Month: September 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.91-21-4,1,2,3,4-Tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

A. 7-Nitro-1,2,3,4-tetrahydro-isoquinoline To 43.1 g (324 mmol) of 1,2,3,4-tetrahydro-isoquinoline was added 160 mL of concentrated sulfuric acid with ice bath cooling. Potassium nitrate 35.2 g (348 mmol) was added in portions to the stirring mixture, while maintaining an internal temperature below 5 C. The mixture was allowed to stand at ambient temperature for 72 h, and then basified with aqueous ammonia and extracted four times with chloroform. The combined organics were dried over MgSO4 and concentrated to give a dark brown oil. The oil was dissolved in 240 mL of ethanol and 40 mL of concentrated hydrochloric acid was added to the mixture with cooling. The precipitated material was collected by filtration and washed with cold ethanol to give 25.0 g of a tan solid. The crude material was partitioned between 1 N NaOH and ethyl acetate. The ethyl acetate layer was washed once with brine, dried over Na2 SO4 and concentrated. The dinitrated tetrahydroisoquinoline was removed by crystallization from ether/hexanes. The mother liquor was concentrated to give 2.19 g of 7-Nitro-1,2,3,4-tetrahydro-isoquinoline. B.[{1-[1-(R)-Benzyloxymethyl-2-(7-nitro-3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-ethylcarbamoyl]-1-methyl-ethyl]-carbamic acid tert-butyl ester According to General Procedure A, 100 mg (0.57 mmol) of 6A and 228 mg (0.60 mmol) of 3 were coupled, and the product was purified by silica gel chromatography (99:1 v/v CH2 Cl2:MeOH) to give 220 mg of 6B as a white foam., 91-21-4

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

Reference£º
Patent; Pfizer Inc; US5936089; (1999); A;,
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.33537-99-4,6-Chloro-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,33537-99-4

General procedure: 1,2,3,4-Tetrahydro-isoquinoline(1g, 7.5 mmol) was dissolved in 5 mL of anhydrous acetonitrile. Then to thissolution was slowly added 2-chloro- or 2-bromo-benzyl compound (7.5 mmol) and the reaction was carried out overnight at room temperature. The solvent wasremoved under reduced pressure. The residue was resuspended in 1 ml of DMSO andpurified using C18 flash chromatography as described above.

The synthetic route of 33537-99-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Farha, Maya A.; Koteva, Kalinka; Gale, Robert T.; Sewell, Edward W.; Wright, Gerard D.; Brown, Eric D.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 3; (2014); p. 905 – 910;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

99365-69-2, 7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

99365-69-2, 10percent Pd/C (1.9 g) was added to a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (19 g; 1 equiv.) in 300 ml of methanol, and the reaction mixture was hydrogenated for 2 hours at 60 PSI. When the conversion was complete, filtration over Celite was carried out, the filter cake was then washed 4 times with methanol, the filtrate was concentrated under reduced pressure, and the residue was taken up in 100 ml of water. The aqueous solution was adjusted to a pH value of 8-9 with potassium hydroxide solution and extracted 3.x. with chloroform. The combined organic phases were dried over sodium sulfate and reduced under reduced pressure. 1,2,3,4-Tetrahydroisoquinoline-7-amine (9 g; 69.2percent) was obtained in the form of a pale-brown solid.

The synthetic route of 99365-69-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Gruenenthal GmbH; US2010/234340; (2010); 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

a. 2-[(4-cyanophenyl)-acetyl]-7-nitro-1,2,3,4-tetrahydro-isoquinoline 4.0 g (22.5 mmol) of 7-nitro-1,2,3,4-tetrahydro-isoquinoline are dissolved in 100 ml of chlorobenzene, mixed with 4.24 g (25 mmol) of 4-cyanophenylacetic acid chloride and refluxed for 2 hours. After cooling to ambient temperature the mixture is diluted with 11 of petroleum ether and filtered. The residue is dissolved in ethyl acetate and chromatographed on silica gel, eluding first with methylene chloride, later with methylene chloride/ethanol (50:1 and 25:1). The desired fractions are combined and evaporated down. Yield: 3.80 g (53% of theory), Rf -value: 0.50 (silica gel; methylene chloride/ethanol=19:1).

42923-79-5, As the paragraph descriping shows that 42923-79-5 is playing an increasingly important role.

Reference£º
Patent; Boehringer Ingelheim KG; US6121308; (2000); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

923591-51-9, 5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,923591-51-9

Intermediate AA: 5-Bromo-N-(l,2,4-thiadiazol-5-yl)-3,4-dihydroisoquinoline-2(lH)- sulfonamide To a 50 mL flask containing sodium l,2,4-thiadiazol-5-ylsulfamate (Intermediate A, 96 mg, 0.472 mmol) and 10 mL of DCM was added PC15 (Aldrich, St. Louis, MO, 245 mg, 1.179 mmol). The resutling slurry was heated at 50 C for 1.5 hours. LCMS showed conversion to the methyl sulfamate (following quench into methanol). The reaction was cooled to rt and was quenched with the addition of 5 drops of brine. The resulting slurry was stirred vigorously for 5 minutes before being filtered through a plug of diatomaceous earth, washing well with DCM. The mixture was concentrated under reduced pressure. The derived oil was taken up in 1 mL of DCM and was added to a solution of 5-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (ASW Medchem, 50 mg, 0.236 mmol) and TEA (164 mu, 1.179 mmol) in 2 mL of DCM at 0 C. Another 0.164 mL of TEA was added and the reaction allowed to warm to room temeprature where it was maintained for 2 hours. LCMS showed clean conversion to sulfonamide. The reaction was allowed to stir overnight before being diluted with saturated sodium bicarbonate (10 mL) and poured into a separatory funnel containing methylenechloride (10 mL). The layers were separated and the aqueous layer was extracted with methylenechloride (2 x 25 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under a vacuum to provide a yellow oil that was purified by silica gel chromatography (Redi-Sep pre-packed silica gel column (12 g), 0-10% methanol in methylenechloride) to provide 5-bromo-N-(l,2,4-thiadiazol-5-yl)-3,4- dihydroisoquinoline-2(lH)-sulfonamide as an off white solid. [M+H]+ = 375.0 XH NMR (400 MHz, Acetone)8 ppm 8.28 (s, 1H), 7.96 (s, 1H), 7.45 – 7.50 (m, 1H), 7.09 – 7.20 (m, 2H), 4.32 (s, 2H), 3.48 (t, J = 6.1 Hz, 2H), 2.86 – 2.92 (m, 2H)

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

215798-14-4, 6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,215798-14-4

Under nitrogen, to N-(4-bromo-3-fluoro-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide (158 mg, 0.500 mmol, 1.00 equiv) in toluene (2.5 mL) at 23 C. were added 6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloric acid salt (178 mg, 0.750 mmol, 1.50 equiv), DavePhos (47 mg, 0.12 mmol, 24 mol %), Pd2(dba)3 (37 mg, 0.040 mmol, 8.0 mol %), and t-BuOK (168 mg, 1.50 mmol, 3.00 equiv). After stirring for 1 hr at 100 C., the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc to afford 72 mg the title compound (33% yield).NMR Spectroscopy: 1H NMR (300 MHz, CDCl3, 23 C., delta): 7.40-7.32 (m, 2H), 7.14 (d, J=8.7 Hz, 1H), 6.79-6.70 (m, 1H), 6.54 (br s, 1H), 4.25 (br s, 2H), 3.37 (t, J=6.0 Hz, 2H), 3.03 (t, J=6.0 Hz, 2H), 2.23 (s, 2H), 2.13-2.08 (m, 6H), 1.08 (s, 9H).

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

Reference£º
Patent; SciFluor Life Sciences, Inc.; EDWARDS, D. Scott; ASKEW, Ben C.; FURUYA, Takeru; (64 pag.)US2017/355679; (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.22990-19-8,1-Phenyl-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,22990-19-8

Racemic mixture of 1 -phenyl- 1, 2,3, 4-tetrahydroisoquinoline (40 g, 191 mmol) and D-(-)-tartaric acid (28.61 g, 191 mmol, ee 99%) are suspended in methanol (240 niL). The solution is heated to reflux, until the whole amount of solid is completely dissolved. The heating bath is being removed and to the clear solution water (120 mL) is added; the resulting mixture is left at ambient temperature (240C) for 24 h. Crystalline solid is filtered off (21.45 g). -17.02 (c=l%, H2O).Obtained crystalline solid is suspended in the mixture of 10% NaOHaq (120 mL) and ethyl acetate (50 mL), the solution is stirred at ambient temperature (240C) for about 10 min. until the whole amount of solid is dissolved. The reaction mixture is transferred into separatory flask, organic layer is separated and water phase is extracted with ethyl acetate (2×30 mL). Combined organic extracts are washed with water (1×40 mL), dried and condensed under vacuum to dryness. (S)-1-Phenyl- 1,2,3, 4-tetrahydroisoquinoline is obtained as crystalline solid (12 g, 30%), of enantiomeric excess ee = 100%. Chemical purity (HPLC): 99.96%; [alpha]25D = 38.20 (c=l%, CH2Cl2).

22990-19-8 1-Phenyl-1,2,3,4-tetrahydroisoquinoline 100137, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; ZAKLADY FARMACEUTYCZNE POLPHARMA SA; WO2009/142521; (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.42923-79-5,7-Nitro-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,42923-79-5

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

Reference£º
Patent; ENVIVO PHARMACEUTICALS, INC.; WO2005/108367; (2005); 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,42923-77-3

In a 25 ml round-bottom flask compound is added in 5A (200 mg, 1 . 23mmol), compound 5B (273 mg, 1 . 11mmol), ethyl acetate (2 ml), stirring, add three acetoxy nabh (284 mg, 1 . 34mmol). Stir at room temperature overnight, TLC detection raw material the reaction is complete. Saturated sodium bicarbonate aqueous solution for quenching the reaction, then using ethyl acetate extraction, combined with the organic layer, dry anhydrous sodium sulfate, concentrated after the silica gel column chromatography, with petroleum ether: ethyl acetate (4:1) as eluant, get white solid product 5 (186 mg, yield: 42.7%)

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

Reference£º
Patent; Chengdu Biological Technology Co., Ltd. Kerry Bass; Li, Dequn; (92 pag.)CN105777632; (2016); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

22990-19-8, 1-Phenyl-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 a compound 3-benzylaza-bicyclo[3.1.0]hexan-6-amine (0.2 g, 0.001 mol) [prepared following the procedure as described in Synlett, 1097-1102 (1996)] in acetonitrile (10 ml), was added p-nitrophenyl chloroformate (0.216 g, 0.001 mol) and triethylamine (0.214 g, 0.00212 mol). The resulting reaction mixture was stirred at room temperature for 3 hours followed by the addition of 1 -phenyl- 1,2,3, 4- tetrahydroisoquinoline (0.2 Ig, 0.001 mol). The reaction mixture was refluxed for 12 hours followed by cooling it to room temperature. The contents of the reaction mixture were poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue thus obtained was purified by column chromatography using ethyl acetate and hexane solvent mixture to furnish the title compound. Yield: 0.11 g.1H NMR (CDCl3): 7.37-7.06 (m, 14H), 6.30 (s, IH), 4.84 (bs, IH), 3.58 (s, 2H), 3.56-3.49 (m, 2H), 3.11-2.74 (m, 7H), 1.26 (s, 2H); IR (DCM): 1622 cm”1

22990-19-8, 22990-19-8 1-Phenyl-1,2,3,4-tetrahydroisoquinoline 100137, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; RANBAXY LABORATORIES LIMITED; WO2006/35280; (2006); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem