160893-07-2|2-Chloro-5-methoxyquinoline| Ambeed

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Quality Control of [ 160893-07-2 ] Purity: 95% SDS Specification

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Product Details of [ 160893-07-2 ]

CAS No. :	160893-07-2
Formula :	C₁₀H₈ClNO
M.W :	193.63
SMILES Code :	COC1=C2C=CC(Cl)=NC2=CC=C1
MDL No. :	MFCD22394142
InChI Key :	ACMDJXKHEUGSIS-UHFFFAOYSA-N
Pubchem ID :	11019719

Safety of [ 160893-07-2 ]

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

Computational Chemistry of [ 160893-07-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
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	53.25
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.	2.39
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	3.12
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.9
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.	2.05
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	3.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.7

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.51
Solubility	0.0599 mg/ml ; 0.00031 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.	-3.25
Solubility	0.108 mg/ml ; 0.000558 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	-4.45
Solubility	0.00692 mg/ml ; 0.0000357 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.	-5.27 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	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<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 [ 160893-07-2 ]

* 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 [ 160893-07-2 ]

[ 160893-07-2 ] Synthesis Path-Downstream 1~35

1
[ 186581-53-3 ]
[ 124467-35-2 ]
[ 160893-07-2 ]

References: [1]Heterocycles,1994,vol. 38,p. 2615 - 2620.

2
[ 160893-07-2 ]
[ 160893-04-9 ]

References: [1]Heterocycles,1994,vol. 38,p. 2615 - 2620.

3
(E)-N-(3-methoxyphenyl)-3-ethoxypropenamide [ No CAS ]
[ 49609-15-6 ]
[ 160893-07-2 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3130 - 3137.

4
[ 927804-72-6 ]
[ 160893-07-2 ]
Ethyl 3-(5-methoxyquinolin-2-ylamino)furo[2,3-c]pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride;XPhos; In 1,4-dioxane;Heating / reflux;	Step A: Ethyl 3-(5-methoxyquinolin-2-ylamino)furo[2,3-c]pyridine-2-carboxylate: <strong>[160893-07-2]2-chloro-5-methoxyquinoline</strong> (0.123 g, 0.635 mmol) and ethyl 3-aminofuro[2,3-c]pyridine-2-carboxylate (0.144 g, 0.70 mmol) were suspended in p-dioxane (6.0 mL) and degassed with Ar for 15 minutes. To this was added 1,3-bis(2,6-diisopropylphenyl)-1H-imidazole-3-ium chloride (0.054 g, 0.127 mmol), Pd2(dba)3 (0.058 g, 0.0635 mmol), and KOt-Bu (0.107 g, 0.953 mmol). The reaction was degassed with Ar for another 15 minutes and then reflux under Ar overnight, then cooled to ambient temperature, filtered through GF/F paper, rinsed with dichloromethane and concentrated. The crude product was purified by flash column chromatography, eluting with hexanes/ethyl acetate (4:1) to give the desired product (265 mg, 99%). MS (APCI) m/z 364.1 (M+1).

References: [1]Patent: US2007/49603,2007,A1 .Location in patent: Page/Page column 66-67.

5
[ 860434-15-7 ]
[ 160893-07-2 ]
C₃₂H₃₃N₃O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4232 - 4241.

6
[ 90924-16-6 ]
[ 160893-07-2 ]

Yield	Reaction Conditions	Operation in experiment
40.1 mg	With trichlorophosphate; In dichloromethane; at 60℃; for 3h;Inert atmosphere;	To solution of 5-methoxyquinoline 2a (104 mg, 0.66 mmol) in CH2Cl2 (3 mL) was added meta-chloroperoxybenzoic acid (195 mg, 1.13 mmol) at 0 C for 30 min. The mixture was allowed to warm to room temperature and stirred for additional 3 h. The reaction is queched with 4 N NaOH and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure to give the crude N-oxide, which was directly used for the next step without purification. To solution of the resulting N-oxide in CH2Cl2 (2.5 mL) was adeed phosphorus oxychloride (0.09 mL, 0.99 mmol). The reaction mixture was refluxed at 60 C for 3 h, allowed to cool to room temperature and poured into ice-water. The resulting mixture was treated with 4 N aqueous NaOH until pH reached to around 10. The organic phase was extracted with CH2Cl2 (3 x 5 mL), washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (EtOA/CH2Cl2/Hexane = 1:2:4) to give 5-methoxy-2chloroquinoline 4a (40.1 mg, 32%)
40.1 mg	With trichlorophosphate; In dichloromethane; at 60℃; for 3h;Inert atmosphere;	General procedure: To solution of 5-methoxyquinoline 6a (104 mg, 0.66 mmol) in CH2Cl2 (3mL) was added meta-chloroperoxybenzoic acid (195 mg, 1.13 mmol) at 0 C for 30 min. The mixture was allowed to warm to room temperature and stirred for additional 3 h. The reaction is queched with 4 N NaOH and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure to give the crude N-oxide, which was directly used for the next step without purification. To solution of the resulting N-oxide in CH2Cl2 (2.5 mL) was adeed phosphorus oxychloride (0.09 mL, 0.99 mmol). The reaction mixture was refluxed at 60 C for 3 h, allowed to cool to room temperature and poured into ice-water. The resulting mixture was treated with 4 N aqueous NaOH until pH reached to around 10. The organic phase was extracted with CH2Cl2 (3 × 5 mL), washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (EtOAc/CH2Cl2/Hexane = 1:2:4) to give 2-chloro-5-methoxy-chloroquinoline 7a (40.1 mg, 32%) as a white solid:1HNMR (CDCl3, 300 MHz) delta 4.01 (s, 3H), 6.88 (dd, J = 7.2,1.5 Hz, 1H), 7.35 (d, J = 8.7 Hz, 1H), 7.59-7.67 (m, 2H),8.51 (d, J = 8.7 Hz, 1H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3307 - 3312.
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1472 - 1476.
[3]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 2304 - 2310.
[4]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.
[5]Chemical Biology and Drug Design,2017,vol. 89,p. 98 - 113.
[6]Patent: KR101778938,2017,B1 .

7
[ 578-67-6 ]
[ 160893-07-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1472 - 1476.
[2]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 2304 - 2310.
[3]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.
[4]Chemical Biology and Drug Design,2017,vol. 89,p. 98 - 113.
[5]Patent: KR101778938,2017,B1 .

8
[ 6931-19-7 ]
[ 160893-07-2 ]

Yield	Reaction Conditions	Operation in experiment
32%		Example 1 2-Chloro-5-methoxyquinoline [0085] After 5-methoxyquinoline (104.3 mg, 0.655 mmol) was dissolved in dichloromethane (3 mL), meta-chloroperbenzoic acid (mCPBA; 195 mg, 1.13 mmol) was added thereto at 0 C., and the resulting mixture was stirred for 30 min. After the stirring for 30 min, the reaction temperature was increased from 0 C. to room temperature, followed by further stirring for 3 hr. The completion of the reaction was confirmed by TLC (EtOAc/MC/Hexane=1:2:4). When the reaction was completed, the reaction mixture was extracted with an aqueous solution of 4 N NaOH and dichloromethane, to thereby separate an organic layer. The organic layer was dried over anhydrous MgSO4 and filtered. The resulting filtrate was concentrated under reduced pressure, to thereby generate a white solid. The thus generated solid was dissolved in dichloromethane (2.5 mL) and added with phosphorous oxychloride (POCl3; 0.09 mL, 0.992 mmol). The resulting mixture was subjected to distillation under reflux at 60 C. for 3 hr. The completion of the reaction was confirmed by TLC (EtOAc/CHCl3/Hexane=1:2:10). When the reaction was completed, the reactant was cooled down to room temperature, followed by further cooling down with the gentle addition of ice. The pH of the resulting mixture was then adjusted to 10 by dropwise addition of an aqueous solution of 4 N NaOH. When the pH was adjusted to 10, the reaction mixture was extracted with distilled water and dichloromethane, to thereby separate an organic layer. The organic layer was dried over anhydrous MgSO4 and filtered. The resulting filtrate was concentrated under reduced pressure and purified by column chromatography (EtOAc/CHCl3/Hexane=1:2:10, R.f: 0.6), to thereby obtain 2-chloro-5-methoxyquinoline (40.1 mg, 32%) as a white solid. [0086] 1H NMR (CDCl3, 300 MHz) delta 4.01 (s, 3H), 6.88 (dd, J=7.2, 1.5 Hz, 1H), 7.35 (d, J=8.7 Hz, 1H), 7.59-7.67 (m, 2H), 8.51 (d, J=8.7 Hz, 1H)

References: [1]Patent: US2014/206876,2014,A1 .Location in patent: Paragraph 0085-0086.
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1472 - 1476.
[3]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 2304 - 2310.
[4]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.
[5]Patent: KR101778938,2017,B1 .

9
[ 536-74-3 ]
[ 160893-07-2 ]
[ 1423778-31-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 80℃; for 24h;Inert atmosphere;	General procedure: To a solution of 2-chloroquinoline (29.7 mg, 0.182 mmole) in THF (1.5 mL) was added PdCl2(PPh3)2 (2.6 mg, 0.0037 mmole), CuI (1.5 mg, 0.0063 mmol). The reaction mixture was stirred for 5 min and triethylamine (0.15 mL) and phenylacetylene (0.03 mL, 0.27 mmol) were added. After the resulting mixture was stirred at 80 C for 24 h, it was allowed to cool to room temperature and filtered through a pad of Celite by the aid of EtOAc. The filtrate was treated with water and extracted with EtOAc (3 x 10 mL). The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel (EtOAc/hexane = 1:10) to give 2-(phenylethynyl)quinoline 5a (25 mg, 60%)
50%		General procedure: To a solution of <strong>[160893-07-2]2-chloro-5-methoxyquinoline</strong> (12.7 mg, 0.0656 mmole) in THF (1.5 mL) was added Pd(PPh3)4 (5.3 mg, 0.00459 mmol), CuI (3.3 mg, 0.017 mmol). The reaction mixture was stirred for 5 min and triethylamine (0.5 mL) and phenylacetylene (0.01 mL, 0.131 mmol) were added. After the resulting mixture was stirred at 80 C for 24 h, it was allowed to cool to room temperature and filtered through a pad of Celite by the aid of EtOAc. The filtrate was treated with water and extracted with EtOAc (3 × 10 mL). The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel (EtOAc/hexane = 1:10) to give 5-methoxy-2-(phenylethynyl)quinoline 3 (8.6 mg, 50%) as a white solid: mp 92-97 C; 1H NMR (CDCl3, 300 MHz) delta 4.05 (s, 3H), 6.91 (d, J= 7.5 Hz, 1H), 7.42-7.44 (m, 3H), 7.62-7.77 (m, 5H), 8.60(d, J = 8.7 Hz, 1H); 13C NMR (CDCl3, 100 MHz) delta 55.8,89.4, 89.9, 104.8, 119.6, 121.5, 122.2, 123.5, 128.4, 129.1,130.0, 131.0, 132.3, 143.9, 149.1, 155.0; GC/MS (EI): m/z:calcd for C18H13NO: 259.10, M+; found: 259.

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1472 - 1476.
[2]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 2304 - 2310.

10
[ 2510-23-8 ]
[ 160893-07-2 ]
[ 1423778-41-9 ]

Yield	Reaction Conditions	Operation in experiment
57%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 80℃; for 24h;Inert atmosphere;	General procedure: To a solution of 2-chloroquinoline (29.7 mg, 0.182 mmole) in THF (1.5 mL) was added PdCl2(PPh3)2 (2.6 mg, 0.0037 mmole), CuI (1.5 mg, 0.0063 mmol). The reaction mixture was stirred for 5 min and triethylamine (0.15 mL) and phenylacetylene (0.03 mL, 0.27 mmol) were added. After the resulting mixture was stirred at 80 C for 24 h, it was allowed to cool to room temperature and filtered through a pad of Celite by the aid of EtOAc. The filtrate was treated with water and extracted with EtOAc (3 x 10 mL). The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel (EtOAc/hexane = 1:10) to give 2-(phenylethynyl)quinoline 5a (25 mg, 60%)

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1472 - 1476.

11
[ 160893-04-9 ]
[ 160893-07-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With trichlorophosphate; for 1h;Reflux;	4.5 2-Chloro-5-methoxyquinoline (4) Phosphorus oxychloride (25.0 mL, 268.0 mmol) was added to compound 3 (2.65 g, 15.15 mmol) at rt and the resulting suspension was heated under reflux for 1 h. The reaction mixture was allowed to cool to rt, poured onto ice cold water (300 mL) and cautiously neutralized with diluted aqueous ammonium hydroxide in ice bath. The mixture was extracted with DCM (3 * 150 mL) and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure to afford the title compound; yellow solid; yield: 2.5 g (86%); 1H NMR (400 MHz, CDCl3) delta 8.46 (d, J = 8.8 Hz, 1H), 7.59 (dd, J = 10.0, 8.0 Hz, 2H), 7.31 (d, J = 8.4 Hz, 1H), 6.84 (t, J = 7.2 Hz, 1H), 3.97 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 155.17, 151.03, 148.61, 133.97, 130.80, 121.07, 120.37, 119.20, 104.81, 55.77.
86%	With trichlorophosphate; for 1h;Inert atmosphere; Reflux;	(5) under an argon atmosphere, manufactured by 5-methoxyquinolin-2(1H)-one (2.7 g, 15.2 mmol) was added phosphorus oxychloride (25.0 mL, 268.0 mmol) and the mixture was refluxed for 1 hour, The completion of the reaction was confirmed by TLC (hexane: ethyl acetate = 1: 1). The reaction mixture was poured into ice water (300 mL), After neutralization with ammonia water (65 mL) and extracted with dichloromethane (3 X 150 mL). The organic solvent layer was washed again with a saturated sodium chloride solution (450 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent to obtain the title compound (2.5 g, 86% yield).

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.
[2]Patent: KR101778938,2017,B1 .Location in patent: Paragraph 0147-0148; 0155; 0180-0182.

12
[ 160893-07-2 ]
4-((2-(3,5-bis(trifluoromethyl)benzamido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

13
[ 160893-07-2 ]
4-((2-(4-chloro-3-(trifluoromethyl)benzamido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

14
[ 160893-07-2 ]
6-chloro-N-(5-((2-(methylcarbamoyl)pyridin-4-yl)oxy)quinolin-2-yl)picolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

15
[ 160893-07-2 ]
N-(5-((2-(methylcarbamoyl)pyridin-4-yl)oxy)quinolin-2-yl)quinoline-6-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

16
[ 160893-07-2 ]
4-((2-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.
[2]Patent: KR101778938,2017,B1 .

17
[ 160893-07-2 ]
4-((2-(3-(2,4-dichlorophenyl)ureido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.
[2]Patent: KR101778938,2017,B1 .

18
[ 160893-07-2 ]
4-((2-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

19
[ 160893-07-2 ]
4-((2-(3-(2-chloro-5-(trifluoromethyl)phenyl)ureido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

20
[ 160893-07-2 ]
4-((2-(3-(3,4-dichlorophenyl)ureido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

21
[ 160893-07-2 ]
4-((2-(3-(4-chlorophenyl)ureido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

22
[ 160893-07-2 ]
4-((2-(3-(4-bromophenyl)ureido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

23
[ 160893-07-2 ]
4-((2-(3-(4-fluorophenyl)ureido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

24
[ 160893-07-2 ]
N-methyl-4-((2-(3-(4-(trifluoromethyl)phenyl)ureido)quinolin-5-yl)oxy)picolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

25
[ 160893-07-2 ]
N-methyl-4-((2-(3-(naphthalen-1-yl)ureido)quinolin-5-yl)oxy)picolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

26
[ 160893-07-2 ]
5-methoxyquinolin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With acetamide; potassium carbonate; In neat (no solvent); at 200℃; for 15h;	4.6 5-Methoxyquinolin-2-amine (5) A mixture of compound 4 (1.0 g, 5.2 mmol), acetamide (6.1 g, 103.3 mmol), and K2CO3 (3.6 g, 25.9 mmol) were fused at 200 C for 15 h. The reaction mixture was cooled, diluted with water (15 mL) and extracted with ethyl acetate (3 * 35 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure and the resultant residue was purified by flash column chromatography (hexane:ethyl acetate, 2:1 v/v) to afford the desired product as yellow solid; yield: 420 mg (47%); 1H NMR (400 MHz, CDCl3) delta 8.31 (d, J = 9.2 Hz, 1H), 7.48 (t, J = 8.4 Hz, 1H), 7.29 (d, J = 8.4 Hz, 1H), 6.68 (d, J = 8.8 Hz, 1H), 6.64 (d, J = 8.0 Hz, 1H), 5.29 (br. s, 2H), 3.96 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 157.30, 155.55, 147.88, 133.10, 130.04, 117.85, 115.11, 110.52, 101.73, 55.59.
47%	With acetamide; potassium carbonate; at 200℃; for 15h;Sealed tube;	To the sealed tube were added <strong>[160893-07-2]2-chloro-5-methoxyquinoline</strong> (1.0 g, 5.2 mmol) prepared in the above step (6), acetamide (6.1 g, 103.3 mnol), potassium carbonate (3.6 g, 25.9 mmol) was added thereto, followed by stirring at 200 C for 15 hours, The completion of the reaction was confirmed by TLC (hexane: ethyl acetate = 2: 1). The reaction mixture was cooled to room temperature, was added to water (15 mL) and extracted with ethyl acetate (3 X 35 mL). The organic solvent layer was washed with saturated sodium chloride solution (110 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The concentrate was separated and purified by column chromatography (hexane: ethyl acetate = 2: 1) to obtain the desired compound (420 mg, 47% yield).

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.
[2]Patent: KR101778938,2017,B1 .Location in patent: Sheet 0147-0148; 0155; 0185-0187.

27
[ 160893-07-2 ]
5-hydroxyquinolin-2-amine [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.
[2]Patent: KR101778938,2017,B1 .

28
[ 160893-07-2 ]
4-((2-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

29
[ 160893-07-2 ]
4-((2-(3-(2,4-difluorophenyl)ureido)quinolin-5-yl)oxy)-N-methylpicolin-amide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

30
[ 160893-07-2 ]
4-((2-aminoquinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.
[2]Patent: KR101778938,2017,B1 .

31
[ 160893-07-2 ]
4-((2-(2,4-dichlorobenzamido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.
[2]Patent: KR101778938,2017,B1 .

32
[ 160893-07-2 ]
4-((2-(3,5-dichlorobenzamido)quinolin-5-yl)oxy)-N-methylpicolinamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 754 - 768.

33
[ 160893-07-2 ]
N-(3-chlorophenyl)-5-hydroxyquinolin-2-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3307 - 3312.
[2]Chemical Biology and Drug Design,2017,vol. 89,p. 98 - 113.

34
[ 160893-07-2 ]
N-(3-(tert-butyl)phenyl)-5-hydroxyquinolin-2-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3307 - 3312.
[2]Chemical Biology and Drug Design,2017,vol. 89,p. 98 - 113.

35
[ 160893-07-2 ]
N-(4-isopropylphenyl)-5-hydroxyquinolin-2-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3307 - 3312.
[2]Chemical Biology and Drug Design,2017,vol. 89,p. 98 - 113.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Nomenclature of Ethers • Preparation of Ethers • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Ethers • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Related Functional Groups of
[ 160893-07-2 ]

Chlorides

A208944 [13676-02-3]

2-Chloro-6-methoxyquinoline

Similarity: 0.97

A173631 [577967-89-6]

2-Chloroquinolin-6-ol

Similarity: 0.92

A118584 [577967-81-8]

2-Chloro-6,7-dimethoxy-3-methylquinoline

Similarity: 0.90

A375530 [31568-91-9]

2-Chloroquinolin-8-ol

Similarity: 0.86

A446998 [70049-46-6]

2,4-Dichloro-6-methoxyquinoline

Similarity: 0.85

Ethers

A208944 [13676-02-3]

2-Chloro-6-methoxyquinoline

Similarity: 0.97

A118584 [577967-81-8]

2-Chloro-6,7-dimethoxy-3-methylquinoline

Similarity: 0.90

A446998 [70049-46-6]

2,4-Dichloro-6-methoxyquinoline

Similarity: 0.85

A264315 [343788-51-2]

8-(Benzyloxy)-2-chloroquinoline

Similarity: 0.84

A567361 [72407-17-1]

2,4-Dichloro-6,7-dimethoxyquinoline

Similarity: 0.83

Related Parent Nucleus of
[ 160893-07-2 ]

Quinolines

A208944 [13676-02-3]

2-Chloro-6-methoxyquinoline

Similarity: 0.97

A173631 [577967-89-6]

2-Chloroquinolin-6-ol

Similarity: 0.92

A118584 [577967-81-8]

2-Chloro-6,7-dimethoxy-3-methylquinoline

Similarity: 0.90

A375530 [31568-91-9]

2-Chloroquinolin-8-ol

Similarity: 0.86

A446998 [70049-46-6]

2,4-Dichloro-6-methoxyquinoline

Similarity: 0.85

Precautionary Statements-General
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P321
P322
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P378
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Storage
Code	Phrase
P401
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P411
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P413
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Disposal
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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Environmental hazards
Code	Phrase
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H401	Toxic to aquatic life
H402	Harmful to aquatic life
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 160893-07-2

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