Heterocyclic Building Blocks-Tetrahydroisoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.170097-67-3,2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,as a common compound, the synthetic route is as follows.

HATU (213 mg, 0.56 mmol) was added to a mixture of (R)-3-amino-N-(3-(cyclopropylmethyl)-7-fluoro-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl)piperidine-1-carboxamide (180 mg, 0.43 mmol), 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid (126 mg, 0.45 mmol) and DIEA (150 muL, 0.86 mmol) in DMF (2.2 mL) at room temperature, and the mixture was stirred at room temperature for 15 hr. To the reaction mixture was added water, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 79?100% ethyl acetate/hexane) to give the title compound (262.6 mg, 0.388 mmol, 90%) as a white amorphous solid. 1H NMR (300 MHz, CDCl3):delta 0.41-0.49(4H,m), 1.28-1.34(1H,m), 1.49(9H,s), 1.60(6H,d,J=7.2 Hz), 1.65-2.02(4H,m), 2.88(2H,t,J=5.7 Hz), 3.49-3.68(5H,m), 3.75-3.83(1H,m), 3.94(2H,d,J=7.2 Hz), 4.13-4.19(1H,m), 4.59(2H,s), 4.93(1H,brs), 6.70-6.75(2H,m), 7.08(1H,d,J=12.8 Hz), 7.18(1H,d,J=8.7 Hz), 7.56-7.62(2H,m), 8.60(1H,d,J=8.7 Hz).

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

Reference£º
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; ODA, Tsuneo; IMADA, Takashi; KONO, Mitsunori; SATO, Ayumu; TOMATA, Yoshihide; OCHIDA, Atsuko; ISHII, Naoki; SASAKI, Yusuke; FUKASE, Yoshiyuki; YUKAWA, Tomoya; FUKUMOTO, Shoji; (200 pag.)EP3192791; (2017); 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.170097-67-3,2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,as a common compound, the synthetic route is as follows.

Intermediate 6: 1 ,1-Dimethylethyl 6-({ri-({5-chloro-2-r(cvclopropylmethyl)oxyl phenyllmethyl)- 5-methyl-1 /-/-pyrazol-3-yl1amino}carbonyl)-3,4-dihvdro-2(1 H)-isoquinolinecarboxylateTo a solution of 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6- isoquinolinecarboxylic acid (200 mg, 0.72 mmol), N-(3-dimethylaminopropyl)-N’- ethylcarbodiimide hydrochloride (158 mg, 0.82 mmol), 1-hydroxybenzotriazole hydrate (1 11 mg, 0.82 mmol) and diisopropylethylamine (1 15 mg, 0.89 mmol) in DCM (15 ml.) was added Intermediate 4 (200 mg, 0.69 mmol) and the mixture was stirred at room temperature for 4 days. The organic phase was then washed with HCI (1 N), NaOH (1 N) and brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM/EtOAc: 90/10 to give the title compound as yellow oil (316 mg, 84%). LC/MS: m/z 551 (M+H)+, Rt: 4.15 min.

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

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/10560; (2009); 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.215798-19-9,6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.

To a solution of 6-bromo- I ,2,3,4-tetrahydroisoquinoline hydrochloride (2.8 g, 11.3 mmol) inMeCN (50 mL) was added benzyl bromide (2.1 g, 12.4 mmol) and Cs2CO3 (11.1 g, 33.9 mmol).After addition, the resulting mixture was heated at reflux for I h. The solvent was evaporatedunder reduced pressure and the residue was dissolved in ethyl acetate (100 mL). The solutionwas then washed with brine (100 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica-gel chromatography (petroleum ether: ethyl acetate = 10:1) to give the title compound (2.7 g, 79% yield) as a colourless oil.

As the paragraph descriping shows that 215798-19-9 is playing an increasingly important role.

Reference£º
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; COTE, Alexandre; GEHLING, Victor; HSIAO-WEI TSUI, Vickie; KIEFER, James, Richard, Jr.; LIANG, Jun; MAGNUSON, Steven; NASVESCHUK, Christopher, G.; PASTOR, Richard; ROMERO, F. Anthony; TAYLOR, Alexander, M.; ZHANG, Birong; (287 pag.)WO2016/112284; (2016); 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.

A mixture of 4-chloro-benzo[4,5]furo[3,2-d]pyrimidine (1.06 g, 5.19 mmol), 6-bromo-l,2,3,4- tetrahydroisoquinoline (1.0 g, 4.7 mmol), potassium carbonate (1.95 g, 14.1 mmol) and sodium iodide (0.71 g, 4.7 mmol) in dioxane (50 mL) was heated at 90 C for 6 hrs. The mixture was diluted with EtOAc and washed with water, brine, dried over Na2S04 and concentrated. The residue was purified by recrystallization with EtOAc to give 4-(6- bromo-3,4-dihydroisoquinolin-2(lH)-yl)benzofuro[3,2-d]pyrimidine (1.2 g, 3.16 mmol, 66.9 % yield). LCMS (M+H): 379.90, 381.90.

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

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

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 6-bromo-1,2,3,4-tetrahydroisoquinoline (1000 mg, 4.7 mmol) and triethylamine (1.0 mL, 7.0 mmol) in DCM (20 mL) was added trimethyl acetyl chloride (0.64 mL, 5.2 mmol) at 0 C and the solution stirred at 25 C for 2 h. Water (60 mL) was added and extracted with DCM (30 mL x3), the combined organics were washed with brine and dried over Na2SO4. The solution was filtered and reduced in vacuo to afford 1-(6-bromo-3,4-dihydro-1H-isoquinolin-2-yl)-2,2-dimethylpropan-1-one (1390 mg, 4.7 mmol, 99% yield) as a light-yellow solid. UPLC-MS (ES+, Method F), 4.02 min, m/z 298.0 [M+H]+

As the paragraph descriping shows that 226942-29-6 is playing an increasingly important role.

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

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.

To a solution of Boc-L-proline (Int-15a, 406 mg, 1.88 mmol) in 10 mL of DMF was added amine Int-16a (400 mg, 1.88 mmol), EDCI (450 mg, 2.35 mmol), HOBT (317 mg, 2.35 mmol), and diisopropylethylamine (0.65 mL, 3.76 mmol). The resulting reaction was heated at 85 0C and allowed to stir at this temperature for 16 hours. The reaction mixture was cooled to room temperature and was then partitioned between EtOAc and water. The organic phase was separated and the aqueous phase was further extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to provide a crude residue which was purified using (ISCO) flash column chromatography (EtO Ac/Hex, 0 to 50% EtOAc eluent ) to provide Compound Int-16b (680 mg, 88%).

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

Reference£º
Patent; SCHERING CORPORATION; ZENG, Qingbei; CHEN, Kevin, X.; ANILKUMAR, Gopinadhan, N.; ROSENBLUM, Stuart, B.; KOZLOWSKI, Joseph, A.; NJOROGE, F., George; WO2010/138791; (2010); 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.42923-77-3,6-Methoxy-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

Example 53D /erf-butyl 6-methoxy-3,4-dihydroisoquinoline-2(lH)-carboxylate To a solution of the product of Example 53C (1.88 g, 11.5 mmol) in dichloromethane (40 mL) was added triethylamine (2.3 g, 23 mmol) and di-teri-butyl dicarbonate (3 g, 13.8 mmol). After stirring for 16 hours, the mixture was poured into water (50 mL) and extracted with dichloromethane (2 chi 100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash chromatography eluting with 10: 1 hexane:ethyl acetate to give the title compound. MS : 264 (M+H+).

The synthetic route of 42923-77-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; WU, Fengchun; SHEN, Yan; LIU, Cuihua; ZOU, Zhenguang; WO2012/97684; (2012); 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.923591-51-9,5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.

5-Bromo-3.4-dihvdroisoquinoline-2(lH)-carbaldehyde5-Bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride was suspended in diethyl ether and washed with IN NaOH, dried with Na2SO4 and concentrated to give the free amine as an oil. The amine (405 mg, 1.9 mmol) was mixed with ethyl formate (1 mL) and stirred at 80 0C for 2h. The mixture was concentrated to give the product as a white solid (0.45 g, 100%). 1H NMR (300 MHz, CDCl3): delta 8.26 and 8.21 (s, IH), 7.52 – 7.42 (m, IH), 7.14 – 7.04 (m, 2H), 4.70 and 4.54 (s, 2H), 3.83 and 3.68 (t, J= 6.2 Hz, 2H), 2.98 – 2.85 (m, 2H); APCI-MS m/z: 240/242 1:1 [MH+].

As the paragraph descriping shows that 923591-51-9 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/7747; (2009); 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.42923-77-3,6-Methoxy-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

General procedure: step 1:The non-lipid compound (see Table 1 for specific substances) and the 1,2,3,4-tetrahydroisoquinoline compound (specificThe substance is shown in Table 1) added to the reaction vessel,Copper-containing compounds (see Table 1 for specific substances),Additives (see Table 1 for specific substances) and organic solvents (see Table 1 for specific substances) were added to the reaction vessel.Step 2: uniformly heat the reaction vessel (such as oil bath) to the temperature described in Table 1,The oxime compound and the 1,2,3,4-tetrahydroisoquinoline compound are reacted in an organic solvent and continue for the time described in Table 1;The reaction atmosphere to be described can be reacted by selecting air.Of course, the amount of oxygen required is 15-30%.Step 3: Purification step.

42923-77-3 6-Methoxy-1,2,3,4-tetrahydroisoquinoline 39356, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; Xiangtan University; Huang Huawen; Qu Zhonghua; Deng Guojun; Xiao Fuhong; Chen Shanping; (32 pag.)CN110294758; (2019); A;,
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

Example 16 Preparation of intermediate 6-bromomethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (D-1) To a solution of 3,4-dihydro-1H-isoquinoline-2,6-dicarboxylic acid 2-tert-butyl ester (12.50 g, 45.08 mmol) in dry THF (125.0 mL), under nitrogen at 25 C., is added via syringe borane THF complex (99.17 mL, 99.17 mmol) The mixture is stirred at 25 C. for 16 h then water (10.0 mL) is slowly added followed by 2.0 M Na2CO3 (15.0 mL). This mixture is stirred for 15 min and then is diluted with EtOAc and the organic layers are collected. The organics are rinsed with 1M HCl, dried over MgSO4, and concentrated under reduced pressure to afford an oil. The oil is purified by silica gel chromatography to yield D-1-1 (11.8 g, 99.3% yield), as a white solid. To a solution of alcohol, D-1-1, (9.50 g, 36.1 mmol) and N,N-diisopropylethylamine (9.43 mL, 54.1 mmol) in dichloromethane (200.0 mL) is added triphenylphosphine dibromide (23.79 g, 54.11 mmol) at 0 C. The reaction is stirred for 1 h then concentrated under reduced pressure. The resulting residue is purified by silica gel chromatography to yield D-1 (8.74 g, 74% yield), as a white solid.

As the paragraph descriping shows that 170097-67-3 is playing an increasingly important role.

Reference£º
Patent; Boehringer Ingelheim International GmbH; BRENNEMAN, Jehrod Burnett; GINN, John David; HOPKINS, Tamara Denise; LOWE, MIchael D.; SARKO, Christopher Ronald; WESTBROOK, John A.; YU, Maolin; ZHANG, Zhonghua; (233 pag.)US2016/24059; (2016); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem