Tag: M.W:200-300

Name is 6-Bromo-1,2,3,4-tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 226942-29-6, its synthesis route is as follows.,226942-29-6

5-Cyclopropyl-2,6-dimethyl-7-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)oxazolo[4,5-c]- quinolin-4-one (Intermediate B) (69 mg, 0.18 mmol), [1 , T- bis(diphenylphosphino)ferrocene]palladium(ll) chloride dichloromethane complex (14 mg, 0.02 mmol), CS2CO3 (178 mg, 0.55 mmol), and 6-bromo-1 ,2,3,4-tetrahydroisoquinoline (38 mg, 0.18 mmol) were dissolved in a mixture of monoglyme (1 mL) and H2O (0.3 mL). The reaction solution was then irradiated with microwaves at 60C for 30 min. The solution was diluted with MeOH, filtered, dry-loaded onto silica and purified by flash chromatography using a gradient of 0-10% MeOH in DCM. The fractions containing the required product were then concentrated in vacuo to give 5-cyclopropyl-2,6-dimethyl-7-(1 , 2,3,4- tetrahydroisoquinolin-6-yl)oxazolo[4,5-c]-quinolin-4-one (2 mg, 3 %) as a pale yellow solid. 1 H NMR (Method A) (CDC ): delta 7.70 (d, J = 8.0 Hz, 1 H), 7.23 (d, J = 8.0 Hz, 1 H), 7.19 – 7.10 (m, 3H), 4.15 (s, 2H), 3.62 (m, 1 H), 3.25 (t, 2H), 2.93 (t, 2H), 2.68 (s, 3H), 2.53 (s, 3H), 1.31 – 1.26 (m, 2H), 0.71 – 0.65 (m, 2H); LC-MS (Method D) 386.4 [M+H]+; RT 1.68 min

With the complex challenges of chemical substances, we look forward to future research findings about 6-Bromo-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; REDX PHARMA PLC; HUXLEY, Anthony; KIRK, Ralph; RATCLIFFE, Andrew; LYTH, David; (112 pag.)WO2017/46605; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is Methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate hydrochloride, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 1029689-82-4, its synthesis route is as follows.,1029689-82-4

To a solution of methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate hydrochloride (12.37 g) and Example 1.1.11 (15 g) in dimethyl sulfoxide (100 mL) was added N,N-diisopropylethylamine (12 mL). The mixture was stirred at 50 C. for 24 hours. The mixture was then diluted with ethyl acetate (500 mL), washed with water and brine, and dried over Na2SO4. Filtration and evaporation of the solvent gave a residue that was purified by silica gel chromatography, eluting with 20% ethyl acetate in heptane, to give the title compound. MS (ESI) m/e 448.4 (M+H)+.

With the complex challenges of chemical substances, we look forward to future research findings about Methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate hydrochloride

Reference£º
Patent; AbbVie Inc.; Boghaert, Erwin R.; Bruncko, Milan; Doherty, George; Frey, Robin R.; Judd, Andrew S.; Phillips, Andrew C.; Song, Xiaohong; Souers, Andrew J.; Sullivan, Gerard M.; Tao, Zhi-Fu; US2019/153107; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO14,mainly used in chemical industry, its synthesis route is as follows.,22990-19-8

A round bottom flask was loaded with IQL (50 g), IPA (350 ml), and water (150 ml). The mixture was heated to 60 C. for dissolution. Then D-tartaric acid (36 g) was added, and the solution was cooled to 25 C. The product was isolated after 2.5 hours by vacuum filtration, washed with IPA (2¡Á50 ml), dried in a vacuum oven at 50 C. over the weekend to obtain (S)-IQL tartrate (33.5 g, 80% yield, 100% enantiomeric purity). ; A round bottom flask was loaded ask was loaded with IQL (10 g), IPA, and water. The mixture was heated to 60 C. for dissolution. Then D-tartaric acid was added, and the solution was cooled and stirred. Where applicable, seeding was performed during the cooling step. The product was isolated by vacuum filtration, washed with a mixture of water and IPA, and dried in vacuum oven at 50 C. over the TABLE 1 Tartaric Stirring acid Acid time (molar IPAH2O addition after Cooling equiv. (ml/g (ml/g temp. cooling temp. Enantiomeric Yield to IQL) of IQL) of IQL) ( C.) Seeding (hrs) ( C.) Purity (%) 1 7 3 60 – 2.5 RT 98.4 83.5 1 6 3 60 – 2.5 RT 98.6 81.4 1 7 2 60 – 2.5 RT 98.8 87.1 1 7 4 60 – 2.5 RT 97.7 75.5 1 5.6 2.4 60 – 2.5 RT 98.2 85.0 1 8.4 3.6 60 – 2.5 RT 99.8 77.1 1 7 3 40 – 2.5 RT 98.1 80.0 1 7 3 25 – 2.5 RT 97.6 79.0 1 7 3 60 + 2.5 RT 98.7 77.9 1 7 3 60 – 5 RT 98.7 79.2 1 7 3 60 – 15 RT 89.9 85.4 1 7 3 60 – 2.5 15 C. 99.6 91.8 1 7 3 60 – 2.5 5 C. 99.5 92.0 weekend to obtain (S)-IQL tartrate. The experiments and results are summarized in Table 1.

With the synthetic route has been constantly updated, we look forward to future research findings about 1-Phenyl-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; Perlman, Nurit; Nidam, Tamar; US2008/91023; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, name is 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride, and cas is 215798-19-9, its synthesis route is as follows.,215798-19-9

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).

With the complex challenges of chemical substances, we look forward to future research findings about 215798-19-9,belong tetrahydroisoquinoline compound

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/105206; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, name is 6-Bromo-1,2,3,4-tetrahydroisoquinoline, and cas is 226942-29-6, its synthesis route is as follows.,226942-29-6

Boc2O (3.52 g, 16.14 mmol) was added to a solution of 6-bromo-1,2,3,4-tetrahydroisoquinoline (3.26 g, 15.37 mmol) in THF (45 mL) at room temperature, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0?8% ethyl acetate/hexane) to give tert-butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (5.05 g, 16.18 mmol, quant.) as a colorless oil. 1H NMR (300 MHz, CDCl3):delta 1.49(9H,s), 2.80(2H,t,J=5.9 Hz), 3.62(2H,t,J=5.9 Hz), 4.51(2H,s), 6.97(1H,d,J=8.7 Hz), 7.28-7.32(2H,m).

With the complex challenges of chemical substances, we look forward to future research findings about 226942-29-6,belong tetrahydroisoquinoline compound

Reference£º
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; ODA, Tsuneo; IMADA, Takashi; KONO, Mitsunori; SATO, Ayumu; TOMATA, Yoshihide; OCHIDA, Atsuko; ISHII, Naoki; SASAKI, Yusuke; FUKASE, Yoshiyuki; YUKAWA, Tomoya; FUKUMOTO, Shoji; (200 pag.)EP3192791; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 170097-67-3, its synthesis route is as follows.,170097-67-3

General procedure: To a solution of corresponding acids (1.0mmol) in DCM (6mL) was added EDCI (1.5mmol), HOBt (1.5mmol), Et3N (3.0mmol) and corresponding amines (1.0mmol). The mixture was stirred at room temperature for 4h. The reaction mixture was diluted with saturated sodium bicarbonate aqueous solution (10mL) and extracted with DCM (3¡Á10mL). The combined organic layers were then dried and concentrated. The residue was purified by silica gel chromatography (dichloromethane/methanol, v/v, 90:10) to give the desired product.

With the complex challenges of chemical substances, we look forward to future research findings about 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

Reference£º
Article; Shao, Jingwei; Zhu, Kongkai; Du, Daohai; Zhang, Yuanyuan; Tao, Hongrui; Chen, Zhifeng; Jiang, Hualiang; Chen, Kaixian; Luo, Cheng; Duan, Wenhu; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 317 – 333;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO468,mainly used in chemical industry, its synthesis route is as follows.,170097-67-3

Example 24: 1 ,1-Dimethylethyl 6-r({1-r(3,4-dichlorophenyl)methvH-1 /-/-pyrazol-4- yl}amino)carbonyll-3,4-dihvdro-2(1 H)-isoquinolinecarboxylate;To a solution of 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6-isoquinoline carboxylic acid (138 mg, 0.5 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (114 mg, 0.6 mmol), 1-hydroxybenzotriazole hydrate (81 mg, 0.6 mmol) and triethylamine (60 mg, 0.6 mmol) in DCM (10 ml.) was added 1-[(3,4- dichlorophenyl)methyl]-1 H-pyrazol-4-amine (Intermediate 7) (120 mg, 0.5 mmol) and the reaction mixture was stirred at room temperature overnight. The organic phase was then washed with a 1 N sodium hydroxide solution, with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM/MeOH: 95/5 to give the title compound as a white solid (190 mg, 77%) after recrystallization from CH3CN. LC/MS: m/z 501 (M+H)+, Rt: 3.65 min.

With the synthetic route has been constantly updated, we look forward to future research findings about 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,belong tetrahydroisoquinoline compound

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/74824; (2008); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid,cas is 151838-62-9, mainly used in chemical industry, its synthesis route is as follows.

Step 1 3(R)-Carboethoxy-1,2,3,4-tetrahydroisoquinoline The title compound was obtained from N-Boc-D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Bachem) using standard amino acid chemical procedures.

151838-62-9, As the rapid development of chemical substances, we look forward to future research findings about 151838-62-9

Reference£º
Patent; Merck & Co., Inc.; US5977134; (1999); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 6-Bromo-1,2,3,4-tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 226942-29-6, its synthesis route is as follows.,226942-29-6

To a solution of 6-bromo-1,2,3,4-tetrahydroisoquinoline (1.25 g, 5.88 mmol) in DCM (25 mL) was added 2-chloro-6-methylbenzaldehyde (1.0 g, 6.5 mmol) and acetic acid (0.337 mL, 5.88 mmol) inDCM (25 mL). Then sodium triacetoxyborohydride (1.62 g, 7.64 mmol) was added. Themixture was stirred at r.t for 16 hrs. The mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by recrystallization with EtOAc to give 6-bromo- 2-(2-chloro-6-methylbenzyl)-1,2,3,4-tetrahydroisoquinoline (1.44 g, 4.11 mmol, 69.8%yield). LCMS (M+H): 350.00, 352.00.

With the complex challenges of chemical substances, we look forward to future research findings about 6-Bromo-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; EASTMAN, Kyle J.; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PATEL, Manoj; SIVAPRAKASAM, Prasanna; TU, Yong; (275 pag.)WO2017/25915; (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.923591-51-9,5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.,923591-51-9

Step 1 : 5-Bromo-N-(thiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide A solution of imidazole (1.530 g, 22.47 mmol) and thiazol-2 -amine (0.750 g, 7.49 mmol) in 8 mL DCM was cooled to -78 C and was treated with sulfuryl chloride (0.609 ml, 7.49 mmol). After stirring for 20 minutes, the cooling bath was removed and the reaction mixture was allowed to stir for an additional 30 minutes. 5-Bromo-l,2,3,4- tetrahydroisoquinoline hydrochloride (ASW Medchem, Brunswick, NJ, 1.396 g, 5.62 mmol) was added, followed by triethylamine (7.31 ml, 52.4 mmol). The reaction mixture was then heated to 80 C for 30 minutes. The mixture was cooled to rt and poured into IN citric acid solution before being extracted into EtO Ac. The organics were dried over MgS04 and concentrated. Purification of the residue by silica gel column chromatography (0 to 100% EtO Ac/heptane) gave 5-bromo-N-(thiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide (1.092 g, 2.92 mmol). [M+H]+ = 375.6.

As the paragraph descriping shows that 923591-51-9 is playing an increasingly important role.

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