Heterocyclic Building Blocks-Tetrahydroisoquinoline

57196-62-0, 6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Titanium tetrachloride at 0 of dichloromethane (80mL) (8.8mL, 15.2g, 80mmol) was added, and then, dichloromethyl methyl ether (7.2mL, 9.2g, 80mmol) was added dropwise and, followed on 6-methoxy-1,2,3,4-tetrahydro – isoquinoline hydrochloride (4.0 g, 20 mmol) was added portionwise, followed by stirring for 3 hours the mixture at 0 C.. The reaction was stopped by slowly adding 2N HCl (50 mL), and the layers were separated. The organic layer was extracted with 1N hydrochloric acid (2 ¡Á 10 mL), and the acidic aqueous layer combined was washed with dichloromethane (1x20mL). Dichloromethane (100 mL) was added to the aqueous layer, and was adjusted to 10 with pH 10 N sodium hydroxide with ice-cooling a mixture of two layers (70 mL). Di -tert- butyl (4.8 g, 22 mmol) After addition, the mixture was stirred overnight. Dilute the reaction with dichloromethane (120 mL) and water (200 mL), and extracted with dichloromethane (2 ¡Á 100 mL) and the aqueous layer was separated. The combined organic layers were washed with water (3 ¡Á 150 mL), dried over magnesium sulfate, and concentrated. The residue oil was chromatographed on silica (200 g), first 8: 1 mixture of the n- hexane and ethyl acetate, followed by the same solvent 4: 2 with a mixture of 1, and, finally: 1 and eluted with a mixture of. The appropriate fractions were combined and concentrated and the residue triturated with n- hexane, first 5-formyl-6-methoxy-3,4-dihydro -1H- isoquinoline-2-carboxylic acid tert- butyl ester (1.72g, 5.9mmol, 29.5%), and then 7-formyl-6-methoxy-3,4-dihydro -1H- isoquinoline-2-carboxylic acid tert- butyl ester (2.88 g,. 9 .9mmol, yield 49.5%) as a colorless solids., 57196-62-0

57196-62-0 6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 2920335, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; MANNKIND CORPORATION; ZENG, QINGPING; TORO, ANDRAS; PATTERSON, JOHN BRUCE; WADE, WARREN STANFIELD; ZUBOVICS, ZOLTAN; YANG, YUN; WU, ZHIPENG; (403 pag.)JP2015/214548; (2015); A;,
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-6-carboxylic acid,cas is 170097-67-3, mainly used in chemical industry, its synthesis route is as follows.

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.

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

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.81237-69-6,5-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,81237-69-6

o a solution of 5-bromo-1,2,3,4-tetrahydroisoquinoline (1.0 g, 4.72 mmol) in ethylene glycol (15mL) was added copper(I) iodide (898 mg, 4.72 mmol), K3P04 (3.0 g, 14.15 mmol) and 4-iodo-1-methyl-1H-pyrazole (1.96 g, 9.43 mmol). The reaction mixture was heated to 120 C for 3 hunder a nitrogen atmosphere. After cooling to room temperature, the mixture was filtered andconcentrated in vacuo. Water (50 mL) was added and extracted with DCM (30 mL x 3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether / EtOAc = 1: 1) to give the title compound (0.28 g, 42% purity) as a brown solid which was further purifiedby reverse phase chromatography (acetonitrile 5-35/0.05% HC1 in water) to give the titlecompound (0.05 g, 4%, HC1 salt) as a light yellow solid. ?H NMR (400 IVIFIz, DMSO-d6) 9.77(s, 1H), 8.65 (s, 1H), 8.26 (s, 1H), 8.11 (d, J 8.0 Hz, 1H), 7.99 (d, J 7.2 Hz, 1H), 7.60-7.54(m, 1H), 4.55 (t, J= 8.0 Hz, 2H), 3.95 (s, 3H), 3.38 (t, J= 8.0 Hz, 2H), 2.54 (s, 2H). LCMS M/Z(M+H) 292.

The synthetic route of 81237-69-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is 7-Nitro-1,2,3,4-tetrahydroisoquinoline,cas is 42923-79-5, mainly used in chemical industry, its synthesis route is as follows.

a. 2-[(4-cyanophenyl)-acetyl]-7-nitro-1,2,3,4-tetrahydro-isoquinoline 4.0 g (22.5 mmol) of 7-nitro-1,2,3,4-tetrahydro-isoquinoline are dissolved in 100 ml of chlorobenzene, mixed with 4.24 g (25 mmol) of 4-cyanophenylacetic acid chloride and refluxed for 2 hours. After cooling to ambient temperature the mixture is diluted with 11 of petroleum ether and filtered. The residue is dissolved in ethyl acetate and chromatographed on silica gel, eluding first with methylene chloride, later with methylene chloride/ethanol (50:1 and 25:1). The desired fractions are combined and evaporated down. Yield: 3.80 g (53% of theory), Rf -value: 0.50 (silica gel; methylene chloride/ethanol=19:1).

42923-79-5, As the rapid development of chemical substances, we look forward to future research findings about 42923-79-5

Reference£º
Patent; Boehringer Ingelheim KG; US6121308; (2000); 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.99365-69-2,7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.

99365-69-2, Example 11: Synthesis of 3-[l-(3,4-dimethoxy-benzoyl)-pyrrolidin-2-yl]-N-(l,2,3,4- tetrah dro-isoquinolin-7-yl)-benzamide trifluoroacetic acid (Compound 45).; To a solution of 7-nitro-l,2,3,4-tetrahydroisoquinoline hydrochloride (11.0 g, 51.25 mmol) in EtOAc (150 mL) at 0 ¡ãC in an ice bath add a solution of K2C03 (15.65 g, 113.25 mmol) in water (150 mL) followed by benzyl chloroformate (8.37 mL, 56.37 mmol) and vigorously stir the reaction at room temperature for 24 h. Separate the layers and extract the aqeuous with more EtOAc (150 mL). Wash the organics with sat.NaHC03 (200 mL), sat. NH4C1 (200 mL) and water (200 mL), then dry (Na2S04).Concentrate in vacuo to give 14.70 g of 7-nitro-3,4-dihydro-lH-isoquinoline-2- carboxylic acid benzyl ester as an oil which partially crystallizes.

As the paragraph descriping shows that 99365-69-2 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GINN, John David; MARSHALL, Daniel Richard; SIBLEY, Robert; SORCEK, Ronald John; YOUNG, Erick Richard Roush; ZHANG, Yunlong; WO2012/6202; (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.57060-88-5,Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride,as a common compound, the synthetic route is as follows.,57060-88-5

Step A: Preparation of Methyl 1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline-3-carboxylate Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride (2.3 g, 10 mmol) in 200 ml absolute ethanol is hydrogenated at 50 psi, room temperature, using 0.6 g 5% Rh/C catalyst. After the theoretical amount of hydrogen is taken up (36 hours), the catalyst is filtered and the filtrate is evaporated to dryness. The residue is dissolved in methylene chloride and washed with a saturated solution of sodium carbonate. The organic phase is dried (Na2 SO4) and acidified with ethanolic HCl. Evaporation of the solvent yields 2.0 g of the product as a diastereomeric mixture which is used without further separation.

57060-88-5 Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride 12248067, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Merck & Co., Inc.; US4381302; (1983); 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.877861-62-6,Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride,as a common compound, the synthetic route is as follows.

877861-62-6, A mixture of ammonium thiocyanate (0.105 g, 1.384 mmol), 6-methoxycarbonyl- 1,2,3,4-tetrahydroisoquinoline hydrochloride (0.3 g, 1.3176 mmol) and THF (2 mL) was heated in a CEM microwave reactor for 1 h at 100 0C. Upon cooling to room temperature, the reaction mixture was diluted with EtOAc, and washed with H2O, 1 N HCl, saturated aqueous NaHCO3 and brine respectively, dried over anhydrous MgSO4, and concentrated under reduced pressure to afford methyl 2- (aminocarbonothioyl)-l,2,3,4-tetrahydroisoquinoline-6-carboxylate (0.33 g, 47%) as a white solid. LCMS: (FA) ES+ 251.

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.; BLACKBURN, Christopher; CIAVARRI, Jeffrey; GIGSTAD, Kenneth; XU, He; WO2010/151318; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

170097-67-3,170097-67-3, 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

General procedure: To a solution of 15 6 (60mg, 0.2mmol) in 57 CH2Cl2 (4mL) were added EDCI (58mg, 0.3mmol) and 16 DMAP (4 mg, 0.03mmol). The solution was stirred at room temperature for 0.5h and compound 715 (97mg, 0.18mmol) was added. The resulting mixture was stirred for another 8h and 58 water was added. The layers were separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated under vacuo. The residue was prified by chromatography (CH2Cl2/CH3OH 40:1) to provide 17 8 as white solid (108mg, 73%).

170097-67-3,2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acidbelongs to tetrahydroisoquinoline compound, is more and more widely used in various fields. and we look forward to future research findings.

Reference£º
Article; Liu, Xiaohua; Zhang, Yu; Huang, Wenjing; Tan, Wenfu; Zhang, Ao; Bioorganic and Medicinal Chemistry; vol. 26; 2; (2018); p. 443 – 454;,
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.

(12-1) The raw material 7-nitro-1,2,3,4-tetrahydroisoquinoline was prepared according to Heterocyclic Chemistry,22, 329 (1985). In 20 ml of ethanol, 2.89 g of 7-nitro-1,2,3,4-tetrahydroisoquinoline was dissolved, 3.9 ml of triethylamine and 2.25 g of ethyl bromoacetate were added, and the mixture was refluxed by heating for an hour. After 1 hour, most of the solvent was distilled off under reduced pressure. The concentrated residue was extracted with ethyl acetate and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The crude product obtained was purified by silica gel column chromatography using a mixture, ethyl acetate:n-hexane=1:3, as a developer and successively treated with a hydrochloric acid/dioxane solution to give 2.14 g of ethyl 7-nitro-1,2,3,4-tetrahydroisoquinoline-2-acetate hydrochloride.

42923-79-5, The synthetic route of 42923-79-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Mitsui Toatsu Chemicals, Inc.; US5629321; (1997); 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.91-21-4,1,2,3,4-Tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,91-21-4

1,2,3,4-tetrahydroiosquinoline (Aldrich Tl,300-5, 100 gm) (11.6 g, 84.8 mmol) is added dropwise with care to stirred ice-cold concentrated H2S04 (42.0 mL). Potassium nitrate (9.40 g. , 93 mmol) is then added in small portions, taking care that the temperature of the reaction mixture does not rise above 5 C. After stirring overnight at room temperature the dark brown reaction mixture is added carefully to a stirred ice-cold concentrated NH40H solution. The basic red reaction mixture is extracted with chloroform (three times), and the combined chloroform extracts is washed with brine and dried over anhydrous Na2S04. Evaporation of the solvent gives a dark brown oil (14.6 g) which was taken up in EtOH (65 mL) and cooled in an ice bath. Treatment of this reddish solution with concentrated HCI (11 mL) yields a viscous yellow precipitate of the hydrochloride salt which is filtered and crystallized from methanol (250 mL) to yield the product compound (2) as a solid (5.36 g, ~30% yield). Alternatively, flash chromatography may be used to purify the crude reaction mixture before crystallization.

The synthetic route of 91-21-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ENVIVO PHARMACEUTICALS, INC.; WO2005/108367; (2005); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem