Month: October 2020

As a common heterocyclic compound, it belong tetrahydroisoquinoline compound,1,2,3,4-Tetrahydroisoquinoline,91-21-4,Molecular formula: C9H11N,mainly used in chemical industry, its synthesis route is as follows.,91-21-4

To 11 mL of 9 concentrated sulfuric acid in an ice bath was added 0 1,2,3,4-tetrahydroisoquinoline (2.9 g, 21 mmol), and 0 potassium nitrate (2.4 g, 24 mmol) was added slowly. The mixture was allowed to increase to room temperature and react overnight. Then the reaction liquid was poured into ice water, and pH was adjusted to around 10 with concentrated aqueous ammonia. After extraction with DCM three times, organic layers were combined and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated under reduced pressure to obtain oil. The oil was dissolved in 16 mL of ethanol in an ice bath, and 3 mL of concentrated HCl was added to generate plenty of solid, which was subjected to suction filtration and drying. After recrystallization with methanol, 1.9 g of beige solid was obtained with a yield of 42percent.

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

Reference£º
Patent; Peking University; Zhengzhou Granlen Pharmatech. Ltd.; LI, Runtao; AN, Haoyun; HAN, Liqiang; GE, Zemei; CUI, Jingrong; CHENG, Tieming; (52 pag.)EP3363803; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 170097-67-3, its synthesis route is as follows.,170097-67-3

Add 4-(4,6-dimethoxy- 1,3 ,5-triazin-2-yl)-4-methylmorpholinium chloride (26.34 g, 94.86 mmol) to solution of 2-tert-butoxycarbonyl-3 ,4-dihydro- 1H-isoquinoline-6- carboxylic acid (18.79 g, 67.76 mmol), N,O-dimethylhydroxylamine hydrochloride (7.93g, 81.31 mmol) and N-methylmorpholine (13.71 g, 14.95 mL, 135.51 mmol) in methanol (563.70 mL). Stir the mixture at room temperature overnight. Concentrate under reduced pressure. Then add ethyl acetate (250 mL) and water (250 mL) to the mixture. Separate the layers and extract the aqueous layer with ethyl acetate (150 mL). Combine the organic layers, wash with aqueous hydrochloric acid solution (2 M, 200 mL), wash withsaturated aqueous sodium chloride (200 mL) and dry over sodium sulfate. Concentrate under reduced pressure to afford the title compound (24.28 g, 75.78 mmol). MS (m/z):321 (M+1).

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

Reference£º
Patent; ELI LILLY AND COMPANY; BURKHOLDER, Timothy Paul; DEL PRADO, Miriam Filadelfa; FERNANDEZ, Maria Carmen; HEINZ II, Lawrence Joseph; PRIETO, Lourdes; ZHAO, Genshi; WO2015/54060; (2015); 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.

Into a 250-mL round-bottom flask, was placed 6-bromo-l,2,3,4-tetrahydroisoquinoline (6.0 g, 28.3 mmol) in MeOH (100 mL) under N2. To the stirred solution was added HCHO (1.02 g, 34 mmol) in portions at RT. The resulting solution was stirred for 4 h, then NaBLbCN (3.56 g, 56.6 mmol) was added in portions at RT. The resulting solution was stirred overnight at RT. The reaction was then quenched by the addition of water (100 mL) and extracted with 3×150 mL ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was eluted from a silica gel column with acetate/petroleum ether (1 : 1). This resulted in 5 g (78.2%) of the title compound as a white solid. MS-ESI: 226/228 (M+l)., 226942-29-6

The synthetic route of 226942-29-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

57060-88-5,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.

To a solution of Boc-Dmt-OH (309 mg, 1 mmol), HBTU (379 mg, 1 mmol) and DIEA (348 muL, 2 mmol) in 5 mL DMF was added a solution of HCl x H-Tic-OMe (227.5 mg, 1 mmol) and DIEA (174 muL, 1 mmol) in 5 mL DMF. The reaction mixture was stirred for 5 h at room temperature and progress of the reaction was monitored by TLC. After solvent evaporation in vacuo, the residue was dissolved in 50 mL AcOEt and the resulting solution was washed with 5% KHSO4 (aq.), saturated NaHCO3 (aq.) and brine. The organic phase was dried (MgSO4), filtered and evaporated to dryness, yielding 430 mg of crude product (90% yield). The crude Boc-protected dipeptide ester was deprotected by treatment with aqueous TFA (95% vv) for 45 min under stirring and cooling with ice. After TFA evaporation in vacuo, the TFA salt of the dipeptide ester was precipitated with ether (Et2O), affording 300 mg (90% yield) of crude product which was purified by preparative HPLC. TFA x H-Dmt-Tic-OMe: TLC Rf (I) 0.55; MS [M+H]+ 383.

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

Reference£º
Article; Weltrowska, Grazyna; Nguyen, Thi M.-D.; Chung, Nga N.; Wilkes, Brian C.; Schiller, Peter W.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 18; (2013); p. 5082 – 5085;,
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.42923-79-5,7-Nitro-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

To a stined solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline (5 g, 28.09 mmol) in DMF (20 mL) was added K2C03 (15.5 g, 112.36 mmol) followed by ethyl iodide (4.4 mL, 56.18 mmol). The reaction was stined at RT for 3 h. Water (50 mL) was added, and the mixture was extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine (25 mL), dried (Na2SO4) and concentrated in vacuo. The resulting crude residue was purified by column chromatography (Si02, 30% EA/pet. ether) to afford 2- ethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline (3.1 g, 54%) as a pale yellow liquid. MS (ESI) mlz 207.1 [M+H].

42923-79-5, As the paragraph descriping shows that 42923-79-5 is playing an increasingly important role.

Reference£º
Patent; ZENO ROYALTIES & MILESTONES, LLC; HUANG, Peter, Qinhua; BOREN, Brant, Clayton; BUNKER, Kevin, Duane; LIU, Hui; PALIWAL, Sunil; (99 pag.)WO2019/28008; (2019); 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

Example 2methyl 2-(4-bromobenzyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate Intermediate-2; To a solution of methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride (500.0 mg, 2.00 mmol) in DMF (17.0 mL) was added 4-bromobenzylbromide (604 mg, 2.42 mmol) and K2CO3 (910 mg, 6.59 mmol). The resulting mixture was stirred overnight at rt. EtOAc and water were added, and the phases were separated. The organic phase was dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography (SiO2, 0-40% EtOAc in hexane) to give methyl 2-(4-bromobenzyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (753 mg, 100%). LC-MS: (FA) ES+ 361; 1H NMR (300 MHz, CDCl3) delta 7.86-7.70 (m, 2H), 7.46 (dd, J=8.7, 2.1 Hz, 2H), 7.36-7.21 (m, 2H), 7.04 (d, J=8.0 Hz, 1H), 3.89 (d, J=3.8 Hz, 3H), 3.64 (s, 4H), 2.93 (t, J=5.8 Hz, 2H), 2.83-2.64 (m, 2H).

The synthetic route of 877861-62-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Millennium Pharmaceuticals, Inc.; US2012/165316; (2012); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 7-Chloro-1,2,3,4-tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 82771-60-6, its synthesis route is as follows.,82771-60-6

To a mixture of 7-chloro- l,2,3,4-tetrahydroisoquinoline (200 mg, 1.19 mmol), 5-bromo-2- pyrimidin-2-yl-pyrimidine (226 mg, 954 muiotaetaomicron, the product of step 3 in Example 1) and CS2CO3 (1.94 g, 5.97 mmol) in dioxane (15 mL) was added Brettphos Pd G3 (216 mg, 239 muiotaetaomicron, CAS registry number: 1470372-59-8). The resulting mixture was heated at 120 C with stirring for 48 hrs under N2 and filtered. The filtrate was concentrated in vacuo. The residue was purified by prep-HPLC to give 7-chloro-2-(2-pyrimidin-2-ylpyrimidin-5-yl)-3,4-dihydro- lH-isoquinoline (0436) (26 mg) as light yellow solid. XH NMR (400 MHz, Methanol-^) delta ppm: 8.87-8.99 (m, 2H), 8.55- 8.70 (m, 2H), 7.45-7.59 (m, IH), 7.25-7.38 (m, IH), 7.21 (s, 2H), 4.62 (s, 2H), 3.76 (t, 2H), 3.02 (s, 2H). MS obsd. (ESI+) [(M+H)+] : 324

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

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 belong tetrahydroisoquinoline compound,6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,215798-19-9,Molecular formula: C9H11BrClN,mainly used in chemical industry, its synthesis route is as follows.,215798-19-9

Step A: Preparation of 2-(6-Bromo-3,4-dihydroisoquinolin-2(lH)-yl)-2-oxoethyl Acetate. To a solution of 6-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (0.400 g, 1.609 mmol) and triethylamine (1.122 mL, 8.05 mmol) in DCM (10 mL)was added 2-chloro-2- oxoethyl acetate (0.242 g, 1.770 mmol). The reaction was stirred at room temperature for 30 min. The mixture was diluted with DCM, washed with 1 M HCl, brine, dried over Na2SO4, and concentrated to give the title compound without further purification

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

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

Into a 20 mL vial was charged 7-nitro-l,2,3,4-tetrahydroisoquinoline, hydrochloric acid salt (0.300 g, 1.398 mmol), methoxyacetyl chloride (0.141 ml, 1.537 mmol), triethylamine (0.429 ml, 3.07 mmol), and dichloromethane (6.99 ml). The reaction was stirred at room temperature for 2 hours. The reaction was diluted with dichloromethane, washed with IN HC1, saturated aqueous sodium bicarbonate, and brine. The organic layer was dried over MgS04, filtered and concentrated to provide the title compound. MS (DCI(+)) m/e 251 (M+H)+.

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

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

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 R)-1 -phenyl-1 ,2,3,4-tetrahydroisoquinoline (25 g) recovered from the filtrate of the resolution step, potassium hydroxide (15.5 g), water (12.5 mL), and dimethyl sulfoxide (50 mL) were placed into a clean and dry round bottom flask and stirred for 5 minutes. The reaction mixture was heated to reflux and maintained for 11 hours, 45 minutes. The reaction mass was cooled to 28C and chilled water (375 ml) was added to the reaction mixture and stirred for 35 minutes. The separated solid was then filtered, washed with water (25 mL) and dried at about 55C to afford 13 g of the title compound.

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.; WO2008/128028; (2008); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem