Category: 33537-99-4

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Integrating Hydrogen Production with Aqueous Selective Semi-Dehydrogenation of Tetrahydroisoquinolines over a Ni2P Bifunctional Electrode

Exploring an alternative anodic reaction to produce value-added chemicals with high selectivity, especially integrated with promoted hydrogen generation, is desirable. Herein, a selective semi-dehydrogenation of tetrahydroisoquinolines (THIQs) is demonstrated to replace the oxygen evolution reaction (OER) for boosting H2 evolution reaction (HER) in water over a Ni2P nanosheet electrode. The value-added semi-dehydrogenation products, dihydroisoquinolines (DHIQs), can be selectively obtained with high yields at the anode. The controllable semi-dehydrogenation is attributed to the in situ formed NiII/NiIII redox active species. Such a strategy can deliver a variety of DHIQs bearing electron-withdrawing/donating groups in good yields and excellent selectivities, and can be applied to gram-scale synthesis. A two-electrode Ni2P bifunctional electrolyzer can produce both H2 and DHIQs with robust stability and high Faradaic efficiencies at a much lower cell voltage than that of overall water splitting.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics.In a document type is Article, the author is Farha, Maya A. and a compound is mentioned, 33537-99-4, 6-Chloro-1,2,3,4-tetrahydroisoquinoline, introducing its new discovery. 33537-99-4

Designing analogs of ticlopidine, a wall teichoic acid inhibitor, to avoid formation of its oxidative metabolites

The thienopyridine antiplatelet agent, ticlopidine and its analog, clopidogrel, have been shown to potentiate the action of beta-lactam antibiotics, reversing the methicillin-resistance phenotype of methicillin-resistant Staphylococcus aureus (MRSA), in vitro. Interestingly, these thienopyridines inhibit the action of TarO, the first enzyme in the synthesis of wall teichoic acid, an important cell wall polymer in Gram-positive bacteria. In the human body, both ticlopidine and clopidogrel undergo a rapid P450-dependent oxidation into their respective antiplatelet-active metabolites, resulting in very low plasma concentrations of intact drug. Herein, a series of analogs of ticlopidine and clopidogrel that would avoid oxidative metabolism were designed, prepared and evaluated as inhibitors of TarO. Specifically, we replaced the P450-labile thiophene ring of ticlopidine and clopidogrel to a more stable phenyl group to generate 2-(2-chlorobenzyl)-1,2,3,4-tetrahydro- isoquinoline) (6) and (2-chloro-phenyl)-(3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid methyl ester (22), respectively. The latter molecules displayed inhibitory activity against TarO and formed the basis of a library of analogs. Most synthesized compounds exhibited comparable efficacy to ticlopidine and clopidogrel. So far, it was introduction of a trifluoromethyl group to compound 6, to generate 2-(2-trifluoromethyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline (13) that exhibited enhanced activity against TarO. Compound 13 represents a novel stable inhibitor of TarO with synergistic impact on beta-lactam antibiotics against MRSA and low potential for P-450 metabolism.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

In an article, published in an article,authors is Bojarski, Andrzej J., once mentioned the application of 33537-99-4, Name is 6-Chloro-1,2,3,4-tetrahydroisoquinoline,molecular formula is C9H10ClN, is a conventional compound. this article was the specific content is as follows. 33537-99-4

Substituted 2-(1,2,3,4-tetrahydroisoquinoline)-butyl derivatives of azaspiro[4.5]decane-7,9-dione and phthalimide as new 5-HT1a and 5-HT2a receptor ligands

Two series of 2-butyl-8-azaspiro[5,4]decane-7,9-dione (a) and N-phthalimidobutyl (b) derivatives of 1,2,3,4-tetrahydroisoquinoline (THIQ) were synthesized. The impact of substituent variations in the aromatic part of the THIQ moiety on 5-HT1A and 5-HT2A receptor affinities, as well as in vivo functional properties of the investigated compounds are discussed. It was found that those modifications improved 5-HT2A receptor affinity, but also slightly reduced the binding affinity for 5-HT1A receptors (in comparison with the unsubstituted THIQ derivatives 3a and 3b). The most active compound (8-Br,5-OCH3-THIQ – 8a) showed features of a 5-HT1A (postsynaptic)/5-HT2A receptor antagonist. Additionally, all chloro derivatives with high and equal affinity for 5-HT1A receptors revealed different functional properties, i.e. an agonistic activity of presynaptic 5-HT1A receptors (4a) and a partial agonistic activity of postsynaptic 5-HT1A receptors (4a, 6a) or an antagonistic activity of postsynaptic ones (5a).

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, name is 6-Chloro-1,2,3,4-tetrahydroisoquinoline, and cas is 33537-99-4, its synthesis route is as follows.

33537-99-4, To a solution of 6-chloro-1 ,2,3,4-tetrahydroisoquinoline (18.5 g, 0.1 1 mol) in CH3CN (180 mL) was added compound 2,3-dimethyl-1 -((2-methyl-1 H-imidazol-1 -yl)sulfonyl)- 1 H-imidazol-3-ium trifluoromethanesulfonate (43.5 g, 0.1 1 mol, Reference: J. Org. Chem. 2002, 68, 1 15-1 19.). The reaction mixture was stirred overnight at 30 C. The solvent was removed and the residue was purified by column chromatography on silica gel (0400) (EtOAc/Petroleum ether = 1 :1 ) to provide 6-chloro-2-(2-methyl-1 /-/-imidazol-1 -ylsulfonyl)- 1 ,2,3,4-tetrahydroisoquinoline. 1 H NMR (400 MHz, CDCI3): d 7.21 (m, 1 H), 7.18 (s, 1 H), 7.02 (m, 1 H), 6.94 (m, 1 H), 4.45 (s, 2H), 3.62 (m, 2H), 2.92 (m, 2H), 2.67 (s, 3H).

33537-99-4 is used more and more widely, we look forward to future research findings about 6-Chloro-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; KEZAR LIFE SCIENCES; JOHNSON, Henry; (166 pag.)WO2019/178510; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

6-Chloro-1,2,3,4-tetrahydroisoquinoline, cas is 33537-99-4, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

General procedure: 1,2,3,4-Tetrahydro-isoquinoline(1g, 7.5 mmol) was dissolved in 5 mL of anhydrous acetonitrile. Then to thissolution was slowly added 2-chloro- or 2-bromo-benzyl compound (7.5 mmol) and the reaction was carried out overnight at room temperature. The solvent wasremoved under reduced pressure. The residue was resuspended in 1 ml of DMSO andpurified using C18 flash chromatography as described above.

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Reference£º
Article; Farha, Maya A.; Koteva, Kalinka; Gale, Robert T.; Sewell, Edward W.; Wright, Gerard D.; Brown, Eric D.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 3; (2014); p. 905 – 910;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

33537-99-4, 6-Chloro-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0232] To a stirring solution of 23 (1 mmol, 200mg) in dichloromethane and triethylamine (2mmol, 0.3ml) at roomtemperature was added N-bromosuccinimide (1.1mmol, 200mg). The reaction mixture was stirred at room temperaturefor 30min. Then 2.0 M NaOH aqueous solution was added and the reaction mixture was stirred at rt for another 1 h. Thereaction mixture as extracted with DCM. The combined organic layer was over MgSO4. The solvent was removed invacuo. The crude product 24 was used in the next step without further purification.

33537-99-4, As the paragraph descriping shows that 33537-99-4 is playing an increasingly important role.

Reference£º
Patent; Merck Sharp & Dohme Corp.; MA, Yao; SHIZUKA, Manami; GUZI, Timothy, J.; TIAN, Yuan; LAHUE, Brian, R.; WANG, Yaolin; SHIPPS, Gerald, W., Jr.; BOGEN, Stephane, L.; NAIR, Latha, G.; PAN, Weidong; VOSS, Matthew, E.; KIROVA-SNOVER, Margarita; CLAYTON, W. Brent; MICCOY, Mark, A.; LIU, Yuan; GIBEAU, Graig, R.; (152 pag.)EP2793890; (2016); B1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, name is 6-Chloro-1,2,3,4-tetrahydroisoquinoline, and cas is 33537-99-4, its synthesis route is as follows.,33537-99-4

A mixture of 5-bromo-2-pyrimidin-2-yl-pyrimidine (150 mg, 633 muiotaetaomicron, the product of step 3 in Example 1), 6-chloro-l,2,3,4-tetrahydroisoquinoline (127 mg, 759 muiotaetaomicron), Ruphos (11.8 mg, 25.3 muiotaetaomicron), Pd2(dba)3 (11.6 mg, 12.7 muiotaetaomicron) and sodium iert-butoxide (122 mg, 1.27 mmol) in dioxane (10 mL) was heated at 110 C with stirring overnight. After being cooled to rt, the resulting mixture was diluted with H20 and extracted with EA (50 mL) for three times. The combined EA layer was dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by prep-HPLC to give 6-chloro-2-(2-pyrimidin-2-ylpyrimidin-5-yl)-3,4-dihydro- lH-isoquinoline (10 mg) as light yellow solid. XH NMR (400 MHz, CDC13) delta ppm: 2.99 – 3.08 (m, 2 H), 3.72 (s, 2 H), 4.55 (s, 2 H), 7.15 – 7.20 (m, 1 H), 7.23 (s, 2 H), 7.31 – 7.36 (m, 1 H), 8.60 (s, 2 H), 8.96 (d, 2 H). MS obsd. (ESI+) [(M+H)+] : 324.

With the complex challenges of chemical substances, we look forward to future research findings about 6-Chloro-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

33537-99-4,33537-99-4, 6-Chloro-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 5-bromo-2-pyrimidin-2-yl-pyrimidine (150 mg, 633 muiotaetaomicron, the product of step 3 in Example 1), 6-chloro-l,2,3,4-tetrahydroisoquinoline (127 mg, 759 muiotaetaomicron), Ruphos (11.8 mg, 25.3 muiotaetaomicron), Pd2(dba)3 (11.6 mg, 12.7 muiotaetaomicron) and sodium iert-butoxide (122 mg, 1.27 mmol) in dioxane (10 mL) was heated at 110 C with stirring overnight. After being cooled to rt, the resulting mixture was diluted with H20 and extracted with EA (50 mL) for three times. The combined EA layer was dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by prep-HPLC to give 6-chloro-2-(2-pyrimidin-2-ylpyrimidin-5-yl)-3,4-dihydro- lH-isoquinoline (10 mg) as light yellow solid. XH NMR (400 MHz, CDC13) delta ppm: 2.99 – 3.08 (m, 2 H), 3.72 (s, 2 H), 4.55 (s, 2 H), 7.15 – 7.20 (m, 1 H), 7.23 (s, 2 H), 7.31 – 7.36 (m, 1 H), 8.60 (s, 2 H), 8.96 (d, 2 H). MS obsd. (ESI+) [(M+H)+] : 324.

33537-99-4,6-Chloro-1,2,3,4-tetrahydroisoquinolinebelongs to tetrahydroisoquinoline compound, is more and more widely used in various fields. and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 6-Chloro-1,2,3,4-tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 33537-99-4, its synthesis route is as follows.,33537-99-4

To a solution of (/:?)-A/-(3-aminobutyl)-4-(dimethylamino)benzenesulfonamide (0.88 g, 4.0 mmol) in CH3CN (10 ml.) was added 6-chloro-1 ,2,3,4-tetrahydroisoquinoline (1.98 g, 4.0 mmol). The reaction mixture was stirred at ambient temperature overnight. The mixture was concentrated and the residue was purified by column chromatography to provide (/:?)-6-chloro-A/-(4-(4-(dimethylamino)phenylsulfonamido)butan-2-yl)-3,4- dihydroisoquinoline-2(1 /-/)-sulfonamide.

With the complex challenges of chemical substances, we look forward to future research findings about 6-Chloro-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; KEZAR LIFE SCIENCES; JOHNSON, Henry; (166 pag.)WO2019/178510; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

6-Chloro-1,2,3,4-tetrahydroisoquinoline, cas is 33537-99-4, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

[0232] To a stirring solution of 23 (1 mmol, 200mg) in dichloromethane and triethylamine (2mmol, 0.3ml) at roomtemperature was added N-bromosuccinimide (1.1mmol, 200mg). The reaction mixture was stirred at room temperaturefor 30min. Then 2.0 M NaOH aqueous solution was added and the reaction mixture was stirred at rt for another 1 h. Thereaction mixture as extracted with DCM. The combined organic layer was over MgSO4. The solvent was removed invacuo. The crude product 24 was used in the next step without further purification.

33537-99-4, As the rapid development of chemical substances, we look forward to future research findings about 33537-99-4

Reference£º
Patent; Merck Sharp & Dohme Corp.; MA, Yao; SHIZUKA, Manami; GUZI, Timothy, J.; TIAN, Yuan; LAHUE, Brian, R.; WANG, Yaolin; SHIPPS, Gerald, W., Jr.; BOGEN, Stephane, L.; NAIR, Latha, G.; PAN, Weidong; VOSS, Matthew, E.; KIROVA-SNOVER, Margarita; CLAYTON, W. Brent; MICCOY, Mark, A.; LIU, Yuan; GIBEAU, Graig, R.; (152 pag.)EP2793890; (2016); B1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem