Heterocyclic Building Blocks-Tetrahydroisoquinoline

42923-77-3,42923-77-3, 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 42D 1,2,3,4-tetrahydro-6-isoquinolinol A solution of boron tribromide (1.2 mL, 12.5 mmol) in dichloromethane (12.5 mL) was added dropwise to a -78 C. solution of 6-methoxytetrahydroisoquinoline (1.0 g, 5.0 mol, prepared as described in Org. Synth 1988, 67, 60) in dichloromethane (38 mL) The mixture was stirred for 1 hour, warmed to 0 C., stirred for 1 hour, warmed to room temperature, and stirred for 1 hour. The mixture was cooled to -78 C., treated dropwise with methanol (20 mL), warmed to room temperature, stirred for 1 hour, and concentrated to provide the desired product. MS (DCI/NH3) m/e 150 (M+H)+.

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; Bruncko, Milan; McClellan, William J.; US6504031; (2003); 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.215798-14-4,6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.,215798-14-4

To a 1,4-dioxane solution (300 muL) of 4-(methylthio)-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (30.7 mg, 0.100 mmol) synthesized in Reference Synthesis Example 33, 6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (35.6 mg, 0.150 mmol) and triethylamine (27.9 muL, 0.200 mmol) were added and the resultant reaction solution was stirred for 4 hours under reflux by heating. After completion of the reaction, the reaction solution was concentrated and the obtained residue was purified by silica gel (amino-based) column chromatography (hexane/ethyl acetate = 1/1) to obtain the title compound (Ex1) (28.1 mg, yield 61 %) as a colorless solid.

As the paragraph descriping shows that 215798-14-4 is playing an increasingly important role.

Reference£º
Patent; Nissan Chemical Industries, Ltd.; NIWA, Masatoshi; INABA, Yusuke; IWAMOTO, Toshimasa; SHINTANI, Yusuke; NAGAI, Hiroshi; EGI, Jun; ADACHI, Michiaki; HIRAI, Yuichi; (84 pag.)EP3053917; (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.186390-62-5,7-Bromo-6-nitro-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

7-Bromo-6-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 115 g (0.447 mol) of 7-bromo-6-nitro-1,2,3,4-tetrahydroisoquinoline, 45.2 g (0.447 mol) of TEA, 97.5 g (0.447 mol) of di-tert-butyl dicarbonate, 3.2 liter of dioxane and 0.5 liter of water were combined and stirred at ambient temperature for 1.5 hrs. The reaction was concentrated to remove the dioxane, 1 liter of saturated sodiumbicarbonate was added and extracted two times with 1 liter of dichloromethane. The organic layer was extracted with brine, dried over magnesium sulfate and concentrated. The resulting solid was recrystallized from isopropanol to yield 118 g of a solid. 1H NMR (250 MHz, DMSO) delta 7.89 (s, 1H); 7.81 (s, 1H); 4.58 (s, 2H); 3.56 (t, 2H); 2.81 (t, 2H); 1.42 (s, 9H)., 186390-62-5

As the paragraph descriping shows that 186390-62-5 is playing an increasingly important role.

Reference£º
Patent; PFIZER INC.; EP1181954; (2002); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

215798-19-9, 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,215798-19-9

To a dry microwave vial under nitrogen was added 4-chloropyrido[3′,2′:4,5]furo[3,2- d]pyrimidine (200 mg, 0.973 mmol), 6-bromo-l,2,3,4-tetrahydroisoquinoline,HCl (300 mg, 1.207 mmol) and acetonitrile (12 mL). The reaction was then treated with Hunig’s base (510 mu, 2.92 mmol), capped, heated 85 C (sand bath) then placed in a microwave reactor at 130 C for 4 h. The resulting solid was colledted by filtration to afford 4-(6- bromo-3,4-dihydroisoquinolin-2(lH)-yl)pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine, 32 mg (87%). LCMS (M+l) = 381.0 and 383.0. NMR (500 MHz, CDCb) delta 8.67 (s, IH), 8.64 (dd, J=4.9, 1.7 Hz, IH), 8.55 (dd, J=7.6, 1.7 Hz, IH), 7.49 (dd, J=7.6, 4.9 Hz, IH), 7.40 – 7.36 (m, 2H), 7.17 (d, J=8.7 Hz, IH), 5.20 (s, 2H), 4.40 (t, J=5.7 Hz, 2H), 3.08 (t, J=5.9 Hz, 2H).

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

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

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

The reaction flask was added A1-4 (60mg, 0.18mmol), A25-4 (194mg, 0.92mmol), diisopropylethyl amine (119mg, 0.92mmol)And N- methylpyrrolidinone (1.5mL). The reaction at 120 8h, cooled to room temperature, water was added, extracted three times with ethyl acetate, the combined organic phases with saturated chlorineAqueous solution of sodium, dried over anhydrous sodium sulfate, and the solvent was evaporated, and purified by column chromatography (petroleum ether: ethyl acetate = 5: 1-3: 1) to give an oily compound (40mg,44%). After parsing NMR spectrum (map data in Table 1), the resulting solid was compound, 81237-69-6

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

Reference£º
Patent; Suzhou Yunxuan Pharmaceutical Co., Ltd.; Zhang, Xiaohu; (54 pag.)CN105254613; (2016); A;,
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

tert-butyl 6-bromo-3,4-dihydroisoquinoline-2(1 H)-carboxylate (1913) A solution of di-terf-butyldicarbonate (1.1 1 mL, 4.76 mmol) in DCM (4 mL) was added dropwise to a suspension of 6-bromo-1 ,2,3,4-tetrahydroisoquinoline (0.990 g, 4.67 mmol) in DCM (6 mL) and the mixture was stirred at room temperature for 3 h. The solvent was removed in vacuo to give ferf-butyl 6-bromo-3,4-dihydroisoquinoline-2(1 H)-carboxylate (1.564 g, 4.66 mmol, 100%) as an orange oil. The product was used without further purification in the next step. 1H NMR (DMSO-d6) delta: 7.39 (1 H, d), 7.36 (1 H, dd), 7.14 (1 H, d), 4.45 (2H, s), 3.53 (2H, dd), 2.77 (2H, dd), 1.43 (9H, s).

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

Reference£º
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); 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.,42923-79-5

To a stifled solution of 7-nitro-i,2,3,4-tetrahydroisoquinoline (4 g, 22.41 mmol) in 1 ,4-dioxane: H20 (2:1, 60 mL) was added 1 N NaOH (20 mL) at 0 C. After 5 mm, di-tert-butyl dicarbonate (5.66 mL, 24.68 mmol) was added at 0 C, and the reaction was stined at RT for 2 h. The reaction was acidified with KHSO4 (pH: 2-3), then the mixture was extracted with EA (2 x 100 mL). The combined organic layers were washed with water (25 mL), dried (Na2SO4) and concentrated. The resulting crude was purified by column chromatography (Si02, 20% EA/pet. ether) to afford tert-butyl 7-nitro-3 ,4- dihydroisoquinoline-2(1H)-carboxylate (4.8 g, 77%) as a pale yellow solid. MS (ESI) mlz 223.2 [M-C4H8+H].

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

Reference£º
Patent; ZENO ROYALTIES & MILESTONES, LLC; HUANG, Peter, Qinhua; BOREN, Brant, Clayton; BUNKER, Kevin, Duane; LIU, Hui; PALIWAL, Sunil; (99 pag.)WO2019/28008; (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

Intermediate 16: 1,1-dimethylethyl 6-({[1-(2-biphenylylmethyl)-5-methyl-1H-pyrazol-3-yl]amino}carbonyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate; To a solution of 1-(2-biphenylylmethyl)-5-methyl-1H-pyrazol-3-amine (Intermediate 6) (76 mg, 0.29 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (66 mg, 0.34 mmol), 1-hydroxybenzotriazole hydrate (46 mg, 0.34 mmol) and diisopropylethylamine (48 mg, 0.37 mmol) in DCM (10 mL) was added 2-{[(1,1-dimethylethyl)oxy]carbonyl}-1,2,3,4-tetrahydro-6-isoquinolinecarboxylic acid (84 mg, 0.3 mmol) and the mixture was stirred at room temperature for 4 days. The organic phase was then washed with NaOH (1N) and brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM to DCM/MeOH: 96/4 to give the title compound as a colorless oil (73 mg, 49%).LC/MS: m/z 523 (M+H)+, Rt: 4.03 min., 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; Bouillot, Anne Marie Jeanne; Daugan, Alain Claude-Marie; Dean, Anthony William; Fillmore, Martin Christian; US2010/22486; (2010); 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

To a solution of 6-bromo-1,2,3,4-tetrahydroisoquinoline (1.00 g, 4.72 mmol) in DCM (20 mL) was added TEA (1.314 mL, 9.43 mmol) followed by di-tertbutyldicarbonate (1.31 mL, 5.66 mmol) and the reaction mixture was stirred at ambient temperature for 12 h. The reaction was quenched with water and extracted with DCM (2 x 50 mL). The combined organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude was purified by CombiFlash (Redi sep-12 g, 15 % EtOAc/n-hexanes) to obtain Intermediate 1-22 (1.10 g, 74.7 %), as alight brown liquid. ?HNIVIR (300 MHz, DMSO-d6) oe ppm 1.42 (s, 9 H), 2.77 (t, J 5.85 Hz, 2 H), 3.52 (t, J= 5.85 Hz, 2 H), 4.45 (s, 2 H), 7.14 (d, J= 7.93 Hz, 1 H), 7.33-7.40 (m, 2 H). LCMS (MethodE): retention time 3.41 mi [M+H] 316.0.

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; RICHTER, Jeremy; YADAV, Navnath Dnyanoba; PANDA, Manoranjan; GODESI, Sreenivasulu; (132 pag.)WO2017/184662; (2017); 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.,42923-77-3

Referential Example 138 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride In dimethylsulfide (20 ml), 6-methoxy-1,2,3,4-tetrahydroisoquinoline (7.75 g) was dissolved, followed by the addition of aluminum chloride (19.0 g) under ice cooling. The resulting mixture was stirred at room temperature for 3 hours. Dichloromethane and dilute hydrochloric acid were added to the reaction mixture. A saturated aqueous solution of sodium bicarbonate was added to the water layer so separated to make it weakly alkaline, followed by the extraction with dichloromethane. After drying over anhydrous sodium sulfate, the solvent was then distilled off under reduced pressure. The residue was dissolved in saturated ethanol hydrochloride (100 ml) and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue and the solid so precipitated was collected by filtration, whereby the title compound (7.91 g, 90%) was obtained. 1H-NMR (DMSO-d6) delta: 3.06(2H,t,J=5.9 Hz), 3.43(2H,m), 4.25(2H,s), 6.76(1H,d,J=2.0 Hz), 6.83(1H,dd,J=8.3,2.0 Hz), 7.15(1H,d,J=8.3 Hz), 9.71(3H,br s). MS (FAB) m/z: 150 (M+H)+.

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

Reference£º
Patent; Daiichi Pharmaceutical Co., Ltd.; US6525042; (2003); B1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem