65202-50-8|Methyl 6-chloropyridazine-3-carboxylate| Ambeed

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Quality Control of [ 65202-50-8 ] Purity: 98% SDS Specification

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Product Details of [ 65202-50-8 ]

CAS No. :	65202-50-8
Formula :	C₆H₅ClN₂O₂
M.W :	172.57
SMILES Code :	ClC1=CC=C(N=N1)C(=O)OC
MDL No. :	MFCD08694876
InChI Key :	FPKXYXKLOWAIOX-UHFFFAOYSA-N
Pubchem ID :	12379801

Safety of [ 65202-50-8 ]

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

Computational Chemistry of [ 65202-50-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	38.32
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.08 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.65
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	-0.25
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.92
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.	0.56
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	1.38
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.85

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.02
Solubility	16.3 mg/ml ; 0.0946 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.	-0.39
Solubility	71.0 mg/ml ; 0.412 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	-2.34
Solubility	0.789 mg/ml ; 0.00457 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	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.	-7.53 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)	1.8

Application In Synthesis of [ 65202-50-8 ]

* 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 [ 65202-50-8 ]

[ 65202-50-8 ] Synthesis Path-Downstream 1~35

1
[ 960492-41-5 ]
[ 65202-50-8 ]
methyl 6-(3-[2-(trifluoromethyl)benzyl]oxy}azetidin-1-yl)pyridazine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetra-(n-butyl)ammonium iodide; potassium carbonate; In 1,4-dioxane; at 95℃; for 16h;	:p 3: Methyl 6-(3- { [2-(trifluoromethyl)benzylloxyl azetidin- 1 -yl)pyridazine-3- carboxylate; A suspension of 3-[2-(trifluoromethyl)benzyl]oxy}azetidine (595 mg, 2.58 mmol), methyl beta-chloropyridazine-S-carboxylate (450 mg, 2.58 mmol), potassium carbonate (715 mg, 5.15 mmol) and tetrabutylammonium iodide (20 mg, 0.052 mmol) in dioxane (10 mL) was heated to 95 °C for 16 h. The cooled reaction mixture was poured into a 125 mL separatory funnel containing water (50 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. Purification by column chromatography through silica gel gave the title compound.1H NMR (J6-acetone, 400 MHz) delta 7.86-7.80 (2H, m), 7.75-7.51 (3H, m), 6.79 (IH, d, J= 9.5 Hz), 4.78-4.76 (3H, m), 4.49 (2H, dd, J= 10.0, 6.5 Hz), 4.15 (2H, dd, J= 10.0, 4.0 Hz), 3.88 (3H, s).MS (ESI, Q+) m/z 368 (M+ 1).

References: [1]Patent: WO2007/143823,2007,A1 .Location in patent: Page/Page column 37.

2
[ 82622-46-6 ]
[ 65202-50-8 ]
methyl 6-{3-[2-(trifluoromethyl)phenoxy]azetidin-1-yl}pyridazine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tert-butyl alcohol; for 48h;Heating / reflux;	Step 3: Methyl 6-{3-r2-(trifluoromethyl)phenoxy1azetidin-l-yl)pyridazine-3-carboxylate; Into a flame-dried 100 mL round-bottom flask equipped with a magnetic stirring bar and under N2 was added <strong>[65202-50-8]methyl 6-chloropyridazine-3-carboxylate</strong> (935 mg, 5.42 mmol), 3- [2-(trifluoromethyl)phenoxy]azetidine hydrochloride (1.25 g, 4.93 mmol) and potassium carbonate (2.04 g, 14.8 mmol) in tert-butanol (20 mL). The suspension was heated to reflux for 2 d. The reaction mixture was concentrated and purified by column chromatography through silica gel to give the indicated product as an off-white solid.1H NMR (CDCl3, 400 MHz): delta 7.94 (IH, d, J= 9.5 Hz), 7.64 (IH, d, J= 8.0 Hz), 7.53 (IH, t, J = 8.0 Hz), 7.11 (IH, t, J= 8.0 Hz), 6.76 (IH, d, J= 8.0 Hz), 6.60 (IH, d, J= 9.5 Hz), 5.27 (IH, tt, J = 6.5, 4.0 Hz), 4.70 (2H, dd, J= 10.0, 6.5 Hz), 4.38 (2H, dd, J= 10.0, 4.0 Hz), 4.01 (3H, s). MS (ESI, Q+) m/z 354 (M + 1).

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 479 - 483.
[2]Patent: WO2007/143823,2007,A1 .Location in patent: Page/Page column 39.

3
[ 960492-73-3 ]
[ 65202-50-8 ]
methyl 6-{3-[(2-bromophenyl)oxy]azetidin-1-yl}pyridazine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In 1,4-dioxane; for 16h;Heating / reflux;	Methyl 6-{3-r(2-bromophenyl)oxylazetidin-l-yl}pyridazine-3-carboxylate; Into a flame-dried 100 mL round-bottom flask equipped with a magnetic stirring bar and under N2 was added <strong>[65202-50-8]methyl 6-chloropyridazine-3-carboxylate</strong> (848 mg, 4.91 mmol), 3- [(2-bromophenyl)oxy]azetidine hydrochloride (1.3 g, 4.91 mmol) and potassium carbonate (2.04 g, 14.7 mmol) in dioxane (30 mL). The reaction mixture was heated to reflux for 16 h overnight. The reaction mixture was cooled to room temperature and quenched with water (10 mL). The reaction mixture was concentrated and a beige solid precipitated out of solution. The solid was diluted with water (20 mL) and filtered through WhatmanNo.l paper on a Hirsch funnel, washing with water. The resulting beige solid was dried on the vacuum pump overnight, giving the desired product.MS (ESI, Q+) m/z 364 (M + 1, 79Br), 366 (M + 1, 81Br).

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 479 - 483.
[2]Patent: WO2007/143823,2007,A1 .Location in patent: Page/Page column 46.

4
[ 960492-85-7 ]
[ 65202-50-8 ]
methyl 6-{3-[2-(trifluoromethyl)benzyl]azetidin-1-yl}pyridazine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In 1,4-dioxane; for 48h;Heating / reflux;	Step 5: Methyl 6-{3-[2-(trifluoromethyl)benzyllazetidin-l-vUpyridazine-3-carboxylate; To a solution of 3-[2-(trifluoromethyl)benzyl]azetidine hydrochloride (327 mg, 1.3 mmol) and methyl beta-chloropyridazine-S-carboxylate (329 mg, 1.3 mmol) in 5 mL of dioxane was added potassium carbonate (539 mg, 3.9 mmol). It was heated to reflux for 2 days. The reaction mixture was allowed to cool to room temperature and poured into a separatory funnel containing KH2PO4 buffer. The aqueous layer was extracted with 3 portions of ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give the desired product.

References: [1]Patent: WO2007/143823,2007,A1 .Location in patent: Page/Page column 50-51.

5
4-(2-chloro-phenoxy)-piperidine hydrochloride [ No CAS ]
[ 65202-50-8 ]
[ 944808-13-3 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3086 - 3100.

6
[ 65202-50-8 ]
[ 165601-61-6 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2925 - 2937.

7
[ 65202-50-8 ]
2-butyl-4-<6-(methoxycarbonyl)pyridazin-3-yl>-1-<<2'-(1H-tetrazol-5-yl)<1,1'-biphenyl>-4-yl>methyl>-1H-imidazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2925 - 2937.

8
[ 65202-50-8 ]
6-{2-Butyl-1-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-imidazol-4-yl}-1-oxy-pyridazine-3-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2925 - 2937.

9
[ 65202-50-8 ]
[ 165601-63-8 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2925 - 2937.

10
[ 65202-50-8 ]
6-{2-Butyl-1-[2'-(1-trityl-1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-imidazol-4-yl}-1-oxy-pyridazine-3-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2925 - 2937.

11
[ 65202-50-8 ]
[ 89967-28-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 4549 - 4553.
[2]Heterocycles,1992,vol. 34,p. 225 - 228.

12
[ 65202-50-8 ]
[ 89967-34-0 ]