[ CAS No. 403-19-0 ] {[proInfo.proName]}

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Quality Control of [ 403-19-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 403-19-0 ]

SDS Specification

Alternatived Products of [ 403-19-0 ]

Product Citations

Quinolone-3-amidoalkanol: A New Class of Potent and Broad-Spectrum Antimicrobial Agent

Dube, Phelelisiwe S. ; Angula, Klaudia T. ; Legoabe, Lesetja J. , et al. ACS Omega,2023,8(19):17086-17102. DOI: 10.1021/acsomega.3c01406 PubMed ID: 37214682

Abstract: Herein, we describe 39 novel quinolone

Purchased 98% after 30 min in the presence of human, rat, and mouse liver microsomes. Several compounds thus reported here are promising leads for the treatment of diseases caused by infectious agents.

from AmBeed: class="">403-19-0 ; class="">636-93-1 ; class="">5847-59-6 ; class="">87-13-8 ; class="">1548-61-4 ; class="">99-53-6 ; class="">402-49-3 ; class="">619-08-9 ; class="">18880-00-7 ; class="">111-41-1 ; class="">619-10-3 ; class="">766-80-3 ; class="">140-75-0 ; class="">823-78-9 ; class="">622-95-7 ; class="">402-23-3 ; class="span_more span_less">141776-91-2 class="keywords_more email-color more_span" onclick="change_span_more(this)">...More

Product Details of [ 403-19-0 ]

CAS No. :	403-19-0	MDL No. :	MFCD00051970
Formula :	C₆H₄FNO₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	ORPHLVJBJOCHBR-UHFFFAOYSA-N
M.W :	157.10	Pubchem ID :	9825
Synonyms :

Calculated chemistry of [ 403-19-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	37.24
TPSA :	66.05 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.18
Log Po/w (XLOGP3) :	2.12
Log Po/w (WLOGP) :	1.86
Log Po/w (MLOGP) :	0.7
Log Po/w (SILICOS-IT) :	-0.35
Consensus Log Po/w :	1.1

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.49
Solubility :	0.512 mg/ml ; 0.00326 mol/l
Class :	Soluble
Log S (Ali) :	-3.14
Solubility :	0.114 mg/ml ; 0.000727 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.47
Solubility :	5.34 mg/ml ; 0.034 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.64

Safety of [ 403-19-0 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501	UN#:	3077
Hazard Statements:	H302-H315-H317-H318-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 403-19-0 ]

* 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.

Upstream synthesis route of [ 403-19-0 ]
Downstream synthetic route of [ 403-19-0 ]

[ 403-19-0 ] Synthesis Path-Upstream 1~1

1
[ 403-19-0 ]
[ 13790-39-1 ]
[ 228559-87-3 ]

Reference： [1] Patent: EP1243582, 2002, A1,

[ 403-19-0 ] Synthesis Path-Downstream 1~10

1
[ 455-93-6 ]
[ 403-19-0 ]

Reference： [1]Journal of the Chemical Society,1949,p. 642,645

2
[ 403-19-0 ]
[ 168268-00-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4686 - 4691
[2]Chinese Chemical Letters,2010,vol. 21,p. 1326 - 1329
[3]Patent: WO2005/30140,2005,A2
[4]Molecules,2019,vol. 24

3
[ 403-19-0 ]
[ 455-93-6 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 2557 - 2564

4
[ 7583-53-1 ]
[ 403-19-0 ]
[ 837421-40-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; at 60℃; for 2.5h;Product distribution / selectivity;	General Scheme J; General Method J; Preparation of 3- (2-Fluoro-4-nitrophenoxymethyl)-1-methylpiperidine; 3-Hydroxymethyl-l-methylpiperidine (2 g, 9.66 mmol) was dissolved in DCM (15 mL), the solution was cooled to 0 °C and methanesulfonyl chloride (0.9 mL, 11.6 mmol) was added dropwise. The reaction was then allowed to warm up to room temperature and left stirring for 24 h. After this time water (20 mL) was added to the reaction and the organic layer was separated, dried over Na2S04, filtered and solvent removed to give a colorless oil. 1H NMR indicated a mixture of the starting piperidine and the desired product. This was then dissolved in acetonitrile (30 mL) along with 2-fluoro-4-nitrophenol (1.52 g. , 9.66 mmol) ; potassium carbonate (2.67 g. , 19.32 mmol) was added and the reaction was heated at 90 °C for 18 h, then allowed to cool to room temperature. The solids were filtered and solvent removed from the filtrate. This gave 3.5 g of an orange oil. Column chromatography (5percent MeOH/DCM) gave a yellow solid which was shown to be a mixture of 2-fluoro-4-nitrophenol and 3-(2-fluoro-4-nitrophenoxymethyl)-1- methylpiperidine. The material was partitioned between DCM (30 mL) and saturated potassium carbonate solution (30 mL). The DCM layer was removed and washed with 5M HC1 (20 mL). The acidic layer was then basified to pH 10 and extracted twice with DCM (30 mL). The organics combined, dried over Na2SO4, filtered and solvent removed to give 3-(2-fluoro-4-nitrophenoxymethyl)-1- methylpiperidine as a yellow oil. 1NMR (400 MHz, (CD30D) 8.16-8. 06 (2 H, m), 7. 33 (1 H, t, J8. 8), 4.17 (1 H, m), 4.09 (1 H, m), 3. 32 (1 H, d, J 10. 8), 3.02 (1 H, t, J 11.5), 2.47 (3 H, s), 2.22 (3 H, m), 1. 89 (3 H, m), 1.75 (1 H, m), 1. 28 (1 H, m).; Alternatively, the nitro derivative was prepared as follows: 3,4-Difluoronitro phenol (3 g, 18. 7 mmol) and 3-hydroxy-1-methylpiperidine (2.5 g, 19.3 mmol) were dissolved in dry THF (100 mL) under nitrogen. Sodium hydride (60percent, 1 g, 25 mmol) was slowly added under positive nitrogen pressure. The resulting light yellow solution was heated at 60 °C for 2.5 h. The dark-red solution was left to cool to room temperature and quenched with a solution of acetic acid (0.3 mL, 5.2 mmol) in methanol (10 mL). Solvent was removed under reduced pressure to yield an orange solid that was purified by column chromatography using DCM: MeOH (75: 25) as eluent to yield 3- (2-fluoro-4-nitro phenoxymethyl)-l- methylpiperidine as an orange oil.

Reference： [1]Patent: WO2005/42518,2005,A2 .Location in patent: Page/Page column 68-69

5
[ 455-93-6 ]
[ 403-19-0 ]
[ 636-93-1 ]
[ 452-11-9 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 1925 - 1934

6
[ 68500-37-8 ]
[ 403-19-0 ]
[ 1039046-51-9 ]

Yield	Reaction Conditions	Operation in experiment
64.1%	With N-ethyl-N,N-diisopropylamine; In toluene; for 24h;Reflux;	Add <strong>[68500-37-8]4-chloro-7-methoxyquinoline</strong> 5.0g (25.91mmol), 2-fluoro-4-nitrophenol 4.1g (25.91mmol), toluene 50mL and DIPEA 10.1g (77.73mmol) in a 100 mL single-necked flask. After 24 hours of reflux reaction, the reaction was complete by TLC.The reaction liquid was cooled to room temperature, and sand was obtained. Column chromatography gave 5.2 g of pale yellow solid, yield 64.1%
49%	With pyridine; dmap; In 1,4-dioxane; at 110℃; for 16h;Inert atmosphere;	To <strong>[68500-37-8]4-chloro-7-methoxyquinoline</strong> (0.900 g, 4.6 mmol), 2-fluoro-4-nitrophenol (2.3 g, 14 mmol), and N,N-dimethylpyridin-4-amine (0.068 g, 0.56 mmol) was added dioxane (10 mL) and pyridine (6.4 ml, 79 mmol). The resulting mixture was heated at 110 0C in an argon-purged sealed tube for 16 hours. An aliquot was analyzed by LCMS and indicated the presence of desired product. The reaction mixture was concentrated in vacuo and diluted with 2 N NaOH. The resulting solid was filtered, and the filtrate was extracted with CH2CI2. The organic layers were dried over sodium sulfate and filtered through a pad of silica gel along with the solids using 10% MeOH/CH2Cl2 as eluent. The collected fractions were concentrated in vacuo to yield 4-(2-fluoro-4-nitrophenoxy)-7- methoxyquinoline (0.900 g, 2.3 mmol, 49% yield) as a brownish solid. Calcd for Ci6H11FN2O4: [M]+= 314. Found: [M+H]+= 315.

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3688 - 3691
[2]Patent: CN109896997,2019,A .Location in patent: Paragraph 0067; 0078-0080
[3]Patent: WO2010/19473,2010,A1 .Location in patent: Page/Page column 31

7
[ 188577-69-7 ]
[ 403-19-0 ]
[ 1415797-76-0 ]

Yield	Reaction Conditions	Operation in experiment
16%	With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; at 120℃; for 24.0h;	<strong>[188577-69-7]3,4-dichloro-2-aminopyridine</strong> (500 mg, 3.07 mmol, prepared with reference to document: Synthetic Communications, 1997, 27(5), 861-870.) and 2-fluoro-4-nitrophenol (1.928 g, 12.27 mmol) were heated to 120 C. and melted, and stirred for 24 hrs. The molten was cooled to room temperature, and subjected to silica gel column chromatography (the eluent was dichloromethane to dichloromethane/methanol=50/1) for purification, to obtain a white solid (137 mg, 16%). 1H NMR (DMSO-d6, 300 MHz) delta 8.38 (dd, 1H, J=10.5, 2.4 Hz), 8.148.09 (m, 1H), 7.86 (d, 1H, J=5.4 Hz), 7.427.36 (m, 1H), 6.60 (br, 2H), 6.27 (d, 1H, J=5.4 Hz).

Reference： [1]Patent: US2014/206679,2014,A1 .Location in patent: Paragraph 0214; 0215

8
[ 403-19-0 ]
[ 74420-05-6 ]
C₁₄H₁₀FN₃O₃ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 143,p. 266 - 275
[2]Bioorganic and medicinal chemistry letters,2019

9
[ 403-19-0 ]
[ 1394820-98-4 ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 6277 - 6292
[2]European Journal of Medicinal Chemistry,2020,vol. 192

10
[ 417721-36-9 ]
[ 403-19-0 ]
C₁₇H₁₂FN₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 160℃; for 2h;	Compound 4 (1.8 g, 7.63 mmol), NMP (40 mE), Compound la (1.797 g, 11.45 mmol) and DIPEA(5.9 g, 45.78 mmol) were sequentially added to a 150 mE three-necked flask. The mixture was heated to 160 C. for 2 hours. Afier cooling to room temperature, the reaction mixture was added to water to precipitate a solid. The mixture was filtered, and the filter cake was washed with water and dried to give Intermediate 5 (2.2 g, 80% yield) as a gray solid. ECMS showed a molecular ion peak mIz[MH]: 358.1.

Reference： [1]Patent: US2019/169163,2019,A1 .Location in patent: Paragraph 0041; 0042; 0044

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Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Chan-Lam Coupling Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Friedel-Crafts Reaction ? Halogenation of Phenols ? Hydrogenolysis of Benzyl Ether ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Reactions of Benzene and Substituted Benzenes ? Reimer-Tiemann Reaction ? Vilsmeier-Haack Reaction

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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
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. 403-19-0 ] {[proInfo.proName]}

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[ 403-19-0 ] Synthesis Path-Upstream 1~1

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Fluorinated Building Blocks

Aryls

Nitroes

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