridinvl) methanedivl diacetate; Concentrated sulfuric acid (3 drops) was added to a suspension of 2, 5-dichloro-4- pyridinecarbaldehyde (Intermediate 8,4. 0g) in acetic anhydride (25ml) and the mixture was stirred at room temperature for 20h. The acetic anhydride was removed under vacuum to give the title compound as a pale brown oil. LC-MS: Rt 2.94min, MH+ 278

References: [1]Patent: WO2005/73232,2005,A1 .Location in patent: Page/Page column 35.

2
[ 16110-09-1 ]
[ 68-12-2 ]
[ 102645-33-0 ]

Yield	Reaction Conditions	Operation in experiment
56%		2,5-dichloropyridine-4-carbaldehvde A solution of 2,5-dichloropyridine (27.0 g, 180 mmol) in THF (65 mL) was added via cannula to a cooled solution of LDA (100 mL of a 1 .8 M solution, 180 mmol) in THF (80 mL) at -78 C. The mixture was stirred at -78 C for 30 mins, then a solution of DMF (21.1 mL, 271 mmol) in THF (25 mL) was added slowly via syringe. The reaction was stirred at -78 C for 3 hours and was then warmed to R.T. gradually. The solution was poured into a mixture of ice (800 mL) and cone. HCI (150 mL) and stirred for 20 mins before being basified with NaOH (3.0 M) to pH 9-10, and extracted with Et20 (2 x 500 mL). The combined organic layers were dried over MgS04 and concentrated to give the crude product as pale yellow solid. This solid was suspended in n-hexane with trace EtOAc and boiled for 5 mins. The liquors were decanted and stripped to yield a yellow solid which was purified by Biotage flash chromatography (65i, loaded in DCM / EtOAc, eluted with heptane - 20 % EtOAc / heptane over 8 CV, then holding for 5 CV) to afford the title compound (17.9 g, 56 %) as a pale yellow solid, 1H NMR (400 MHz, DMSO-d6) delta 7.85 (s, 1 H) 8.76 (s, 1 H) 10.22 (s, 1 H).
	With n-butyllithium;	2,5-Dichloropyridine-4-carboxaldehyde was prepared from 2.5-dichloropyridine using the procedure described in Eur. J. Org. Chem. 2001, 1371-1376 (E. Marzi, A. Bigi, M. Schlosser ) and converted to 2-(2,5-dichloro-pyridin-3-yl)-lH- benzoimidazole using the method in route 1 step 4. This was aminated as described for compound 34 and the aminopyridine converted to compound 38 using the method in route 1 step 1
		Intermediate 8: 2, 5-Dichloro-4-pyridinecarbaldehyde; Diisopropylamine (7. 5ml) was dissolved in THF (47ml) and the solution was cooled to -35C. n-Butyl lithium (1.6M in hexanes, 44ml) was added slowly maintaining the temperature below-30C. After the addition the reaction mixture was cooled to-75C and a solution of 2, 5-dichloropyridine (8.9g) in THF (27ml) was added dropwise. The mixture was stirred at-75C for a further 30min and a solution of DMF (7. Oml) in THF (14ml) was added dropwise. The reaction mixture was stirred at-75C for 1.5h then allowed to warm to 10C over 2.5h. The solution was poured onto a mixture of ice (500ml) and concentrated hydrochloric acid (45ml) and stirred for 15min. The mixture was basified to pH8 with sodium hydroxide (2N), extracted with ether (x3) and the combined organic extracts were washed with brine, dried (magnesium sulfate) and reduced to dryness under vacuum. The resulting oil was applied to a silica column (50g) and eluted with cyclohexane/ethyl acetate (100: 0 to 80: 20) The product obtained was recrystallised from cyclohexane to give the title compound as beige needles (6.65g). NMR: [8H d6-DMSO] 10.20 (1H, s), 8.75 (1H, s), 7.83 (1H, s)

References: [1]Patent: WO2011/27249,2011,A2 .Location in patent: Page/Page column 58.
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6578 - 6581.
[3]Patent: WO2006/50506,2006,A1 .Location in patent: Page/Page column 132.
[4]Patent: WO2005/73232,2005,A1 .Location in patent: Page/Page column 34.

Yield	Reaction Conditions	Operation in experiment
		The organic solutions were combined, washed with saturated NaCl solution, dried and evaporated to dryness to give about 22 g of 2,5-dichloro-4-pyridinecarboxaldehyde.

4
[ 102645-33-0 ]
2,5-dichloro-4-pyridinecarboxaldehyde oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22.8 g (85%)	With hydrogenchloride; hydroxylamine hydrochloride; In isopropyl alcohol;	This aldehyde was dissolved in 100 ml of 2-propanol, mixed with 13.8 g of hydroxylamine hydrochloride and 20 drops of concentrated HCl and heated on a steambath for 1 hour. The mixture was then poured onto 200 g of ice, stirred well and filtered leaving a solid residue. The solid was vacuum dried to give 22.8 g (85%) of the desired <strong>[102645-33-0]2,5-dichloro-4-pyridinecarboxaldehyde</strong> oxime STR6 m.p. 173-174 C.

References: [1]Patent: US4558134,1985,A .

5
[ 102645-33-0 ]
[ 102645-34-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6578 - 6581.

6
[ 102645-33-0 ]
[ 4760-34-3 ]
[ 1269771-37-0 ]