Month: August 2020

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-Methanesulfonyl-l52,354-tetrahydro-isoquinolin-7-ylamine was prepared as follows: A solution of l5253,4-tetrahydro-isoquinolin-7-ylamine (1.255g)[ prepared from 1,2,3,4-tetrahydroisoquinoline according to J. Med. Chem., 2003, 46(5), pp831- 7.], NEt3 (l.lmL) and methanesulfonylchloride (0.6mL) in dry CH2Cl2 (2OmL) was stiired at R.T. overnight. Aqueous work-up followed by purification on silica gave 2- methanesulfonyl-7-nitro-l,25354-tetrahydro-isoquinoline (1.435g).

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

Reference£º
Patent; LUDWIG INSTITUTE FOR CANCER RESEARCH; CANCER RESEARCH TECHNOLOGY LIMITED; INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; ASTELLAS PHARMA INC; PIRAMED LIMITED; WO2007/42806; (2007); 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

To 11 mL of 9 concentrated sulfuric acid in an ice bath was added 0 1,2,3,4-tetrahydroisoquinoline (2.9 g, 21 mmol), and 0 potassium nitrate (2.4 g, 24 mmol) was added slowly. The mixture was allowed to increase to room temperature and react overnight. Then the reaction liquid was poured into ice water, and pH was adjusted to around 10 with concentrated aqueous ammonia. After extraction with DCM three times, organic layers were combined and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated under reduced pressure to obtain oil. The oil was dissolved in 16 mL of ethanol in an ice bath, and 3 mL of concentrated HCl was added to generate plenty of solid, which was subjected to suction filtration and drying. After recrystallization with methanol, 1.9 g of beige solid was obtained with a yield of 42percent.

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Reference£º
Patent; Peking University; Zhengzhou Granlen Pharmatech. Ltd.; LI, Runtao; AN, Haoyun; HAN, Liqiang; GE, Zemei; CUI, Jingrong; CHENG, Tieming; (52 pag.)EP3363803; (2018); 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

tert-Butyl 3,4-dihydro-7-nitroisoquinoline-2(1H)-carboxylate A mixture of 1,2,3,4-Tetrahydro-7-nitroisoquinoline (2.5 g, 11.6 mmol), 1,4-dioxane (24 mL), H2O (12 mL) and 1N NaOH (12 mL) was cooled in an ice-bath, and Boc2O (2.8 g, 12.8 mmol) was added. The mixture was stirred at room temperature for 2.5 h, acidified with a 5% KHSO4 solution to pH 2-3, and then extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give tert-butyl 3,4-dihydro-7-nitroisoquinoline-2(1H)-carboxylate (3.3 g, quant.), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) delta 8.13 (d, J=2.3 Hz, 1H), 8.03 (dd, J=8.4, 2.5 Hz, 1H), 7.45 (d, J=8.5 Hz, 1H), 4.63 (s, 2H), 3.60-3.57 (m, 2H), 2.90 (t, J=5.9 Hz, 2H), 1.44 (s, 9H); HPLC ret. time 3.51 min, 10-99% CH3CN, 5 min run; ESI-MS 279.2 m/z (MH+).

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

Reference£º
Patent; Vertex Pharmaceuticals Incorported; US2011/98311; (2011); 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.226942-29-6,6-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

Step 2 Sodium bicarbonate (1.21 kg) and Boc2O (2.62 kg) were added to a solution of 6-bromo-1,2,3,4tetrahydroisoquinoline (2.55 kg, 12.02 mol, 1.00 equivalent) in ethyl acetate (12.5 L) and water (12.5 L) at 20 C., and the reaction solution was stirred at 20 C. for 12 hours. After the reaction was completed, the reaction mixture was allowed to stand for layering, and the aqueous phase was extracted again with ethyl acetate (10 L*2). The organic phases were combined and washed once with water (10 L), dried over anhydrous sodium sulfate, filtered and concentrated to give N-tert-butoxycarbonyl-6bromo-1,2,3,4-tetrahydroisoquinoline (3.5 kg, 11.21 mol, yield of 91.4%, purity of 98%) as a yellow oil. m/z 256, 258 (1:1) [M+H-56]+; 1H NMR (400 MHz, CDCl3) delta=7.29 (m, 2H), 6.98 (d, 1H), 4.51 (s, 2H), 3.63 (t, 2H), 2.81 (t, 2H), 1.49 (s, 9H).

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

Reference£º
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; YAN, Xiaobing; HUANG, Wei; LI, Dan; DING, Charles Z.; LIU, Fei; ZHANG, Xiquan; (26 pag.)US2019/284146; (2019); 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.877861-62-6,Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride,as a common compound, the synthetic route is as follows.

A mixture of methyl 1,2,3,4-tetrahydroisoquino- line-6-carboxylate hydrochloride (230 mg, 1.01 mmol), bromobenzene (230 mg, 1.47 mmol), and cesium carbonate (0.66 g, 2.02 mmol) in 1,4-dioxane (10 mE) was purged with nitrogen. RuPhos precatalyst (15mg, 0.020 mmol) was added and the reaction mixture was heated at 80 C. for 30 mm, then 120 C. for 16 h. The solvent was removed under vacuum. The residue was diluted with water (30 mE), poured into a separatory flannel, and washed with ethyl acetate (3×50 mE). The combined organic layers were dried over sodium sulfate and the solvent was removed under vacuum and the crude mixture was purified on silica gel using a gradient of 0-100% ethyl acetate/hexanes, to give methyl 2-phenyl-1 ,2,3,4-tet- rahydroisoquinoline-6-carboxylate(200mg, 74%). 1HNMR (400 MHz, CDC13) oe 8.00-7.76 (m, 2H), 7.30-7.12 (m, 3H), 6.75 (d, 2H), 6.75 (t, 1H), 4.35 (s, 2H), 3.84 (s, 3H), 3.39 (t, 2H), 2.94 (t, 2H) ppm. LCMS: (ESI) mlz 268 [M+H].

The synthetic route of 877861-62-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Forma Therapeutics, Inc.; Ioannidis, Stephanos; Talbot, Adam Charles; Follows, Bruce; Buckmelter, Alexandre Joseph; Wang, Minghua; Campbell, Ann-Marie; Schmidt, Darby Rye; Guerin, David Joseph; Caravella, Justin A.; Diebold, R. Bruce; Ericsson, Anna; Lancia, JR., David; (225 pag.)US2016/185785; (2016); 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 94: 1.1-dimethylethyl 6-r({1-r(3.4-dichlorophenyl)methyll-5-methyl-1 H-1.2.3- triazol-4-yl}amino)carbonyl1-3,4-dihvdro-2(1 H)-isoquinolinecarboxylate; A mixture of 1-[(3,4-dichlorophenyl)methyl]-5-methyl-1 H-1 ,2,3-triazol-4-amine (Intermediate 69) (0.1g, 0.39mmol), 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6- isoquinolinecarboxylic acid (0.1 1g, 0.37mmol), HATU (0.19g, O.deltammol) and DIPEA (88mul_, O.deltammol) in DMF (5mL) was stirred at room temperature overnight. The mixture was evaporated. The residue was washed with water and extracted with DCM. The organic phase was dried over Na2SO4, filtered and concentrated. The title compound was obtained as a white solid after purification by flash column chromatography eluting with DCM/MeOH: 98//2 and crystallisation from isopropyl ether (86mg, 43 %). HRMS calculated for C25H27CI2N5O3 (M+H)+ 516.1569, found: 516.1591 , Rt: 3.13 min.

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

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/16216; (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.42923-77-3,6-Methoxy-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

A mixture of 6-methoxy- 1,2,3,4-tetrahydroisoquinoline (1.0 g, 6.13 mmol), ethyl 3-iodobenzoate (2.03 g, 7.35 mmol), Pd(dba)2(352 mg, 0.61 mmol), Cs2C03(7.98 g, 24.5 mmol) and X-phos (584 mg, 1.23 mmol) in DMF (15 mL) was degassed and purged with nitrogen for three times. The resulting mixture was stirred at 100C for 2 hours under nitrogen. The reaction mixture was cooled to room temperature and diluted with H20 (30 mL), and extracted with EA (20 mL X 2). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using 5-10% EA in PE as eluent to give the title compound (1.12 g, 58.7%) as a yellow liquid. +ESI-MS: m/z 311.7 [M +H]+.

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

Reference£º
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; (56 pag.)WO2017/147047; (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.215798-14-4,6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.

Step 4: (S)-N-[I -Benzyl-2-oxo-2-(6-trifluoromethyl-3,4-dihydro-1 H-isoquinolin-2-yl)-ethyl]- N-(4-pyridin-2-yl-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide A mixture of (S)-3-phenyl-2-{(4-pyridin-2-yl-benzyl)-[3-(4-trifluoromethyl-phenyl)-acryloyl]- amino}-propionic acid (50 mg, 0.094 mmol), TBTU (30.3 mg, 0.094 mmol), and DIPEA (0.08 mL, 0.471 mmol) in dry DMF (1 mL) was stirred at rt for 30 min. Then a solution of 6- trifluoromethyl-1 ,2,3,4-tetrahydro-isoquinoline hydrochloride in dry DMF (1 ml.) was added and the reaction mixture was stirred overnight at rt and directy purified by preparativeHPLC.LC-MS: tR = 1.04 min; [M+H]+ = 714.15.

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Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/141782; (2009); 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

Preparation of intermediate 6-bromomethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (4-19) Compound 4-17 (12.50 g, 45.08 mmol) is dissolved in dry THF (125.0 mL) under nitrogen at 25 C. Borane THF complex (99.17 mL, 99.17 mmol) is added via syringe and the mixture is stirred at 25 C. for 16 h. Water (10.0 mL) is slowly added and then 2.0 M Na2CO3 (15.0 mL). This mixture is stirred for 15 min and then is diluted with EtOAc and the organic layers are collected. The organics are rinsed with 1.0 M HCl, dried over MgSO4, and concentrated in vacuo to afford an oil. The oil is purified by silica gel chromatography using a gradient of 10-80% EtOAc in heptane to yield the desired product, 4-18 (11.78 g), as a white solid.

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Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BRENNEMAN, Jehrod Burnett; GINN, John; LOWE, Michael D.; SARKO, Christopher Ronald; TASBER, Edward S.; ZHANG, Zhonghua; US2014/73629; (2014); 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.

EXAMPLE 14 STR20 2-(2-chloropropionyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline By procedures described in Example 1 (Method A), phenethylamine and benzoyl chloride were converted to 1-phenyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.0 g of this isoquinoline compound, 5 ml 10% sodium hydroxide and 50 ml methylene chloride. With this mixture stirred, 1 ml 2-chloropropionyl chloride was added dropwise to the mixture. The mixture was stirred for 10 minutes, then water was added. The organic extract was dried with magnesium sulfate, stripped of solvent and subjected to Kugelrohr distillation (170 C. a 0.1 mm Hg) to provide 2.3 g of a viscous yellow oil product having the elemental analysis reported in Table I.

The synthetic route of 22990-19-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Monsanto Company; US4755218; (1988); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem