63010-71-9|8-Fluoroquinolin-4-ol| Ambeed

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Quality Control of [ 63010-71-9 ] Purity: 98% SDS Specification

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Product Details of [ 63010-71-9 ]

CAS No. :	63010-71-9
Formula :	C₉H₆FNO
M.W :	163.15
SMILES Code :	OC1=CC=NC2=C(F)C=CC=C12
MDL No. :	MFCD00272395
InChI Key :	HTELWJVKZKSAQI-UHFFFAOYSA-N
Pubchem ID :	2737334

Safety of [ 63010-71-9 ]

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

Computational Chemistry of [ 63010-71-9 ] 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	3.0
Num. H-bond donors	1.0
Molar Refractivity	43.72
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	33.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.39
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	1.08
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.5
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.	1.61
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	2.38
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.79

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.15
Solubility	1.16 mg/ml ; 0.0071 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.	-1.37
Solubility	7.0 mg/ml ; 0.0429 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	-3.4
Solubility	0.0657 mg/ml ; 0.000403 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.	-6.53 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)	1.33

Application In Synthesis of [ 63010-71-9 ]

* 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 [ 63010-71-9 ]

[ 63010-71-9 ] Synthesis Path-Downstream 1~30

2
[ 63010-71-9 ]
[ 63010-72-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1015 - 1018.

3
[ 369395-32-4 ]
[ 63010-71-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1015 - 1018.

4
[ 63010-71-9 ]
N,N-diethyl-N'-(8-fluoro-quinolin-4-yl)-propane-1,3-diamine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1015 - 1018.

5
[ 63010-71-9 ]
[ 358-23-6 ]
8-fluoroquinolin-4-yl trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere;	To a solution of <strong>[63010-71-9]8-fluoroquinolin-4-ol</strong> (20 g, 122 mmol) in DCM (100 mL) and Et3N (25 g, 122.6 mmol) was slowly dropwised Tf2O (42g, 147 mmol) at 0 under N2. The mixture was stirred overnight at r.t. The mixture was quenched by H2O (30 mL) and extracted with DCM (100 mL 3). The organic layer was dried over with Na2SO4, filtered and concentrated to give crude product which was further purified by column chromatography, eluting with EA: PE=1: 10 to give the product (16.1 g, 45%). [M+H] +=296. To a solution of <strong>[63010-71-9]8-fluoroquinolin-4-ol</strong> (20 g, 123 mmoL) in DCM (200 mL) was added DIPEA (24 g, 185 mmol) at room temperature, followed by addition of trifluoromethanesulfonic anhydride (52 g, 185 mmol) drop wise at 0 and the mixture was stirred for 1 hour. Saturated aqueous of NaHCO3was added and extracted with DCM (100 mL×3) , combined the organic layer and the organic layer was evaporated under reduced pressure to give crude product, which was further purified by column chromatography (PE: EA=10: 1) to give product as an oil (24 g in 66%yield) .1H NMR (400 MHz, DMSO-d6) deltaH9.15 (d, J= 4.8 Hz, 1H) , 7.93 (dd, J= 1.2 Hz, J = 4.8 Hz, 1H) , 7.82-7.88 (m, 3H) , MS (ESI) m/e [M+1]+=295.9.

References: [1]Patent: WO2018/54365,2018,A1 .Location in patent: Paragraph 0348; 0349.
[2]Patent: WO2005/82871,2005,A2 .Location in patent: Page/Page column 102.

6
[ 63010-71-9 ]
8-fluoro-4-hydroxy-3-hydroxymethylquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With formaldehyd; In sodium hydroxide;	(a) 8-Fluoro-4-hydroxyquinoline was reacted with formaldehyde in aqueous sodium hydroxide to give the novel compound 8-fluoro-4-hydroxy-3-hydroxymethylquinoline, m.p. 176-178 (from dichloromethane).

References: [1]Patent: US4442109,1984,A .

7
[ 71083-06-2 ]
[ 63010-71-9 ]

References: [1]Collection of Czechoslovak Chemical Communications,2006,vol. 71,p. 978 - 990.

8
[ 63010-71-9 ]
[ 350-30-1 ]
[ 1033810-03-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16.0h;	2-Chloro-1-fluoro-4-nitrobenzene (2.15 g) and <strong>[63010-71-9]8-fluoroquinolin-4-ol</strong> (2.0 g) were dissolved in N,N-dimethylformamide (12 mL). Potassium carbonate (2.54 g) was added, and the mixture was stirred at room temperature for 16 hr. The mixture was partitioned between ethyl acetate (100 mL) and water (80 mL), and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=90:10?20:80) to give the title compound (3.27 g) as a white powder. 1H-NMR (DMSO-d6) delta: 6.96 (1H, d, J= 5.0 Hz), 7.60-7.80 (3H, m), 8.00-8.10 (1H, m), 8.30-8.40 (1H, m), 8.61 (1H, d, J= 3.0 Hz), 8.83 (1H, d, J= 5.0 Hz)

References: [1]Patent: EP2103620,2009,A1 .Location in patent: Page/Page column 93.

9
[ 63010-71-9 ]
trans-{4-[(8-fluoroquinolin-4-yl)oxy]cyclohexyl}methylamine [ No CAS ]

References: [1]Patent: WO2014/1247,2014,A1 .

10
[ 63010-71-9 ]
N-({trans-4-[(8-fluoroquinolin-4-yl)oxy]cyclohexyl}methyl)-4-fluorobenzamide [ No CAS ]

References: [1]Patent: WO2014/1247,2014,A1 .

11
[ 63010-71-9 ]
N-({trans-4-[(8-fluoroquinolin-4-yl)oxy]cyclohexyl}methyl)-3-methylisoxazole-4-carboxamide [ No CAS ]

References: [1]Patent: WO2014/1247,2014,A1 .

12
[ 63010-71-9 ]
tert-butyl N-[(cis-4-hydroxycyclohexyl)methyl]carbamate [ No CAS ]
tert-butyl N-({trans-4-[(8-fluoroquinolin-4-yl)oxy]cyclohexyl}methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;	General procedure: Building block Bl ieri-butyl-Ai-({ ira5-4-[(8-fluoroquinolin-4-yl)oxy]cyclohexyl }methyl)carbamate 8-Fluoroquinolin-4-ol (948 mg, 5.81 mmol), triphenylphosphine (1.52 g, 5.81 mmol) and DIAD (1.17 g, 5.81 mmol) were dissolved in tetrahydrofuran (140 mL). After adding ieri-butyl-.V-[(d.y-4- hydroxycyclohexyl)methyl]carbamate (1.11 g, 4.84 mmol), the reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, extracted with ethyl acetate and the combined organic phases were dried over sodium sulphate. After removal of the solvent residues and chromatographic purification of the residue, the product was obtained at 42% yield (960 mg). NMR (300 MHz, DMSO-d6) delta [ppm] 1.05 - 1.19 (m, 2 H), 1.35 (s, 9 H), 1.38 - 1.52 (m, 2 H), 1.70 - 1.82 (m, 2 H), 2.08 - 2.20 (m, 2 H), 2.80 (t, 2 H), 4.52 - 4.69 (m, 1 H), 6.84 (t, 1 H), 7.16 (d, 1 H), 7.39 - 7.61 (m, 2 H), 7.83 - 7.93 (m, 1 H), 8.69 (d, 1 H)

References: [1]Patent: WO2014/1247,2014,A1 .Location in patent: Page/Page column 28.

13
[ 63010-71-9 ]
(+/-)-(2-(2H-1,2,3-triazol-2-yl)phenyl)((2R,5S)-5-hydroxy-2-methylpiperidin-1-yl)methanone [ No CAS ]
C₂₄H₂₂FN₅O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 444 - 450.

14
[ 63010-71-9 ]
[ 1222491-29-3 ]
C₂₄H₂₂FN₅O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 444 - 450.

15
[ 63010-71-9 ]
[ 25294-59-1 ]
3-fluoro-8,8-dimethylfuro[3',4':5,6]pyrano[2,3,4-de]quinolin-10(8H)-one [ No CAS ]

References: [1]Chemical Communications,2017,vol. 53,p. 7824 - 7827.

16
[ 63010-71-9 ]
8-fluoro-4-(1,4-dioxaspiro[4.5] dec-7-en-8-yl)quinoline [ No CAS ]

References: [1]Patent: WO2018/54365,2018,A1 .

17
[ 63010-71-9 ]
4-(8-fluoroquinolin-4-yl)cyclohex-3-en-1-one [ No CAS ]

References: [1]Patent: WO2018/54365,2018,A1 .

18
[ 63010-71-9 ]
4-(8-fluoroquinolin-4-yl)cyclohexan-1-one [ No CAS ]