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[ CAS No. 766-80-3 ] {[proInfo.proName]}

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Chemical Structure| 766-80-3

Chemical Structure| 766-80-3

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Quality Control of [ 766-80-3 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 766-80-3 ]

Product Citations

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

More

Abstract: Herein, we describe 39 novel quinolone compounds bearing a hydrophilic amine chain and varied substituted benzyloxy units. These compounds demonstrate broad-spectrum activities against acid-fast bacterium, Gram-pos. and -neg. bacteria, fungi, and leishmania parasite. Compound 30 maintained antitubercular activity against moxifloxacin-, isoniazid-, and rifampicin-resistant Mycobacterium tuberculosis, while 37 exhibited low micromolar activities (<1 μg/mL) against World Health Organization (WHO) critical pathogens: Cryptococcus neoformans, Acinetobacter baumannii, and Pseudomonas aeruginosa. Compounds in this study are metabolically robust, demonstrating % remnant of >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.

Purchased from AmBeed: 403-19-0 ; 636-93-1 ; 5847-59-6 ; 87-13-8 ; 1548-61-4 ; 99-53-6 ; 402-49-3 ; 619-08-9 ; 18880-00-7 ; 111-41-1 ; 619-10-3 ; 766-80-3 ; 140-75-0 ; 823-78-9 ; 622-95-7 ; 402-23-3 ; 141776-91-2 ...More

Product Details of [ 766-80-3 ]

CAS No. :	766-80-3	MDL No. :	MFCD00000597
Formula :	C₇H₆BrCl	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	LZIYAIRGDHSVED-UHFFFAOYSA-N
M.W :	205.47	Pubchem ID :	69838
Synonyms :

Safety of [ 766-80-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 766-80-3 ]

* 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 [ 766-80-3 ]
Downstream synthetic route of [ 766-80-3 ]

[ 766-80-3 ] Synthesis Path-Upstream 1~1

Reference： [1] Liebigs Annalen der Chemie, 1989, p. 1215 - 1232

[ 766-80-3 ] Synthesis Path-Downstream 1~12

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 3163 - 3168

Reference： [1]Liebigs Annalen der Chemie,1989,p. 1215 - 1232

3
[ 766-80-3 ]
[ 89-20-3 ]

Reference： [1]Journal of Organic Chemistry,1961,vol. 26,p. 2310 - 2316

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2942 - 2945

5
[ 93247-78-0 ]
[ 766-80-3 ]
C₁₇H₁₄ClNO₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3760 - 3763

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2230 - 2234

7
[ 1303587-99-6 ]
[ 766-80-3 ]
2-chloro-8-(3-chlorobenzyl)-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0℃; for 1h;Inert atmosphere;	Synthesis of 2-chloro-8-(3-chlorobenzyl)-7 , 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0455] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (100 mg, 0.58 mmol) in DMF (1 mL) under argon atmosphere was added sodium hydride (27 mg, 1.16 mmol) at 0 C. After stirring for 10 mins, l-(bromomethyl)-3-chlorobenzene (92 mg, 0.70 mmol) was added to the reaction mixture at 0 C and stirred for 1 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford 2-chloro-8-(3- chlorobenzyl)-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (160 mg, 93%) as an off- white solid. 1H-NMR (CD3OD, 400 MHz): delta 7.61 (s, 1H), 7.39-7.22 (m, 4H), 4.52 (s, 2H), 4.20-4.18 (m, 2H), 3.53-3.50 (m, 2H); LCMS: 295.8 (M+1); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 muiotaeta); RT 3.79 min 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 60% EtOAc/hexane (R 0.5).

Reference： [1]Patent: WO2015/66697,2015,A1 .Location in patent: Paragraph 0455

8
[ 185613-91-6 ]
[ 766-80-3 ]
4-(benzo[d][1,3]dioxol-5-yl)-N-(3-chlorobenzyl)thiazole-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.4%		4-(Benzo[d][1,3] dioxol-5-yl)thiazol-2-amine(2) (1.00 g, 4.54 mmol) and NaH (0.164 g, 6.82 mmol) to THF (15 ml) todissolved and then allowed to react at room temperature for 1 hour under a nitrogen stream. After dropwise addition of 3-chlorobenzylbromide (1.40 g, 6.82 mmol) slowly at room temperature and reacted for 10 minutes. After the reaction wasfinished, it was concentrated under reduced pressure and extracted three times into a saturated solution of NaHCO3 isdissolved in ethyl acetate. The ethyl acetate layer was separated and dried with anhydrous Na2SO4, then purified by columnchromatography (Ethyl acetate: Hexane = 1: 5) to give the compound 1f to give. Yield 17.4%
17%		General procedure: A solution of <strong>[185613-91-6]4-(benzo[d][1,3]dioxol-5-yl)thiazol-2-amine</strong> (1.0 equiv) and NaH (1.5 equiv) in THF was stirred at room temperature. After 1 h, benzyl bromide (1.5 equiv) was added and stirring was continued for 10 more min. The reaction progress was monitored by TLC. After completion of the reaction, quenched with saturated NH4Cl solution and extracted with EtOAc, the organic layer was dried over MgSO4, filtered, concentrated invacuo. The residue was purified by silica gel column chromatography (16% EtOAc/hexanes) to afford desired product.

Reference： [1]Patent: KR101651208,2016,B1 .Location in patent: Paragraph 0145-0147
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4854 - 4857

9
[ 766-80-3 ]
[ 186663-74-1 ]
tert-butyl (2-((3-chlorobenzyl)oxy)phenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃;Inert atmosphere;	General procedure: To a solution of the corresponding N-Boc-aminophenol (1 mmol) in DMF (2 mL), K2CO3 (207 mg,1.5 mmol) and the required benzyl bromide (1 mmol) were added. The mixture was stirred at 60 Cuntil no starting material was observed by TLC. A saturated aqueous solution of ammonium chloridewas added (5 mL) and the resulting mixture extracted with EtOAc (10 mL ×3), the organic extractswashed with brine (20 mL) and dried over MgSO4. The crude product was purified by FC eluting withhexane/EtOAc (95:5 ? 9:1).

Reference： [1]Synlett,2017,vol. 28,p. 471 - 474

10
[ 57611-47-9 ]
[ 766-80-3 ]
methyl (R)-1-benzyl-3-(3-chlorobenzyl)-4-oxopiperidine-3-carboxylate [ No CAS ]
methyl (S)-1-benzyl-3-(3-chlorobenzyl)-4-oxopiperidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a 10 mL reaction tube was added <strong>[57611-47-9]methyl 1-benzyl-4-oxopiperidine- 3-carboxylate</strong> 2c (49.5 mg, 0.2 mmol), 50% aq. KOH (112 mg, 1 mmol, 5 eq) and phase transfer catalyst 1k (12.1 mg, 0.02 mmol, 10 mol%) followed by p-xylene (1 mL). After the mixture was stirred at rt for 30 min, BnBr (71.3 uL, 0.6 mmol, 3 eq) was added, and the stirring was continued at rt for additional 12 h (monitored by TLC analysis). The crude product was purified by column flash chromatography (eluting with 20:1 hexane/EtOAc) to afford 3c (256 mg, 76% yield) as colorless transparent liquid.

Reference： [1]Synthetic Communications,2018,vol. 48,p. 2260 - 2271

11
[ 766-80-3 ]
[ 436-77-1 ]
C₅₈H₅₇Cl₃N₂O₆⁽²⁺⁾*2Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: The mixture of stirred DTET (100 mg, 0.16 mmol) and NaH (20 mg,0.83 mmol) was dissolved in 2 mL DMF at 0 C. Then, R1Br (0.5 mmol)dissolved in 0.5 mL DMF was added to the DTET solution, and themixture was stirred at 0 C for 6 h, then heated to 92 C until the TLCanalysis showed that the reaction was completed. The temperature ofthe mixture was cooled to room temperature and vacuum evaporated.The residue was purified using aluminum column chromatography, and4a-4 h were obtained using CH2Cl 2/CH3OH as the eluent.

Reference： [1]Bioorganic Chemistry,2019

12
[ 766-80-3 ]
[ 436-77-1 ]
C₄₄H₄₅ClN₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.1%		General procedure: The mixture of stirred DTET (100 mg, 0.16 mmol) and NaH (20 mg,0.83 mmol) was dissolved in 2 mL DMF at 0 C. Then, R1Br (0.18 mmol)dissolved in 0.5 mL DMF was added to the DTET solution, and themixture was stirred until the TLC analysis showed that the reaction wascompleted. The temperature of the mixture was cooled to room temperatureand vacuum evaporated. The residue was purified using aluminumcolumn chromatography, and 3a-3m were obtained usingCH2Cl2/CH3OH as the eluent

Reference： [1]Bioorganic Chemistry,2019

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Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Alkylbenzene ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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