Month: October 2020

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.

To a 250 mL three neck flask water (70 mL) and (R/S)-l -phenyl- 1,2,3,4- tetrahydroisoquinoline (20 g) were charged. Reaction mixture was heated to 65-70 C. D-(-)-tartaric acid dissolved in water (20 mL) was added to the reaction mixture at 65- 70 C and stirred for 30 minutes. The reaction mixture was further heated to 90-95 C and stirred for 1 h. The reaction mixture was cooled to 55 C. To the clear solution 0.250 g seeding of (S)-l-phenyl-l,2,3,4-tetrahydroisoquinoline was added. Reaction mixture was further cooled to 32-35 C and stirred for 30 minutes. Solid product was filtered and washed with cold water. It was dried in a fan dryer at 70-80 C till constant weight obtained. The (S)-l -phenyl- 1,2,3,4-tetrahydroisoquinoline was obtained. (Yield- 40.0 %, % Chemical purity-98.0 %, % Chiral purity of S-isomer-97.2 %).

22990-19-8, 22990-19-8 1-Phenyl-1,2,3,4-tetrahydroisoquinoline 100137, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; CADILA HEALTHCARE LIMITED; KOTHARI, Himanshu M.; DAVE, Mayank Ghanshyambhai; PANDEY, Bipin; WO2011/48607; (2011); 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: C8H14ClNO330,mainly used in chemical industry, its synthesis route is as follows.,81237-69-6

The reaction flask was added A1-4 (60mg, 0.18mmol), A25-4 (194mg, 0.92mmol), diisopropylethyl amine (119mg, 0.92mmol)And N- methylpyrrolidinone (1.5mL). The reaction at 120 8h, cooled to room temperature, water was added, extracted three times with ethyl acetate, the combined organic phases with saturated chlorineAqueous solution of sodium, dried over anhydrous sodium sulfate, and the solvent was evaporated, and purified by column chromatography (petroleum ether: ethyl acetate = 5: 1-3: 1) to give an oily compound (40mg,44%). After parsing NMR spectrum (map data in Table 1), the resulting solid was compound

With the synthetic route has been constantly updated, we look forward to future research findings about 5-Bromo-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; Suzhou Yunxuan Pharmaceutical Co., Ltd.; Zhang, Xiaohu; (54 pag.)CN105254613; (2016); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, name is 6-Bromo-1,2,3,4-tetrahydroisoquinoline, and cas is 226942-29-6, its synthesis route is as follows.

226942-29-6, A mixture of 6-bromo-1,2,3,4-tetrahydroisoquinoline (800 mg, 3.8 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (1051 mg, 4.5 mmol) and potassium carbonate (1043 mg, 7.5 mmol) in NMP (10 mL) was stirred at 40 oC for 18 h. The reaction mixture was filtered and the filtrate was reduced in vacuo. The residue was purified by silica column chromatography eluting with 2% EtOAc in Pet. Ether to afford 6-bromo-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline (800 mg, 2.72 mmol, 72% yield) as a white solid.1H NMR (400 MHz, DMSO-d6) delta 7.36- 7.26 (m, 2H), 7.03 (d, J = 8.1 Hz, 1H), 3.79- 3.74 (m, 2H), 3.38- 3.28 (m, 2H), 2.90 (m, 2H), 2.82 (m, 2H).

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

Reference£º
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

A mixture of 7-nitro-l,2,3,4-tetrahydro-isoquinoline(1.5g, 8.38 mmole) and 10% Pd/C (300 mg) in diethyleneglycol (5 mL) was reacted in a Smith Synthesizer undermicrowave radiation at 220 2C for 25 min. The resultingmixture was diluted with MeOH and filtered. The filtrate wasconcentrated and diluted with CH2C12, washed with sat. aq.NH4C1 and dried over Na2S04. After filtration andconcentration, the title compound was isolated through flashchromatography (eluted with CH2Cl2:MeOH 9:1) as an orangesolid. MS: (ES+) 145(M+H). Calc’d. for C9H8N2 – 144.07.

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

Reference£º
Patent; AMGEN INC.; WO2006/12374; (2006); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is Methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate hydrochloride,cas is 1029689-82-4, mainly used in chemical industry, its synthesis route is as follows.,1029689-82-4

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)+.

As the rapid development of chemical substances, we look forward to future research findings about 1029689-82-4

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

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

Intermediate I: 5-Bromo-N-(5-fluorothiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)- sulfonamide A solution of 5-fluorothiazol-2-amine hydrochloride (Milestone Pharmatech, Brunswick, NJ, 6.22 g, 40.2 mmol) and IH-imidazole (10.96 g, 161 mmol) in 200 mL DCM was cooled to -78 C and was treated with sulfuryl chloride (3.27 ml, 40.2 mmol). After stirring for 10 minutes, the reaction mixture was placed into a 0 C bath and was allowed to stir for an additional hour. To this mixture was added 30 mL of heptane and the solvent was decanted. The remaining solid was treated with 5-bromo- 1,2,3,4-tetrahydroisoquinoline hydrochloride (ASW Medchem, Brunswick, NJ, 5.00 g, 20.12 mmol) then treated sequentially with 100 mL THF and DIPEA (42.2 ml, 241 mmol). The reaction mixture was heated to reflux for one hour before being cooled and poured into IN citric acid. The desired product was extracted with ethyl acetate. The organics were concentrated and the resulting residue was purified directly by silioca gel column chromatography (0 to 100% EtO Ac/heptane, 2% MeOH) yielding 5-bromo-N-(5-fluorothiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide (3.25 g, 8.29 mmol). [M+H]+ = 393.9

With the complex challenges of chemical substances, we look forward to future research findings about 5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride

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

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

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]+.

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

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

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

Resolution of (R:S)-1 -phenyl- 1,2,3,4-tetrahydroisoquinoline (100 g) was carried out using (D)-(-)-tartaric acid in water as per the literature method known in the art (Ref 1.- J. Chem. Soc. Perkin. Trans I, (4), 869-73 (1988), Ref. 2.- Monatshefte Fur. Chemie, vol. 53-54:956-962(1929)) and diastereomeric (D)-(-)-tartaric acid salt of (1S)- 1 -phenyl- 1,2,3,4-tetrahydroisoquinoline was filtered out as a solid. The filtrate containing enantiomerically enriched (D)-(-)-tartaric acid salt of (lR)-l-phenyl-l,2,3,4- tetrahydroisoquinoline was collected and a clear aqueous solution 40 % aq. sodium hydroxide (NaOH, 85 mL) was added at room temperature when solid was precipitated. The precipitated solid was filtered and washed with water and dried. The weight of enantiomerically enriched (lR)-l-phenyl-l,2,3,4-tetrahydroisoquinoline was 61.0 g. (% Purity by HPLC-97.0 %; % Chiral purity of R-isomer -79.0 %).

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

Reference£º
Patent; CADILA HEALTHCARE LIMITED; KOTHARI, Himanshu M.; DAVE, Mayank Ghanshyambhai; PANDEY, Bipin; WO2011/48607; (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.226942-29-6,6-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

In a pressure vessel equipped with a magnetic stirring bar was added 6-bromo-l,2,3,4- tetrahydroisoquinoline (1.328 g, 6.26 mmol), and 2-chloro-4-(pyridin-3-yl)pyrimidine (1 g, 5.22 mmol) in acetonitrile (25 mL). Hunig’s base (2.73 mL, 15.66 mmol) was added and the mixture was heated to 80 C in a preheated oil bath and allowed to stir for 16 hours overnight. Reaction appears complete by LC/MS, cooled to RT and filtered solids, washed with ethyl acetate, concentrated in vacuo to a solid. Took up solid in EtOAc: heated to dissolve most material in minimum amount of solvent, filtered while hot, and allowed to cool to RT. After filtration and drying under vacuum, 1.5g (87%) of 6-bromo- 2-(4-(pyridin-3-yl)pyrimidin-2-yl)-l,2,3,4-tetrahydroisoquinoline was obtained as a light brown solid. LCMS (M+l) = 366.7 and 368.6., 226942-29-6

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

Reference£º
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; DESKUS, Jeffrey; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (220 pag.)WO2018/127801; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem