Heterocyclic Building Blocks-Tetrahydroisoquinoline

7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride, cas is 99365-69-2, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

99365-69-2, 1) Production of 2-(7-nitro-3,4-dihydroisoquinolin-2(1H)-yl)ethanol: An acetonitrile solution (30 mL) of 3 g of the compound obtained in Production Example 22-1), 2.3 g of 2-chloroethanol and 3.9 g of potassium carbonate was stirred at 100¡ãC for 15 hours. The reaction liquid was cooled, diluted with chloroform and washed with saturated saline water. The organic layer was washed with saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting crude product was purified through basic silica gel column chromatography (hexane/ethyl acetate) and further through silica gel column chromatography (hexane/ethyl acetate) to obtain 1.5 g of the entitled compound as a colorless solid. 1H-NMR (CDCl3) delta: 8.00 (1H, dd, J=8.5, 2.2 Hz), 7.93 (1H, d, J=2.2 Hz), 7.28-7.25 (1H, m), 3.78 (2H, s), 3.74 (2H, t, J=5.5 Hz), 3.00 (2H, t, J=5.9 Hz), 2.86 (2H, t, J=5.9 Hz), 2.76 (2H, t, J=5.5 Hz) ESI-MS Found: m/z [M+H] 223

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

Reference£º
Patent; Banyu Pharmaceutical Co., Ltd.; EP2168966; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belong tetrahydroisoquinoline compound,2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid,151838-62-9,Molecular formula: C15H19NO4,mainly used in chemical industry, its synthesis route is as follows.,151838-62-9

Example 23 A. Podophyllotoxin-4-O-ester of N-BOC-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid [000302] ; The mixture of podophyllotoxin (20 mg, 0.048 mmol), N-BOC-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (22 mg, 0.07 mmol), EDCI (25 mg, 0.13 mmol), DMAP (2 mg, 0.02 mmol) and dichloromethane (3 ml) were stirred in the room temperature for 20 h, then dichloromethane (20 ml) was added to the solution. Organic layer was washed with water (20 ml), saturated NaHCO3 aqueous solution (10 ml) and brine (20 ml), and then dried over MgSO4. After the solvent was removed under reduced pressure, the resulting liquid was separated by column chromatography (eluent: ethyl acetate and petroleum ether) to afford 15 mgPodophyllotoxin-4-O-ester of N-BOC-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid. [0242] The chemical structure analysis was performed by 1HNMR (CDCl3, 600 MHz):

With the synthetic route has been constantly updated, we look forward to future research findings about 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid,belong tetrahydroisoquinoline compound

Reference£º
Patent; Yang, Li-Xi; US2005/4169; (2005); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 166591-85-1, its synthesis route is as follows.,166591-85-1

2,3-Dihydro-1H-inden-2-amine (0.240 g, 1.803 mmol) was added to a solution of 2-{tert- butoxycarbonyl)-l,2,3,4-tetrahydroisoquinoline-l-carboxylic acid (0.S g, 1.803 mmol) in DCM (10 mL) then EDC.HC1 (0.519 g, 2.70 mmol), HOAT (0.446 g, 2.70 mmol) and TEA (0.627 mL, S.41 mmol) were added under nitrogen. The reaction was stirred at room temperature for 18 h. The reaction mixture was washed with water, IN HCI, and sat. NaHCCh, dried (MgS04) and concentrated in vacuo to afford the title compound. (0870) ‘H NMR (400 MHz, DMSO-d6) delta ppm 1.28 – 1.51 (m, 9 H) 2.58 – 3.26 (m, 6 H) 3.46 – 3.63 (m, 1 H) 3.74 – 3.93 (m, 1 H) 4.28 – 4.47 (m, 1 H) 5.20 (s, 1 H) 7.05 – 7.30 (m, 7 H) 7.36 – 7.51 (m, l H) 8.57 (m, 1 H) (0871) MS ES+: 293 (M-BOC)

With the complex challenges of chemical substances, we look forward to future research findings about 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; LIWICKI, Gemma; MACK, Stephen; STEPHENSON, Anne; TEALL, Martin; WHITE, Kathryn; (168 pag.)WO2018/47983; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

As a common heterocyclic compound, it belong tetrahydroisoquinoline compound,2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,170097-67-3,Molecular formula: C15H19NO4,mainly used in chemical industry, its synthesis route is as follows.,170097-67-3

A mixture of 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid (0.40 g, 1.4 mmol), and NMM (0.238 mL, 2.16 mmol) in THF (14.4 mL) was treated with IBCF (0.227 mL, 1.73 mmol) ) at 0 C, and the reaction mixture was stirred for 5 minutes. A solution of NaBH4 (0.218 g, 5.77 mmol) dissolved in 5 mL of water was then added portionwise. The reaction mixture was allowed to warm to rt and was stirred for 2 h. The reaction mixture was quenched with saturated aq. ammonium chloride, and extracted 3x with EtOAc. The chombined extracts were washed with brine, dried with Na2SO4, filtered and concentrated to yield 1A as a yellow oil which was used in the next step without further purification. MS (ESI) m/z 263.9 (M+H) 207.9 (M-tBu).

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; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne M.; HU, Carol Hui; VALENTE, Meriah Neissel; SHAW, Scott A.; VOKITS, Benjamin P.; HALPERN, Oz Scott; (137 pag.)WO2017/160632; (2017); A1;,
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,22990-19-8

(10 mmol) of 3,4-dimethoxyphenethylamine (1.1 mmol) and DIPEA (2.2 mmol) was slowly added to a THF solution (10 ml) of triphosgene (0.44 mmol) And stirred for 30-45 minutes. Then, a solution of 1-phenyl-1,2,3,4-tetrahydroisoquinoline (1.1 mmol) in THF (10 ml) was added and stirred overnight. The salt was filtered, and the filtrate was evaporated and column chromatography (EA: Hexane) was carried out to obtain the title compound.

The synthetic route of 22990-19-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CHUNGNAM NATIONAL UNIVERSITY INDUSTRY & ACADEMIC COOPERATION (IAC); JUNG, SANG HUN; WOO, SUN HEE; KIM, SANG KYUM; JEON, EUN SEOK; LEE, YOU JUNG; MANICKAM, MANOJ; JALANI HITESHKUMAR, HITESHKUMAR; SHARMA, NITI; (234 pag.)KR2015/111825; (2015); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

42923-79-5,7-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.

Step A: 2-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline 7-Nitro-1,2,3,4-tetrahydroisoquinoline (4.15 g, 23.3 mmol) was combined with paraformaldehyde (3.7 g, 116 mmol), HOAc (6.7 mL, 116 mmol), sodium cyanoborohydride (7.3 g, 116 mmol) in DCE (300 mL) and heated at reflux for 15 h. The reaction was cooled and quenched by stirring with saturated aqueous NaHCO3. The organic layer was dried with MgSO4. The solvent was removed under vacuum and the crude oil was purified by silica gel flash column chromatography (40-100% EtOAc/hexanes). Purification yielded 3.0 g (67%) of the title compound as an oil. 1H NMR (400 MHz, DMSO-d6) delta 8.14 (s, 1H), 8.09 (dd, J=8.5, 2.4 Hz, 1H), 7.52 (d, J=8.2 Hz, 1H), 4.22 (s, 2H), 3.29-3.23 (m, 2H), 3.16-3.08 (m, 2H), 2.67 (s, 3H).

42923-79-5 is used more and more widely, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; Uehling, David Edward; Hubbard, Robert Dale; Waterson, Alex Gregory; Petrov, Kimberly; Bifulco, JR., Neil; Wilson, Joseph Wendell; Badiang, Jennifer Gabriel; Cheung, Mui; Yamabe, Mariko; US2009/149456; (2009); 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: C8H14ClNO65,mainly used in chemical industry, its synthesis route is as follows.,42923-79-5

A mixture of 1,2,3,4-Tetrahydro-7-nitroisoquinoline (2.5 g, 11.6 mmol), 1,4-dioxane (24 mL), H2O (12 mL) and 1N NaOH (12 mL) was cooled in an ice-bath, and Boc2O (2.8 g, 12.8 mmol) was added. The mixture was stirred at room temperature for 2.5 h, acidified with a 5% KHSO4 solution to pH 2-3, and then extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give tert-butyl 3,4-dihydro-7-nitroisoquinoline-2(1H)-carboxylate (3.3 g, quant.), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) delta 8.13 (d, J=2.3 Hz, 1H), 8.03 (dd, J=8.4, 2.5 Hz, 1H), 7.45 (d, J=8.5 Hz, 1H), 4.63 (s, 2H), 3.60-3.57 (m, 2H), 2.90 (t, J=5.9 Hz, 2H), 1.44 (s, 9H); HPLC ret. time 3.51 min, 10-99% CH3CN, 5 min run; ESI-MS 279.2 m/z (MH+).

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; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); 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: C8H14ClNO433,mainly used in chemical industry, its synthesis route is as follows.,42923-77-3

EXAMPLE 88 5-(3,4-Dimethoxybenzylamino)-2-(2-furyl)-8-(6-methoxy-1,2,3,4-tetrahydroisoquinolin-2-ylmethyl)[1,2,4]triazolo[1,5-c]pyrimidine (Compound 88) The subject compound (94%) was obtained as a pale brown oily matter from 5-(3,4-dimethoxybenzylamino)-8-formyl-2-(2-furyl)[1,2,4]triazolo[1,5-c]pyrimidine and 6-methoxy-1,2,3,4-tetrahydroisoquinoline in a manner similar to that in Example 1. 1H NMR (CDCl3, delta, ppm): 2.85-2.89 (m, 4H), 3.72 (s, 2H), 3.77 (s, 3H), 3.88 (s, 3H), 3.88 (s, 3H), 3.99 (s, 2H), 4.76 (d, J=5.6 Hz, 2H), 6.41 (t, J=5.6 Hz, 1H), 6.56 (dd, J=1.7, 3.4 Hz, 1H), 6.63-6.70 (m, 2H), 6.85 (d, J=8.0 Hz, 1H), 6.90-6.94 (m, 1H), 6.96 (s, 1H), 6.97 (d, J=8.0 Hz, 1H), 7.22 (d, J=3.4 Hz, 1H), 7.60 (d, J=1.7 Hz, 1H), 8.01 (s, 1H)

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

Reference£º
Patent; Uesaka, Noriaki; Imma, Hironori; Kashima, Hajime; Kurokawa, Masako; Nonaka, Hiromi; Kanda, Tomoyuki; Kuwana, Yoshihisa; Toki, Shinichiro; Shimada, Junichi; US2004/110826; (2004); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

1-Phenyl-1,2,3,4-tetrahydroisoquinoline, cas is 22990-19-8, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

EXAMPLE 1 Preparation of phenyl 1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate (II) A solution of racemic 1-phenyl-1,2,3,4-tetrahydro-isoquinoline (100 mg, 0.48 mmols) in tetrahydrofuran (500 mul) is added with diphenyl carbonate (102.36 mg, 0.48 mmols) and dimethylaminopyridine in catalytic amount and refluxed. After completion of the reaction, the solvent is evaporated off under reduced pressure and the product is isolated by flash chromatography. The title product is obtained as a yellow oil in 75% yield. 1-H-NMR (400 MHz, CDCl3) delta 2.85-2.94 (1H, m), 3.10-3.21 (1H, m), 3.35-3.56 (1H, br s), 4.22-4.31 (1H, m), 6.54-6.59 (1H, s), 7.09-7.44 (15H, m)., 22990-19-8

22990-19-8 is used more and more widely, we look forward to future research findings about 1-Phenyl-1,2,3,4-tetrahydroisoquinoline

Reference£º
Patent; Dipharma Francis S.r.l.; US2009/203915; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

75416-51-2, 8-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Boc2O (25.73 g, 117.88 mmol) was added dropwise to a solution of intermediate 21 (25.00 g, 117.88 mmol) and TEA (32.83 mL, 236.00 mmol) in DCM (300 mL) at 0 ¡ãC. The resulting mixture was stirred at room temperature for 30 minutes. Sat. citric acid was added to quench the reaction and layers were separated. The organic layer was washed with brine, dried over Mg504, filtered and evaporated in vacuo. The crude residue was purified by silica gel column (mobile phase: Petroleum ether/EtOAc, 3/1, v/v) to give 35 g of intermediate 22 (95percent yield)., 75416-51-2

75416-51-2 8-Bromo-1,2,3,4-tetrahydroisoquinoline 12630420, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; PILATTE, Isabelle, Noelle, Constance; QUEROLLE, Olivier, Alexis, Georges; ANGIBAUD, Patrick, Rene; BERTHELOT, Didier, Jean-Claude; COUPA, Sophie; DEMESTRE, Christophe, Gabriel, Marcel; MEERPOEL, Lieven; MERCEY, Guillaume, Jean, Maurice; MEVELLEC, Laurence, Anne; MEYER, Christophe; PASQUIER, Elisabeth, Therese, Jeanne; PONCELET, Virginie, Sophie; (104 pag.)WO2017/216293; (2017); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem