Month: August 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.226942-29-6,6-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

The compound (2.253 g) obtained in Example 17-1 was dissolved in anhydrous THF (11 ml) and added with a 1 mol/l borane-THF complex/THF solution (manufactured by Kanto Chemical Co., Inc.) (55.4ml). The whole was refluxed overnight under heating. After the whole was left for cooling, methanol was added thereto and the solvent was distilled off. The resultant was added with 1 mol/l hydrochloric acid and refluxed under heating for 3 hours. After completion of the reaction, the solution was cooled with ice and added with a 1 mol/l sodium hydroxide aqueous solution and 27% ammonium water, followed by extraction with chloroform. The extract was dried with magnesium sulfate and the solvent was distilled off. The resultant was dissolved in anhydrous dichloromethane (40 ml), added with triethylamine (1.53 ml), and cooled with ice. Trifluoroacetic anhydride (1.55 ml) was added thereto and the whole was stirred at room temperature for 1 hour. After completion of the reaction, the resultant was added with a saturated aqueous sodium hydrogen carbonate solution, subjected to extraction with chloroform, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure, thereby obtaining the subject compound (2.23 g) as a white solid. MS(FAB,Pos.):m/z=308,310[M+H]+

As the paragraph descriping shows that 226942-29-6 is playing an increasingly important role.

Reference£º
Patent; Kureha Corporation; EP1724263; (2006); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride, cas is 923591-51-9, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

2-Acetyl-5-bromo-l,2,3,4-tetrahydroisoquinoline5-Bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (2.0 g, 8.0 mmol) was taken up in diethyl ether (20 mL) and washed with NaOH (aq, IN), dried (Na2SO4) and concentrated to give the free amine (1.67 g) that was dissolved in pyridine (15 mL) and cooled to 0 0C. Acetic anhydride (0.82 mL, 8.7 mmol) was added dropwise and the reaction was stirred at RT overnight. Azeotropic evaporation with toluene several times gave the product as a white solid (1.9 g, 94%).1H NMR (SOO MHz, DMSO-d6): delta 7.53 – 7.46 (m, IH), 7.27 – 7.11 (m, 2H), 4.66 and 4.61 rotamers 4:6 (s, 2H), 3.73 – 3.66 (m, 2H), 2.83 and 2.71 rotamers 6:4 (t, J= 6.1 Hz, 2H), 2.09 and 2.07 rotamers 6:4 (s, 3H); APCI-MS m/z: 254/256 1:1 [MH+].

With the rapid development of chemical substances, we look forward to future research findings about 923591-51-9

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/7747; (2009); A2;,
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.42923-77-3,6-Methoxy-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

General procedure: To a dried sealed vessel was added 1,2,3,4-tetrahydroisoquinoline (5 mL, 40 mmol), anhydrous K2CO3 (8.34 g,60 mmol), CuI (0.8 g, 4 mmol), L-Proline (0.92 g, 8 mmol), ethyl 6-bromopicolinate (4.32 g, 20 mmol), and DMSO (25 mL). Then themixture was stirred at 80 C for 16 h under N2 environment. Aftercooling to room temperature, water (100 mL) was added andextracted with EtOAc. Then, the combined organic layer was driedover MgSO4, filtered, and concentrated. The residue was purified bysilica gel flash chromatography (hexane/EtOAc = 5/1) to providecompound 14 as a white oil (3.94 g, 70%).

The synthetic route of 42923-77-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Fang, Yuying; Zhou, Huihao; Gu, Qiong; Xu, Jun; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 133 – 145;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

To a solution of 2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-lH-isoquinoline-6- carboxylic acid (CAS-RN 170097-67-3; 300 mg, 1.08 mmol) in N,N-dimethylformamide (5 ml) was added 4-methylmorpholine (547 mg, 5.41 mmol), 4,5,6,7-tetrahydro-lH-[l,2,3]triazolo[4,5- c]pyridine (CAS-RN 706757-05-3; 141 mg, 1.08 mmol) and 0-(7-azabenzotriazol-l-yl)- Nu,Nu,Nu’,Nu’-tetramethyluronium hexafluoro-phosphate (411 mg, 1.08 mmol) at room temperature, then after 18 h the reaction mixture was partitioned between sat. aq. sodium hydrogen carbonate solution and a mixture of ethyl acetate and 2-methyltetrahydrofuran. The organic layer was washed with ammonium chloride solution and brine, dried over magnesium sulfate, filtered and evaporated. Chromatography (silica gel, gradient dichloromethane to dichloromethane / methanol / 25% aq. ammonia solution 90 : 10 : 2.5) produced the title compound (278 mg, 67%). White foam, MS: 384.3 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 170097-67-3

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; MATTEI, Patrizio; RUDOLPH, Markus; SCHMITZ, Petra; DI GIORGIO, Patrick; (81 pag.)WO2018/167113; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

5-Bromo-1,2,3,4-tetrahydroisoquinoline, cas is 81237-69-6, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

(R)-perfluorophenyl (1,1,1-trifluoro-3-((4-methoxybenzyl)oxy)propan-2-yl) carbonate (60 mg, 0.13 mmol) in acetonitrile (2 mL) was added into cold 0 C. solution of 5-bromo, 1,2,3,4-tetrahydroisoquinoline (30 mg, 0.14 mmol) and N,N-diisopropylethylamine (0.05 mL, 0.39 mmol) in acetonitrile (4 mL). The resulting reaction mixture was allowed to come to room temperature and stirred for 1 hour. Then, the reaction was diluted in dichloromethane (25 mL) and washed with water (2*15 mL). The organic extracts were dried over anhydrous NaSO4. The solvents were removed under vacuum and the residue was purified on silica gel (Biotage; eluting solvents hexanes:EtOAc 4/1 ratio) to afford (R)-1,1,1-trifluoro-3-((4-methoxybenzyl)oxy)propan-2-yl 5-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate as colorless oil. 1H NMR (400 MHz, CDCl3) delta ppm 7.46-7.45 (m, 1H), 7.25-7.16 (m, 2H), 7.08-7.06 (m, 2H), 6.84-6.82 (m, 2H), 5.52-5.51 (sept, 1H), 4.64-4.61 (m, 2H), 4.52-4.44 (m, 2H), 3.78 (s, 3H), 3.76-3.71 (m, 3H), 2.90-2.87 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 81237-69-6

Reference£º
Patent; Malamas, Michael; Makriyannis, Alexandros; Lamani, Manjunath; Farah, Shrouq I.; US2019/152917; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

91-21-4, 1,2,3,4-Tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1,2,3,4-Tetrahydroisoquinoline (50 g; 1 equiv.) was added at 0¡ã C., in the course of 90 minutes, to 185 ml of sulfuric acid, and the reaction mixture was stirred for 30 minutes at 0¡ã C. Potassium nitrate (40.7 g; 1.2 equiv.) was then added in portions, and stirring was carried out for 15 hours at room temperature. When the conversion was complete, the reaction mixture was shaken on 500 g of ice and adjusted to pH 8-9 with ammonia solution. Extraction with chloroform was then carried out 3 times, and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The residue was taken up in IPA (500 ml) and cooled to 0¡ã C., and hydrochloric acid (2 equiv.) was added. The resulting solid was filtered out and recrystallised from methanol. 7-Nitro-1,2,3,4-tetrahydroisoquinoline (35 g; 52.3percent) was obtained in the form of a white solid.

As the paragraph descriping shows that 91-21-4 is playing an increasingly important role.

Reference£º
Patent; Gruenenthal GmbH; US2010/234340; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

215798-14-4, 6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 1,4-dioxane solution (300 mL) of 4-(methylthio)-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (30.7 mg, 0.100 mmol) synthesized in Reference Synthesis Example 33, 6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinolinehydrochloride (35.6 mg, 0.150 mmol) and triethylamine (27.9 mL, 0.200 mmol) were added and theresultant reaction solution was stirred for 4 hours under reflux by heating. After completion of the reaction, the reactionsolution was concentrated and the obtained residue was purified by silica gel (amino-based) column chromatography(hexane/ethyl acetate = 1/1) to obtain the title compound (Ex1) (28.1 mg, yield 61 %) as a colorless solid.

#N/A

Reference£º
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; NIWA, MASATOSHI; INABA, YUSUKE; IWAMOTO, TOSHIMASA; SHINTANI, YUSUKE; NAGAI, HIROSHI; EGI, JUN; ADACHI, MICHIAKI; HIRAI, YUICHI; (176 pag.)TW2016/7941; (2016); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride, cas is 215798-14-4, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

A mixture of (S)-3-phenyl-2-{(4-pyridin-2-yl-benzyl)-[3-(4-trifluoromethyl-phenyl)-acryloyl]-amino}propionic acid (50 mg, 0.094 mmol), TBTU (30.3 mg, 0.094 mmol), and DIPEA (0.08 mL, 0.471 mmol) in dry DMF (1 mL) was stirred at rt for 30 min. Then a solution of 6-trifluoromethyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride in dry DMF (1 mL) was added and the reaction mixture was stirred overnight at rt and directly purified by preparative HPLC.LC-MS: tR=1.04 min; [M+H]+=714.15.

With the rapid development of chemical substances, we look forward to future research findings about 215798-14-4

Reference£º
Patent; Aissaoui, Hamed; Boss, Christoph; Corminboeuf, Olivier; Frantz, Marie-Celine; US2011/281869; (2011); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

186390-62-5, 7-Bromo-6-nitro-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7-Bromo-6-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (5) A 115 g (0.447 mol) sample of 7-bromo-6-nitro-1,2,3,4-tetrahydroisoquinoline, 45.2 g (0.447 mol) of triethylamine, 97.5 g (0.447 mol) of di-tert-butyl dicarbonate, 3.2 liter of dioxane and 0.5 liter of water were combined and stirred at ambient temperature for 1.5 hrs. The reaction was concentrated to remove the dioxane, 1 liter of saturated sodium bicarbonate was added and the mixture was extracted two times with 1 liter of methylene chloride. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The resulting solid was recrystallized from isopropanol to yield 118 g of a solid. 1 H NMR (250 MHz, DMSO) delta7.89 (s, 1H); 7.81 (s, 1H); 4.58 (s, 2H); 3.56 (t, 2H); 2.81 (t, 2H); 1.42 (s, 9H).

186390-62-5 7-Bromo-6-nitro-1,2,3,4-tetrahydroisoquinoline 23296211, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; Pfizer Inc; US6121283; (2000); 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.1029689-82-4,Methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate hydrochloride,as a common compound, the synthetic route is as follows.

To a solution of methyl l,2,3,4-tetrahydroisoquinoline-8-carboxylate hydrochloride (12.37 g) and Example 1.4.4 (15 g) in dimethyl sulfoxide (100 mL) was added N,N-diisopropylethylamine(12 mL). The mixture was stirred at 50 C for 24 hours. The mixture was diluted with ethyl acetate (500 mL), washed with water and brine, and dried over Na2S04. After filtration and evaporation of the solvent, the crude material was purified via silica gel column chromatography, eluting with 20% ethyl acetate in hexane, to give the title compound. MS (ESI) m/e 448.4 (M+H)+.

1029689-82-4 Methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate hydrochloride 45074000, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; ABBVIE INC.; BENATUIL, Lorenzo; BRUNCKO, Milan; JUDD, Andrew, S.; LI, Yingchun; MCCLUSKEY, Andrew; PHILLIPS, Andrew, C.; PHILLIPS, Darren, C.; SEAGAL, Jane; SOUERS, Andrew, J.; (608 pag.)WO2017/214458; (2017); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem