Month: November 2020

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.,42923-79-5

tert-Butyl 3,4-dihydro-7-nitroisoquinoline-2(1H)-carboxylate A mixture of 1,2,3,4-Tetrahydro-7-nitroisoquinoline (2.5 g, 11.6 mmol), 1,4-dioxane (24 mL), H2O (12 mL) and 1N NaOH (12 mL) was cooled in an ice-bath, and Boc2O (2.8 g, 12.8 mmol) was added. The mixture was stirred at room temperature for 2.5 h, acidified with a 5% KHSO4 solution to pH 2-3, and then extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give tert-butyl 3,4-dihydro-7-nitroisoquinoline-2(1H)-carboxylate (3.3 g, quant.), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) delta 8.13 (d, J=2.3 Hz, 1H), 8.03 (dd, J=8.4, 2.5 Hz, 1H), 7.45 (d, J=8.5 Hz, 1H), 4.63 (s, 2H), 3.60-3.57 (m, 2H), 2.90 (t, J=5.9 Hz, 2H), 1.44 (s, 9H); HPLC ret. time 3.51 min, 10-99% CH3CN, 5 min run; ESI-MS 279.2 m/z (MH+).

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; Vertex Pharmaceuticals Incorported; US2011/98311; (2011); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

Example 62 : 5 -(3 ‘,4’-difluoro-3 -methoxy- [1, 1 ‘-biphenyl] -4-yl)-N-( 1 ,3 ,4-thiadiazol-2-yl)-3 ,4- dihydroisoquinoline-2( 1 H)-sulfonamide Step 1 : 5-bromo-N-(l,3,4-thiadiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide A solution of l, l”-sulfonyldiimidazole (0.588 g, 2.97 mmol) and l,3,4-thiadiazol-2- amine (0.300 g, 2.97 mmol) in 6 mL of DMF was cooled to 0C. NaH (60% in mineral oil) (0.238 g, 9.91 mmol) was added. After 30 minutes, the reaction mixture was heated to 80C for one hour. 5-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (0.737 g, 2.97 mmol) and n,n-diisopropylethylamine (2.59 ml, 14.83 mmol) were added, and the reaction mixture was heated to 110C for an additional 3 hours. The reaction mixture was then diluted with DCM and washed with IN citric acid solution. The organics were dried over MgSC^ and concentrated. Purification of the crude residue by reverse phase column chromatography [Redisep Gold C18, 10-100% (0.1%NH4OH in MeOH)/(0.1%NH4OH in water)] gave 5- bromo-N-(l,3,4-thiadiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide (0.520 g, 1.386 mmol, 46.7 % yield). (M+H)+= 375.0.

923591-51-9 is used more and more widely, 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

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 dry microwave vial under nitrogen was added 2,4-dichloro-6-methyl-l,3,5-triazine (150 mg, 0.915 mmol), 6-bromo-l,2,3,4-tetrahydroisoquinoline (195 mg, 0.919 mmol) and anhydrous NMP (2.5 mL). The reaction was flushed with nitrogen, then treated with triethylamine (400 mu, 2.87 mmol), capped and allowed to stir at room temp for 30 min. The reaction was then treated with morpholine (800 mg, 9.18 mmol) and stirred at room temp for 2 h. The resulting white solid was collected by vacuum filtration to afford 4-(4- (6-bromo-3,4-dihydroisoquinolin-2(lH)-yl)-6-methyl-l,3,5-triazin-2-yl)mophiholine, 200 mg (54%). LCMS (M+l) = 390.1, 392.1. NMR (500 MHz, DMSO-de) delta 7.41 (d, J=1.7 Hz, 1H), 7.38 (dd, J=8.2, 2.1 Hz, 1H), 7.23 (d, J=8.2 Hz, 1H), 4.86 – 4.77 (m, 2H), 3.93 (br s, 2H), 3.78 – 3.69 (m, 4H), 3.62 (br d, J=4.6 Hz, 4H), 2.84 (br t, J=5.6 Hz, 2H), 2.20 (s, 3H).

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

42923-79-5,7-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.

A mixture of 7-nitro-1,2,3,4-tetrahydroisoquinoline (0.55 g, 3.1 mmole), di-t-butyldicarbonate (0.70 g, 3.2 mmole), triethylamine (1.0 mL, 7.7 mmole) in dichloromethane (8 mL) was stirred at rt for 8 h. The reaction mixture was diluted with water (50 mL) and stirred for 1 h. The organic phase was separated and washed with brine. Concentration of the organic phase gave 2-(t-butoxycarbonyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline. 1H NMR (CDCl3): delta 8.03-7.95 (m, 2H), 7.28 (d, 1H, J=8.4 Hz), 4.66 (s, 2H), 3.68 (t, 2H, J=6.0 Hz), 2.92 (t, 2H, J=6.0 Hz), 1.49 (s, 9H).

42923-79-5 is used more and more widely, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; RIGEL PHARMACEUTICALS, INC.; Singh, Rajinder; Argade, Ankush; Payan, Donald; Molineaux, Susan; Holland, Sacha; Clough, Jeffrey; Keim, Holger; Bhamidipati, Somasekhar; Sylvain, Catherine; Li, Hui; Rossi, Alexander; US2015/266828; (2015); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 7-Methoxy-1,2,3,4-tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 43207-78-9, its synthesis route is as follows.,43207-78-9

To a solution OF 7-METHOXY-3, 4-DIHYDRO-2H-ISOQUINOLIN-1-ONE (200mg) in THF (8mL) is added LiAIH4 (76mg) and stirred for 3hr under reflux, and diluted with THF. The reaction mixture is added sodium sulfate decahydrate and filtration through celite pad. The filtrate is concentrated in vacuo. The residue is dissolved in Et20, then HCI in EtOAc is added the Et20. White precipitate is collected. by filtration to provide the title compound; 1 H NMR (CDCI3, 6 (ppm) ); 2.92 (dd, 2H), 3.30-3. 35 (m, 2H), 3.72 (s, 3H), 4.18-4. 23 (m, 2H), 6.81- 6.86 (m, 2H), 7.12 (d, 1H), 9.45 (brs, 2H).

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

Reference£º
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/69256; (2004); 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

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

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

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 quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO84,mainly used in chemical industry, its synthesis route is as follows.,42923-79-5

Combined solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline (1.0 g, 5.61 mmol), Boc2O (2 mL, 8.42 mmol) and Et3N (1.5 mL, 11.22 mmol) dissolved in THF (12 mL) was stirred at room temperature for 2 h. After reaction completion, quenched with water, extracted with chloroform (3 X 50 mL). Evaporation of the solvent and purification of the resulting crude by silica gel column chromatography provided the desired product as a colorless viscous oil in 87% yield.1H NMR (400 MHz, Chloroform-d) delta 8.04 – 7.98 (m, 2H), 7.29 (d, J = 8.2 Hz, 1H), 4.66 (s, 2H), 3.69 (t, J = 5.9 Hz, 2H), 2.93 (t, J = 5.9 Hz, 2H), 1.50 (s, 9H). Yield: 87%.

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

Reference£º
Patent; SOUTHERN RESEARCH INSTITUTE; OYAGEN, INC.; ANANTHAN, Subramaniam; AUGELLI-SZAFRAN, Corinne E.; BENNETT, Ryan P.; SMITH, Harold C.; VENUKADASULA, Phanindra Krishna Mohan; (227 pag.)WO2019/133666; (2019); 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