Month: October 2020

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

Name is 7-Nitro-1,2,3,4-tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 42923-79-5, its synthesis route is as follows.,42923-79-5

1H NMR (400 MHz, DMSO-d6) delta 8.45 (dd, J = 7.9, 1.3 Hz, 1H), 8.21 (d, J = 2.4 Hz, 1H), 8.16 (dt, J = 8.1, 1.0 Hz, 1H), 8.09 (dd, J = 8.4, 2.5 Hz, 1H), 7.98 (ddd, J = 8.1, 7.3, 1.1 Hz, 1H), 7.87 (ddd, J = 8.4, 7.3, 1.4 Hz, 1H), 7.54 (d, J = 8.5 Hz, 1H), 4.74 (s, 2H), 3.73 (t, J = 5.9 Hz, 2H), 3.32 – 3.26 (m, 2H), 2.49-2.42 (m, 1H), 1.24 -1.11 (m, 4H). HRMS: (0603) C21H18N6O2 calculated (M+H)+ = 387.15640 m/z; found (M+H)+ = 387.15630. Yield: 50%.

With the complex challenges of chemical substances, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; SOUTHERN RESEARCH INSTITUTE; OYAGEN, INC.; ANANTHAN, Subramaniam; AUGELLI-SZAFRAN, Corinne E.; BENNETT, Ryan P.; SMITH, Harold C.; VENUKADASULA, Phanindra Krishna Mohan; (227 pag.)WO2019/133666; (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

Name is 8-Chloro-1,2,3,4-tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 75416-50-1, its synthesis route is as follows.,75416-50-1

A mixture of 8-chloro-1,2,3,4-tetrahydroisoquinoline (4.5 g, 22.0 mmol), 3-trifluoromethylbenzaldehyde (3.25 mL, 24.3 mmol), sodium acetate (1.81 g, 22.0 mmol), and acetic acid (0.63 mL, 11.0 mmol) in ethanol was stirred for 1 hour. Sodium triacetoxyborohydride (5.60 g, 26.5 mmol) was added a little at a time over a period of 30 min, and the mixture was then stirred for 15 hours. The reaction solution was diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was then distilled off at reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=10:1), the resulting oily substance was dissolved in isopropyl alcohol (30 mL), and 4 N hydrogen chloride/ethyl acetate (5 mL) was added. The precipitated crystals were filtered off to give 5.89 g of the titled compound (yield 74%). Melting point: 217-218 C.1H-NMR (DMSO-d6) delta: 3.00-3.40 (4H, m), 4.20-4.40 (2H, m), 4.50-4.80 (2H, m), 7.25 (1H, d, J=7.5 Hz), 7.32 (1H, d, J=7.2 Hz), 7.38 (1H, t, J=7.2 Hz), 7.74 (1H, t, J=7.5 Hz), 7.80-7.90 (1H, m), 7.90-8.00 (1H, m), 8.10 (1H, s), 11.24 (1H, br s).

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

Reference£º
Patent; Takeda Pharmaceutical Company Limited; US2010/41891; (2010); 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

1-Methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride, cas is 111635-08-6, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

D. l . Synthesis of N-(2,6-dichlorophenyl)-1 -methyl-3,4-dihydroisoquinoline-2(1 H)-carbox- amide 118 and enantiomers. CAS RN 39920-37-1 CAS RN 4965-09-7 8 commercial commercial To a solution of 1 -methyl-1 ,2,3,4-tetrahydroisoquinoline hydrochloride (commercial, 500 mg, 2.72 mmol) in THF (5 mL) were added TEA (1 .2 mL, 8.5 mmol) and 1 ,3-dichloro-2- isocyanatobenzene (commercial, 522 mg, 2.72 mmol). The mixture was stirred overnight at 60 C, then concentrated under vacuum. The residue was taken up with DCM (100 mL), then the solution was successively washed with a 1 N aqueous solution of NaOH (50 mL) and a 1 N aqueous solution of HCI (50 mL). The organic layer was dried over MgS04, filtered and concentrated under vacuum. The residue was purified by reverse phase chromatography (basic mode, standard LC) to afford 273 mg of N-(2,6-dichlorophenyl)-1 – methyl-3,4-dihydroisoquinoline-2(1 H)-carboxamide 118 as a white solid. Yield: 30% LCMS (ES+): 335/337/339 (M+H)+, 98.8% purity.

111635-08-6, With the rapid development of chemical substances, we look forward to future research findings about 1-Methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reference£º
Patent; UCB BIOPHARMA SPRL; VALADE, Anne; JNOFF, Eric; ATES, Ali; BURSSENS, Pierre; SKOLC, David; (211 pag.)WO2016/55479; (2016); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, name is 6-Methoxy-1,2,3,4-tetrahydroisoquinoline, and cas is 42923-77-3, its synthesis route is as follows.,42923-77-3

6-Methoxy-l,2,3,4-tetrahydroisoquinoline (14.7 g, 90 mmol) is dissolved in hydrobromic acid (48%, 300 ml), and the mixture is heated at 120 0C for 16 h. The solvent is removed under reduced pressure to give the title compound as the hydrobromate.

With the complex challenges of chemical substances, we look forward to future research findings about 42923-77-3,belong tetrahydroisoquinoline compound

Reference£º
Patent; NEUROGEN CORPORATION; WO2007/146122; (2007); A2;,
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

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

6-Chloro-1,2,3,4-tetrahydroisoquinoline, cas is 33537-99-4, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

[0232] To a stirring solution of 23 (1 mmol, 200mg) in dichloromethane and triethylamine (2mmol, 0.3ml) at roomtemperature was added N-bromosuccinimide (1.1mmol, 200mg). The reaction mixture was stirred at room temperaturefor 30min. Then 2.0 M NaOH aqueous solution was added and the reaction mixture was stirred at rt for another 1 h. Thereaction mixture as extracted with DCM. The combined organic layer was over MgSO4. The solvent was removed invacuo. The crude product 24 was used in the next step without further purification.

33537-99-4, As the rapid development of chemical substances, we look forward to future research findings about 33537-99-4

Reference£º
Patent; Merck Sharp & Dohme Corp.; MA, Yao; SHIZUKA, Manami; GUZI, Timothy, J.; TIAN, Yuan; LAHUE, Brian, R.; WANG, Yaolin; SHIPPS, Gerald, W., Jr.; BOGEN, Stephane, L.; NAIR, Latha, G.; PAN, Weidong; VOSS, Matthew, E.; KIROVA-SNOVER, Margarita; CLAYTON, W. Brent; MICCOY, Mark, A.; LIU, Yuan; GIBEAU, Graig, R.; (152 pag.)EP2793890; (2016); B1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

7-Nitro-1,2,3,4-tetrahydroisoquinoline, cas is 42923-79-5, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

1,2,3,4-tetrahydroiosquinoline (Aldrich Tl,300-5, 100 gm) (11.6 g, 84.8 mmol) is added dropwise with care to stirred ice-cold concentrated H2S04 (42.0 mL). Potassium nitrate (9.40 g. , 93 mmol) is then added in small portions, taking care that the temperature of the reaction mixture does not rise above 5 ¡ãC. After stirring overnight at room temperature the dark brown reaction mixture is added carefully to a stirred ice-cold concentrated NH40H solution. The basic red reaction mixture is extracted with chloroform (three times), and the combined chloroform extracts is washed with brine and dried over anhydrous Na2S04. Evaporation of the solvent gives a dark brown oil (14.6 g) which was taken up in EtOH (65 mL) and cooled in an ice bath. Treatment of this reddish solution with concentrated HCI (11 mL) yields a viscous yellow precipitate of the hydrochloride salt which is filtered and crystallized from methanol (250 mL) to yield the product compound (2) as a solid (5.36 g, ~30percent yield). Alternatively, flash chromatography may be used to purify the crude reaction mixture before crystallization.

42923-79-5, With the rapid development of chemical substances, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; ENVIVO PHARMACEUTICALS, INC.; WO2005/108367; (2005); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem