Month: September 2020

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

General procedure: A mixture of CuI (10 mmol%) and K3PO4 (3.0 equiv.) was taken in a two necked round bottom flask evacuated and backfilled with nitrogen and fitted on oil bath. 2-Propanol (10 mL), ethylene glycol (1.1 mL), 1,2,3,4-tetrahydroisoqunoline (15 mmol, 2.0mL) and aryl iodide (10 mmol, 1.12 mL) were added successively by microsyring at rt. The reaction mixture was heated at 80-90 oC with stirring for 24-36 h. After the completion of the reaction was allowed to cool at rt. Diethyl ether (20 mL) and water (20 mL) was added to reaction mixture. The organic layer was extracted by diethyl ether (2 ¡Á 20mL). The combined organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by rotary evaporator and the crude product was purified by column chromatography on silica gel with a mixture of hexane/ethyl acetate as eluent to afford an analytically pure sample of substrates 1.

82771-60-6,7-Chloro-1,2,3,4-tetrahydroisoquinolinebelongs to tetrahydroisoquinoline compound, is more and more widely used in various fields. and we look forward to future research findings.

Reference£º
Article; Yadav, Arvind K.; Yadav, Lal Dhar S.; Tetrahedron Letters; vol. 56; 48; (2015); p. 6696 – 6699;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

75416-50-1, 8-Chloro-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,75416-50-1

General procedure: A mixture of alkylating agent (1equiv), appropriate amine (1.1equiv) K2CO3 (1.1equiv), and KI (catalytic) in DME or CH3CN (50mL) was placed in a round bottomed flask with a stirrer was heated to reflux on a heating plate for 24-28 h. The reaction was monitored by TLC for product formation. After reaction was complete, the resulting crude mixture was directly purified on silica gel by flash chromatography (gradient up to 70% EtOAc in hexanes) to afford the final compounds. The free base where necessary, was converted to the HCl or HBr salt and crystallized out of a mixture of MeOH-Et2O.

As the paragraph descriping shows that 75416-50-1 is playing an increasingly important role.

Reference£º
Article; Ofori, Edward; Zhu, Xue Y.; Etukala, Jagan R.; Bricker, Barbara A.; Ablordeppey, Seth Y.; Bioorganic and Medicinal Chemistry; vol. 24; 22; (2016); p. 5730 – 5740;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

The tetrahydroisoquinoline compound, cas is 91-21-4 name is 1,2,3,4-Tetrahydroisoquinoline, mainly used in chemical industry, its synthesis route is as follows.

Example 1: Synthesis of 3′-hydroxy-biphenyl-4-carboxylic acid 3-(2-methyl-l,2,3,4- tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide (Compound 1, Table 1); To concentrated H2S04 (100 mL) at 4C add 1,2,3 ,4-tetrahydro-isoquinoline (24.01 g, 180.3 mmol) dropwise keeping the temp below 15C. To the stirring mixture at 4C add NaNC>3 (20.04 g, 198.2 mmol) carefully keeping internal temp below 10 C and stir the mixture overnight at rt. Carefully add the reaction to stirring NH4OH (300 mL) to a final pH = 8. Extract the mixture with DCM (3 x 200 mL) and wash the organic phase with brine (100 mL). Dry the mixture (Na2S04), filter and concentrate. Dissolve the crude residue in EtOH (80 mL) and add concentrated HC1 (25 mL) resulting in a light brown solid which crystallizes in MeOH to give the desired product 7-nitro-l,2,3,4-tetrahydro- isoquinoline (21.91 g, 123.0 mmol)., 91-21-4

With the rapid development of chemical substances, we look forward to future research findings about 91-21-4

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KOWALSKI, Jennifer A.; LI, Xiang; MARSHALL, Daniel Richard; SCHLYER, Sabine; SIBLEY, Robert; SMITH-KEENAN, Lana Louise; SOLEYMANZADEH, Fariba; SORCEK, Ronald John; YOUNG, Erick Richard Roush; ZHANG, Yunlong; WO2012/6203; (2012); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

The tetrahydroisoquinoline compound, cas is 81237-69-6 name is 5-Bromo-1,2,3,4-tetrahydroisoquinoline, mainly used in chemical industry, its synthesis route is as follows.

(b) A stirred, ice-cooled solution of the above 2:1 mixture (14.3 g) in dichloromethane (150 ml) was saturated with hydrogen chloride and then evaporated under reduced pressure to afford the corresponding hydrochloride salt which was collected and dried. A stirred mixture of platinum oxide (1g) and a solution of the preceding hydrochloride salt in ethanol (150 ml) was hydrogenated for 30 hours at 50 psi (3.45 bar) and room temperature, then filtered. The filtrate was evaporated under reduced pressure and the residue chromatographed on silica gel, using a mixture of dichloromethane:methanol: 0.880 aqueous ammonia solution (90:10:1) as eluent, to give an 85:15 mixture (5.62 g) of 5-methyl-1,2,3,4-tetrahydroisoquinoline and 5-bromo-1,2,3,4-tetrahydroisoquinoline as an oil; major component: Rf 0.32 (SS 9), m/e 148 (M+H)+. The above 85:15 mixture was converted to the corresponding 2-trifluoroacetyl derivative mixture, using the procedure described in Preparation 3(b), to afford an oil; major component: Rf 0.90 (SS 10), m/e 244 (M+H)+.

81237-69-6, With the rapid development of chemical substances, we look forward to future research findings about 81237-69-6

Reference£º
Patent; Pfizer Inc.; US5750520; (1998); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

The tetrahydroisoquinoline compound, cas is 215798-19-9 name is 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride, mainly used in chemical industry, its synthesis route is as follows.

To a mixture of 6-bromo-l,2,3,4-tetrahydro-isoquinoline (10.60 g, 50 mmol) and t- butyl bromoacetate (9.95 g, 51 mmol, 1.02 eq.) in aceto?itrile (100 ml) are added sodium carbonate (10.6 g, 100 mmol, 2.0 eq.) and NaI ( 375 mg, 2.5 mmol, 0.05 eq.). The resulting mixture is stirred at rt for 16 hr. Water (100 ml) is added to quench the reaction, and the acetonitrile is evaporated. The residue is extracted with EtOAc (100 ml x 3), and the combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by silica gel flash chromatography (EtOAc/hexane, 1 :4) to give the title compound.MS (+VE) m/z 326.10 (M++l)., 215798-19-9

With the rapid development of chemical substances, we look forward to future research findings about 215798-19-9

Reference£º
Patent; NEUROGEN CORPORATION; WO2007/106349; (2007); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

The tetrahydroisoquinoline compound, cas is 215798-19-9 name is 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride, mainly used in chemical industry, its synthesis route is as follows.

6-bromo- 1 ,2,3,4-tetrahydroisoquinoline hydrochloride (1. 5g, 6 mmol),and potassium carbonate (1.7g, 12 mmol) were taken in acetone (100 mL). 2,4,6- tnmethylbenzenesulfonyl chloride (1.6g, 7.2 mmol) was added to the reaction mixture andstirred at ambient temperature for 1 6h. Crude reaction mixture was concentrated under reduced pressure, extracted with saturated bicarbonate and brine, dried and concentrated. The crude mixture was purified on silica using ethyl acetate-hexane (3 0-70) to obtain the title compound (2.OOg, 85% yield). ?H NMR (400 MHz, DMSO-d6) oe ppm 2.27 – 2.29 (m, 3 H)2.54 (s, 6 H) 2.81 (t, J=6.00 Hz, 2 H) 3.39 (t, J=5.99 Hz, 2 H) 4.25 (s, 2 H) 7.09 (s, 3 H) 7.16(d, J8.31 Hz, 2 H) 7.33 – 7.36 (m, 2 H) 7.38 (m, J=2.00 Hz, 2 H). MS (m/z): 396.0, 397.0(M+H) for two bromine isomers., 215798-19-9

With the rapid development of chemical substances, we look forward to future research findings about 215798-19-9

Reference£º
Patent; SAINT LOUIS UNIVERSITY; BURRIS, Thomas; WALKER, Jonn, K.; FLAVENY, Colin; CHATTERJEE, Arindam; (117 pag.)WO2017/223514; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

The tetrahydroisoquinoline compound, cas is 170097-67-3 name is 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid, mainly used in chemical industry, its synthesis route is as follows.

Intermediate 16: 1,1-dimethylethyl 6-({[1-(2-biphenylylmethyl)-5-methyl-1H-pyrazol-3-yl]amino}carbonyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate; To a solution of 1-(2-biphenylylmethyl)-5-methyl-1H-pyrazol-3-amine (Intermediate 6) (76 mg, 0.29 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (66 mg, 0.34 mmol), 1-hydroxybenzotriazole hydrate (46 mg, 0.34 mmol) and diisopropylethylamine (48 mg, 0.37 mmol) in DCM (10 mL) was added 2-{[(1,1-dimethylethyl)oxy]carbonyl}-1,2,3,4-tetrahydro-6-isoquinolinecarboxylic acid (84 mg, 0.3 mmol) and the mixture was stirred at room temperature for 4 days. The organic phase was then washed with NaOH (1N) and brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM to DCM/MeOH: 96/4 to give the title compound as a colorless oil (73 mg, 49%).LC/MS: m/z 523 (M+H)+, Rt: 4.03 min., 170097-67-3

With the rapid development of chemical substances, we look forward to future research findings about 170097-67-3

Reference£º
Patent; Bouillot, Anne Marie Jeanne; Daugan, Alain Claude-Marie; Dean, Anthony William; Fillmore, Martin Christian; US2010/22486; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

5-Bromo-1,2,3,4-tetrahydroisoquinoline, cas is 81237-69-6, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

Sodium triacetoxyborohydride (5.81 g, 27.4 mmol) was added to a THF (100 mL)-DMF (10 mL) mixed solution of 5-bromo-1,2,3,4-tetrahydroisoquinoline (2.90 g, 13.7 mmol) and 3-(trifluoromethyl)benzaldehyde (2.74 mL, 20.6 mmol), and the mixture was stirred for 15 hours at room temperature. The reaction solution was treated with the addition of water and 1 N sodium hydroxide aqueous solution, and was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and then concentrated at reduced pressure. The residue was purified by silica gel column chromatography to give 4.77 g of the titled compound (yield 94%) in the form of an oily substance.1H-NMR (CDCl3) delta: 2.72-2.80 (2H, m), 2.82-2.92 (2H, m), 3.62 (2H, s), 3.72 (2H, s), 6.91-6.96 (1H, m), 6.96-7.03 (1H, m), 7.40 (1H, dd, J=7.5, 1.3 Hz), 7.46 (1H, d, J=7.5 Hz), 7.51-7.56 (1H, m), 7.58 (1H, d, J=7.5 Hz), 7.65 (1H, s), 81237-69-6

With the rapid development of chemical substances, we look forward to future research findings about 81237-69-6

Reference£º
Patent; Takeda Pharmaceutical Company Limited; US2010/41891; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

Intermediate 94: 1.1-dimethylethyl 6-r({1-r(3.4-dichlorophenyl)methyll-5-methyl-1 H-1.2.3- triazol-4-yl}amino)carbonyl1-3,4-dihvdro-2(1 H)-isoquinolinecarboxylate; A mixture of 1-[(3,4-dichlorophenyl)methyl]-5-methyl-1 H-1 ,2,3-triazol-4-amine (Intermediate 69) (0.1g, 0.39mmol), 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6- isoquinolinecarboxylic acid (0.1 1g, 0.37mmol), HATU (0.19g, O.deltammol) and DIPEA (88mul_, O.deltammol) in DMF (5mL) was stirred at room temperature overnight. The mixture was evaporated. The residue was washed with water and extracted with DCM. The organic phase was dried over Na2SO4, filtered and concentrated. The title compound was obtained as a white solid after purification by flash column chromatography eluting with DCM/MeOH: 98//2 and crystallisation from isopropyl ether (86mg, 43 %). HRMS calculated for C25H27CI2N5O3 (M+H)+ 516.1569, found: 516.1591 , Rt: 3.13 min., 170097-67-3

With the rapid development of chemical substances, we look forward to future research findings about 170097-67-3

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/16216; (2009); 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,226942-29-6

To a solution of 6- bromo-l,2,3,4-tetrahydroisoquinoline (1.25 g, 5.88 mmol) in DCM (25 mL) was added 2- chloro-6-methylbenzaldehyde (1.0 g, 6.5 mmol) and acetic acid (0.337 mL, 5.88 mmol) in DCM (25 mL). Then sodium triacetoxyborohydride (1.62 g, 7.64 mmol) was added. The mixture was stirred at r.t for 16 hrs. The mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2S04and concentrated. The residue was purified by recrystallization with EtOAc to give 6-bromo- 2-(2-chloro-6-methylbenzyl)-l,2,3,4-tetrahydroisoquinoline (1.44 g, 4.11 mmol, 69.8 % yield). LCMS (M+H): 350.00, 352.00. 1H NMR (400MHz, DMSO-d6) delta 7.32 – 7.14 (m, 5H), 6.99 (d, 7=8.1 Hz, 1H), 3.77 (s, 2H), 3.56 (s, 2H), 2.78 – 2.72 (m, 2H), 2.71 – 2.66 (m, 2H), 2.41 (s, 3H).

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; EASTMAN, Kyle J.; KADOW, John F.; PARCELLA, Kyle E.; NAIDU, B. Narasimhulu; WANG, Tao; YIN, Zhiwei; ZHANG, Zhongxing; (121 pag.)WO2017/25917; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem