Heterocyclic Building Blocks-Tetrahydroisoquinoline

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

Step 1 Conc. sulfuric acid (80 ml) was added by small portions to tetrahydroisoquinoline (24.4 g, 183 mmol) under ice-cooling for dissolution. Then, 60percent nitric acid (18 ml) was added dropwise from a funnel and the mixture was stirred under ice-cooling for 3 hr. The mixture was stirred at room temperature for 18 hr. The reaction mixture was diluted with water under ice-cooling, and 35percent aqueous sodium hydroxide solution was added to adjust the solution to pH 12. After extraction with chloroform, the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ethanol (180 ml) and conc. hydrochloric acid (20 ml) was added under ice-cooling. The precipitated brown crystals were collected by filtration with suction to give 7-nitrotetrahydroisoquinoline hydrochloride (7.18 g, 22percent).

The synthetic route of 91-21-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Japan Tobacco Inc.; US6410561; (2002); B1;,
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.

Into a 50 mL Erlenmeyer flask were added 202.8 mg (0.22 mmol) of troxerutin azelate and 359 mg (2.20 mmol) of 6-methoxy-1,2,3,4-tetrahydroisoquinoline, [HPy ] BF4 (N-n-hexylpyridinium tetrafluoroborate) 20 mL, 60 C air bath Oscillator, 150rpm constant temperature oscillation, the reaction 36h. Ethyl acetate extraction, the extract was concentrated, the product was isolated by column chromatography, The eluent was ethyl acetate / methanol / water (20/3/1, v / v). 170 mg of pale yellow solid was obtained in a yield of 73%.

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

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

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-Bromo-2-methyl-1,2,3,4-tetrahydroisoquinolineTo a solution of 6-bromo-1 ,2,3,4-tetrahydroisoquinoline (1 g, 4.72 mmol) in formic acid (10 mL, 261 mmol) was added formaldehyde (37%) (2 mL, 72.6 mmol). The reaction was stirred at 150 C for 15 min in a microwave reactor. T he reaction mixture was concentrated under vaccum, cooled to 0 C, quenched with saturated NaHC03solution, extracted with EtOAc (2X), The organic layer washed with brine, dried under anhydrous Na2S04and filtered. The filtrate was reduced under pressure to afford 6-bromo-2-methyl- 1 ,2,3,4-tetrahydroisoquinoline (900 mg, 3.85 mmol, 82 % yield). LC-MS m/z 226 (M+H)+, 1.29 min (ret. time). The crude compound was used for next step without further purification.

226942-29-6 6-Bromo-1,2,3,4-tetrahydroisoquinoline 15885183, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); 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

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.

The synthetic route of 215798-14-4 has been constantly updated, and we look forward to future research findings.

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

17680-55-6, 7-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 251; 4- [7-(3 -aminophenyl)-3 ,4-dihydroisoquinolin-2( 1 H)-yI] – 1 -hydroxy- 1 , 8-naphthyridin-2( 1 H)-one; Stepl : l-(benzyloxy)-4-(7-bromo-3,4-dihydroisoquinolin-2(lH)-yl)-l,8-naphthyridin-2(l)-one; l-(benzyloxy)-2-oxo-l,2-dihydro-l,8-naphthyridin-4-yltrifluoromethanesulfonate (Example 2, Stepl: 500 mg, 1.249mmol) and 7-bromo-l,2,3,4-tetrahydroisoquinoline (1007 mg, 4.75 mmol) in DMF (10 ml) was heated at 110 C and stirred for 90 minutes. The crude mixture was dissolved in DCM and purified by SGC (30-100 % EtOAc-hexanes) to give the title compound. MS: m/z = 462.3 (M), 464.3 (M+2).

The synthetic route of 17680-55-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; WO2008/10964; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

42923-79-5, 7-Nitro-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7-Nitro-1,2,3,4-tetrahydroisoquinoline (1600 mg, 8.979 mmol) was treated with trifluoromethanesulfonic acid (5 mL). The mixture was cooled to 0 C. To the mixture was added 1-iodopyrrolidine-2,5-dione (2.3 g, 10.22 mmol) portionwise and the reaction mixture was stirred at room temperature overnight. The reaction mixture was added to ice and stirred for 10 minutes. To this mixture was added sodium hydroxide (20 mL of 6 M, 120.0 mmol) until a yellow precipitate was formed. The precipitate was filtered, washed with water, and dried to yield crude 5-iodo-7-nitro-1,2,3,4-tetrahydroisoquinoline (2.2 g, 80.95%). ESI-MS m/z calc.303.97, found 304.89 (M+1)+; Retention time: 0.59 minutes. The product was utilized in the next step without further purification.

As the paragraph descriping shows that 42923-79-5 is playing an increasingly important role.

Reference£º
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BETHIEL, Randy Scott; CAO, Jingrong; COLLIER, Philip, N.; DAVIES, Robert J.; DOYLE, Elisabeth; FRANTZ, James Daniel; GOLDMAN, Brian Anthony; GREY, Ronald Lee; GRILLOT, Anne-laure; GU, Wenxin; KOLPAK, Adrianne Lynne; KRAUSS, Paul Eduardo; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MESSERSMITH, David; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; WANG, Jian; (491 pag.)WO2018/106646; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of Boc-L-proline (Int-5a, 406 mg, 1.88 mmol) in 10 mL of DMF was added amine Int-6a (400 mg, 1.88 mmol), EDCI (450 mg, 2.35 mmol), HOBT (317 mg, 2.35 mmol), and Hunig’s base (0.65 mL, 3.76 mmol). The resulting reaction was heated at 85 0C and allowed to stir at this temperature for 16 hours. The reaction mixture was cooled to room temperature and was then partitioned between EtOAc and water. The organic phase was separated and the aqueous phase was further extracted with EtOAc. The combined organic phases were dried (MgSO4) and concentrated in vacuo to provide a crude residue which was purified using (ISCO) flash column chromatography (EtO Ac/Hex, 0 to 50% EtOAc eluent ) to provide compound Int-6b (680 mg, 88%).

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

Reference£º
Patent; SCHERING CORPORATION; ROSENBLUM, Stuart, B.; CHEN, Kevin, X.; KOZLOWSKI, Joseph, A.; NJOROGE, F., George; COBURN, Craig, A.; WO2010/132538; (2010); A1;,
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.170097-67-3,2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,as a common compound, the synthetic route is as follows.

29a 6-(Methoxy-methyl-carbamoyl)-3,4-dihydro-1/-/-isoquinoline-2-carboxylic acid te/f-butyl esterTo 2.00 g (7.21 mmol) 3,4-dihydro-1 /-/-isoquinoline-2,6-dicarboxylic acid 2-te/f-butyl ester in 70 mL MeOH is added at RT 844 mg (8.65 mmol) O,lambda/-dimethyl-hydroxylamine and 1.59 mL (14.4 mmol) 4-methyl-morpholine. The mixture is stirred at RT and then 2.10 g (7.57 mmol) 4- (4,6-dimethoxy-1 ,3,5-triazin-2-yl)-4-methyl-morpholin-4-ium chloride hydrate is added and the mixture is stirred overnight at RT. The residue is directly purified via reverse HPLC chromatography (Waters XBridge, C18; water (0.3 % NH4OH)/acetonitrile (0.3 % NH4OH) 90:10 to 10:90). Yield: 2.30 g (100% of theory) ESI Mass spectrum: [M+H]+ = 321Retention time HPLC: 1.7 min (method K).

As the paragraph descriping shows that 170097-67-3 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/22979; (2008); A1;,
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.215798-19-9,6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.

6-bromo- 1 ,2,3,4-tetrahydroisoquinoline hydrochloride (1. 5g, 6 mmol),and potassium carbonate (1.7g, 12 mmol) were taken in acetone (100 mL). 2,4,6- tnmethylbenzenesulfonyl chloride (1.6g, 7.2 mmol) was added to the reaction mixture andstirred at ambient temperature for 1 6h. Crude reaction mixture was concentrated under reduced pressure, extracted with saturated bicarbonate and brine, dried and concentrated. The crude mixture was purified on silica using ethyl acetate-hexane (3 0-70) to obtain the title compound (2.OOg, 85% yield). ?H NMR (400 MHz, DMSO-d6) oe ppm 2.27 – 2.29 (m, 3 H)2.54 (s, 6 H) 2.81 (t, J=6.00 Hz, 2 H) 3.39 (t, J=5.99 Hz, 2 H) 4.25 (s, 2 H) 7.09 (s, 3 H) 7.16(d, J8.31 Hz, 2 H) 7.33 – 7.36 (m, 2 H) 7.38 (m, J=2.00 Hz, 2 H). MS (m/z): 396.0, 397.0(M+H) for two bromine isomers.

215798-19-9 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride 22570216, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; SAINT LOUIS UNIVERSITY; BURRIS, Thomas; WALKER, Jonn, K.; FLAVENY, Colin; CHATTERJEE, Arindam; (117 pag.)WO2017/223514; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of the acid structural unit S27 (1.5 g) in dichloromethane (5 ml/mmol) there was added at 0 C. diisopropylethylamine (2.5 eq.), followed by N-hydroxybenzotriazole (HOBt) (1 eq.) and N-ethyl-N’-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) (1.5 eq.). The resulting reaction mixture was stirred for 15 min. at 23 C. It was then cooled to 0 C., and 6-bromo-1,2,3,4-tetrahydroisoquinoline (1.2 eq., dissolved in dichloromethane) was added dropwise. The reaction mixture was stirred for 16 h at 25 C. until the reaction was complete. The mixture was diluted with dichloromethane (100 ml) and extracted with saturated ammonium chloride solution, saturated sodium chloride solution, saturated sodium hydrogen carbonate solution and again with saturated sodium chloride solution. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (5% ethyl acetate in dichloromethane). Yield: 80%

The synthetic route of 226942-29-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Gruenenthal GmbH; US2008/153843; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem