Author: Jessica.F

As a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, name is 6-Methoxy-1,2,3,4-tetrahydroisoquinoline, and cas is 42923-77-3, its synthesis route is as follows.,42923-77-3

To a cooled (0 oC) solution of 1,1?-carbonyldiimidazole (350 mg, 2.20 mmol) in anhydrous MeCN (25 mL) was added THIQ 14 (326 mg, 2.00 mmol) and K2CO3 (4.00 mmol). The resulting mixture was stirred at 24 oC for 18 h and then concentrated under reduced pressure to afford a residue which was purified by column chromatography (100% EtOAc) to give imidazole 15 (493 mg, 96%) as a colourless oil, Rf 0.31 (100% EtOAc). This intermediate was immediately used without further purification in the next synthetic step. 1H NMR (300 MHz, CDCl3): deltaH 7.86 (d, J 0.9 Hz, 1H, imidazole-H), 7.20 (d, J 1.4 Hz, 1H, imidazole-H), 7.05 (d, J 1.4 Hz, 1H, imidazole-H), 6.95-6.92 (m, 1H, ArH), 6.71-6.64 (m, 2H, ArH), 4.61 (s, 2H, ArCH2N), 3.78-3.67 (m, 5H, overlapping signals – NCH2 and OMe), 2.90 (t, J 6.0 Hz, 2H, ArCH2CH2). 13C NMR (75 MHz, CDCl3): deltaC 29.1 (ArCH2CH2), 44.7 (CH2CH2N), 48.3 (ArCH2N), 55.6 (OMe), 113.3 (ArCH), 113.9 (ArCH), 118.2 (ArCH), 124.1 (ArC), 127.6 (ArCH), 130.1 (ArCH), 135.3 (ArC), 137.1 (ArCH), 151.4 (C-O), 159.0 (C=O).

With the complex challenges of chemical substances, we look forward to future research findings about 42923-77-3,belong tetrahydroisoquinoline compound

Reference£º
Article; Mabank, Tanya; Alexandre, Kabamba B.; Pelly, Stephen C.; Green, Ivan R.; van Otterlo, Willem A.L.; Arkivoc; vol. 2019; 4; (2019);,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, name is 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid, and cas is 170097-67-3, its synthesis route is as follows.,170097-67-3

Intermediate 6: 1 ,1-Dimethylethyl 6-({ri-({5-chloro-2-r(cvclopropylmethyl)oxyl phenyllmethyl)- 5-methyl-1 /-/-pyrazol-3-yl1amino}carbonyl)-3,4-dihvdro-2(1 H)-isoquinolinecarboxylateTo a solution of 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6- isoquinolinecarboxylic acid (200 mg, 0.72 mmol), N-(3-dimethylaminopropyl)-N’- ethylcarbodiimide hydrochloride (158 mg, 0.82 mmol), 1-hydroxybenzotriazole hydrate (1 11 mg, 0.82 mmol) and diisopropylethylamine (1 15 mg, 0.89 mmol) in DCM (15 ml.) was added Intermediate 4 (200 mg, 0.69 mmol) and the mixture was stirred at room temperature for 4 days. The organic phase was then washed with HCI (1 N), NaOH (1 N) and brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM/EtOAc: 90/10 to give the title compound as yellow oil (316 mg, 84%). LC/MS: m/z 551 (M+H)+, Rt: 4.15 min.

With the complex challenges of chemical substances, we look forward to future research findings about 170097-67-3,belong tetrahydroisoquinoline compound

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/10560; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 57196-62-0, its synthesis route is as follows.,57196-62-0

(a) 6-Methoxy-2-(4-phenylbenzyl)-1,2,3,4-tetrahydroisoquinoline 4.0 g of 6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride, 4.1 g of 4-chloromethylbiphenyl and 6.0 g of finely powdered potassium carbonate in 50 ml of dimethylformamide are stirred at 80 for 5 hours. The solvent is removed in vacuo, the residue is taken up in water/methylene chloride, the organic phase is shaken twice with water, and the organic phase is dried with magnesium sulfate and evaporated in a rotary evaporator. The crude product, which is only slightly impure, can be reacted further without further purification. A sample recrystallized from ethyl acetate has a melting point of 120.

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

Reference£º
Patent; Hoechst Aktiengesellschaft; US4717724; (1988); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO434,mainly used in chemical industry, its synthesis route is as follows.,42923-77-3

EXAMPLE 27 3-(6-methoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methyl-1H-pyrrolo[2,3-b]pyridine A mixture of 6-methoxy-1,2,3,4-tetrahydroisoquinoline (prepared by the method of Helfer, Helv. Chim. Acta, 1924, 7, 945) (0.55 g, 3.36 mmol) and 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (0.59 g, 3.36 mmol) in toluene (3 ml) was heated at reflux under nitrogen for 18 h. The mixture was allowed to cool and the crystallized product collected. Recrystallisation from toluene afforded the title compound (0.31 g, 32%), m.p. 144-146 C.; (Found: C, 73.04; H, 6.43; N, 14.10. C18 H19 N3 O.0.1H2 O requires C, 73.24; H, 6.55; N, 14.23%); deltaH (DMSO-d6) 2.67 (2H, br s, CH2), 2.76 (2H, t, J 5.4 Hz, CH2), 3.49 (2H, s, CH2), 3.69 (3H, s, OCH3), 3.78 (2H, s, CH2), 6.65 (2H, m, ArH), 6.89 (1H, d, 9 Hz, ArH), 7.01 (1H, dd, J 7.9, 4.7 Hz, 5-H), 7.40 (1H, d, J 2.2 Hz, ArH), 8.03 (1H, dd, J 7.7, 1.3 Hz, 4-H), 8.19 (1H, dd, J 4.6, 1.4 Hz, 6-H), and 11.47 (1H, br s, NH); m/z (CI+, NH3) 294 (M+1)+.

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Methoxy-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; Merck Sharp & Dohme, Ltd.; US5700809; (1997); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is 7-Nitro-1,2,3,4-tetrahydroisoquinoline,cas is 42923-79-5, mainly used in chemical industry, its synthesis route is as follows.

The mixture of 7-nitro-l,2,3,4-tetrahydroisoquinoline and 6-nitro-l,2,3,4- tetrahydroisoquinoline (1.Og, 5.6mmol, 1 equiv) was dissolved in a mixture of aqueous ammonium chloride [(2.4g, 44.8mmol, 8 equiv) in 6 ml of water] and ethanol (4ml). Iron powder (1.3g, 23.3mmol, 4 equiv) was added and the reaction mixture was stirred at 60C for 24hrs. The mixture was cooled down to room temperature and then filtered throughCelite. The filter cake was washed with ethanol (50ml). The orange solution was filtered again to remove any inorganics, concentrated in vacuum and azeotroped with toluene. The residue was stirred in ethanol (50ml) at 40C and filtered. The filtrate was concentrated to give the title mixture as a yellow solid ( 0.85g, 100%).1H NMR (MeOD, 400MHz) delta= 6.95 (m, IH), 6.66 (m, IH), 6.63 (m, IH), 4.2 (m, 2H), 3.4 (m, 2H), 3.0 (m, 2H).

42923-79-5, As the rapid development of chemical substances, we look forward to future research findings about 42923-79-5

Reference£º
Patent; CELLZOME AG; WO2009/62658; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO137,mainly used in chemical industry, its synthesis route is as follows.,17680-55-6

EXAMPLE 105; To a solution of Intermediate 21 (150 mg, 0.43 mmol) in dichloromethane (10 mL) was added EDC (170 mg, 0.86 mmol), HOAt (59 mg, 0.43 mmol) and Intermediate 21 (91 mg, 0.43 mmol) and the resulting mixture was stirred at room temperature for 3 days. The reaction was quenched with water and diluted with 20 mL of dichloromethane. The organic layer was separated and the aqueous layer was extracted with DCM (2¡Á20 mL). The organics were combined, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by preparative TLC (eluant: 7% ethanol: 92% dichloromethane: 1.0% NH4OH) to yield 121 mg (50%) of the final desired product as a mixture of two cis isomers. LC-MS for C29H36BrFN2O calculated 526.28, found [M+H]+ 527 and [(M+2)+H]+ 529.

With the complex challenges of chemical substances, we look forward to future research findings about 7-Bromo-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; Butora, Gabor; Goble, Stephen D.; Pastemak, Alexander; Yang, Lihu; Zhou, Changyou; Moyes, Christopher R.; US2008/81803; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO354,mainly used in chemical industry, its synthesis route is as follows.,42923-77-3

In a 50 mL Erlenmeyer flask, 190 mg (0.22 mmol) of troxerutin and glutaryl vinyl ether was added,359 mg (2.20 mmol) of 6-methoxy-1,2,3,4-tetrahydroisoquinoline, [TOMA] [Tf2N](N-hexylpyridine bistrifluoromethanesulfonimide salt) 20mL,60 air bath oscillator, 150rpm constant temperature oscillation, the reaction 30h. Ethyl acetate extraction, the extract was concentrated, column chromatography The product was obtained and the eluent was ethyl acetate / methanol / water (20/3/1, v / v) to give the troxerutamide derivative containing methoxytetrahydroisoquinoline. The product was a light yellow solid, 155 mg, 71% yield.

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Methoxy-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; Henan University of Technology; Xiao Yongmei; Mao Pu; Yang Shuoye; Yang Liangru; Qu Lingbo; Yuan Jinwei; (17 pag.)CN107163096; (2017); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.81237-69-6,5-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

81237-69-6, To a solution of 5-bromo-l,2,3,4-tetrahydroisoquinoline (1.06 g, 10 mmol) in DMF (3 mL) was added zinc cyanide (875 mg, 7.5 mmol) and Pd(P(Ph3)4 (577 mg, 0.5 mmol). The resulting mixture was heated at 100 C and stirred for 15 hrs under N2, then poured into water (30 mL) and extracted with EA (50 mL) twice. The organic layers were combined and washed with water and brine, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by column (eluting with DCM: MeOH =20: 1, v:v) to give l,2,3,4-tetrahydroisoquinoline-5- carbonitrile (400 mg) as a yellow solid.

As the paragraph descriping shows that 81237-69-6 is playing an increasingly important role.

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

As a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, name is 7-Nitro-1,2,3,4-tetrahydroisoquinoline, and cas is 42923-79-5, its synthesis route is as follows.,42923-79-5

General procedure: A mixture of the required 1,2,3,4-tetrahydroisoquinoline derivative (1 equivalent), NaHCO3 (2 equivalents), and the appropriate substituted nitroaryl derivative or 2-chloro-3,5-dinitropyridine (1 equivalent) was heated at reflux in a mixture of ethanol : water (2:1) with stirring (15 hours). After cooling to room temperature, the ethanol was evaporated and the residue was poured onto ice yielding a solid. The solid was collected and dried in a vacuum desiccator over P2O5 giving the crude N-(nitroaryl)-1,2,3,4-tetrahydroisoquinoline derivative or 1,2,3,4-tetrahydro-2-(3,5-dinitropyridin-2-yl)isoquinoline 12.

With the complex challenges of chemical substances, we look forward to future research findings about 42923-79-5,belong tetrahydroisoquinoline compound

Reference£º
Article; Burke, Philip J.; Chun Wong, Lai; Jenkins, Terence C.; Knox, Richard J.; Stanforth, Stephen P.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 24; (2011); p. 7447 – 7450;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem