20146-59-2|4-Chloroquinolin-2(1H)-one| Ambeed

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Quality Control of [ 20146-59-2 ] Purity: 96% SDS Specification

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NMR

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Product Details of [ 20146-59-2 ]

CAS No. :	20146-59-2
Formula :	C₉H₆ClNO
M.W :	179.60
SMILES Code :	O=C1NC2=C(C=CC=C2)C(Cl)=C1
MDL No. :	MFCD00234492
InChI Key :	YJXTZWWKNXVRHA-UHFFFAOYSA-N
Pubchem ID :	298329

Safety of [ 20146-59-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H320-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 20146-59-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	49.58
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	32.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.77
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	1.68
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.18
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.	2.22
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	3.22
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.21

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.63
Solubility	0.422 mg/ml ; 0.00235 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.	-1.98
Solubility	1.86 mg/ml ; 0.0104 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	-4.22
Solubility	0.0108 mg/ml ; 0.00006 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	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.	-6.2 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)	1.5

Application In Synthesis of [ 20146-59-2 ]

* 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 [ 20146-59-2 ]

[ 20146-59-2 ] Synthesis Path-Downstream 1~35

1
[ 67-56-1 ]
[ 74857-00-4 ]
[ 20146-59-2 ]
[ 4295-05-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 493 - 499.

2
[ 20146-59-2 ]
[ 2759-28-6 ]
[ 91300-75-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 2100 - 2110.

3
[ 74857-00-4 ]
[ 20146-59-2 ]
[ 4295-05-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 493 - 499.

5
[ 703-61-7 ]
[ 105-13-5 ]
[ 20146-59-2 ]
[ 733053-60-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7154 - 7159.

6
[ 20146-59-2 ]
[ 109-76-2 ]
[ 913253-72-2 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7154 - 7159.

7
[ 20146-59-2 ]
[ 934687-48-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sulfuric acid; nitric acid; at 0℃; for 1h;	A mixture of 4-chloro-1/-/-quinolin-2-one (from step 1 ; 17.8 g, 98.9 mmol) in sulfuric acid (52.7 mL, 989 mmol) was cooled to 0 C. Nitric acid (70%) (9.9 mL, 109 mmol) was added dropwise. The solution was stirred at 0 C for 1 h and then poured onto ice water. The yellow precipitate that formed was filtered and washed with water, methanol, ethyl acetate and diethyl ether before being stirred under vacuum at 120 C for approx. 10 min affording 4-chloro-6-nitroquinolin-2(1/-/)-one (21.5 g, 97%) as a pale yellow solid. LCMS (Method T2) RT 1.27 min; m/z 225.01 [M+H]+.
21.5 g	With sulfuric acid; nitric acid; at 0℃; for 1h;	A mixture of 4-chloro-1 H-quinolin-2-one (17.8 g, 98.9 mmol) in sulfuric acid (52.7 mL, 989 mmol) was cooled to 0 00. Nitric acid (70%) (9.90 mL, 109 mmol) was added dropwise. The solution was stirred at 0 00 for 1 h and then poured onto ice water. The yellow precipitate that formed was filtered and washed with water, methanol, ethyl acetate and diethyl ether before being stirred under vacuum at 120 00 for -10 mins affording 4-chloro-6-nitro-1H- quinolin-2-one (21.5 g) as a pale yellow solid. LCMS (Method T2) Rt = 1.27 mins, mlz 225.01 [M+H]+.

References: [1]Patent: WO2019/197842,2019,A1 .Location in patent: Paragraph 00349.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1527 - 1531.
[3]Patent: WO2018/215798,2018,A1 .Location in patent: Paragraph 00342.

8
[ 703-61-7 ]
[ 20146-59-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride; In 1,4-dioxane; water; for 18h;Reflux;	To a stirred solution of 2,4-dichloroquinoline (24.9 g, 126 mmol) in 1 ,4-dioxane (126 ml_) was added cone. HCI (83.8 ml_, 1.01 mol) dropwise. The reaction mixture was refluxed for 18h. The mixture was cooled to room temperature, poured into excess ice water and allowed to stir for 1 h. The precipitate was filtered and dried under vacuum to afford 4- chloroquinolin-2(1/-/)-one (19.2 g, 85%) as an off-white solid. LCMS (Method T2) RT 1.25 min; m/z 180.03 [M+H]+.
	With hydrogenchloride; In 1,4-dioxane;Heating / reflux;	To a solution of optionally substituted 2,4-dichloroquinoline (10.0 mmol) in 1,4- dioxane (20 mL) was added HCl (6 N, 30 mL). The mixture was refluxed overnight. After cooling, 200 mL of water was added and precipitate was formed. The precipitate was collected and dried under vacuum. To the dry solid was added anhydrous acetone (50 mL), K2CO3 (2 equiv.) and MeI (5 equiv.). The mixture was heated to reflux overnight. The insoluble solid was filtered off and the solution was dried and purified on a column. The yields were around 50% for the two steps.
19.2 g	With hydrogenchloride; water; In 1,4-dioxane; for 19h;Reflux;	To a stirred solution of 2,4-dichloroquinoline (24.9 g, 126 mmol) in 1,4-dioxane (126 mL) was added conc. HCl (83.8 mL, 1.01 mol) drop-wise. The reaction mixture was refluxed for 18 h. The mixture was cooled to room temperature, poured into excess ice water and allowed to stir for 1 h. The precipitate was filtered and dried under vacuum to afford 4-chloro- 1 H-quinolin-2-one (19.2 g) as an off-white solid. LCMS (Method T2) Rt = 1.25 mins, mlz 180.03 [M+H]+.

References: [1]Patent: WO2019/197842,2019,A1 .Location in patent: Paragraph 00348.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 5419 - 5434.
[3]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 5995 - 6005.
[4]Patent: WO2008/24423,2008,A2 .Location in patent: Page/Page column 40-41.
[5]Patent: WO2018/215798,2018,A1 .Location in patent: Paragraph 00341.
[6]Bioorganic Chemistry,2019,vol. 90.
[7],2020.

9
[ 20146-59-2 ]
[ 74-88-4 ]
[ 1009360-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone;Heating / reflux;	To a solution of optionally substituted 2,4-dichloroquinoline (10.0 mmol) in 1,4- dioxane (20 mL) was added HCl (6 N, 30 mL). The mixture was refluxed overnight. After cooling, 200 mL of water was added and precipitate was formed. The precipitate was collected and dried under vacuum. To the dry solid was added anhydrous acetone (50 mL), K2CO3 (2 equiv.) and MeI (5 equiv.). The mixture was heated to reflux overnight. The insoluble solid was filtered off and the solution was dried and purified on a column. The yields were around 50% for the two steps.

References: [1]Patent: WO2008/24423,2008,A2 .Location in patent: Page/Page column 40-41.

10
[ 4637-59-6 ]
[ 20146-59-2 ]

Yield	Reaction Conditions	Operation in experiment
	With water; potassium carbonate; p-toluenesulfonyl chloride; In chloroform; at 20℃; for 5h;	To 30 mL of a chloroform solution containing 910 mg of 4-chloroquinoline N-oxide, 1.21 g of p-toluenesulfonyl chloride and 10 mL of an aqueous solution containing 2.47 g of potassium carbonate were added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was added with water, the organic layer was separated, the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; chloroform : methanol = 4 : 1] to obtain 560 mg of a pale yellow solid, 4-chloroquinolin-2(1H)-one. 1H-NMR (CDCl3) delta: 6.88 (1H, s), 7.27-7.37 (1H, m), 7.38-7.45 (1H, m), 7.54-7.65 (1H, m), 7.97 (1H, dd, J=8.4, 1.3 Hz)

References: [1]Patent: EP1900732,2008,A1 .Location in patent: Page/Page column 112.

11
[ 20146-59-2 ]
6-amino-4-chloro-2(1H)-quinolinone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1527 - 1531.

12
[ 20146-59-2 ]
6-[bis-(2,2,2-trifluoro-ethyl)-amino]-4-chloro-1<i>H</i>-quinolin-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1527 - 1531.

13
[ 20146-59-2 ]
4-[3-(3,4-dichloro-benzylamino)-propylamino]-1<i>H</i>-quinolin-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7154 - 7159.

14
[ 62-53-3 ]
α-chloro-propionic acid amide [ No CAS ]
[ 20146-59-2 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7154 - 7159.

15
[ 20146-59-2 ]
[ 91300-80-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 2100 - 2110.

16
[ 20146-59-2 ]
[ 93392-72-4 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 2100 - 2110.

17
[ 20146-59-2 ]
[ 93392-71-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 2100 - 2110.

18
[ 20146-59-2 ]
[ 881204-44-0 ]
C₂₅H₂₂N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	at 130 - 160℃;	A mixture of 4-chloro- 2(lH)-quinolinone (0.0011 mol) and intermediate 2 (0.0016 mol) was stirred at 13O0C for 5 hours, then stirred at 16O0C overnight and brought to room temperature. The residue was purified by column chromatography over silica gel (35-70mum) (eluent: DCMZMeOHZNH4OH 95Z5Z0.1). The pure fractions were collected and the solvent was evaporated. The residue (0.12g) was taken up in acetonitrile. The precipitate was filtered off and dried, yielding 0.045g (10%) of compound 3, melting point 2380C.

References: [1]Patent: WO2006/32631,2006,A1 .Location in patent: Page/Page column 66.

19
[ 4360-63-8 ]
[ 20146-59-2 ]
[ 917835-14-4 ]

Yield	Reaction Conditions	Operation in experiment
		To 20 mL of an N,N-dimethylformamide solution containing 540 mg of <strong>[20146-59-2]4-chloroquinolin-2(1H)-one</strong>, 376 mg of 60% sodium hydride was added, and the mixture was stirred at room temperature for 1 hour. Thereto was added 3.2 mL of 2-bromomethyl-1,3-dioxolane, and the mixture was stirred at 90C for 16 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and 1 mol/L hydrochloric acid were added thereto. The organic layer was separated, the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate : hexane = 1 : 1] to obtain 165 mg of a white solid, 1-(1,3-dioxolan-2-ylmethyl)-<strong>[20146-59-2]4-chloroquinolin-2(1H)-one</strong>. 1H-NMR (CDCl3) delta: 3.84-3.92 (2H, m), 3.99-4.05 (2H, m), 4.54 (2H, d, J=4.4 Hz), 5.25 (1H, t, J=4.4 Hz), 6.91 (1H, s), 7.24-7.37 (1H, m), 7.60-7.68 (2H, m), 8.02 (1H, d, J=7.9 Hz)

References: [1]Patent: EP1900732,2008,A1 .Location in patent: Page/Page column 112-113.

20
[ 20146-59-2 ]
[ 110216-76-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 5995 - 6005.

21
[ 20146-59-2 ]
[ 105-39-5 ]
[ 1380598-33-3 ]
[ 1380598-41-3 ]

Yield	Reaction Conditions	Operation in experiment
20%; 80%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 14h;	General procedure: To a solution of starting <strong>[20146-59-2]4-chloro-1H-quinolin-2-one</strong>s (0.005 mol, 1e, 1.045 g) in 40 mL of DMF and K2CO3, chloroacetamide (0.01 mol) or ethylchloroacetate (0.01 mol) was added. The resulting solution was stirred at room temperature for 14-18 h. After completion of the reaction, it was checked by TLC, and the mixture was poured into crushed ice and then filtered, dried. The mixture was purified by column chromatography using petroleum ether and ethyl acetate (95:5) as eluent.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3230 - 3232.

22
[ 20146-59-2 ]
[ 79-07-2 ]
[ 1380598-38-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h;	General procedure: To a solution of starting <strong>[20146-59-2]4-chloro-1H-quinolin-2-one</strong>s (0.005 mol, 1e, 1.045 g) in 40 mL of DMF and K2CO3, chloroacetamide (0.01 mol) or ethylchloroacetate (0.01 mol) was added. The resulting solution was stirred at room temperature for 14-18 h. After completion of the reaction, it was checked by TLC, and the mixture was poured into crushed ice and then filtered, dried. The mixture was purified by column chromatography using petroleum ether and ethyl acetate (95:5) as eluent.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3230 - 3232.

23
[ 20146-59-2 ]
[ 74-88-4 ]
[ 32262-17-2 ]