Tag: M.W:200-300

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, To a solution of 5-bromo-l,2,3,4-tetrahydroisoquinoline (1.06 g, 10 mmol) in DMF (3 mL) was added zinc cyanide (875 mg, 7.5 mmol) and Pd(P(Ph3)4 (577 mg, 0.5 mmol). The resulting mixture was heated at 100 C and stirred for 15 hrs under N2, then poured into water (30 mL) and extracted with EA (50 mL) twice. The organic layers were combined and washed with water and brine, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by column (eluting with DCM: MeOH =20: 1, v:v) to give l,2,3,4-tetrahydroisoquinoline-5- carbonitrile (400 mg) as a yellow solid.

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); 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

3,4-Dimethoxybenzoic acid (100 mg, 0.55 mmol) was dissolved in DMF (1 mL). EDC (124.6 mg, 0.65 mmol) and HOBt (81 mg, 0.6 mmol) were added, followed by N- methylmorpholine (0.71 mL, 0.65 mmol). The resulting solution was agitated for 1 h. 3- Aminomethylphenyl-carbamic acid tert-butyl ester (111 mg, 0.5 mmol) was then added and the resulting mixture was agitated overnight. The reaction mixture was diluted with 4 mL dichloromethane, and the resulting mixture was washed with 1 N HCl (2 x 5 mL), NaHCO3 (saturated aqueous, 2 x 5 mL), and brine (1 x 5 mL), dried, and the solvents were evaporated to provide 190 mg (quantitative yield) of (3-[(3,4-dimethoxy-benzoylamino)- methyl]-phenyl}-carbamic acid tert-butyi ester, which was dissolved in dichloromethane (2 mL). SCX (1.14 g, 1.0 mmol) was added and the resulting mixture was agitated for 48 h. The reaction mixture was filtered and the solids were washed with dichloromethane (2 x 2 mL) and methanol (2 x 2 mL). The product was eluted with NH3 in methanol (7 N, 2 x 2 mL). The solvents were evaporated to provide 112 mg (78% yield) of 7V-(3-amino- benzyl)-3,4-dimethoxy-benzamide as a white solid, which was used directly. 3,4-Dihydro- lH-isoquinoline-2,6-dicarboxylic acid 2-tert-buty{ ester (19.1 mg, 0.069 mmol), EDC (19.2 mg, 0.1 mmol), and HOBt (12.2 mg, 0.09 mmol) were combined in a reaction tube, and DMF (1 mL) was added. To the resulting solution was added N-methylmorpholine (0.013 mL, 0.12 mmol), and the mixture was agitated for 1 h. The intermediate prepared above, Lambda/-(3-amino-benzyl)-3,4-dimethoxy-benzamide (17 mg, 0.059 mmol), was then added as a solution in DMF (0.3 mL), and the reaction mixture was agitated overnight. The reaction mixture was diluted with 6 mL dichloromethane, and the resulting mixture was washed with 1 N HCl (2 x 2 mL), NaHCO3 (saturated aqueous, 2 x 2 mL), and brine (1 x 2 mL), dried, and concentrated to 32 mg of 6-{3-[(3,4-dimethoxy-benzoylamino)- methyl]-phenylcarbamoyl}-3,4-dihydro-lH-isoquinoline-2-carboxylic acid tert-butyl ester as an oil, which was redissolved in dichloromethane (1 mL) and treated with SCX (284 mg, 0.25 mmol). The resulting mixture was agitated overnight. The reaction mixture was filtered and the solids were washed with dichloromethane (2 x 2 mL) and methanol (2 x 2 mL). The product was eluted with NH3 in methanol (7 N, 2 x 2 mL), and the eluant was evaporated. The resulting residue was purified by preparative HPLC using an acetonitrile/water/formic acid gradient providing the title compound as a formate salt (20 mg, 77% yield – 2 steps), MS analysis electrospray, 446 (M+H).

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/86047; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

Into a 500 mL erlenmeyer flask was charged 7-nitro-l,2,3,4-tetrahydroisoquinoline hydrochloride (5 g, 23.30 mmol) and 1,2-dichloroethane (250 mL). The solution was treated with 1 N NaOH (~50 mL) and stirred 10 minutes. The layers were separated and the organic layer was treated with paraformaldehyde (3.50 g, 116 mmol), acetic acid (6.67 mL, 24.48 mmol) and sodium cyanoborohydride (5.42 g, 86 mmol). The reaction was heated at 90 ¡ãC for 16 hours. The reaction was cooled to ambient temperature and saturated sodium bicarbonate (60 mL) was added. The bilayer was stirred for 1 hour and charged to a separatory funnel. The organic layer was dried ( a2S04) and concentrated. The concentrate was purified by flash chromatography on a 130 g silica gel column with a gradient of from 0percent to 1percent methanol in CH2C12 to provide the title compound. MS (DCI(+)) m/e 193.0 (M+H)+.

With the complex challenges of chemical substances, we look forward to future research findings about 99365-69-2,belong tetrahydroisoquinoline compound

Reference£º
Patent; ABBOTT LABORATORIES; BA-MAUNG, Nwe Y.; CLARK, Richard F.; ERICKSON, Scott A.; FIDANZE, Steve D.; KAWAI, Megumi; MANTEI, Robert A.; SHEPPARD, George S.; SORENSON, Bryan K.; WANG, Gary T.; WO2011/53476; (2011); 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.

99365-69-2, 7-nitro-1,2,3,4-tetrahydroiso-quinoline hydrochloride (1.8 g, 8.4 mmol) is dissolved in water(30 mL), followed by adding potassium carbonate (3.5 g, 25.4 mmol), and the reaction mixture is stirred at room temperature for 30 min, then extracted with ethyl acetate (20 mL * 3), dried with anhydrous Na2SO4, filtered and rotated to dryness, so as to obtain a brown solid. The solid is dissolved in methanol (20 mL), followed by adding 10percent Pd/C (220 mg), and the reaction mixture reacts at room temperature for 16 hrs under the hydrogen protection. Then the resulting substance is filtered with sillceousearth, washed and rotated to remove the solvent, so as to obtain a yellow solid compound of 1.2 g, that is 7-amino-1,2,3,4-tetrahydroiso-quinoline with a yield of 96percent. The product is directly used for the next reaction without purification.

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

Reference£º
Patent; Guangzhou Henovcom Bioscience Co. Ltd.; ZHANG, Jiancun; ZOU, Qingan; CHEN, Yanwei; (64 pag.)EP3401315; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

877861-62-6,Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride, cas is 877861-62-6, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

Step B: 3,4-Dihydro-1 H-isoquinoline-2,6-dicarboxylic acid 2-tert-butyl ester 6-methyl ester. To a solution of 6-methoxycarbonyl-1 ,2,3,4-tetrahydroisoquinoline hydrochloride (5.00 g, 22.0 mmol) in MeOH (220 ml_) was added di-tert-butyl dicarbonate (7.20 g, 33.0 mmol) and triethylamine (TEA; 9.20 ml_, 66.0 mmol). After 24 h, the mixture was concentrated to provide a yellow oil. This oil was dissolved in ethyl acetate (EtOAc; 200 ml_) and washed with 0.25 M HCI (200 ml_). The aqueous layer was extracted with EtOAc. The combined organic layers were dried and concentrated to provide 6.84 g (100%) of the title compound as a colorless oil.

With the rapid development of chemical substances, we look forward to future research findings about Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/109336; (2008); A1;,
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

To a suspension of 3,4-dihydro-1H-isoquinoline-2,6-dicarboxylic acid 2-tert-butyl ester (96 mg, 0.348 mmol) in toluene (4 mL) is added SOCl2 (254 muL, 10 eq.). The mixture is heated to reflux for 3 hours. All the solvent is removed under reduced pressure. The residue is redissolved in toluene and evaporated to dryness twice to remove excess HCl and is dried under high vacuum for 2 hours to give crude 6-chlorocarbonyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester.

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

Reference£º
Patent; Novartis AG; PAN, Shifeng; GRAY, Nathanael S.; FAN, Yi; GAO, Wenqi; MI, Yuan; EP1644367; (2015); B1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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.

Example 1.1: Preparation of (lambda)-6-(4-(2-(2-Methylpyrrolidin-l-yl)ethyl)phenyl)-l,2,3,4- tetrahydroisoquinoline. To a round-bottom flask was added 6-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (2.00 g, 8.05 mmol), (lambda)-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 Na2SO4, and concentrated. The residue was taken up in 1 M HCl solution and washed with ethyl acetate. The aqueous layer was basifed 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]+; 1H NMR (400 MHz, DMSO-J6) delta ppm 0.99-1.04 (m, 3H), 1.22-1.33 (m, IH), 1.59-1.69 (m, 2H), 1.81-1.92 (m, IH), 2.13 (q, J = 8.67 Hz, IH), 2.20-2.34 (m, 2H), 2.65- 2.83 (m, 5H), 2.94-3.04 (m, 3H), 3.10-3.18 (m, IH), 3.91 (s, 2H), 7.09 (d, J= 8.08 Hz, IH), 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

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

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/105206; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride, cas is 877861-62-6, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

877861-62-6, A mixture of ammonium thiocyanate (0.105 g, 1.384 mmol), 6-methoxycarbonyl- 1,2,3,4-tetrahydroisoquinoline hydrochloride (0.3 g, 1.3176 mmol) and THF (2 mL) was heated in a CEM microwave reactor for 1 h at 100 0C. Upon cooling to room temperature, the reaction mixture was diluted with EtOAc, and washed with H2O, 1 N HCl, saturated aqueous NaHCO3 and brine respectively, dried over anhydrous MgSO4, and concentrated under reduced pressure to afford methyl 2- (aminocarbonothioyl)-l,2,3,4-tetrahydroisoquinoline-6-carboxylate (0.33 g, 47%) as a white solid. LCMS: (FA) ES+ 251.

As the rapid development of chemical substances, we look forward to future research findings about 877861-62-6

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.

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, 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.877861-62-6,Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride,as a common compound, the synthetic route is as follows.,877861-62-6

Example 1methyl 2-{[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate Intermediate 1; A solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (0.830 g, 3.41 mmol) and triethylamine (0.792 mL, 5.68 mmol) in DMF (11.0 mL) was treated with TFFH (1.13 g, 4.26 mmol). The resulting mixture was stirred at rt for 30 min and then methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride (0.647 g, 2.84 mmol) and triethylamine (0.792 mL, 5.68 mmol) were added. The reaction mixture was stirred at rt for 2 days and then extracted with EtOAc three times. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the resulting residue by column chromatography (SiO2, 0-100% EtOAc in hexane) provided methyl 2-{[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (0.959 g, 82%). LC-MS: (FA) ES+ 439 (M+Na); 1H NMR (400 MHz, CDCl3) delta 7.85 (dd, J=10.1, 2.2 Hz, 2H), 7.19 (d, J=8.0 Hz, 1H), 4.79 (s, 2H), 3.95-3.77 (m, 5H), 3.67 (d, J=38.1 Hz, 2H), 3.21 (s, 2H), 2.92 (t, J=5.7 Hz, 2H), 2.24-2.10 (m, 2H), 1.61 (d, J=10.8 Hz, 1H), 1.44 (d, J=5.0 Hz, 10H), 1.33 (d, J=3.6 Hz, 3H).

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.; US2012/165316; (2012); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem