Month: November 2020

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.

Step A: Preparation of l-(6-Bromo-3,4-dihydroisoquinolin-2(lH)-yl)-2- hydroxyethanone. A magnetically stirred flask equipped with a drying tube was charged with a solution of6-bromo-l,2,3,4-tetrahydroisoquinoline (3.43 g, 16.2 mmol) in anhydrous toluene (40 mL), to which was added 2,2-dimethyl-l,3-dioxolan-4-one (1.9 g, 16.2 mmol). The resulting solution was refluxed for 20 h. The reaction mixture was cooled, extracted with 1 N HCl (30 mL), followed by brine (20 mL), and the organic extract was dried over MgSO4. The resulting solution was reduced in volume to about 25 mL, and heptane (25 mL) was gradually added over 20 min as precipitate formed. The resulting white solid was collected by filtration and rinsed with 1 : 1 toluene/heptane to provide the title compound. LCMS m/z = 270.1 [M+H]+; 1H NMR (400 MHz, CDCl3) delta 2.48 (bs, IH), 2.87-2.94 (m, 2H), 3.55 (t, J= 5.9 Hz, 1.2H), 3.89 (t, J= 6.1 Hz, 0.8H), 4.26 (s, 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), 7.32-7.39 (m, 2H).

226942-29-6, As the rapid development of chemical substances, we look forward to future research findings about 226942-29-6

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-Methoxy-1,2,3,4-tetrahydroisoquinoline, and cas is 42923-77-3, its synthesis route is as follows.,42923-77-3

General procedure: The synthesis of the intermediate 13 was carried out by 3-p-benzoic acid ethyl ester (2.76 g, 10 mmol) and Intermediate 5 (2.45 g, 15 mmol) by the above method, and purified by column chromatography ( petroleum ether: ethyl acetate = 20:3) Obtained white oil intermediate 13 (2.17 g, 70%)

With the complex challenges of chemical substances, we look forward to future research findings about 42923-77-3,belong tetrahydroisoquinoline compound

Reference£º
Patent; Sun Yat-sen University; Gu Qiong; Xu Jun; Fang Yuying; (20 pag.)CN109879856; (2019); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

42923-77-3,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.

a Ethyl (6-Methoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)acetate A solution of 6-methoxy-1,2,3,4-tetrahydroisoquinoline, Sall and Grunewald, J. Med. Chem. 1987, 30, 2208-2216 (1.1 mmol), ethyl chloroacetate (1.17 mmol), and K2 CO3 (1.17 mmol) in CH3 CN (10 mL) is stirred for 18 h. The mixture is partitioned between EtOAc and H2 O. The organic phase is concentrated to an oil, which is purified by chromatography (silica gel, gradient, 20-80% EtOAc/hexane) to afford the title compound.

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; SmithKline Beecham Corporation; US6159964; (2000); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

General procedure: The mixtures of 4-(bromomethyl)benzoic acid (200 mg, 0.93 mmol, 1 equiv.) and correspondingtetrahydroisoquinolines A (1.86 mmol, 2 equiv.) in 8 mL anhydrous THF were refluxed for 8 h,and the progress of the reaction was followed using TLC. After completion of the reaction, the reactionmixture was cooled to room temperature and the solvent was removed under vacuo. The resultantsolid was dissolved in 1N NaOH (20 mL) and then extracted with CH2Cl2 (3 20 mL). The aqueouslayer was acidified to pH = 1 using 10% HCl (20 mL), resulting in precipitation of the final compounds.

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

Reference£º
Article; Jiang, Cheng-Shi; Ge, Yong-Xi; Cheng, Zhi-Qiang; Wang, Yin-Yin; Tao, Hong-Rui; Zhu, Kongkai; Zhang, Hua; Molecules; vol. 24; 14; (2019);,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride, cas is 215798-14-4, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.,215798-14-4

5-Fluoro-2-nitroaniline (0.219 g, 1.40 mmole) was dissolved in anhydrous dimethylsulfoxide (6 mL). 6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.50 g, 2.1 mmole) was added triethylamine (0.66 mL) and solid iodine (1 mg). The mixture was heated at reflux for 5 h. under argon. The reaction was dissolved in dichloromethane (10 mL) and extracted with water (10 mL). The organic layer was washed with 3*30 mL water and then dried through a 1PS filter and evaporated to dryness. The crude material was chromatographed on a silica gel column (10 g) packed in hexanes. The column polarity was increased to 100% ethyl acetate over 10 CV, at 12 mL/min. Fractions (22 mL each) containing the product were pooled and stripped to give 2-nitro-5-(6-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)aniline (0.23 g, 42% yield).

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

Reference£º
Patent; SciFluor Life Sciences, Inc.; EDWARDS, D. Scott; ASKEW, Ben C.; FURUYA, Takeru; (64 pag.)US2017/355679; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 6-Methoxy-1,2,3,4-tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 42923-77-3, its synthesis route is as follows.,42923-77-3

General procedure: To a dried sealed vessel was added 1,2,3,4-tetrahydroisoquinoline (5 mL, 40 mmol), anhydrous K2CO3 (8.34 g,60 mmol), CuI (0.8 g, 4 mmol), L-Proline (0.92 g, 8 mmol), ethyl 6-bromopicolinate (4.32 g, 20 mmol), and DMSO (25 mL). Then themixture was stirred at 80 C for 16 h under N2 environment. Aftercooling to room temperature, water (100 mL) was added andextracted with EtOAc. Then, the combined organic layer was driedover MgSO4, filtered, and concentrated. The residue was purified bysilica gel flash chromatography (hexane/EtOAc = 5/1) to providecompound 14 as a white oil (3.94 g, 70%).

With the complex challenges of chemical substances, we look forward to future research findings about 6-Methoxy-1,2,3,4-tetrahydroisoquinoline

Reference£º
Article; Fang, Yuying; Zhou, Huihao; Gu, Qiong; Xu, Jun; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 133 – 145;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is 7-Chloro-1,2,3,4-tetrahydroisoquinoline,cas is 82771-60-6, mainly used in chemical industry, its synthesis route is as follows.

82771-60-6, 7- Chloro-1,2,3,4-tetrahydroisoquinoline (75.0 mg) was dissolved in DMF (0.7 mL). MA6-019 (86.0 mg) and DIPEA (a56.8 muL) were added into the mixture and stirred for 16 h. Purification by washing with aq. NaHCO3 (5 mL) and trituration from ethyl acetate/hexanes gave MA7-074 as a biege solid (77 mg, 62%). HPLC: >99% [tR = 11.6 min, 15% MeOH, 85 water (with 0.1% TFA), 20 min]. 1H NMR (400 MHz, DMSO) delta 10.71 (s, 1H), 7.17-7.11 (m , 3H), 3.94 (d, J = 16 Hz, 1H), 3.79 (d, J = 16 Hz, 1H), 3.65 (dd J = 8.0, J = 4.0, 1H), 2.90-2.95 (m, 1H), 2.90-2.81 (m, 1H), 2.70-2.80 (m, 2H), 2.65-2.50 (m, 2H), 2.20-2.08 (m, 1H), 1.95-1.85 (m, 1H). HRMS (ESI+): m/z calcd for C14H16ClN2O2 (M+H)+ 279.0894, found 279.0894, m/z calcd for C14H15ClN2O2Na (M+Na)+ 301.0714, found 301.0711. HPLC-MS: HPLC-MS (ESI+): m/z 279.2 [40%, (M+H)+], 277.1 [100%, (M-H)-].

As the rapid development of chemical substances, we look forward to future research findings about 82771-60-6

Reference£º
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; BURNETTE, Pearlie; LAWRENCE, Harshani; LAWRENCE, Nicholas J.; (285 pag.)WO2017/161119; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 6-Methoxy-1,2,3,4-tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 42923-77-3, its synthesis route is as follows.,42923-77-3

General procedure: To a dried sealed vessel was added 1,2,3,4-tetrahydroisoquinoline (5 mL, 40 mmol), anhydrous K2CO3 (8.34 g,60 mmol), CuI (0.8 g, 4 mmol), L-Proline (0.92 g, 8 mmol), ethyl 6-bromopicolinate (4.32 g, 20 mmol), and DMSO (25 mL). Then themixture was stirred at 80 C for 16 h under N2 environment. Aftercooling to room temperature, water (100 mL) was added andextracted with EtOAc. Then, the combined organic layer was driedover MgSO4, filtered, and concentrated. The residue was purified bysilica gel flash chromatography (hexane/EtOAc = 5/1) to providecompound 14 as a white oil (3.94 g, 70%).

With the complex challenges of chemical substances, we look forward to future research findings about 6-Methoxy-1,2,3,4-tetrahydroisoquinoline

Reference£º
Article; Fang, Yuying; Zhou, Huihao; Gu, Qiong; Xu, Jun; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 133 – 145;,
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

To a white suspension of 6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (CAS-RN 2 15798-14-4; 500 mg, 2.04 mmol) and pyridine (339 mg, 4.29 mmol) in dichloromethane (5 mL) was added dropwise a solution of triphosgene (273 mg, 918 j.imol,) in dichioromethane (5 mL) at 0C. After 30 mm the ice bath was removed, then after 16 h the reaction mixture was partitioned between 1 M aq. hydrochloric acid solution and dichloromethane. The organic layer was washed with breind, dried over magnesium sulfate, filtered, and evaporated to produce the title compound (546 mg, quant.) as a yellow oil.

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; MATTEI, Patrizio; HUNZIKER, Daniel; DI GIORGIO, Patrick; HERT, Jerome; RUDOLPH, Markus; WANG, Lisha; WO2015/78803; (2015); 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 hydrochloride, and cas is 215798-19-9, its synthesis route is as follows.,215798-19-9

Step F: Preparation of l-(6-Bromo-3,4-dihydroisoquinolin-2(lH)-yl)ethanone. To a stirred slurry of 6-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (2.460 g, 9.90 mmol) in THF (39.6 mL) was added triethylamine (4.14 mL, 29.7 mmol). The reaction mixture was cooled in an ice-bath, and acetyl chloride (0.880 mL, 12.37 mmol) was added slowly. The ice-bath was removed and the mixture was stirred at room temperature for 30 min. The mixture was diluted with ethyl acetate and washed with 1 M HCl and brine. The ethyl acetate layer was dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (1.983 g). LCMS m/z = 256.3 [M+H]+. 1H NMR (400 MHz, CDCl3) delta ppm 2.17 (d, J = 1.52 Hz, 3H), 2.78-2.91 (m, 2H), 3.60-3.86 (m, 2H), 4.53-4.70 (m, 2H), 6.94-7.06 (m, IH), 7.28-7.36 (m, 2 H).

With the complex challenges 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