Category: tetrahydroisoquinoline

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO126,mainly used in chemical industry, its synthesis route is as follows.,42923-79-5

To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline (33.1) (4 g, 22.44 mmol) in THF (100 mL) was added TEA (2.27 g, 22.45 mmol) and tert-butoxycarbonyl tert-butyl carbonate (5.4 g, 24.74 mmol) . The reaction mixture was stirred at room temperature for 2h. TLC showed the reaction was complete. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (DCM) to afford tert-butyl 7-nitro-3,4-dihydroisoquinoline-2(1H)-carboxylate (33.2) as a yellow liquid (4.4 g, 70.4%). [00535] LCMS: 279.1 [M+1]+. [00536] 1HNMR (400 MHz, CDCl3): delta 1.50 (s, 9H), 2.93 (t, 2H), 3.69 (t, 2H), 4.66 (s, 2H), 7.29 (t, 1H), 8.03-8.02 (m, 2H).

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

Reference£º
Patent; CELGENE AVILOMICS RESEARCH, INC.; SCHWARTZ, C., Eric; SURAPANENI, Sekhar, S.; WORM, Karin Irmgard; (266 pag.)WO2016/90079; (2016); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

Example 285A ethyl 4-(6-methoxy-3,4-dihydroisoquinolin-2(1H)-yl)benzoate The desired product was prepared by subtituting 6-methoxy-1,2,3,4-tetrahydroisoquinoline (prepared according to the procedure described in U.S. Pat. No. 1,845,403) for 1,4-dioxa-8-azasprio(4,5)decane in Example 158A. MS (DCI) m/e 312 (M+H)+.

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

Reference£º
Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/86887; (2002); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride, cas is 877861-62-6, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

877861-62-6, To a solution of 6-methoxycarbonyl-l ,2,3,4-tetrahydroisoquinoline hydrochloride (34.2 mg, 0.15 mmol) and triethylamine (83.6 muL, 0.6 mmol) in N,N-dimethylformamide (1 mL, 13 mmol) and water (25 muL, 1.39 mmol) was added benzyl bromide (16 muL, 0.135 mmol). The reaction was allowed to stir overnight at room temperature. The solvent was removed in vacuo and the residue obtained was partitioned between DCE (3 x 5 mL) and saturated aqueous sodium bicarbonate (5 mL). The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. LCMS confirmed formation of intermediate [(FA) ES+282].

As the rapid development of chemical substances, we look forward to future research findings about 877861-62-6

Reference£º
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BLACKBURN, Christopher; CIAVARRI, Jeffrey; GIGSTAD, Kenneth; XU, He; WO2010/151318; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

Intermediate 13: 1 ,1-Dimethylethyl 6-({ri-(1-naphthalenylmethyl)-1 /-/-pyrazol-4- vHamino)carbonyl)-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-(1- naphthalenylmethyl)-1 H-pyrazol-4-amine (11 1 mg, 0.5 mmol) and the reaction mixture was stirred at room temperature overnight. The organic phase was diluted with an additional volume of DCM then washed with a saturated sodium hydrogeno carbonate solution, with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM/MeOH: 97/3 to give the title compound as an orange oil (180 mg, 81%). LC/MS: m/z 483 (M+H)+, Rt: 3.53 min.

With the complex challenges of chemical substances, we look forward to future research findings about 170097-67-3,belong tetrahydroisoquinoline compound

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

67123-97-1, 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,67123-97-1

A solution of chiral monomer 5 [(R)- and (R)-1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid] (4.27 g, 20 mmol) in methanol (20 mL) was cooled to 0 C, and added drop wise with 5.2 mL thionyl chloride. The reaction mixture was stirred for overnight at ambient temperature. The solvent was removed by rotary evaporator under vacuum to give compound 6 (5.29 g), yield: 94.4%. 1H NMR (300 MHz, D2O, r.t.) delta 7.45-7.24 (m, 4H), 4.60 (d, J = 5.5 Hz, 1H), 4.56 (d, J = 5.4 Hz, 1H), 4.53 (br s, 1H), 3.93 (s, 3H), 3.53 (dd, J = 17.4, 5.5 Hz, 1H), 3.53 (dd, J = 17.4, 5.5 Hz, 1H), 3.32 (dd, J = 17.3, 10.9 Hz, 1H), 3.32 (dd, J = 17.3, 10.9 Hz, 1H). HR ESIMS: m/z 192.1028 [M + H]+ (calcd. 192.1025).

The synthetic route of 67123-97-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Liang, Chuanpeng; Hao, Huilin; Wu, Xingkang; Li, Zhenyu; Zhu, Jing; Lu, Chunhua; Shen, Yuemao; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 272 – 282;,
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

A mixture of4-chloro-benzo[4,5]furo[3 ,2-d]pyrimidine (1.06 g, 5.19 mmol), 6-bromo- 1,2,3,4-tetrahydroisoquinoline (1.0 g, 4.7 mmol), potassium carbonate (1.95 g, 14.1 mmol) and sodium iodide (0.71 g, 4.7 mmol) in dioxane (50 mL) was heated at 90 C for 6 hrs. The mixture was diluted with EtOAc and washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by recrystallization with EtOAc to give 4-(6- bromo-3 ,4-dihydroisoquinolin-2( 1H)-yl)benzofuro[3 ,2-d]pyrimidine (1.2 g, 3.16 mmol,66.9 % yield). LCMS (M+H): 379.90, 381.90.

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

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 6-bromo-l,2,3,4-tetrahydroisoquinoline (2 g, 9.43 mmol), Boc20 (2.26 g, 2.41 mL, 10.4 mmol) and Et3N (1.91 g, 2.63 mL, 18.9 mmol) in THF (30 mL) was stirred at rt. For 3 hrs. The resulting mixture was diluted with aqueous Na2C03 solution and extracted with EA (30 mL) twice. The combined organic layer was washed with brine, dried over aqueous Na2S04, filtered, and concentrated in vacuo to afford tert-butyl 6-bromo-3,4-dihydro-lH- isoquinoline-2-carboxylate (2.9 g) as white solid which was directly used in the next step without any further purification, 226942-29-6

The synthetic route of 226942-29-6 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

7-Bromo-1,2,3,4-tetrahydroisoquinoline, cas is 17680-55-6, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.,17680-55-6

EXAMPLE 251; 4- [7-(3 -aminophenyl)-3 ,4-dihydroisoquinolin-2( 1 H)-yI] – 1 -hydroxy- 1 , 8-naphthyridin-2( 1 H)-one; Stepl : l-(benzyloxy)-4-(7-bromo-3,4-dihydroisoquinolin-2(lH)-yl)-l,8-naphthyridin-2(l)-one; l-(benzyloxy)-2-oxo-l,2-dihydro-l,8-naphthyridin-4-yltrifluoromethanesulfonate (Example 2, Stepl: 500 mg, 1.249mmol) and 7-bromo-l,2,3,4-tetrahydroisoquinoline (1007 mg, 4.75 mmol) in DMF (10 ml) was heated at 110 C and stirred for 90 minutes. The crude mixture was dissolved in DCM and purified by SGC (30-100 % EtOAc-hexanes) to give the title compound. MS: m/z = 462.3 (M), 464.3 (M+2).

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Bromo-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; MERCK & CO., INC.; WO2008/10964; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belong tetrahydroisoquinoline compound,7-Nitro-1,2,3,4-tetrahydroisoquinoline,42923-79-5,Molecular formula: C9H10N2O2,mainly used in chemical industry, its synthesis route is as follows.,42923-79-5

A solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline (33.1) (200 mg, 1.12 mmol) and cyclobutanone (118 mg, 1.68 mmol) in methanol (15 mL) was stirred at ambient temperature for 2 h. NaBH3CN (141 mg, 2.24 mmol) was added, and the mixture was stirred at ambient temperature for 20 min. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated to afford the crude product. The crude product was purified by column chromatography (DCM/methanol: 10/1) to afford 2-cyclobutyl-7-nitro-1,2,3,4- tetrahydroisoquinoline (46.1) as a yellow oil (170 mg, 65%). [00668] LCMS: 233.1[M+1]+.

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; CELGENE AVILOMICS RESEARCH, INC.; SCHWARTZ, C., Eric; SURAPANENI, Sekhar, S.; WORM, Karin Irmgard; (266 pag.)WO2016/90079; (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.226942-29-6,6-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

Step A: Preparation of l-(6-Bromo-3,4-dihydroisoquinolin-2(lH)-yl)-2- hydroxyethanone. A magnetically stirred flask equipped with a drying tube was charged with a solution of6-bromo-l,2,3,4-tetrahydroisoquinoline (3.43 g, 16.2 mmol) in anhydrous toluene (40 mL), to which was added 2,2-dimethyl-l,3-dioxolan-4-one (1.9 g, 16.2 mmol). The resulting solution was refluxed for 20 h. The reaction mixture was cooled, extracted with 1 N HCl (30 mL), followed by brine (20 mL), and the organic extract was dried over MgSO4. The resulting solution was reduced in volume to about 25 mL, and heptane (25 mL) was gradually added over 20 min as precipitate formed. The resulting white solid was collected by filtration and rinsed with 1 : 1 toluene/heptane to provide the title compound. LCMS m/z = 270.1 [M+H]+; 1H NMR (400 MHz, CDCl3) delta 2.48 (bs, IH), 2.87-2.94 (m, 2H), 3.55 (t, J= 5.9 Hz, 1.2H), 3.89 (t, J= 6.1 Hz, 0.8H), 4.26 (s, 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), 7.32-7.39 (m, 2H).

226942-29-6, 226942-29-6 6-Bromo-1,2,3,4-tetrahydroisoquinoline 15885183, atetrahydroisoquinoline compound, is more and more widely used in various fields.

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