Heterocyclic Building Blocks-Tetrahydroisoquinoline

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

Example 1methyl 2-{[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate Intermediate 1; A solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (0.830 g, 3.41 mmol) and triethylamine (0.792 mL, 5.68 mmol) in DMF (11.0 mL) was treated with TFFH (1.13 g, 4.26 mmol). The resulting mixture was stirred at rt for 30 min and then methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride (0.647 g, 2.84 mmol) and triethylamine (0.792 mL, 5.68 mmol) were added. The reaction mixture was stirred at rt for 2 days and then extracted with EtOAc three times. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the resulting residue by column chromatography (SiO2, 0-100% EtOAc in hexane) provided methyl 2-{[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (0.959 g, 82%). LC-MS: (FA) ES+ 439 (M+Na); 1H NMR (400 MHz, CDCl3) delta 7.85 (dd, J=10.1, 2.2 Hz, 2H), 7.19 (d, J=8.0 Hz, 1H), 4.79 (s, 2H), 3.95-3.77 (m, 5H), 3.67 (d, J=38.1 Hz, 2H), 3.21 (s, 2H), 2.92 (t, J=5.7 Hz, 2H), 2.24-2.10 (m, 2H), 1.61 (d, J=10.8 Hz, 1H), 1.44 (d, J=5.0 Hz, 10H), 1.33 (d, J=3.6 Hz, 3H).

877861-62-6 Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride 42614607, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Millennium Pharmaceuticals, Inc.; US2012/165316; (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.29726-60-1,3-Methyl-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,29726-60-1

To a mixture of pyrazole acid (1 mmol), EDC.HCl (1.2 mmol) and HOBt (1.2 mmol) in dry dichloromethane (10 mL) was added a mixture of amine (1 mmol) and triethyl amine (1.5 mmol) in dichloromethane (5 mL) at 0 C. The mixture was stirred at room temperature till the completion of reaction (judged by TLC). The reaction mixture was diluted with additional DCM (20 mL). The organic layer was washed with water, brine and dried (Na2SO4). Concentration and purification over silica gel (100-200 mesh) afforded the desired compound.

The synthetic route of 29726-60-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Sasmal, Pradip K.; Reddy, D. Srinivasa; Talwar, Rashmi; Venkatesham; Balasubrahmanyam; Kannan; Srinivas; Kumar, K. Shiva; Devi, B. Neelima; Jadhav, Vikram P.; Khan, Sanjoy K.; Mohan, Priya; Chaudhury, Hira; Bhuniya, Debnath; Iqbal, Javed; Chakrabarti, Ranjan; Bioorganic and Medicinal Chemistry Letters; vol. 21; 1; (2011); p. 562 – 568;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

1-Phenyl-1,2,3,4-tetrahydroisoquinoline, cas is 22990-19-8, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

To a reaction flask charged with Pd / C (40 mol% of the substrate in Formula 1), potassium phosphate trihydrate (20 mol% of the substrate in Formula 1) was added 4 ml of acetonitrile in an oxygen atmosphere or in air and stirred at room temperature After a few minutes, 1-phenyl-1,2,3,4-tetrahydroisoquinoline (0. 3 mmol) was added and the reaction was stirred at 60 C for 12-22 hours. Pd / C was filtered and concentrated , And direct column chromatography (eluent: petroleum ether and ethyl acetate = 5: 1 by volume) to give the desired product, 3,4-dihydroisoquinoline, 22990-19-8

With the rapid development of chemical substances, we look forward to future research findings about 1-Phenyl-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; Dalian Institute of Chemical Physics, Chinese Academy of Sciences; Zhou, Yonggui; Shi, Lei; Ji, Yue; Chen, Mu Wang; (10 pag.)CN105566218; (2016); A;,
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

EXAMPLE 20 5-(6-Methoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamine A suspension of 0.80 g (0.00412 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride in 17 ml of dimethylformamide was treated with 1.7 ml (0.0124 mol) of triethylamine and 0.87 g (0.0053 mol) of 6-methoxy-1,2,3,4-tetrahydro-isoquinoline and the mixture was stirred at room temperature under argon for 3 hours. The mixture was completely freed from the solvents and the residue was triturated in 20 ml of water. The resulting crystals were filtered off under suction, chromatographed over silica gel with dichloromethane/methanol 9:1 as the eluent and recrystallized from ethyl acetate/n-hexane. 0.26 g (22%) of 5-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamine was obtained as white crystals; m.p. 142-143.

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

Reference£º
Patent; Hoffmann-La Roche Inc.; US5688798; (1997); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

It is a common heterocyclic compound, the tetrahydroisoquinoline compound, 7-Chloro-1,2,3,4-tetrahydroisoquinoline, cas is 82771-60-6 its synthesis route is as follows.,82771-60-6

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.

With the complex challenges of chemical substances, we look forward to future research findings about 7-Chloro-1,2,3,4-tetrahydroisoquinoline

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

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.,42923-77-3

To a solution of 6-methoxy-l,2,3,4-tetrahydroisoquinoline (2.0 g, 12.3 mmol)in sulfuric acid (10 mL) at -5 C was slowly added guanidine nitrate (750 mg, 6.15 mmol) and the mixture was stirred for 15 min at the same temperature. The reaction was quenched with ice-cold water and basified using potassium carbonate. The aqueous mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 1.7 g of the desired compound. lU NMR (400 MHz, DMSO-de) d 2.76 (t, J= 6.0 Hz, 2H), 2.94 (t, J= 6.0 Hz, 2H), 3.83 (d, J= 6.4 Hz, 2H), 3.87 (s, 3H), 7.07 (s, 1H), 7.60 (s, 1H), 8.32 (s, 1H).

As the paragraph descriping shows that 42923-77-3 is playing an increasingly important role.

Reference£º
Patent; ICHNOS SCIENCES S.A.; CHAUDHARI, Sachin, Sundarlal; GHARAT, Laxmikant, Atmaram; IYER, Pravin; DHONE, Sachin, Vasantrao; ADIK, Bharat, Gangadhar; WADEKAR, Prashant, Dilip; GOWDA, Nagaraj; BAJPAI, Malini; (233 pag.)WO2020/70331; (2020); 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

5-Cyclopropyl-2,6-dimethyl-7-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)oxazolo[4,5-c]- quinolin-4-one (Intermediate B) (69 mg, 0.18 mmol), [1 , T- bis(diphenylphosphino)ferrocene]palladium(ll) chloride dichloromethane complex (14 mg, 0.02 mmol), CS2CO3 (178 mg, 0.55 mmol), and 6-bromo-1 ,2,3,4-tetrahydroisoquinoline (38 mg, 0.18 mmol) were dissolved in a mixture of monoglyme (1 mL) and H2O (0.3 mL). The reaction solution was then irradiated with microwaves at 60C for 30 min. The solution was diluted with MeOH, filtered, dry-loaded onto silica and purified by flash chromatography using a gradient of 0-10% MeOH in DCM. The fractions containing the required product were then concentrated in vacuo to give 5-cyclopropyl-2,6-dimethyl-7-(1 , 2,3,4- tetrahydroisoquinolin-6-yl)oxazolo[4,5-c]-quinolin-4-one (2 mg, 3 %) as a pale yellow solid. 1 H NMR (Method A) (CDC ): delta 7.70 (d, J = 8.0 Hz, 1 H), 7.23 (d, J = 8.0 Hz, 1 H), 7.19 – 7.10 (m, 3H), 4.15 (s, 2H), 3.62 (m, 1 H), 3.25 (t, 2H), 2.93 (t, 2H), 2.68 (s, 3H), 2.53 (s, 3H), 1.31 – 1.26 (m, 2H), 0.71 – 0.65 (m, 2H); LC-MS (Method D) 386.4 [M+H]+; RT 1.68 min

226942-29-6 6-Bromo-1,2,3,4-tetrahydroisoquinoline 15885183, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; REDX PHARMA PLC; HUXLEY, Anthony; KIRK, Ralph; RATCLIFFE, Andrew; LYTH, David; (112 pag.)WO2017/46605; (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

A solution of 35% formaldehyde (2.49 g, 0.034 mol) was added dropwise to 2-(3-methoxyphenyl)ethanamine (5g, 0.033 mol). The warm solution soon deposited an oil and the reaction was completed by heating the mixture for one hour at 100 C. The oil was extracted with toluene (25 ml) and washed with water (3 x 18 ml). The extract was dried over Na2SO4 and the solvent was concentrated to yield a yellow oil. A solution of 20% hydrochloric acid (6 ml) was added to the crude and the mixture was stirred at 100 C for 1 hour. After the evaporation to dryness, the residue was dissolved in a little water, made alkaline with concentrated potassium hydroxide, extracted with dichloromethane (3 x 90 ml) and dried over Na2SO4. After the evaporation of the solvent, the oil was dissolved in ethyl acetate and concentrated hydrochloric acid was added to form the hydrochloride, which was filtered to yield a white solid identified as 6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (5.1 g, 80 % yield). 1H NMR (300 MHz, CHLOROFORM-D) delta ppm 2.80 (t, J=6.01 Hz, 2 H) 3.14 (t, J=6.01 Hz, 2 H) 3.78 (s, 3 H) 3.97 (s, 2 H) 6.63 (d, J=2.50 Hz, 1 H) 6.71 (dd, J=8.42, 2.56 Hz, 1 H) 6.93 (d, J=8.42 Hz, 1H) MS (APCI (M+H)+): 164

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

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; EP1676844; (2006); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 99365-69-2, its synthesis route is as follows.,99365-69-2

7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (2) from Example 1, is placed in a Parr shaker bottle (15.0 g, 69.9 mmol) dissolved in 95percent EtOH (100 mL), and to the Parr shaker bottle is added concentrated HCI (10 mL), water (25 mL), and Pt02 (0.5 g). The mixture is hydrogenated at 50 psi until no further drop in pressure was observed (about 4 hours). The yellowish suspension is filtered through Celite and evaporated to dryness to afford a yellowish solid which is made basic with 10percent NaOH solution (adequate care is exercised in catalyst disposal). Extraction of the basic solution with CHC13 (three times), followed by drying over anhydrous Na2S04 and evaporation of the solvent, yields a reddish yellow solid (9.54 g, 92.2 percent) : mp = 110-112. 7-Amino-1,2,3,4-tetrahydroisoquinoline dihydrochloride (3) is recrystallized from aqueous MeOH as buff colored needles, mp = 290 ¡ãC.

With the complex challenges of chemical substances, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

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