Month: September 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.170097-67-3,2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,as a common compound, the synthetic route is as follows.

3,4-Dimethoxybenzoic acid (100 mg, 0.55 mmol) was dissolved in DMF (1 mL). EDC (124.6 mg, 0.65 mmol) and HOBt (81 mg, 0.6 mmol) were added, followed by N- methylmorpholine (0.71 mL, 0.65 mmol). The resulting solution was agitated for 1 h. 3- Aminomethylphenyl-carbamic acid tert-butyl ester (111 mg, 0.5 mmol) was then added and the resulting mixture was agitated overnight. The reaction mixture was diluted with 4 mL dichloromethane, and the resulting mixture was washed with 1 N HCl (2 x 5 mL), NaHCO3 (saturated aqueous, 2 x 5 mL), and brine (1 x 5 mL), dried, and the solvents were evaporated to provide 190 mg (quantitative yield) of (3-[(3,4-dimethoxy-benzoylamino)- methyl]-phenyl}-carbamic acid tert-butyi ester, which was dissolved in dichloromethane (2 mL). SCX (1.14 g, 1.0 mmol) was added and the resulting mixture was agitated for 48 h. The reaction mixture was filtered and the solids were washed with dichloromethane (2 x 2 mL) and methanol (2 x 2 mL). The product was eluted with NH3 in methanol (7 N, 2 x 2 mL). The solvents were evaporated to provide 112 mg (78% yield) of 7V-(3-amino- benzyl)-3,4-dimethoxy-benzamide as a white solid, which was used directly. 3,4-Dihydro- lH-isoquinoline-2,6-dicarboxylic acid 2-tert-buty{ ester (19.1 mg, 0.069 mmol), EDC (19.2 mg, 0.1 mmol), and HOBt (12.2 mg, 0.09 mmol) were combined in a reaction tube, and DMF (1 mL) was added. To the resulting solution was added N-methylmorpholine (0.013 mL, 0.12 mmol), and the mixture was agitated for 1 h. The intermediate prepared above, Lambda/-(3-amino-benzyl)-3,4-dimethoxy-benzamide (17 mg, 0.059 mmol), was then added as a solution in DMF (0.3 mL), and the reaction mixture was agitated overnight. The reaction mixture was diluted with 6 mL dichloromethane, and the resulting mixture was washed with 1 N HCl (2 x 2 mL), NaHCO3 (saturated aqueous, 2 x 2 mL), and brine (1 x 2 mL), dried, and concentrated to 32 mg of 6-{3-[(3,4-dimethoxy-benzoylamino)- methyl]-phenylcarbamoyl}-3,4-dihydro-lH-isoquinoline-2-carboxylic acid tert-butyl ester as an oil, which was redissolved in dichloromethane (1 mL) and treated with SCX (284 mg, 0.25 mmol). The resulting mixture was agitated overnight. The reaction mixture was filtered and the solids were washed with dichloromethane (2 x 2 mL) and methanol (2 x 2 mL). The product was eluted with NH3 in methanol (7 N, 2 x 2 mL), and the eluant was evaporated. The resulting residue was purified by preparative HPLC using an acetonitrile/water/formic acid gradient providing the title compound as a formate salt (20 mg, 77% yield – 2 steps), MS analysis electrospray, 446 (M+H)., 170097-67-3

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/86047; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

91-21-4, 1,2,3,4-Tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,91-21-4

1g 1,2,3,4-Tetrahydro-isochinolin wurden vorsichtig in 5 ml konzentrierter Schwefelsaeure geloest. Die Salpetersaeure wurde hergestellt durch Loesen von 1g Kaliumnitrat in 5 ml konzentrierter Schwefelsaeure. Zwei 2-ml-Einweg-Kunststoffspritzen wurden mit den beiden Loesungen gefuellt und an einer “Havard Apparatus pump 22” befestigt. Die Einwegspritzen selbst wurden mit einem statischen Siliziummischer verbunden, der wiederum mit einem duennen, 80 cm langen Teflonschlauch mit einem Durchmesser von 0,25 mm verbunden war. Die Reaktion wurde bei Umgebungstemperatur mit einer Durchflussgeschwindigkeit von 5 mul/min durchgefuehrt. Das entstandene Reaktionsgemisch wurde in einem Gefaess gefuellt mit Eistueckchen gesammelt und mit 2N NaOH neutralisiert bevor das gebildete Produkt mit Dichlormethan extrahiert wurde. 1g N-Methoxycarbonyl-1,2,3,4-Tetrahydro-isochinolin, geloest in 5 ml Dichloromethan, wurde wie vorher beschrieben bei Umgebungstemperatur mit 65%iger Salpetersaeure und einer Durchflussgeschwindigkeit von 5 mul/min nitriert. Die Aufarbeitung der organischen Phase erfolgte ohne vorherige Neutralisation. Die gleichen Bedingungen wurden eingestellt fuer einen kontinuierlichen Versuch, der kontinuierlich ueber sechs Tage durchgefuehrt wurde. In diesem Fall wurden zwei Spritzen mit einem jeweiligen Fassungsvermoegen von 50 ml verwendet.

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

Reference£º
Patent; MERCK PATENT GmbH; EP1200375; (2004); 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.17680-55-6,7-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,17680-55-6

EXAMPLE 105; To a solution of Intermediate 21 (150 mg, 0.43 mmol) in dichloromethane (10 mL) was added EDC (170 mg, 0.86 mmol), HOAt (59 mg, 0.43 mmol) and Intermediate 21 (91 mg, 0.43 mmol) and the resulting mixture was stirred at room temperature for 3 days. The reaction was quenched with water and diluted with 20 mL of dichloromethane. The organic layer was separated and the aqueous layer was extracted with DCM (2¡Á20 mL). The organics were combined, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by preparative TLC (eluant: 7% ethanol: 92% dichloromethane: 1.0% NH4OH) to yield 121 mg (50%) of the final desired product as a mixture of two cis isomers. LC-MS for C29H36BrFN2O calculated 526.28, found [M+H]+ 527 and [(M+2)+H]+ 529.

17680-55-6 7-Bromo-1,2,3,4-tetrahydroisoquinoline 10729255, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Butora, Gabor; Goble, Stephen D.; Pastemak, Alexander; Yang, Lihu; Zhou, Changyou; Moyes, Christopher R.; US2008/81803; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

81237-69-6, 5-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,81237-69-6

(R)-perfluorophenyl (1,1,1-trifluoro-3-((4-methoxybenzyl)oxy)propan-2-yl) carbonate (60 mg, 0.13 mmol) in acetonitrile (2 mL) was added into cold 0 C. solution of 5-bromo, 1,2,3,4-tetrahydroisoquinoline (30 mg, 0.14 mmol) and N,N-diisopropylethylamine (0.05 mL, 0.39 mmol) in acetonitrile (4 mL). The resulting reaction mixture was allowed to come to room temperature and stirred for 1 hour. Then, the reaction was diluted in dichloromethane (25 mL) and washed with water (2*15 mL). The organic extracts were dried over anhydrous NaSO4. The solvents were removed under vacuum and the residue was purified on silica gel (Biotage; eluting solvents hexanes:EtOAc 4/1 ratio) to afford (R)-1,1,1-trifluoro-3-((4-methoxybenzyl)oxy)propan-2-yl 5-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate as colorless oil. 1H NMR (400 MHz, CDCl3) delta ppm 7.46-7.45 (m, 1H), 7.25-7.16 (m, 2H), 7.08-7.06 (m, 2H), 6.84-6.82 (m, 2H), 5.52-5.51 (sept, 1H), 4.64-4.61 (m, 2H), 4.52-4.44 (m, 2H), 3.78 (s, 3H), 3.76-3.71 (m, 3H), 2.90-2.87 (m, 2H).

As the paragraph descriping shows that 81237-69-6 is playing an increasingly important role.

Reference£º
Patent; Malamas, Michael; Makriyannis, Alexandros; Lamani, Manjunath; Farah, Shrouq I.; US2019/152917; (2019); 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

To a cooled (0 oC) solution of 1,1?-carbonyldiimidazole (350 mg, 2.20 mmol) in anhydrous MeCN (25 mL) was added THIQ 14 (326 mg, 2.00 mmol) and K2CO3 (4.00 mmol). The resulting mixture was stirred at 24 oC for 18 h and then concentrated under reduced pressure to afford a residue which was purified by column chromatography (100% EtOAc) to give imidazole 15 (493 mg, 96%) as a colourless oil, Rf 0.31 (100% EtOAc). This intermediate was immediately used without further purification in the next synthetic step. 1H NMR (300 MHz, CDCl3): deltaH 7.86 (d, J 0.9 Hz, 1H, imidazole-H), 7.20 (d, J 1.4 Hz, 1H, imidazole-H), 7.05 (d, J 1.4 Hz, 1H, imidazole-H), 6.95-6.92 (m, 1H, ArH), 6.71-6.64 (m, 2H, ArH), 4.61 (s, 2H, ArCH2N), 3.78-3.67 (m, 5H, overlapping signals – NCH2 and OMe), 2.90 (t, J 6.0 Hz, 2H, ArCH2CH2). 13C NMR (75 MHz, CDCl3): deltaC 29.1 (ArCH2CH2), 44.7 (CH2CH2N), 48.3 (ArCH2N), 55.6 (OMe), 113.3 (ArCH), 113.9 (ArCH), 118.2 (ArCH), 124.1 (ArC), 127.6 (ArCH), 130.1 (ArCH), 135.3 (ArC), 137.1 (ArCH), 151.4 (C-O), 159.0 (C=O).

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

Reference£º
Article; Mabank, Tanya; Alexandre, Kabamba B.; Pelly, Stephen C.; Green, Ivan R.; van Otterlo, Willem A.L.; Arkivoc; vol. 2019; 4; (2019);,
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

3,4-Dihydro-lH-isoquinoline-2,6-dicarboxylic acid 2-tert-buty ester (50 mg, 0.18 mmol), EDC (38.3 mg, 0.2 mmol) and EtaOBt (24.3 mg, 0.18 mmol) were combined in a reaction vial, and DMF (1 mL) was added. To the solution thus formed, N-methylmorpholine (0.22 mL, 0.2 mmol) was added and the reaction mixture was agitated for 1 hour. The urea, 1- (3-amino-benzyl)-3-(4-cyano-phenyl)-urea (40 mg, 0.15 mmol), prepared as described above, was then added as a solution in DMF (0.3 mL), and the reaction mixture was agitated for 48 h. The reaction mixture was diluted to 6 mL with dichloromethane, washed with IN HCl (3×2 mL), NaHCO3 (satd. aq., 3×2 mL, and brine (1 x 2 mL), dried and evaporated to 59 mg of an oil (95% yield). This intermediate (6-{3-[3-(4-cyano- phenyl)-ureidomethyl]-phenylcarbamoyl}-3,4-dihydro-lH-isoquinoline-2-carboxylic acid tert-butyl ester) was dissolved in dichloromethane (1 mL) and TFA (0.4 mL) was added. The reaction mixture was stirred for 2 h, then the solvents were evaporated and the resulting residue was purified directly by preparative EtaPLC using an acetonitrile/water/formic acid gradient providing the title compound (20 mg, 48% yield), MS analysis electrospray, 426 (M+Eta).

170097-67-3, The synthetic route of 170097-67-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/86047; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

1029689-82-4, Methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1029689-82-4, [000516] To a solution of methyl l,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)+.

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

Reference£º
Patent; ABBVIE INC.; TAO, Zhi-Fu; DOHERTY, George; WANG, Xilu; SULLIVAN, Gerard M.; SONG, Xiaohong; KUNZER, Aaron R.; WENDT, Michael D.; MARIN, Violeta L.; FREY, Robin R.; CULLEN, Steve C.; WELCH, Dennie S.; SHEN, Xiaoqiang; BENNETT, Nathan B.; HAIGHT, Anthony R.; ACKLER, Scott L.; BOGHAERT, Erwin R.; SOUERS, Andrew J.; JUDD, Andrew S.; (623 pag.)WO2016/94509; (2016); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

42923-79-5, 7-Nitro-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 the required 1,2,3,4-tetrahydroisoquinoline derivative (1 equivalent), NaHCO3 (2 equivalents), and the appropriate substituted nitroaryl derivative or 2-chloro-3,5-dinitropyridine (1 equivalent) was heated at reflux in a mixture of ethanol : water (2:1) with stirring (15 hours). After cooling to room temperature, the ethanol was evaporated and the residue was poured onto ice yielding a solid. The solid was collected and dried in a vacuum desiccator over P2O5 giving the crude N-(nitroaryl)-1,2,3,4-tetrahydroisoquinoline derivative or 1,2,3,4-tetrahydro-2-(3,5-dinitropyridin-2-yl)isoquinoline 12., 42923-79-5

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

Reference£º
Article; Burke, Philip J.; Chun Wong, Lai; Jenkins, Terence C.; Knox, Richard J.; Stanforth, Stephen P.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 24; (2011); p. 7447 – 7450;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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,82771-60-6

To a solution of 3,3-diethyl-5-(2-(4-(4-hydroxyphenyl)piperazin- 1-yl)ethyl)dihydrofuran-2(3H)-one (50 mg, 0.147 mmol, 1 eq.) in acetonitrile (1.5 mL) was added K2C03 (91 mg, 0.658 mmol, 4.5 eq.). Then, 7-chloro-1,2,3,4-tetrahydroisoquinoline (37 mg, 0.220 mmol, 1.5 eq.) was added and the reaction mixture was allowed to stir at reflux for 3 days. The mixture was filtered through a glass pipet packed with glass wool and washed with acetonitrile. The filtrate was concentrated under reduced pressure to afford a crude oil which was purified through flash chromatography (silica; methanol/dichloromethane, 0% 10%) to provide 5-(2-(7-chloro-3,4-dihydroisoquinolin-2( 1 H)-yl)ethyl)-3,3 -diethyldihydrofuran2(3H)-one 5 -(2-(7-chloro-3 ,4-dihydroisoquinolin-2(1 H)-yl)ethyl)-3 ,3 -diethyl-dihydrofuran2(3H)-one: 1 ?H NMR (400 MHz, CDC13) oe 7.02 (dd, J = 2.2, 8.2, 1H), 6.95 (m, 2H), 4.45 (m, 1H), 3.52 (s, 2H), 2.77 (m, 2H), 2.63 (m, 4H), 2.07 (dd, J = 6.7, 13.0, 1H), 1.83 (m, 3H), 1.55 (qd, J= 1.2, 7.3, 4H), 0.85 (dt, J= 7.5, 15.3, 6H) LC/MS [M+Hj= m/z 336.1.

The synthetic route of 82771-60-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TEMPLE UNIVERSITY-OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; CANNEY, Daniel, J.; BLASS, Benjamin, E.; GAO, Rong; BLATTNER, Kevin; (187 pag.)WO2016/183150; (2016); 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.42923-77-3,6-Methoxy-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

General procedure: To a stirred solution of 1,2,3,4-THIQ (1.0 equiv.) in CH2Cl2 (10.0 mL/mmol), triethylamine(1.2 equivalent) was added and then cooled to 0 C. Acyl chloride (1.2 equivalent), sulfonyl chloride(1.2 equivalent), or diethylcarbamoyl chloride (1.2 equivalent) was added slowly at 0 C. The resultingreaction mixture was stirred at room temperature for 2 h under an argon atmosphere and thenpoured onto water (10.0 mL/mmol) and the organic layer was separated. The aqueous layer wasextracted two times with CH2Cl2 (10.0 mL/mmol), and the combined organic layer was washed withbrine (5.0 mL/mmol), dried over sodium sulfate, filtered, and concentrated under reduced pressure.Purification of the crude residue by flash column chromatography on silica gel, using the appropriatemixture of eluents, provided the corresponding N-protected 1,2,3,4-tetrahydroisoquinoline. Spectral data(1H- and 13C-NMR) of compounds (5a, 5c, 5d, 5e, 5g, 5h, 5k, 5l, 5m, 5n, 5o, 5q, 5r) which were reportedpreviously were compared and found in agreement with literature data. Furthermore, references wererepresented in supporting information. The characterization of novel compounds is given.

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

Reference£º
Article; Kim, Hong Pyo; Yu, Heesun; Kim, Hyoungsu; Kim, Seok-Ho; Lee, Dongjoo; Molecules; vol. 23; 12; (2018);,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem