Month: November 2020

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

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).

42923-77-3 is used more and more widely, we look forward to future research findings about 6-Methoxy-1,2,3,4-tetrahydroisoquinoline

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

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

33537-99-4, To a solution of 6-chloro-1 ,2,3,4-tetrahydroisoquinoline (18.5 g, 0.1 1 mol) in CH3CN (180 mL) was added compound 2,3-dimethyl-1 -((2-methyl-1 H-imidazol-1 -yl)sulfonyl)- 1 H-imidazol-3-ium trifluoromethanesulfonate (43.5 g, 0.1 1 mol, Reference: J. Org. Chem. 2002, 68, 1 15-1 19.). The reaction mixture was stirred overnight at 30 C. The solvent was removed and the residue was purified by column chromatography on silica gel (0400) (EtOAc/Petroleum ether = 1 :1 ) to provide 6-chloro-2-(2-methyl-1 /-/-imidazol-1 -ylsulfonyl)- 1 ,2,3,4-tetrahydroisoquinoline. 1 H NMR (400 MHz, CDCI3): d 7.21 (m, 1 H), 7.18 (s, 1 H), 7.02 (m, 1 H), 6.94 (m, 1 H), 4.45 (s, 2H), 3.62 (m, 2H), 2.92 (m, 2H), 2.67 (s, 3H).

33537-99-4 is used more and more widely, we look forward to future research findings about 6-Chloro-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; KEZAR LIFE SCIENCES; JOHNSON, Henry; (166 pag.)WO2019/178510; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

General procedure: Synthesis of intermediate 7: Intermediate 5 (2.45 g, 15 mmol) and ethyl 6-bromopyridine-2-carboxylate (2.30 g, 10 mmol) were synthesized as above and purified by column chromatography ( petroleum ether: acetic acid Ethyl ester = 8:1) to give a white oily intermediate 7 (2.34 g, 75%)

42923-77-3 is used more and more widely, we look forward to future research findings about 6-Methoxy-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; Sun Yat-sen University; Gu Qiong; Xu Jun; Fang Yuying; (20 pag.)CN109879856; (2019); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belong tetrahydroisoquinoline compound,6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,215798-19-9,Molecular formula: C9H11BrClN,mainly used in chemical industry, its synthesis route is as follows.,215798-19-9

As an alternative procedure to that contained within Description 1, a solution of 6-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (6.0 g, 24 mmol) and triethylamine (7.4 ml, 5.36 g, 53 mmol) in dichloromethane (100 ml) was treated with trifluoroacetic anhydride (3.7 ml, 5.54 g, 26.4 mmol) with ice cooling. Mixture was stirred at 20[deg.] C. for 1.5 h. then partitioned between saturated aqueous NaHCO3 (250 ml) and dichloromethane (3*50 ml). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give a solid (8.3 g). A mixture of the latter with copper (I) cyanide (5.1 g, 56.6 mmol) in 1-methyl-2-pyrrolidinone (100 ml) was heated at reflux under argon for 4 h, then cooled and partitioned between water (300 ml), 0.880 aqueous ammonia (100 ml) and dichloromethane (5*200 ml). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give an oil. The latter was dissolved in ether and treated with ethereal HCl to give the title compound (4.47 g, 85%) as a colourless solid. [0130] Mass spectrum (API<+>): Found 159 (MH<+>). C10H10N2 requires 158.

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,belong tetrahydroisoquinoline compound

Reference£º
Patent; SmithKline Beecham, p.l.c.; US2003/191314; (2003); 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

To a mixture of 6-bromo-l,2,3,4-tetrahydro-isoquinoline (10.60 g, 50 mmol) and t- butyl bromoacetate (9.95 g, 51 mmol, 1.02 eq.) in aceto?itrile (100 ml) are added sodium carbonate (10.6 g, 100 mmol, 2.0 eq.) and NaI ( 375 mg, 2.5 mmol, 0.05 eq.). The resulting mixture is stirred at rt for 16 hr. Water (100 ml) is added to quench the reaction, and the acetonitrile is evaporated. The residue is extracted with EtOAc (100 ml x 3), and the combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by silica gel flash chromatography (EtOAc/hexane, 1 :4) to give the title compound.MS (+VE) m/z 326.10 (M++l).

215798-19-9 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride 22570216, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; NEUROGEN CORPORATION; WO2007/106349; (2007); A2;,
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: C8H14ClNO265,mainly used in chemical industry, its synthesis route is as follows.,170097-67-3

HATU (213 mg, 0.56 mmol) was added to a mixture of (R)-3-amino-N-(3-(cyclopropylmethyl)-7-fluoro-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl)piperidine-1-carboxamide (180 mg, 0.43 mmol), 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid (126 mg, 0.45 mmol) and DIEA (150 muL, 0.86 mmol) in DMF (2.2 mL) at room temperature, and the mixture was stirred at room temperature for 15 hr. To the reaction mixture was added water, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 79?100% ethyl acetate/hexane) to give the title compound (262.6 mg, 0.388 mmol, 90%) as a white amorphous solid. 1H NMR (300 MHz, CDCl3):delta 0.41-0.49(4H,m), 1.28-1.34(1H,m), 1.49(9H,s), 1.60(6H,d,J=7.2 Hz), 1.65-2.02(4H,m), 2.88(2H,t,J=5.7 Hz), 3.49-3.68(5H,m), 3.75-3.83(1H,m), 3.94(2H,d,J=7.2 Hz), 4.13-4.19(1H,m), 4.59(2H,s), 4.93(1H,brs), 6.70-6.75(2H,m), 7.08(1H,d,J=12.8 Hz), 7.18(1H,d,J=8.7 Hz), 7.56-7.62(2H,m), 8.60(1H,d,J=8.7 Hz).

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; 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

It is a common heterocyclic compound, the tetrahydroisoquinoline compound, 6-Bromo-1,2,3,4-tetrahydroisoquinoline, cas is 226942-29-6 its synthesis route is as follows.,226942-29-6

A mixture of paraformaldehyde (350 mg, 3.63 mmol, 2.20 equiv) in methanol (1.00 mL) was stirred at 60 C for 1 h and then cooled to 40 C. To the mixture was added AcOH (1 drop) and 6-bromo-l, 2, 3, 4-tetrahydroisoquinoline (350 mg, 1.65 mmol, 1.00 equiv) followed by NaCNBH3 (114 mg, 1.82 mmol, 1.1 equiv). The mixture was stirred at 40C for 1 h and was subsequently filtered and concentrated in vacuo to give a residue. The residue was purified by prep-TLC (petroleum ether/ethyl acetate = 2/1) to afford 6-bromo-2-methyl-3, 4-dihydro -1 H- isoquinoline (360 mg, 1.59 mmol, 96.5% yield) as a yellow oil. 1H NMR (400MHz, CD3OD) d = 7.32 (s, 1H), 7.28 (dd, =2.0, 8.4 Hz, 1H), 7.00 (d, =8.0 Hz, 1H), 3.57 (s, 2H), 2.94 (t, =6.0 Hz, 2H), 2.75 – 2.72 (m, 2H), 2.46 (s, 3H).

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; MIRATI THERAPEUTICS, INC; MARX, Matthew, Arnold; LEE, Matthew, Randolph; BOBINSKI, Thomas, P.; BURNS, Aaron, Craig; ARORA, Nidhi; CHRISTENSEN, James, Gail; KETCHAM, John, Nichael; (225 pag.)WO2019/152419; (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.42923-79-5,7-Nitro-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,42923-79-5

Into a 25 mL round-bottom flask was placed a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline (200 mg, 1.12 mmol) in dichloromethane (10 mL) followed by di-tert-butyl dicarbonate (489 mg, 2.24 mmol) and triethylamine (339 mg, 3.35 mmol). The reaction mixture was stirred overnight at room temperature then concentrated under vacuum. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1 :10). The collected fractions were combined and concentrated under vacuum to yield tert-butyl 7-nitro-3,4-dihydroisoquinoline-2(1H)-carboxylate (290 mg, 93%).

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; LYCERA CORPORATION; AICHER, Thomas Daniel; SKALITZKY, Donald J.; TOOGOOD, Peter L.; VANHUIS, Chad A.; (416 pag.)WO2019/200120; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride, cas is 57196-62-0, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.,57196-62-0

To an ice bath cooled mixture of 6-methoxy-1,2, 3, 4-tetrahydroisoquinoline hydrochloride salt from part a) (23 g, 115.2 [MMOL)] and triethylamine (48 mL) in dichloromethane (400 mL) was added [TRIFLUOROACETIC] anhydride (19.5 mL). The solution was stirred for 1 hour at room temperature before quenching with saturated sodium bicarbonate. The organic layer was removed, dried [(MGS04)] and purified by chromatography on silica eluting with 10% EtOAc/Hexane up to 30% EtOAc/Hexane yielding the title compound D16 as a clear oil (7.75 [G).] MH+ 260.’H NMR [8] (CDCI3) 2.88-2. 98 (2H, t), 3.74-3. 90 (5H, m), 4.63-4. 75 (2H, d), 6.65-6. 84 (2H, m), 7.01-7. 10 (1H, m).

57196-62-0 is used more and more widely, we look forward to future research findings about 6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reference£º
Patent; GLAXO GROUP LIMITED; WO2003/99786; (2003); A2;,
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 1.4.4 (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 diluted with ethyl acetate (500 mL), washed with water and brine, and dried over Na2SO4. After filtration and evaporation of the solvent, the crude material was purified via silica gel column chromatography, eluting with 20% ethyl acetate in hexane, 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.; Ackler, Scott L.; Bennett, Nathan B.; Boghaert, Erwin R.; Cullen, Steve C.; Doherty, George; Frey, Robin R.; Haight, Anthony R.; Judd, Andrew S.; Kunzer, Aaron R.; Shen, Xiaoqiang; Song, Xiaohong; Souers, Andrew J.; Sullivan, Gerard M.; Tao, Zhi-Fu; Wang, Xilu; Welch, Dennie S.; Wendt, Michael D.; (210 pag.)US2016/158377; (2016); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem