Tag: M.W:200-300

6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride, cas is 215798-19-9, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.,215798-19-9

Step A: Preparation of t¡ãrt-Butyl 6-Bromo-3,4-dihydroisoquinoline-2(l//)- carboxylate.To a solution of 6-bromo- 1,2,3, 4-tetrahydroisoquinoline hydrochloride (1.00 g, 4.02 mmol) in EtOH (20 mL) was added sodium hydrogencarbonate (1.69 g, 20.1 mmol) and i-tert- butyl dicarbonate (0.966 g, 4.43 mmol). The reaction mixture was allowed to stir for 16 h at room temperature. The reaction mixture was then concentrated. The residue was diluted with H2O and extracted three times with EtOAc. The combined organics were dried over Na2SO4, filtered, and concentrated to give the title compound (1.15 g) as a clear oil. LCMS m/z = 311.9 [M+H]+; 1H NMR (400 MHz, Methanol-^) delta ppm 1.45-1.51 (m, 9H), 2.81 (t, J= 5.81 Hz, 2H), 3.29-3.34 (m, 2H), 3.61 (t, J= 5.68 Hz, 2H), 4.50 (s, 2H), 7.04 (d, J= 8.08 Hz, IH).

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

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/105206; (2009); 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.

81237-69-6, Preparation of l-(5-bromo-3,4-dihydroisoquinolin-2(lH)-yl)-2-(4-methoxy-7-(3- methyl- IH-1 ,2,4-triazol- 1 -yl)- 1 H-pyrrolo[2,3 -c]pyridin-3-yl)ethane- 1 ,2-dione; [00106] A 20 mL vial was charged with 2-(4-methoxy-7-(3-methyl-lH-l,2,4- triazol-l-yl)-lH-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (0.1 g, 0.332 mmol), 5- bromo-l,2,3,4-tetrahydroisoquinoline (0.083 g, 0.332 mmol), o-benzotriazol-1-yl- N,N,N’,N’-tetramethyluronium tetrafluoroborate (0.133 g, 0.415 mmol), Hunig’s Base (0.580 mL, 3.32 mmol), and DMF (3 mL). The vial was sealed and stirred at rt. After stirring the mixture for 70.5 h, the reaction was quenched with water. The solids that formed were collected by filtration. The mother liquor was concentrated under reduced pressure, and a second batch of solids was collected by recrystallizing from MeOH and water. The expected product, l-(5-bromo-3,4-dihydroisoquinolin-2(lH)- yl)-2-(4-methoxy-7-(3-methyl-lH-l,2,4-triazol-l-yl)-lH-pyrrolo[2,3-c]pyridin-3- yl)ethane-l,2-dione (0.145 g, 0.293 mmol, 88 % yield), was isolated as an off-white solid. LC/MS: m/z 495 (M+H)+, 497.02 (M + 3H)+ 1.935 min (method 1). 1H IMR (500 MHz, DMSO-d6) I’ ppm 12.42 (s, 1 H) 9.22 – 9.27 (m, 1 H) 8.18 – 8.31 (m, 1 H) 7.84 (s, 1 H) 7.09 – 7.59 (m, 3 H) 4.59 – 4.87 (m, 2 H) 3.67 – 3.95 (m, 5 H) 2.73 – 2.96 (m, 2 H) 2.47 – 2.52 (m, 3 H).

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/158396; (2009); 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

General procedure: Pd/C (254 mg, 0.12 mmol) and K3PO4*3H2O (16 mg, 0.06mmol) were placed in a Schlenk tube followed by acetonitrile(1 mL), and the resulting mixture was stirred at room temperaturefor 10 min. A solution of 1-substituted-1,2,3,4- tetrahydroisoquinoline(0.30 mmol) in acetonitrile (4 mL) was thenadded to the reaction mixture, and the Schlenk tube was carefullyand quickly vacuum purged before being filled with oxygenusing an oxygen balloon. The reaction mixture was thenstirred at 60 C until the 1-substituted-1,2,3,4- tetrahydroisoquinolinehad been completely consumed (as determined byTLC analysis). Upon completion of the reaction, the mixturewas slowly cooled to room temperature and filtered throughdiatomite to remove the Pd/C catalyst. The filtrate was thenconcentrated in vacuo to give the crude product as a residue,which was purified by flash chromatography over silica geleluting with petroleum ether and ethyl acetate to give the imineproduct 2. 1-Phenyl-3,4-dihydroisoquinoline (2a): 86% yield, known compound [ 54 ], yellow oil, Rf = 0.75 (ethyl acetate). 1H NMR (400 MHz, CDCl3) delta = 7.60-7.56 (m, 2H), 7.44-7.35 (m, 4H), 7.26-7.21 (m, 3H), 3.85-3.82 (m, 2H), 2.80-2.77 (m, 2H); 13C NMR (100 MHz, CDCl3) delta = 167.3, 139.0, 138.9, 130.7, 129.3, 128.9, 128.8, 128.1, 127.9, 127.4, 126.6, 47.7, 26.3.

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

Reference£º
Article; Ji, Yue; Chen, Mu-Wang; Shi, Lei; Zhou, Yong-Gui; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 36; 1; (2015); p. 33 – 39;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

215798-19-9, 6-Bromo-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 round -bottom flask was added 6-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (2.00 g, 8.05 mmol), (R)-4-(2-(2-methylpyrrolidin-l-yl)ethyl)phenylboronic acid (2.063 g, 8.85 mmol), tetrakis(triphenylphosphine)palladium (0) (0.279 g, 0.241 mmol), benzene (30.00 mL), ethanol (10.00 mL), and 2.0 M aqueous solution of sodium bicarbonate (8.05 mL, 16.09 mmol). The reaction mixture was refluxed for 6 h. Upon completion, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2S04, and concentrated. The residue was taken up in 1 M HC1 solution and washed with ethyl acetate. The aqueous layer was basified with 10% aqueous NaOH to pH~l 1, extracted with ethyl acetate, and concentrated. The residue was purified by silica gel column, eluting with 5-10% 2.0 M ammonia in methanol/DCM to give a yellow solid (1.20 g). LCMS m/z = 321.4 [M+H]+; NMR (400 MHz, DMSO- ) delta ppm 0.99-1.04 (m, 3H), 1.22-1.33 (m, 1H), 1.59-1.69 (m, 2H), 1.81-1.92 (m, 1H), 2.13 (q, J = 8.67 Hz, 1H), 2.20-2.34 (m, 2H), 2.65-2.83 (m, 5H), 2.94-3.04 (m, 3H), 3.10-3.18 (m, 1H), 3.91 (s, 2H), 7.09 (d, J = 8.08 Hz, 1H), 7.29 (d, J = 8.08 Hz, 2H), 7.33-7.40 (m, 2H), 7.53 (d, J = 8.08 Hz, 2H)., 215798-19-9

The synthetic route of 215798-19-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; WEI, Zheng; GROTTICK, Andew J.; MILLS, David M.; SMITH, Brian M.; WO2013/151982; (2013); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

877861-62-6, Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,877861-62-6

: To a mixture of 6-methoxycarbonyl-l,2,3,4-tetrahydroisoquinoline hydrochloride (50 mg, 0.22 mmol) and N^V-dimethylaminopyridine (1 10 mg, 0.9 mmol) in DMF (3.2 mL) was added n- butanesulfonyl chloride (34.4 mg, 0.22 mmol). The reaction was allowed to stir at room temperature overnight. The solvent was removed in vacuo and the residue obtained was partitioned between DCE (3 x 5 mL) and saturated aqueous sodium bicarbonate (5 mL). The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated to yield a white solid. LCMS (FA) ES+ 405.

877861-62-6 Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride 42614607, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BLACKBURN, Christopher; CIAVARRI, Jeffrey; GIGSTAD, Kenneth; XU, He; WO2010/151318; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

To a solution of 6- bromo-l,2,3,4-tetrahydroisoquinoline (4.19 g, 19.7 mmol) in DCM (75 mL) was added 4- fluoro-2-methylbenzaldehyde (3.0 g, 22 mmol) and acetic acid (1.13 mL, 19.7 mmol). Then sodium triacetoxyborohydride (5.4 g, 26 mmol) was added. The mixture was stirred at RT for 16 hrs. The mixture was quenched with water and extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated. The residue was purified by recrystallization with EtOAc to give 6-bromo-2-(4-fluoro-2- methylbenzyl)-l,2,3,4-tetrahydroisoquinoline (3.4 g, 10.17 mmol, 51.5 % yield). LCMS (M+H) = 333.95 and 335.90.

226942-29-6, As the rapid development of chemical substances, we look forward to future research findings about 226942-29-6

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

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

A mixture of N-(4-(1-aminoethyl)pyridin-2-yl)isobutyramide hydrochloride (20 mg, 0.082 mmol, Amine-12), 4-nitrophenyl chloroformate (18 mg, 0.090 mmol), and triethylamine (0.034 mL, 0.25 mmol) in DCM (1 mL) is stirred at rt for 1 hour. Then, 6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (20 mg, 0.082 mmol) and DBU (25 mg, 0.16 mmol) are added. After stirring at rt, the mixture is diluted with EtOAc (3 mL), washed with water (3 mL), dried over sodium sulfate, and concentrated. The residue is diluted with MeOH (4 mL) and applied onto a strong cation exchange cartridge (BondElute(registered trademark)SCX, 1 g/6 mL, Varian Inc.), and the solid phase matrix is rinsed with MeOH (5 mL). The crude mixture is eluted with 1M ammonia in MeOH (5 mL) and concentrated. This is purified by preparative LC-MS to give 9.4 mg (26% yield) of the title compound. MS (ESI) m/z: 435 (M+H)+.

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

Reference£º
Patent; RAQUALIA PHARMA INC.; YAMAGISHI, Tatsuya; KAWAMURA, Kiyoshi; MORITA, Mikio; WO2013/161308; (2013); 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.81237-69-6,5-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,81237-69-6

Intermediate 24A. 5-Bromo-l,4-dihydroisoquinoline: 5-Bromo-l,2,3,4- tetrahydroisoquinoline (0.500 g, 2.36 mmol) in DCM (25 mL) was treated with manganese dioxide (3.69 g, 42.4 mmol). After 15 h, the reaction mixture was filtered through a plug of CELITE and filtrate concentrated. The imine was carried forward as is. MS (ESI) m/z: 209.8 (M+H)+.

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.P.; CLARK, Charles G.; SMITH, II, Leon M.; ORWAT, Michael J.; JEON, Yoon; CORTE, James R.; WO2014/160668; (2014); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

1-phenyl-1 ,2,3,4-tetrahydroisoquinoline (100 g) was taken into a round bottom flask and methanol (400 ml) was added and stirred for about 5 minutes. The reaction mass was then heated to about 40 0C, and D-(-)-tartaric acid (71 .6 g) was added. The reaction mass was further heated to about 64 0C and maintained for about 2 hours. The reaction mass was then allowed to cool to about 28 0C and ethyl acetate (200 ml) was added. The reaction mass was maintained at about 28 0C for about 20 minutes, and then filtered. The filtered solid was washed with methanol (100 ml) and the wet solid was dried at about 55 0C for about 1 hour, 20 minutes.The dry material was taken into another round bottom flask and methanol (270 ml) was added. The reaction mass was heated to about 64 0C and maintained for about 1 hour. The reaction mass was then allowed to cool to about 28 0C and ethyl acetate (136 ml) was added. The reaction mass was maintained at about 28 0C for about 1 hour and the solid was filtered and washed with methanol (68 ml). The wet solid was dried at about 50 0C for about 1 hour. The dry solid was taken into another fresh round bottom flask and water (938 ml) was added. The mixture was stirred for about 10 minutes and the pH of the mixture was adjusted to about 8.9 using 10% aqueous sodium hydroxide solution. The mixture was stirred at about 28 0C for about 1 hour and then filtered. The filtered solid was washed with water (125 ml) and dried at about 53C for about 9 hours to get 35.9 g of the title compound. Purity by HPLC: 99.24% by weight. Chiral purity by HPLC: 99.64% by weight.

With the complex challenges of chemical substances, we look forward to future research findings about 22990-19-8,belong tetrahydroisoquinoline compound

Reference£º
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; WO2008/11462; (2008); A2;,
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

compound VIII 10.5g added to 105.0 ml anhydrous ethanol, adding (S) – (+)-tartaric acid 75.1g heating to reflux reaction 0.5h, then lowering the temperature to the system for 10-20 C crystallization, filtering to obtain solid; the solid using 20 ml of pure water refining, I of the obtained compound (S) – (+)-tartrate. 7. 5g, yield 42.0%.

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; SHANDONG JINCHENG MEDICAL AND CHEMICAL CO., LTD; Sun, bin; Zhao, chengbiao; Ma, qingshuang; Wang, xiaoguang; (7 pag.)CN105541712; (2016); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem