Heterocyclic Building Blocks-Tetrahydroisoquinoline

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

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

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

75416-51-2, 8-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,75416-51-2

(a) 8-bromo-l,2,3,4-tetrahydroisoquinoline (64 mg, 0.3 mmol) was dissolved in acetonitrile, K2C03(166 mg, 1.2 mmol) and ethyl 2-bromoacetate (40 mu^, 0.36 mmol) were added. The mixture was stirred at r.t. over night. The solvent was evaporated off, and the residue was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. Purification through flash chromatography on silica gel eluted with 30percent ethyl acetate in hexane gave intermediate ethyl 2-(8-(2-chloro-4- methoxyphenyl)-3,4-dihydroisoquinolin-2(lH)-yl)acetate 73 mg as a brown oil, yield: 86.8percent. LC/MS: (ESI) [M+H]+= 299.2

The synthetic route of 75416-51-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITY OF WASHINGTON; FAN, Erkang; ZHANG, Zhongsheng; HUANG, Wenlin; BUCKNER, Frederick S.; (180 pag.)WO2018/237349; (2018); 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,42923-77-3

EXAMPLE 2 6-Methoxy-2-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline A mixture of 6-methoxy-1,2,3,4-tetrahydroisoquinoline (1.00 g, 6.2 mmol), 4-(4-phenylbenzoylamino)butyraldehyde (1.64 g, 6.2 mmol), sodium triacetoxyborohydride (1.94 g, 9.2 mmol) and dichloromethane (50 ml) was stirred at 20 C. for 18 h. Resulting solution was partitioned between saturated aqueous NAHCO3 (50 ml) and dichloromethane (3*50 ml). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give a solid. Trituration with 1:1 dichloromethane-ether gave the title compound (0.80 g, 32%). Mass spectrum (API+): Found 415 (MH+). C27H30N2O2 requires 414. 1H NMR (CDCl3)delta: 1.78 (4H, m), 2.59 (2H, m), 2.72 (2H, t, J=6 Hz), 2.87 (2H, t, J=6 Hz), 3.51 (2H, m), 3.55 (2H, s), 3.74 (3H, s), 6.61 (1H, dd, J=2 Hz), 6.70 (1H, dd, J=9, 2 Hz), 6.90 (1H, d, J=9 Hz), 7.30-7.50 (5H, m), 7.55 (2H, m), 7.68 (3H, m).

The synthetic route of 42923-77-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SmithKline Beecham p.l.c.; US6274593; (2001); B1;,
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.226942-29-6,6-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,226942-29-6

A mixture of 6-bromo-1,2,3,4-tetrahydroisoquinoline (800 mg, 3.8 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (1051 mg, 4.5 mmol) and potassium carbonate (1043 mg, 7.5 mmol) in NMP (10 mL) was stirred at 40 oC for 18 h. The reaction mixture was filtered and the filtrate was reduced in vacuo. The residue was purified by silica column chromatography eluting with 2% EtOAc in Pet. Ether to afford 6-bromo-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline (800 mg, 2.72 mmol, 72% yield) as a white solid.1H NMR (400 MHz, DMSO-d6) delta 7.36- 7.26 (m, 2H), 7.03 (d, J = 8.1 Hz, 1H), 3.79- 3.74 (m, 2H), 3.38- 3.28 (m, 2H), 2.90 (m, 2H), 2.82 (m, 2H).

The synthetic route of 226942-29-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

A solution of 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6- isoquinolinecarboxylic acid (555 mg, 2 mmol), HATU (989 mg, 2.6 mmol), triethylamine (0.26 ml_, 2.6mmol) in DMF (15 ml.) and 5-{[(2-chlorophenyl)(methyl)amino]methyl}- 1 ,3,4-thiadiazol-2-amine (Intermediate 240) (509 mg, 2 mmol) was stirred at room temperature overnight. The DMF was evaporated under reduced pressure and the residue was dissolved in DCM. The organic phase was dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with a gradient DCM 100% to DCM/MeOH: 98/2. After evaporation of the right fractions, the material was triturated in hot methyl alcohol, to give after filtration and drying the title compound as a white solid (300 mg, 29%). HRMS calculated for C25H28CIN5O3S (M+H)+ 514.1680, found: 514.1651, Rt: 3.47 min.

170097-67-3, As the paragraph descriping shows that 170097-67-3 is playing an increasingly important role.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/104524; (2008); 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-l,2,3,4-tetrahydroisoquinoline (100 mg, 0.472 mmol) and triethylamine (180 mu, 1.291 mmol) in anhydrous NMP (2.5 mL) was added to 2,4- dichloro-6-mophiholino-l,3,5-triazine (100 mg, 0.425 mmol). The reaction was flushed briefly with nitrogen, capped, stirred at room temp for 30 min at room temp, followed by heating at 80 C for 1 h. The crude reaction was purified via reverse phase Prep HPLC to afford 4-(4-(6-bromo-3,4-dihydroisoquinolin-2( lH)-yl)-6-chloro- l,3,5-triazin-2- yl)morpholine, 150 mg (86%). LCMS (M+l) = 410.1, 412.1. NuMuRhonu (500 MHz, (0186) DMSO-de) delta 7.48 – 7.35 (m, 2H), 7.24 (br dd, J=l 1.8, 8.3 Hz, 1H), 4.79 (br d, J=17.4 Hz, 2H), 3.90 (dt, J=14.6, 5.9 Hz, 2H), 3.76 (br s, 2H), 3.71 – 3.58 (m, 6H), 2.86 (br d, J=6.1 Hz, 2H).

226942-29-6, 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; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; DESKUS, Jeffrey; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (220 pag.)WO2018/127801; (2018); 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.1029689-82-4,Methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate hydrochloride,as a common compound, the synthetic route is as follows.

To a solution of methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate hydrochloride (12.37 g) and Example 1.1.10 (15 g) in dimethyl sulfoxide (100 mL) was added N,N-diisopropylethylamine (12 mL), and the mixture was stirred at 50 C. for 24 hours. The mixture was then diluted with ethyl acetate (500 mL) and washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with 20% ethyl acetate in hexane, to give the title compound. MS (ESI) m/e 448.4 (M+H)+., 1029689-82-4

The synthetic route of 1029689-82-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AbbVie Inc.; Benatuil, Lorenzo; Bruncko, Milan; Chao, Debra; Izeradjene, Kamel; Judd, Andrew S.; Phillips, Andrew C.; Souers, Andrew J.; Thakur, Archana; (556 pag.)US2017/355769; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

923591-51-9, 5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,923591-51-9

Intermediate O: 5-(2-(l-Methyl-lH-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-l,2,3,4- tetrahydroisoquinoline A vial was charged with 5-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (ASW Medchem, Brunswick, NJ, 400.42 mg, 1.367 mmol), (2-(l- methyl-lH-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)boronic acid (Intermediate B, 443 mg, 1.640 mmol), potassium phosphate (1 160 mg, 5.47 mmol), and Pd(AmPhos)2Ci2 (Sigma- Aldrich, St. Louis, MO, 48.4 mg, 0.068 mmol). The vial was flushed with Ar (g), then dioxane (2928 mu) and water (976 mu) were added in sequence. The mixture was heated in a microwave reactor for 30 min at 90 C. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water (and a small amount of brine to break up emulsions, 2x), washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was taken up in MeOH, then loaded onto a 10 g SCX-2 ion exchange column. The column was eluted with MeOH, then with 2M ammonia in MeOH. The basic filtrate was concentrated, and the residue was chromatographed on a 40 g silica gel column with 0 to 10% MeOH/DCM to provide 5-(2-(l -methyl- lH-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-l ,2,3,4- tetrahydroisoquinoline as a pale yellow solid. [M+H]+ = 358.1. XH NMR (400 MHz, DMSO-d6) delta ppm = 7.91 – 7.80 (m, 2 H), 7.56 (d, J= 8.0 Hz, 1 H), 7.28 (d, J= 2.0 Hz, 1 H), 7.09 – 6.95 (m, 2 H), 6.84 (dd, J= 1.3, 7.4 Hz, 1 H), 5.96 (d, J= 1.9 Hz, 1 H), 3.85 (s, 2 H), 3.52 (br. s., 3 H), 2.93 – 2.84 (m, 1 H), 2.79 – 2.67 (m, 1 H), 2.48 – 2.39 (m, 1 H), 2.09 (td, J= 5.3, 16.7 Hz, 1 H).

923591-51-9 5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride 45074003, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); 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.22990-19-8,1-Phenyl-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,22990-19-8

Optically active (S)-mandelic acid (0.5 equiv) was added to the solution of racemic compound 5 (1.0 equiv) in mixture of toluene and methanol solvents at room temperature. The resulting suspension was stirred at 80 C to make homogeneous reaction mixture. The stirring was continued with heating at 80 C until completion of reaction. It was found that after 30 min the reaction was completed. The solution was allowed to cool to room temperature. Mandelic acid resolves diastereomeric mixture to S-form of 5, which was filtered from the solution. The filter cake was washed once with toluene and air-dried to yield compound 6 (S-form) as a white solid in 47 % yield. Compound 6 was treated with 2 M Sodium hydroxide solution and the toluene was added. Two layers were separated. Toluene fraction was dried over anhydrous Na2SO4, concentrated and purified on silica gel column (eluted using mixture of hexane and ethyl acetate) to obtain pure S-isomer.

As the paragraph descriping shows that 22990-19-8 is playing an increasingly important role.

Reference£º
Article; Krishna Rao; Surendra Babu; Basaveswara Rao; Keshavi; Sundara Rao; Eswara Prasad; Murthy; Asian Journal of Chemistry; vol. 29; 5; (2017); p. 1035 – 1038;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem