Author: Jessica.F

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

Step A: Preparation of l-(6-Bromo-3,4-dihydroisoquinolin-2(li/)-yl)-2- hydroxyethanone.A 4 L jacketed reactor equipped with mechanical stirrer, thermocouple, gas inlet, heating/cooling and condenser was charged with 6-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (150 g, 603 mmol), followed by dichloromethane (2.8 L), and the resulting slurry was mechanically stirred. Glycolic acid (55.07 g, 724 mmol) was added, followed by 1- hydroxybenzotriazole hydrate (101.66 g, 672 mmol) and N-(dimethylaminopropyl),N- ethylcarbodiimide hydrochloride (173.5 g, 905 mmol), followed by additional dichloromethane (0.2 L). With efficient stirring, 4-methylmorpholine (134.29 g, 1.327 mol) was slowly added in portions, while cooling to maintain a temperature at or below 25 0C, and then the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was then treated with 1 nu HCl (2 L), resulting in formation of solids, which were removed by filtration. The aqueous layer was then removed, and the organic layer was washed with water (150 mL). The organic extract was dried over MgSO4 filtered, and the solvent was removed from the filtrate to provide a golden yellow oil (190.6 g). The oil was then suspended in 1 nu NaOH (1 L), and stirred until fine colorless solids separated out. The solids were collected by filtration and rinsed with water (2 x 200 mL). A second batch of the same scale was prepared under identical conditions, and the solids were consolidated at this stage. After filtering and rinsing with additional water (4 x 500 mL), the combined solid was dried in a vacuum oven at 45 0C for 48 h to provide the title compound (292 g). LCMS m/z = 270.1 [M+H]+; 1H NMR (400 MHz, CDCl3) delta 2.48 (bs, IH), 2.91 (m, 2H), 3.55 (t, J = 5.9 Hz, 1.2H), 3.89 (t, J= 6.1 Hz, 0.8H), 4.26 (m, 2H), 4.40 (s, 0.8H), 4.75 (s, 1.2H), 7.00 (d, J = 8.3 Hz, 0.4H), 7.07 (d, J= 8.3 Hz, 0.6H), 7.37 (m, 2H).

With the complex challenges of chemical substances, we look forward to future research findings about 215798-19-9,belong tetrahydroisoquinoline compound

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

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

Boc2O (3.52 g, 16.14 mmol) was added to a solution of 6-bromo-1,2,3,4-tetrahydroisoquinoline (3.26 g, 15.37 mmol) in THF (45 mL) at room temperature, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0?8% ethyl acetate/hexane) to give tert-butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (5.05 g, 16.18 mmol, quant.) as a colorless oil. 1H NMR (300 MHz, CDCl3):delta 1.49(9H,s), 2.80(2H,t,J=5.9 Hz), 3.62(2H,t,J=5.9 Hz), 4.51(2H,s), 6.97(1H,d,J=8.7 Hz), 7.28-7.32(2H,m).

With the complex challenges of chemical substances, we look forward to future research findings about 226942-29-6,belong tetrahydroisoquinoline compound

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

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

General procedure: To a solution of corresponding acids (1.0mmol) in DCM (6mL) was added EDCI (1.5mmol), HOBt (1.5mmol), Et3N (3.0mmol) and corresponding amines (1.0mmol). The mixture was stirred at room temperature for 4h. The reaction mixture was diluted with saturated sodium bicarbonate aqueous solution (10mL) and extracted with DCM (3¡Á10mL). The combined organic layers were then dried and concentrated. The residue was purified by silica gel chromatography (dichloromethane/methanol, v/v, 90:10) to give the desired product.

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
Article; Shao, Jingwei; Zhu, Kongkai; Du, Daohai; Zhang, Yuanyuan; Tao, Hongrui; Chen, Zhifeng; Jiang, Hualiang; Chen, Kaixian; Luo, Cheng; Duan, Wenhu; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 317 – 333;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

7-nitrotetrahydroisoquinoline (35.6 mg, 0.2 mmol), graphene oxide (8 mg),And a stirrer is placed in the reaction tube, after replacing the inert gas,Add 1 ml of DMF and seal the reaction tube. Place the reaction tube in a 150C oil bath reaction potThe reaction was stirred for 18 hours; after cooling to room temperature, the catalyst was removed by filtration.The filtrate was diluted with 15 mL of water, diluted with 15 mL of water and extracted 3 times with ethyl acetate, 15 mL each time; the extracts were combined and dried over anhydrous sodium sulfate and filtered.The filtrate was concentrated under reduced pressure, and the crude product was subjected to column chromatography with ethyl acetate:petroleum ether=1:3 (containing 1% triethylamine) as eluent to obtain a pure product.Brown oil, yield 46%.

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; Xiangtan University; Gong Xing; Xie Guilin; Cai Changqun; Zhang Jingyu; (19 pag.)CN107827816; (2018); A;,
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.82771-60-6,7-Chloro-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,82771-60-6

Example 32: 7-Chloro-3,4-dihydroisoquinoline Int-50 [00379] To a solution of 7-chloro-l ,2,3,4-tetrahydro-isoquinoline ( 1.15 g, 6.86 mmol) in DCM (70.0 mL, 1090 mmol) was added Mn02 (5.96 g, 68.6 mmol) at rt, and the mixture was stirred for 16h. The reaction was filtered through a Celite pad and the residual solid was rinsed with DCM several times. The filtrate was concentrated in vacuo and the residue was purified by ISCO silica gel column chromatography (40g, eluting with 50% EtOAc in DCM, 50mL/min flow) to give 915 mg of the title compound as colorless solid. NMR (400 MHz, DMSO-d6) delta 8.35 (t, J = 2.1 Hz, 1H), 7.52 (d, J = 2.2 Hz, 1H), 7.46 (dd, J = 8.0, 2.3 Hz, 1H), 7.28 (d, J = 8.0 Hz, 1H), 3.70 – 3.63 (m, 2H), 2.71 – 2.65 (m, 2H).

As the paragraph descriping shows that 82771-60-6 is playing an increasingly important role.

Reference£º
Patent; DUFFEY, Matthew O.; ENGLAND, Dylan; FREEZE, Scott; HU, Zhigen; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; ONO, Koji; XU, He; (684 pag.)WO2016/4136; (2016); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

42923-77-3,42923-77-3, 6-Methoxy-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: 1,2,3,4-Tetra-hydroisoquinoline(67 mg, 0.5 mmol), compound 11a (125 mg, 0.5 mmol),and potassium carbonate (207 mg, 1.5 mmol) were added to N,Ndimethylformamide,and the mixture was stirred at 100 C for12 h. After the reaction was completed, the mixture was extractedwith EtOAc, washed with water, brine, and dried over Na2SO4. Theorganic phase was concentrated in vacuo. The residues were purifiedby flash column chromatography (EtOAc/hexane = 1:3) to givecompound 3a (90 mg, 52%) as a white solid.

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

Reference£º
Article; Zhao, Chao; Choi, You Hee; Khadka, Daulat Bikram; Jin, Yifeng; Lee, Kwang-Youl; Cho, Won-Jea; Bioorganic and Medicinal Chemistry; vol. 24; 4; (2016); p. 789 – 801;,
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: C8H14ClNO468,mainly used in chemical industry, its synthesis route is as follows.,170097-67-3

Example 24: 1 ,1-Dimethylethyl 6-r({1-r(3,4-dichlorophenyl)methvH-1 /-/-pyrazol-4- yl}amino)carbonyll-3,4-dihvdro-2(1 H)-isoquinolinecarboxylate;To a solution of 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6-isoquinoline carboxylic acid (138 mg, 0.5 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (114 mg, 0.6 mmol), 1-hydroxybenzotriazole hydrate (81 mg, 0.6 mmol) and triethylamine (60 mg, 0.6 mmol) in DCM (10 ml.) was added 1-[(3,4- dichlorophenyl)methyl]-1 H-pyrazol-4-amine (Intermediate 7) (120 mg, 0.5 mmol) and the reaction mixture was stirred at room temperature overnight. The organic phase was then washed with a 1 N sodium hydroxide solution, with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM/MeOH: 95/5 to give the title compound as a white solid (190 mg, 77%) after recrystallization from CH3CN. LC/MS: m/z 501 (M+H)+, Rt: 3.65 min.

With the synthetic route has been constantly updated, we look forward to future research findings about 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,belong tetrahydroisoquinoline compound

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/74824; (2008); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid,cas is 151838-62-9, mainly used in chemical industry, its synthesis route is as follows.

Step 1 3(R)-Carboethoxy-1,2,3,4-tetrahydroisoquinoline The title compound was obtained from N-Boc-D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Bachem) using standard amino acid chemical procedures.

151838-62-9, As the rapid development of chemical substances, we look forward to future research findings about 151838-62-9

Reference£º
Patent; Merck & Co., Inc.; US5977134; (1999); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

42923-77-3, 6-Methoxy-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,42923-77-3

a) To 1.6 g (6.1 mmol) 6-methoxy-1,2,3,4-tetrahydro-isoquinoline in 15 mL AcOH are added 0.34 mL (6.7 mmol) bromine and the mixture is stirred at r.t. for 3 h. The precipitate is filtered off and dried at r.t.C10H12BrNO (M = 242.1 g/mol)ESI-MS: 242 [M-i-H]R (HPLC): 0.74 mm (method A)

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ROTH, Gerald Juergen; FLECK, Martin; HAEBEL, Peter Wilhelm; HEIMANN, Annekatrin; HEINE, Niklas; (172 pag.)WO2016/41845; (2016); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

82771-60-6, 7-Chloro-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,82771-60-6

To a mixture of 7-chloro-1, 2, 3, 4-tetrahydroisoquinoline (20 mg, 0.12 mmol) , 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylacetic acid (40 mg, 0.11 mmol) , DIPEA (100 mg, 0.77 mmol) in DMF (1 mL) was added HATU (50 mg, 0.13 mmol) at rt and the mixture was stirred at rt for 16 hrs. 20 mL of EA was added and the mixture was washed with brine (10 mL x 3) , dried over Na2SO4and concentrated. The resulting residue was purified by prep-TLC (PE/EA = 1: 2) to give the title product (16.0 mg, yield: 28%) .1H NMR (400 MHz, DMSO-d6) delta 8.24 -8.03 (m, 3H) , 7.95 (s, 1H) , 7.50 -7.26 (m, 6H) , 7.24 (s, 1H) , 7.21 -7.03 (m, 2H) , 6.95 -6.88 (m, 1H) , 6.74 (s, 1H) , 4.78 -4.33 (m, 2H) , 3.80 -3.49 (m, 2H) , 2.84 -2.27 (m, 2H) . MS: M/e 525 (M+1)+.

The synthetic route of 82771-60-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BEIGENE, LTD.; ZHANG, Guoliang; SUN, Hanzi; ZHOU, Changyou; (253 pag.)WO2020/20097; (2020); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem