32608-29-0|2,4-Dichloro-8-methoxyquinoline| Ambeed

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Quality Control of [ 32608-29-0 ] Purity: 95% SDS Specification

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Product Details of [ 32608-29-0 ]

CAS No. :	32608-29-0
Formula :	C₁₀H₇Cl₂NO
M.W :	228.08
SMILES Code :	COC1=C2N=C(Cl)C=C(Cl)C2=CC=C1
MDL No. :	MFCD07644554
InChI Key :	YQPQBGCONUUZNN-UHFFFAOYSA-N
Pubchem ID :	28286217

Safety of [ 32608-29-0 ]

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

Computational Chemistry of [ 32608-29-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	10
Fraction Csp3	0.1
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	58.26
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	22.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.47
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	3.75
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.55
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.	2.6
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	3.68
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.21

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.08
Solubility	0.019 mg/ml ; 0.0000833 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.91
Solubility	0.0282 mg/ml ; 0.000124 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	-5.07
Solubility	0.00195 mg/ml ; 0.00000855 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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.	-5.03 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	0.0
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	1.0 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<2.0
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)	1.91

Application In Synthesis of [ 32608-29-0 ]

* 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 [ 32608-29-0 ]

[ 32608-29-0 ] Synthesis Path-Downstream 1~28

1
[ 4843-06-5 ]
[ 32608-29-0 ]

References: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1937,vol. 204,p. 1204,1206.

2
[ 32608-29-0 ]
[ 82613-17-0 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 238 - 239.

4
[ 32608-29-0 ]
[ 82613-19-2 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 238 - 239.

5
[ 32608-29-0 ]
[ 82613-18-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 238 - 239.

6
[ 693-98-1 ]
[ 32608-29-0 ]
[ 1064677-85-5 ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one; at 140℃; for 20h;	A mixture of <strong>[32608-29-0]2,4-dichloro-8-methoxy-quinoline</strong> (0.20 g, 0.88 mmol) and 2-methyl-lH- imidazole (0.11 g, 1.3 mmol) in NMP (0.20 mL) was heated to 140C for 20 h. The solvent was removed in vacuo and the residue was purified by reversed phase HPLC using a gradient of acetonitrile in water with 0.1% TFA to give the title compound as the TFA salt. MS (m/z):419.0 [M+H+].

References: [1]Patent: WO2008/116620,2008,A1 .Location in patent: Page/Page column 151.

7
[ 32608-29-0 ]
[ 20439-47-8 ]
[ 1370730-92-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium t-butanolate;2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); In toluene; at 70℃; for 3.5h;	4Cl8MeOQuinBAM. A 100 mL round bottom flask was charged with Pd(dba)2 (25.2 mg, 43.8 mumol), rac-BINAP (27.3 mg, 43.8 mumol), sodium tert-butoxide (632.0 mg, 6.576 mmol), (R,R)-diaminocyclohexane (250.3 mg, 2.192 mmol), and the quinoline (1.0000 g, 4.385 mmol).1 Toluene (22 mL) was added, and the reaction mixture was heated at 70 C. and stirred for 3.5 h. The reaction was cooled to room temperature, diluted with CH2Cl2, and filtered through celite. The filtrate was concentrated and purified by column chromatography (25-50% ethyl acetate in hexanes) to provide a yellow solid (642.6 mg, 62%). [alpha]D20 +530 (c 0.16, CHCl3); Rf=0.31 (50% EtOAc/hexanes); IR (film) 3240, 2933, 1607, 1545 cm-1; 1H NMR (400 MHz, CDCl3) delta 7.54 (dd, J=8.4, 0.8 Hz, 2H), 7.17 (dd, J=7.6, 0.8 Hz, 2H), 7.01 (dd, J=7.6, 0.8 Hz, 2H), 6.59 (s, 2H), 6.38 (br s, 2H), 4.15-3.95 (m, 2H), 4.04 (s, 6H), 2.45-2.30 (m, 2H), 1.85-1.70 (m, 2H), 1.50-1.30 (m, 4H); 13C NMR (150 MHz, CDCl3) ppm 155.9, 153.2, 142.1, 140.0, 122.2, 121.9, 116.2, 112.7, 109.8, 56.6, 56.2, 32.5, 24.7; HRMS (ESI): Exact mass calcd for C26H27Cl2N4O2 [M+H]+ 497.1511. found 497.1521. 1 Adapted from Wagaw, S.; Rennels, R.; Buchwald, S. J Am. Chem. Soc. 1997, 119, 8451-8458.

References: [1]Organic Process Research and Development,2016,vol. 20,p. 215 - 226.
[2]Patent: US2012/88915,2012,A1 .Location in patent: Page/Page column 17.
[3]Journal of Organic Chemistry,2013,vol. 78,p. 10605 - 10616.
[4]Chemical Communications,2019,vol. 55,p. 14351 - 14354.

8
[ 141-82-2 ]
[ 90-04-0 ]
[ 32608-29-0 ]

Yield	Reaction Conditions	Operation in experiment
78.6%	With trichlorophosphate; at 80 - 100℃; for 5h;	General synthesis route of the compound was described schematicallyin Scheme 1. 2, 4-Dichloro-8-methoxy quinoline, wassynthesized according to literature report [27,28], equimolarmixture of o-anisidine and malonic acid were refluxed with 30 mlof phosphorous oxy chloride on a heating mantle maintained at atemperature of 80e100 C for 5 h. On completion of the reaction(monitored by TLC), the reaction mixture was cooled and pouredslowly onto the crushed ice with continuous stirring. The solidseparated was filtered, dried and washed thoroughly with water.Column purification (95:5 hexaneeEtOAc) of the crude solid gave4-dichloro-8-methoxy quinoline, in a good yield (78.6%).
27%	With trichlorophosphate; at 0℃;Reflux;	To 2-methoxyaniline (5.0 g, 40.6 mmol) and Malonic acid (6.34 g, 60.97 mmol) was added dropwise at 0C phosphoryl chloride (50 ml). The resulting mixture was stirred and heated under reflux overnight. Then, the mixture was cooled, concentrated under reduced pressure and co-evaporated twice with toluene. The residue was then taken up with DCM and washed with cold water. The aqueous layer was extracted with DCM and the combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a brown-solid. The crude product was purified by flash chromatography (gradient Petroleum ether/EtOAC from 8/2 to 5/10) to give 2.5 g (yield 27%) of a yellowish solid corresponding to 2, 4-dichloro-8-methoxyquinoline (6-1). HPLC-MS, Method C: tr = 2.02 min, (ES+) C10H7Cl2NO required 227; found 228 [M+H]. 1H NMR (500 MHz, CDCl3)

References: [1]Journal of Molecular Structure,2017,vol. 1131,p. 51 - 72.
[2]Research on Chemical Intermediates,2014,vol. 40,p. 1851 - 1866.
[3]Organic Process Research and Development,2016,vol. 20,p. 215 - 226.
[4]Patent: EP3620164,2020,A1 .Location in patent: Paragraph 1459; 1460.
[5]Chemical Communications,2019,vol. 55,p. 14351 - 14354.
[6]Journal of Organic Chemistry,2013,vol. 78,p. 10605 - 10616.
[7]Research on Chemical Intermediates,2013,vol. 39,p. 1807 - 1815.
[8]Medicinal Chemistry Research,2013,vol. 22,p. 3185 - 3192.
[9]Molecules,2015,vol. 20,p. 7620 - 7636.

9
[ 32608-29-0 ]
[ 294653-58-0 ]
[ 1386328-65-9 ]

References: [1]Research on Chemical Intermediates,2013,vol. 39,p. 1807 - 1815.

10
[ 90-33-5 ]
[ 32608-29-0 ]
[ 1415232-55-1 ]

References: [1]Medicinal Chemistry Research,2013,vol. 22,p. 3185 - 3192.

11
[ 32608-29-0 ]
[ 1370730-93-0 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 10605 - 10616.
[2]Chemical Communications,2019,vol. 55,p. 14351 - 14354.

12
[ 80-05-7 ]
[ 32608-29-0 ]
[ 1417625-40-1 ]

References: [1]Research on Chemical Intermediates,2013,vol. 39,p. 4259 - 4267.

13
[ 32608-29-0 ]
[ 10354-30-0 ]
[ 1424371-09-4 ]

References: [1]Research on Chemical Intermediates,2014,vol. 40,p. 1851 - 1866.

14
[ 32608-29-0 ]
8-methoxy-2-(4-methyl-1,4-diazepan-1-yl)-N-(1-methylpiperidin-4-yl)quinolin-4-amine [ No CAS ]

References: [1]Molecules,2015,vol. 20,p. 7620 - 7636.

15
[ 41838-46-4 ]
[ 32608-29-0 ]
C₁₆H₂₀ClN₃O [ No CAS ]

References: [1]Molecules,2015,vol. 20,p. 7620 - 7636.

16
4-(3-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester [ No CAS ]
[ 32608-29-0 ]
ethyl 4-(3-(2-chloro-8-methoxyquinolin-4-yloxy)phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃;	General procedure: A mixture of substituted 2,4-dichloroquinolines 2a-j (1mol), powdered K2CO3 (1.2 mol) and 4-(3-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate(1; 1 mol) in DMF was stirred at 70 C for 48 h.The progress of the reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was poured into a beaker containing ice cold water and stirred well, the separated solid filtered to dryness and purified through column chromatography of silica gel (60-120 mesh)using pet. ether and ethyl acetate (7:3) mixture as eluent,which afforded the products 3a-j in pure form.

References: [1]Medicinal Chemistry,2015,vol. 11,p. 789 - 797.

17
[ 141-82-2 ]
[ 90-04-0 ]
[ 32608-29-0 ]
[ 7056-72-6 ]