Month: September 2020

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

2-(tert-Butoxycarbonyl)- 1,2,3 ,4-tetrahydroisoquinoline-6-carboxylic acid (100 mg, 0.361 mmol) was dissolved in THF (5 mL) in an oven dried flask at -78 C. TMEDA (0.174 mL, 1.15 mmol) was added, followed by dropwise addition of a 1.6 M solution of n-BuLi in hexane (0.721 mL, 1.15 mmol) over 1 mm. The reaction mixture was stirred at-78 C for 1 hour, then a solution of Mel (0.090 mL, 1.4 mmol) dissolved in 1 mL of THFwas added. The reaction was allowed to warm to rt, and stirring was continued at rt for 45minutes. The reaction was then quenched with an aq. solution of saturated NH4C1 and extracted 3x with EtOAc. The combined organic extracts were dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to provide 181A(70 mg, 67% yield), as a white solid. MS(ESI)m/z 290.1 (M-H)., 170097-67-3

As the paragraph descriping shows that 170097-67-3 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne, M.; SHAW, Scott, A.; HALPERN, Oz, Scott; HU, Carol, Hui; KICK, Ellen, K.; (311 pag.)WO2017/40449; (2017); 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,91-21-4

Example 101,2,3,4-Tetrahydro-7-nitroisoquinoline hydrochloride1,2,3,4-Tetrahydroisoquinoline (6.3 mL, 50.0 mmol) was added dropwise to a stirred ice-cold solution of concentrated H2SO4 (25 mL). KNO3 (5.6 g, 55.0 mmol) was added portionwise while maintaining the temperature below 5¡ã C.The mixture was stirred at room temperature overnight, carefully poured into an ice-cold solution of concentrated NH4OH, and then extracted three times with CHCl3.The combined organic layers were washed with brine, dried over Na2SO4 and concentrated.The resulting dark brown oil was taken up into EtOH, cooled in an ice bath and treated with concentrated HCl.The yellow precipitate was collected via filtration and recrystallized from methanol to give 1,2,3,4-tetrahydro-7-nitroisoquinoline hydrochloride as yellow solid (2.5 g, 23percent).1H NMR (400 MHz, DMSO-d6) delta 9.86 (s, 2H), 8.22 (d, J=1.6 Hz, 1H), 8.11 (dd, J=8.5, 2.2 Hz, 1H), 7.53 (d, J=8.5 Hz, 1H), 4.38 (s, 2H), 3.38 (s, 2H), 3.17-3.14 (m, 2H); HPLC ret. time 0.51 min, 10-99percent CH3CN, 5 min run; ESI-MS 179.0 m/z (MH+).

As the paragraph descriping shows that 91-21-4 is playing an increasingly important role.

Reference£º
Patent; Vertex Pharmaceuticals Incorported; US2011/98311; (2011); 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

91-21-4, Concentrated sulfuric acid (70 mL) was cooled in an ice-salt bath to 00C. 1,2,3,4- Tetrahydroisoquinoline (96percent, 19.6 g, 141 mmol) was added dropwise in portions over 35 minutes, with the temperature mostly staying below 200C, but occasional brief excursions as high as 400C. The resulting mixture was again cooled in an ice-salt bath to 00C and solid potassium nitrate (15.7 g, 155 mmol) was added in portions over 60 minutes, keeping the temperature mostly below 5¡ãC with occasional brief excursions as high as 7¡ãC. Following completion of addition, the bath was removed and the resulting mixture was allowed to stir overnight at ambient temperature. The mixture was added carefully in small portions over 2 hours to concentrated ammonium hydroxide (200 mL), cooled initially in an ice-salt bath to – 2¡ãC. The resulting mixture was diluted with chloroform (400 mL) and the mixture stirred overnight at ambient temperature. Additional concentrated ammonium hydroxide was added to bring the pH to about 11. The mixture was transferred to a separatory funnel and the organic layer was dried over sodium sulfate and evaporated to give about 25 g of dark red oil. This oil was redissolved in ethanol (100 mL), and to the resulting stirred solution was added concentrated hydrochloric acid (10 mL). The mixture immediately formed a hard solid. Additional ethanol (100 mL) and concentrated hydrochloric acid (10 mL) were added, and after stirring for a few minutes, the resulting precipitate was collected by filtration, washed with ethanol, and air-dried. The precipitate was heated to boiling with methanol (200 mL), and the mixture was allowed to cool to ambient temperature and stand overnight. The precipitate was collected by filtration, washed with methanol, and dried under vacuum to afford 7-nitro-l,2,3,4-tetrahydroisoquinoline hydrochloride as an off-white solid (7.05 g, 23percent yield).

As the paragraph descriping shows that 91-21-4 is playing an increasingly important role.

Reference£º
Patent; ARRAY BIOPHARMA INC.; WO2009/158426; (2009); A1;,
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

A suspension of 6-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (CASNo.226942-29-6 , commercially available from Allichem LLC, 1 g, 4.02 mmol) and di-tert- butyl dicarbonate (1.87 ml, 8.05 mmol) in MeOH (10 ml) at room temperature under nitrogen was treated with triethylamine (2.80 ml, 20.12 mmol) and the resulting mixture was stirred at room temperature for 20 hours then concentrated in vacuo.The residue was partitioned between DCM and a saturated Na2CO3 aqueous solution and the two layers were separated using a phase separator cartridge. The organic phase was concentrated in vacuo and the residue loaded on a SCX column, eluting with MeOH. The combined methanolic fractions were concentrated in vacuo to give 1,1-dimethylethyl 6-bromo-3,4-dihydro-2(1H)-isoquinolinecarboxylate (1.215 g,97%) as a pale yellow gum.LCMS: retention time 1.38 min ; [M+H]+ = 314.02 (1 Br)

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

Reference£º
Patent; GLAXO GROUP LIMITED; SMETHURST, Christian, Alan, Paul; DEMONT, Emmanuel, Hubert; LIN, Xichen; REN, Feng; BAILEY, James, Matthew; WO2010/145202; (2010); 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.82771-60-6,7-Chloro-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,82771-60-6

To a mixture of 7-chloro- l,2,3,4-tetrahydroisoquinoline (200 mg, 1.19 mmol), 5-bromo-2- pyrimidin-2-yl-pyrimidine (226 mg, 954 muiotaetaomicron, the product of step 3 in Example 1) and CS2CO3 (1.94 g, 5.97 mmol) in dioxane (15 mL) was added Brettphos Pd G3 (216 mg, 239 muiotaetaomicron, CAS registry number: 1470372-59-8). The resulting mixture was heated at 120 C with stirring for 48 hrs under N2 and filtered. The filtrate was concentrated in vacuo. The residue was purified by prep-HPLC to give 7-chloro-2-(2-pyrimidin-2-ylpyrimidin-5-yl)-3,4-dihydro- lH-isoquinoline (0436) (26 mg) as light yellow solid. XH NMR (400 MHz, Methanol-^) delta ppm: 8.87-8.99 (m, 2H), 8.55- 8.70 (m, 2H), 7.45-7.59 (m, IH), 7.25-7.38 (m, IH), 7.21 (s, 2H), 4.62 (s, 2H), 3.76 (t, 2H), 3.02 (s, 2H). MS obsd. (ESI+) [(M+H)+] : 324

The synthetic route of 82771-60-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

151838-62-9, 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of Boc-Tic-OH (0.33 g, 1.20 mmol) and 2TFAH2N-CH[(CH2)4-NH- Z]-Bid [benzyl 5-amino-5-(lH-benzo[151838-62-9, As the paragraph descriping shows that 151838-62-9 is playing an increasingly important role.

Reference£º
Patent; GOVERNMENT OF THE UNITED STATES OF AMERICA, represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; WO2008/16913; (2008); 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.57196-62-0,6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.,57196-62-0

To a solution of 5-bromo-3-methyi- 1 -(p-toiyl)- 1H-pyrazoie- 4-carbonitrile (Intermediate Ii, 600 mg, 2.173 rnmol) in DM50 (20 ml) was added6-methoxy-i,2,3,4-teirahvdroisoquinoline hydrochloride (434 mg, 2.173 mmoi), Cs2CO3 (1416 mg, 4.35 rnmol) and Cul (414 ing. 2.173 inmol). The mixture was stirred at 140C for 18 h. The mixture was diluted with water (2×20 mL) and extracted with EtOAc (2 x 50 mL). The combined organic layers were dried over NaSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromalography (PE:EtOAc=50 :1 to 30:1) to yieldthe title compound.

57196-62-0 6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 2920335, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; ADAMS, Gregory, L.; COX, Jason, M.; DEBENHAM, John, S.; EDMONDSON, Scott; GILBERT, Eric, J.; GUO, Yan; JIANG, Yu; JOSIEN, Hubert; KIM, Hyunjin, M.; LAN, Ping; MIAO, Shouwu; PLUMMER, Christopher, W.; RAJAGOPALAN, Murali; SHAH, Unmesh; SUN, Zhongxiang; TRUONG, Quang, T.; UJJAINWALLA, Feroze; VELAZQUEZ, Francisco; VENKATRAMAN, Srikanth; SUZUKI, Takao; WANG, Nengxue; (182 pag.)WO2017/205193; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

170097-67-3,170097-67-3, 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 9: 1 ,1-dimethylethyl 6-({ri-({5-chloro-2-r(2-methylpropyl)oxylphenyl}methyl)-5- ethyl-I H-pyrazol-S-yliaminolcarbonvD-S^-dihydro^d l-D-isoquinolinecarboxylate; To a solution of 1-({5-chloro-2-[(2-methylpropyl)oxy]phenyl}methyl)-5-ethyl-1 H-pyrazol-3- amine (Intermediate 7) (0.5 g, 1.62 mmol) in DMF (1 OmL) was added 2-{[(1 ,1- dimethylethyOoxylcarbonylJ-I ^.S^-tetrahydro-theta-isoquinolinecarboxylic acid (0.41 g, 0.9 eq.), HATU (0.74 g, 1.2 eq.) and DIEA (0.34 ml_,1.2 eq.) and the mixture was stirred at room temperature for 24 hours. The solvent was evaporated under reduced pressure and the residue was diluted with DCM. The organic phase was then washed with water and dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM/EtOAc: 95/5 to give the title compound as an oil (120 mg, 13%). LC/MS: m/z 567 (M+H)+ Rt: 4.23 min.

170097-67-3,2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acidbelongs to tetrahydroisoquinoline compound, is more and more widely used in various fields. and we look forward to future research findings.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/74834; (2008); A2;,
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

0.5 g of 6-methoxy-1,2,3,4-tetrahydroisoquinoline was loaded in 20 mL of DMF in a flask in nitrogen atmosphere, followed by stifling. 1.1 g of cesiumcarbonate was added thereto at room temperature. 30 minutes later, 1.0 g of (S)-ethyl 3-(4-(4-(2-(methylsulfonyloxy)ethyl)benzyloxy)phenyl)hex-4-inoate prepared in Manufacturing Example 16 was added thereto, followed by stirring at room temperature for 12 hours. Upon completion of the reaction, distilled water was slowly added thereto, followed by extraction using ethylacetate. The extract was washed with brine, dried over anhydrous MgSO4, and concentrated. Then, silica gel column chromatography was performed to give the target compound. (0493) 1H NMR (400 MHz, CDCl3): delta 7.35 (2H, d), 7.30 (2H, d), 7.23 (2H, d), 7.00 (1H, d), 6.85 (2H, d), 6.80 (1H, d), 6.70 (1H, d), 5.00 (2H, s), 4.30 (2H, m), 4.13 (2H, m) 4.03 (1H, t), 3.80 (3H, s), 3.58 (6H, m), 3.30 (2H, s), 2.78 (2H, m), 1.86 (3H, d), 1.28 (3H, m).

The synthetic route of 42923-77-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; HYUNDAI PHARM CO., LTD; Yang, Jin; Kim, Jin Woong; Lee, Han Kyu; Kim, Jae Hyun; Son, Chang Mo; Lee, kyu hwan; Choi, Hyung-Ho; Kim, daehoon; Ha, Tae-Young; Rhee, Jaekeol; (62 pag.)US2016/24063; (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.42923-77-3,6-Methoxy-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,42923-77-3

A solution of 35% formaldehyde (2.49 g, 0.034 mol) was added dropwise to 2-(3-methoxyphenyl)ethanamine (5g, 0.033 mol). The warm solution soon deposited an oil and the reaction was completed by heating the mixture for one hour at 100 C. The oil was extracted with toluene (25 ml) and washed with water (3 x 18 ml). The extract was dried over Na2SO4 and the solvent was concentrated to yield a yellow oil. A solution of 20% hydrochloric acid (6 ml) was added to the crude and the mixture was stirred at 100 C for 1 hour. After the evaporation to dryness, the residue was dissolved in a little water, made alkaline with concentrated potassium hydroxide, extracted with dichloromethane (3 x 90 ml) and dried over Na2SO4. After the evaporation of the solvent, the oil was dissolved in ethyl acetate and concentrated hydrochloric acid was added to form the hydrochloride, which was filtered to yield a white solid identified as 6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (5.1 g, 80 % yield). 1H NMR (300 MHz, CHLOROFORM-D) delta ppm 2.80 (t, J=6.01 Hz, 2 H) 3.14 (t, J=6.01 Hz, 2 H) 3.78 (s, 3 H) 3.97 (s, 2 H) 6.63 (d, J=2.50 Hz, 1 H) 6.71 (dd, J=8.42, 2.56 Hz, 1 H) 6.93 (d, J=8.42 Hz, 1H) MS (APCI (M+H)+): 164

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; LABORATORIOS DEL DR. ESTEVE, S.A.; EP1676844; (2006); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem