Heterocyclic Building Blocks-Tetrahydroisoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.43207-78-9,7-Methoxy-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

Lithium aluminium hydride, L. OM solution in THF (Aldrich, 21,277-6) (22mL, 22MMOL) was added drop wise to 7-METHOXY-3, 4-dihydro-2H-isoquinolin-l-one (3. 0g, 17MMOL) in THF (25mL) at RT. After addition the reaction was refluxed for 3HRS. THE reaction was cooled to 0C and quenched by the careful addition of deionised H20 (1ML), 10% OH solution (LML) and deionised H20 (3mL). The basic suspension was filtered through celite and extracted into EtOAc (3XL50ML). The combined extracts were dried over MGS04 and the solvent was removed in vacuo. The residue was purified via flash chromatography eluting with MEOH/CH2CL2 (10: 90) to AFFORD 7-METHOXY-1, 2, 3,4-tetrahydro-isoquinoline. This was dissolved in EtOAc (LOML) and hydrogen chloride, 2. 0m solution in Et2O (Aldrich, 45,518-0) (lOmL) was added drop wise, which formed a white ppte. The solid was filtered off and washed with Et20 to afford 7-methoxy-1,2, 3, 4-TETRALLYDRO- isoquinoline hydrochloride as a white solid. Yield 1.4g (42%). HPLC retention time, 3. 05min. Mass spectrum (ES+) m/z 164 (M + H).

As the paragraph descriping shows that 43207-78-9 is playing an increasingly important role.

Reference£º
Patent; IONIX PHARMACEUTICALS LIMITED; WO2005/5392; (2005); A1;,
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

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.

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

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

215798-14-4, 6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2. Synthesis of 2-(4,6-dimethoxy-5-nitropyrimidin-2-yl)-6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline, 5b 1,8-diazabicyclo[5.4.0]undec-7-ene (0.669 g, 4.4 mmol) was added to a mixture of 4a (0.438 g, 2 mmol) and 6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.487 g, 2.05 mmol) in DMF (5 ml) at 0 C. over 5 minutes. The mixture was stirred for an additional 5 minutes at room temperature. The mixture was washed with brine, extracted with ethyl acetate and chromatographed to yield 5b (0.76 g, 1.98 mmol, 99%).

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Reference£º
Patent; VALEANT PHARMACEUTICALS INTERNATIONAL; US2008/318979; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

29726-60-1, 3-Methyl-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step B: (3R4)-3-Methyl-1,2,3,4-tetraliydroisoquinolineThe product from Step A (4.5 g) is dissolved in a 1:9 isopropanol/heptane mixture (55mL), and the resultant solution is repeat-injected onto an IC Column (50x500mm, 20 urnparticle size), eluting with 5:95 mixture of 2-propanol/heptane containing 0.05% diethylamine, with a flow rate of 50 mi/mm at ambient temperature. Under these conditions the (R,)-isomer eluted as the second fraction.

29726-60-1 3-Methyl-1,2,3,4-tetrahydroisoquinoline 568974, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; DAVIDSON, James, Edward, Paul; MURRAY, James, Brooke; CHEN, I-Jen; WALMSLEY, Claire; DODSWORTH, Mark; MEISSNER, Johannes, W., G.; BROUGH, Paul; FEJES, Imre; TATAI, Janos; NYERGES, Miklos; KOTSCHY, Andras; SZLAVIK, Zoltan; GENESTE, Olivier; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; HENLIN, Jean-Michel; STARCK, Jerome-Benoit; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; WO2015/11164; (2015); 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

A solution of 6-bromo tetrahydroisoquinoline (300 mg, 1.42 mmol) in CH2Cl2 (8 mL) was cooled to 0 C, and i-Pr2NEt (243 mg, 1.88 mmol) and CbzCl (322 mg, 1.88 mmol) were added. The reaction was stirred at room temperature for 16 h. The reaction was diluted with CH2Cl2 (10 mL) and poured into water (20 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (3 x 20 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The crude mixture was purified via flash column chromatography eluting with EtOAc:hexanes (5:95) to give 400 mg (81%) of 9 as a colorless oil: 1H NMR (400 MHz) delta 7.41 – 7.27 (comp, 7 H), 6.97 (d, J = 10.3 Hz, 1 H), 5.18 (s, 2 H), 4.59 (s, 2 H), 3.70 (br s, 2 H), 2.82 (br s, 2 H); HRMS (ESI) m/z C17H16BrNO2 (M+Na)+ calcd for 368.0257 and 370.0238; found 368.0257 and 370.0238.

As the paragraph descriping shows that 226942-29-6 is playing an increasingly important role.

Reference£º
Article; Linkens, Kathryn; Schmidt, Hayden R.; Sahn, James J.; Kruse, Andrew C.; Martin, Stephen F.; European Journal of Medicinal Chemistry; vol. 151; (2018); p. 557 – 567;,
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.

Intermediate 67; Methyl 2-(phenylmethyl)-1,2,3.4-tetrahvdro-6-isoquinolinecarboxylate; To a solution of methyl 1 ,2,3,4-tetrahydro-6-isoquinolinecarboxylate hydrochloride (230 mg, 1.01 mmol) in ethanol (10 ml) was added triethylamine (380 mul, 2.02 mmol) and (bromomethyl)benzene (120 mul, 1.01 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was concentrated and the residue was diluted with a saturated solution of NaHCO3 and dichloromethane. The organic phase was extracted, dried over Na2SO4, filtered and concentrated to give the title compound as yellow oil (260 mg, 86%). LC/MS : m/z 282 (M+H)+, Rt: 3.47.

As the paragraph descriping shows that 877861-62-6 is playing an increasingly important role.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/47240; (2009); 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.215798-19-9,6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.

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).

As the paragraph descriping shows that 215798-19-9 is playing an increasingly important role.

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/105206; (2009); 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.215798-19-9,6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.

As an alternative procedure to that contained within Description 1, a solution of 6-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (6.0 g, 24 mmol) and triethylamine (7.4 ml, 5.36 g, 53 mmol) in dichloromethane (100 ml) was treated with trifluoroacetic anhydride (3.7 ml, 5.54 g, 26.4 mmol) with ice cooling. Mixture was stirred at 20[deg.] C. for 1.5 h. then partitioned between saturated aqueous NaHCO3 (250 ml) and dichloromethane (3*50 ml). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give a solid (8.3 g). A mixture of the latter with copper (I) cyanide (5.1 g, 56.6 mmol) in 1-methyl-2-pyrrolidinone (100 ml) was heated at reflux under argon for 4 h, then cooled and partitioned between water (300 ml), 0.880 aqueous ammonia (100 ml) and dichloromethane (5*200 ml). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give an oil. The latter was dissolved in ether and treated with ethereal HCl to give the title compound (4.47 g, 85%) as a colourless solid. [0130] Mass spectrum (API<+>): Found 159 (MH<+>). C10H10N2 requires 158.

As the paragraph descriping shows that 215798-19-9 is playing an increasingly important role.

Reference£º
Patent; SmithKline Beecham, p.l.c.; US2003/191314; (2003); 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.42923-79-5,7-Nitro-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

2-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline (252). Formic acid (9.4 mL, 250 mmol) was added dropwise to Ac2O (19 mL, 202 mmol) at 0 0C. The solution was stirred at 50 0C for 45 min, then cooled to -18 0C, diluted with THF (100 mL) and a solution of 7-nitro- 1 ,2,3,4-tetrahydroisoquinoline [(a) Tercel, M.; et al., J. Med. Chem. 1996, 39, 1084-1094; (b) Zhu, Z., et al., J. Med. Chem. 2003, 46, 831-837] (251) (13.8 g, 5.0 mmol) in THF (100 mL) was added and stirred at -15 to -18 0C for 30 min. The solution was warmed to 20 0C, the solvent evaporated and the residue partitioned between saturated aqueous NaHCO3 solution (250 mL) and EtOAc (250 mL). The aqueous fraction was extracted with EtOAc (3 x 250 mL), dried and the solvent evaporated. The residue was dissolved in THF (200 mL), EPO cooled to 10 0C and BH3 DMS solution (10 M, 19.4 mL, 194 mmol) was added. The solution was stirred at 20 0C for 1 h, diluted with MeOH (30 mL) and acidified with HCI solution (1 M, 45 mL). The solution was stirred at 40 0C for 15 min, the solvent evaporated and the residue partitioned between saturated aqueous NaHCO3 solution (250 mL) and EtOAc (250 mL). The aqueous fraction was extracted with EtOAc (3 x 250 mL), dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (2-5%) of MeOH/DCM, to give isoquinoline 252 (12.6 g, 85%) as an orange solid: 1H NMR delta 8.09 (dd, J = 8.4, 2.3 Hz, 1 H, H-6), 7.95 (d, J = 2.3 Hz, 1 H, H-8), 7.37 (d, J = 8.4 Hz, 1 H, H-5), 4.27 (d, J = 16.1 Hz1 1 H, H-1), 3.94 (d, J = 16.1 Hz, 1 H, H-1), 3.23-3.34 (m, 2 H, CH2), 2.99-3.18 (m, 2 H, CH2), 2.17 (s, 3 H, NCH3); MS (APCI) m/z 193 (MH+, 100%).

42923-79-5 7-Nitro-1,2,3,4-tetrahydroisoquinoline 6424833, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; AUCKLAND UNISERVICES LIMITED; WO2006/104406; (2006); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

57060-88-5, Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of Boc-Dmt-OH (309 mg, 1 mmol), HBTU (379 mg, 1 mmol) and DIEA (348 muL, 2 mmol) in 5 mL DMF was added a solution of HCl x H-Tic-OMe (227.5 mg, 1 mmol) and DIEA (174 muL, 1 mmol) in 5 mL DMF. The reaction mixture was stirred for 5 h at room temperature and progress of the reaction was monitored by TLC. After solvent evaporation in vacuo, the residue was dissolved in 50 mL AcOEt and the resulting solution was washed with 5% KHSO4 (aq.), saturated NaHCO3 (aq.) and brine. The organic phase was dried (MgSO4), filtered and evaporated to dryness, yielding 430 mg of crude product (90% yield). The crude Boc-protected dipeptide ester was deprotected by treatment with aqueous TFA (95% vv) for 45 min under stirring and cooling with ice. After TFA evaporation in vacuo, the TFA salt of the dipeptide ester was precipitated with ether (Et2O), affording 300 mg (90% yield) of crude product which was purified by preparative HPLC. TFA x H-Dmt-Tic-OMe: TLC Rf (I) 0.55; MS [M+H]+ 383.

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

Reference£º
Article; Weltrowska, Grazyna; Nguyen, Thi M.-D.; Chung, Nga N.; Wilkes, Brian C.; Schiller, Peter W.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 18; (2013); p. 5082 – 5085;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem