Month: August 2020

1,2,3,4-Tetrahydroisoquinoline, cas is 91-21-4, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

A. 7-Nitro-1,2,3,4-tetrahydro-isoquinoline To 43.1 g (324 mmol) of 1,2,3,4-tetrahydro-isoquinoline was added 160 mL of concentrated sulfuric acid with ice bath cooling. Potassium nitrate 35.2 g (348 mmol) was added in portions to the stirring mixture, while maintaining an internal temperature below 5 C. The mixture was allowed to stand at ambient temperature for 72 h, and then basified with aqueous ammonia and extracted four times with chloroform. The combined organics were dried over MgSO4 and concentrated to give a dark brown oil. The oil was dissolved in 240 mL of ethanol and 40 mL of concentrated hydrochloric acid was added to the mixture with cooling. The precipitated material was collected by filtration and washed with cold ethanol to give 25.0 g of a tan solid. The crude material was partitioned between 1 N NaOH and ethyl acetate. The ethyl acetate layer was washed once with brine, dried over Na2 SO4 and concentrated. The dinitrated tetrahydroisoquinoline was removed by crystallization from ether/hexanes. The mother liquor was concentrated to give 2.19 g of 7-Nitro-1,2,3,4-tetrahydro-isoquinoline. B.[{1-[1-(R)-Benzyloxymethyl-2-(7-nitro-3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-ethylcarbamoyl]-1-methyl-ethyl]-carbamic acid tert-butyl ester According to General Procedure A, 100 mg (0.57 mmol) of 6A and 228 mg (0.60 mmol) of 3 were coupled, and the product was purified by silica gel chromatography (99:1 v/v CH2 Cl2:MeOH) to give 220 mg of 6B as a white foam., 91-21-4

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Reference£º
Patent; Pfizer Inc; US5936089; (1999); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

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., 42923-79-5

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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

7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride, cas is 99365-69-2, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

(4-2-1) To 125 ml of suspension in ethanol of 136 g of 7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride was added 98 ml of triethylamine and 83 ml of ethyl acrylate, and the solution was heated and stirred overnight under reflux. The solution was concentrated under reduced pressure, and the residue was extracted with ethyl acetate, washed with water, and dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the filtrate was concentrated under reduced pressure to obtain 2-(2-(ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline.

99365-69-2, With the rapid development of chemical substances, we look forward to future research findings about 99365-69-2

Reference£º
Patent; Terumo Kabushiki Kaisha; US5789595; (1998); 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.57196-62-0,6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.,57196-62-0

5.84 3-{4-[4-(6-METHOXY-3,4-DIHYDRO-1H-ISOQUINOLIN-2-YLMETHYL)-BENZYLOXY]-1-OXO-1,3-DIHYDRO-ISOINDOL-2-YL}-PIPERIDINE-2,6-DIONE To the CH3CN (10 ml) solution of 3-(4-(4-(bromomethyl)benzyloxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (0.365 g, 0.823 mmol) was added 6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.247 g, 1.235 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.408 ml, 2.470 mmol) at room temperature overnight. Solvent was evaporated and the residue was stirred in CH2Cl2 (100 ml) and washed with sat NaHCO3 (2*30 ml), brine (20 ml) and evaporated to an oil, which was purified by silica gel column (MeOH/CH2Cl2) to give 3-{4-[4-(6-Methoxy-3,4-dihydro-1,1-isoquinolin-2-ylmethyl)-benzyloxy]-1-oxo-1,3-dihydro-isoindol-2-yl}-piperidine-2,6-dione (0.26 g, 60% yield); mp, 169-171 C. HPLC: Waters Symmetry C-18, 3.9*150 mm, 5 mum, 1 mL/min, 240 nm, gradient from 10/90 to 70/30 in 5 min, isocratic at 70/30 for 5 min (CH3CN/0.1% H3PO4), 4.72 min (98.3%). 1H NMR (DMSO-d6) delta 1.90-2.06 (m, 1H, CHH), 2.32-2.46 (m, 1H, CHH), 2.53-2.71 (m, 3H, CH2, CHH), 2.71-2.83 (m, 2H, CH2), 2.83-3.02 (m, 1H, CHH), 3.46 (br. s., 2H, CH2), 3.55-3.81 (m, 5H, CH2, CH3), 4.18-4.50 (m, 2H, CH2), 5.12 (dd, J=5.2, 13.3 Hz, 1H, NCH), 5.23 (br. s., 2H, CH2), 6.58-6.74 (m, 2H, Ar), 6.89 (d, J=9.1 Hz, 1H, Ar), 7.24-7.62 (m, 7H, Ar), 10.98 (br. s., 1H, NH). 13C NMR (DMSO-d6) delta 22.36, 28.94, 31.21, 45.10, 50.12, 51.58, 54.92, 61.51, 69.45, 111.91, 112.93, 114.97, 115.24, 126.73, 127.26, 127.72, 128.82, 129.81, 129.94, 131.81, 133.31, 135.22, 138.28, 153.51, 157.45, 168.01, 169.07, 170.96, 172.83. LC/MS m/e=526. Anal Calcd for C31H31N3O5 (+1.1 H2O): C, 68.27; H, 6.14; N, 7.70. Found: C, 68.08; H, 5.92; N, 7.47.

The synthetic route of 57196-62-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Man, Hon-Wah; Muller, George W.; Ruchelman, Alexander L.; Khalil, Ehab M.; Chen, Roger Shen-Chu; Zhang, Weihong; US2011/196150; (2011); 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.22990-19-8,1-Phenyl-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

22990-19-8, A solution of 3,4-dimethoxyphenethylamine (1.1 mmol) and DIPEA (2.2 mmol) in THF (10 ml) was slowly added to a THF solution (10 ml) of triphosgene (0.44 mmol) And stirred for 30-45 minutes. Then, a solution of 1-phenyl-1,2,3,4-tetrahydroisoquinoline (1.1 mmol) in THF (10 ml) was added and stirred overnight. The salt was filtered, and the filtrate was evaporated and column chromatography (EA: Hexane) was carried out to obtain the title compound.

As the paragraph descriping shows that 22990-19-8 is playing an increasingly important role.

Reference£º
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
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.

2-(tert-Butoxycarbonyl)- 1,2,3 ,4-tetrahydroisoquinoline-6-carboxylic acid (100 mg, 0.361 mmol) was dissolved in THF (5 mL) in an oven dried flask at -78 C. TMEDA (0.174 mL, 1.15 mmol) was added, followed by dropwise addition of a 1.6 M solution of n-BuLi in hexane (0.721 mL, 1.15 mmol) over 1 mm. The reaction mixture was stirred at-78 C for 1 hour, then a solution of Mel (0.090 mL, 1.4 mmol) dissolved in 1 mL of THFwas added. The reaction was allowed to warm to rt, and stirring was continued at rt for 45minutes. The reaction was then quenched with an aq. solution of saturated NH4C1 and extracted 3x with EtOAc. The combined organic extracts were dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to provide 181A(70 mg, 67% yield), as a white solid. MS(ESI)m/z 290.1 (M-H)., 170097-67-3

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Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne, M.; SHAW, Scott, A.; HALPERN, Oz, Scott; HU, Carol, Hui; KICK, Ellen, K.; (311 pag.)WO2017/40449; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

1-Phenyl-1,2,3,4-tetrahydroisoquinoline, cas is 22990-19-8, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

General procedure: To a solution of alcohol 1 (1.0 mmol) in DMSO (2 mL), was added at 0 C propylphosphonic anhydride (T3P) (1.0 mmol, 50 % solution in ethyl acetate) and the resulting reaction mixture was stirred at room temperature for 1-2 h under nitrogen atmosphere. The reaction was monitored by TLC, after the completion of reaction, the solvent was removed under reduced pressure. The crude product was taken in toluene, amine 2 (1.2 mmol) and acetic acid (0.5 equiv) was added and stirred further for 1-2 h. After completion of the reaction, the mixture was diluted with water (20 mL) and neutralized with 10 % NaHCO3 solution. The product was extracted with ethyl acetate (10 mL) and the combined organic phase was washed with water (10 mL) and brine solution. The organic phase was dried over anhydrous Na2SO4. The solvent was dried under reduced pressure to afford a crude product, which was purified on silica gel using ethyl acetate and petroleum ether (Scheme-I)., 22990-19-8

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Reference£º
Article; Dinesha; Mantelingu; Asian Journal of Chemistry; vol. 31; 2; (2019); p. 261 – 267;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

170097-67-3, 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,170097-67-3

Borane-tetrahydrofuran complex in tetrahydrofuran (1.0 M, 15.87 mL, 15.87 mmol) was added dropwise to a stirred solution of 2-(tert-butoxycarbonyl)-1,2,3,4- tetrahydroisoquinoline-6-carboxylic acid (2.0 g, 7.21 mmol) in tetrahydrofuran (50 mL) at ambient temperature under argon in a sealed flask. After stirring for 3 hours, the mixture was carefully quenched with water and sodium hydrogen carbonate solution was added. The mixture was extracted with ethyl acetate (x2) and the combined extracts were washed with brine, dried (anhydrous Na2SO4) and evaporated to give tert-butyl 6- (hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (2.0 g). LCMS m/z = 207.9 [M+H-isobutylene]+.

The synthetic route of 170097-67-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Nicholas David; BENOWITZ, Andrew B.; RUEDA BENEDE, Maria Lourdes; EVANS, Karen Anderson; FOSBENNER, David T.; KING, Bryan Wayne; LI, Mei; MILLER, William Henry; REIF, Alexander Joseph; ROMERIL, Stuart Paul; SCHMIDT, Stanley J.; WIGGALL, Kenneth; (1283 pag.)WO2017/216726; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride, cas is 57060-88-5, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

Methyl 1 ,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride (3g, 13.17 mmol) and potassium carbonate (3.6g, 26.34 mmol) were taken in acetone (250 mL). 2,4,6-trimethylbenzenesulfonyl chloride (3.5g, 15.8 mmol) was added to the reaction mixture and stirred at ambient temperature for 1 6h. Crude reaction mixture was concentratedunder reduced pressure, extracted with saturated bicarbonate and brine, dried and concentrated. The crude mixture was purified on silica using ethyl acetate-hexane (40-60) to obtain the title compound (4.5g, 92% yield). ?H NMR (400 MHz, DMSO-d6) oe ppm 2.27 (s, 3 H) 2.54 (s, 6 H) 3.14 (d, J=3.42 Hz, 3 H) 4.32 – 4.50 (m, 2 H) 4.77 – 4.83 (m, 1 H) 7.08 (s, 2 H) 7.17 (s, 4H). MS (m/z): 374.1 (M+H)., 57060-88-5

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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

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.

Step 1 : 5-Bromo-N-(thiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide A solution of imidazole (1.530 g, 22.47 mmol) and thiazol-2 -amine (0.750 g, 7.49 mmol) in 8 mL DCM was cooled to -78 C and was treated with sulfuryl chloride (0.609 ml, 7.49 mmol). After stirring for 20 minutes, the cooling bath was removed and the reaction mixture was allowed to stir for an additional 30 minutes. 5-Bromo-l,2,3,4- tetrahydroisoquinoline hydrochloride (ASW Medchem, Brunswick, NJ, 1.396 g, 5.62 mmol) was added, followed by triethylamine (7.31 ml, 52.4 mmol). The reaction mixture was then heated to 80 C for 30 minutes. The mixture was cooled to rt and poured into IN citric acid solution before being extracted into EtO Ac. The organics were dried over MgS04 and concentrated. Purification of the residue by silica gel column chromatography (0 to 100% EtO Ac/heptane) gave 5-bromo-N-(thiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide (1.092 g, 2.92 mmol). [M+H]+ = 375.6., 923591-51-9

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Reference£º
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem