Heterocyclic Building Blocks-Tetrahydroisoquinoline

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.

EXAMPLE 14 STR20 2-(2-chloropropionyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline By procedures described in Example 1 (Method A), phenethylamine and benzoyl chloride were converted to 1-phenyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.0 g of this isoquinoline compound, 5 ml 10% sodium hydroxide and 50 ml methylene chloride. With this mixture stirred, 1 ml 2-chloropropionyl chloride was added dropwise to the mixture. The mixture was stirred for 10 minutes, then water was added. The organic extract was dried with magnesium sulfate, stripped of solvent and subjected to Kugelrohr distillation (170 C. a 0.1 mm Hg) to provide 2.3 g of a viscous yellow oil product having the elemental analysis reported in Table I.

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

Reference£º
Patent; Monsanto Company; US4755218; (1988); 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.877861-62-6,Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride,as a common compound, the synthetic route is as follows.

Methyl 1 ,2,3,4-tetrahydro-6-isoquinolinecarboxylate hydrochloride (3.071 g, 13.5mmol), BOC-anhydride (4.42g, 20.3mmol) and triethylamine (3.76ml, 27.0mol) were stirred in DCM (70ml) under argon for 18 hours, evaporated to dryness, redissolved in ethyl acetate, washed with saturated sodium bicarbonate twice, once with brine and dried (MgSO4). The organic solution was filtered, evaporated to a solid and purified by flash chromatography using ethyl acetate and hexane to yield the title compound (3.6g) LC/MS Rt = 3.24min [MH+] 236

The synthetic route of 877861-62-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2006/114313; (2006); 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.170097-67-3,2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,as a common compound, the synthetic route is as follows.

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).

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.; 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

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.

General procedure: A mixture of the required 1,2,3,4-tetrahydroisoquinoline derivative (1 equivalent), NaHCO3 (2 equivalents), and the appropriate substituted nitroaryl derivative or 2-chloro-3,5-dinitropyridine (1 equivalent) was heated at reflux in a mixture of ethanol : water (2:1) with stirring (15 hours). After cooling to room temperature, the ethanol was evaporated and the residue was poured onto ice yielding a solid. The solid was collected and dried in a vacuum desiccator over P2O5 giving the crude N-(nitroaryl)-1,2,3,4-tetrahydroisoquinoline derivative or 1,2,3,4-tetrahydro-2-(3,5-dinitropyridin-2-yl)isoquinoline 12.

The synthetic route of 42923-79-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Burke, Philip J.; Chun Wong, Lai; Jenkins, Terence C.; Knox, Richard J.; Stanforth, Stephen P.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 24; (2011); p. 7447 – 7450;,
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

General procedure: 1007511 To a mixture of Compound 61F (250 mg, 0.5 mmol) and Cs2CO3 (326 mg, 1 mmol) in DMF (20 mL) was added Mel (142 mg, 1 mmol) and stirred at 60 C for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 50% v/v) to afford Compound 63A. LC-MS (ESI) m/z: 518 [M+H]t

The synthetic route of 226942-29-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
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 2- {4- [2-AMINO-3- (4- FLUOROPHENYL)-PROPIONYL]-3-CYCLOPROPYLMETHYL-2-OXO-PIPERAZIN-1-YL}-N-METHYL-3-NAPHTHALEN-2-YL- propionamide, 18, (44 mg, 0. 068 MMOL) in DMF (1 mL) are added 3, 4-DIHYDRO-1H-ISOQUINOLINE- 2, 3-dicarboxylic acid 2-tert-butyl ester (21 mg, 0.079 MMOL), 1-HYDROXYBENZO-TRIAZOLE (20 mg, 0,148 mmol), N-methylmorpholine (41 mg, 0.41 MMOL) and 1- (3-DIMETHYLAMINO-PROPYL)-3- ETHYLCARBODIIMIDE (16 mg, 0.083 mmol) consecutively. The reaction mixture is stirred for 3 hours, quenched with aqueous NH4CI and extracted several times with ethyl acetate. The combined extracts are dried over NA2SO4, filtered and concentrated in vacuo to a residue, which is purified over silica gel (CH2CI2/CH30H, 13: 1) to afford the desired product.

151838-62-9 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 2735649, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; THE PROCTER & GAMBLE COMPANY; WO2004/37797; (2004); 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.170097-67-3,2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,as a common compound, the synthetic route is as follows.

To a flask charged with ethanol (180 mL), cooled to 0 C, is added 4.0 mL (56 mmol) of acetyl chloride. The mixture is stirred at 0 C. for 30 min then 5.00 g (18.0 mmol) of 3,4-dihydro-1H-isoquinoline-2,6-dicarboxylic acid 2-tert-butyl ester is added. The mixture is heated to 70 C. and stirred for 2 days. The mixture is cooled to room temperature and filtered through diatomaceous earth. The filtrate is concentrated under reduced pressure to provide D-13-1 (3.47 g, 79.6%) as a white powder.

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Reference£º
Patent; Boehringer Ingelheim International GmbH; BRENNEMAN, Jehrod Burnett; GINN, John David; HOPKINS, Tamara Denise; LOWE, MIchael D.; SARKO, Christopher Ronald; WESTBROOK, John A.; YU, Maolin; ZHANG, Zhonghua; (233 pag.)US2016/24059; (2016); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

A solution of 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6- isoquinolinecarboxylic acid (0.68 g, 2.45 mmol), HATU (1 g, 2.64 mmol), DIPEA (0.76 ml_, 4.4 mmol ) and 5-[(4-chlorophenyl)methyl]-1 ,3-thiazol-2-amine (0.5 g, 2.2 mmol) in DMF (5 ml.) was stirred at room temperature for one week. The volatiles were removed under reduced pressure and the residue was dissolved in dichloromethane. The organic phase was then washed with water, with a 1 N NaOH solution, dried over Na2SO4, filtered and evaporated under reduced pressure. The solid was triturated with acetonitrile and recrystallised from methanol/dichloromethane to give the title compound as a white solid (0.67 g, 63%). LC/MS: m/z 484 (M+H)+, Rt : 3.86 min.

The synthetic route of 170097-67-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/150196; (2009); 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

A solution of 6-methoxy- 1,2,3 ,4-tetrahydroisoquinoline (200 mg, 1.23 mmol) in HBr (3.16 g, 47% wt. in H20, 18.4 mmol) was stirred at 100 C overnight. After the reaction wascompleted, the mixture was concentrated in vacuo and triturated with EtOAc. The mixture wasfiltered and the solid was collected and dried in vacuo to give 1,2,3,4-tetrahydroisoquinolin-6- ol;hydrobromide (170 mg, 93%) as a brown solid. MS obsd. (ESIj [(M+H)]: 150.

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; LIANG, Chungen; LIU, Yongfu; TAN, Xuefei; WU, Jun; WANG, Jianping; (134 pag.)WO2020/79106; (2020); 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.

General procedure: To a solution of bromoacetyl chloride (1.40g, 8.17mmol) in10mL of dry THF cooled at 0C, under argon atmosphere, was added dropwise, under vigorous stirring, a solution of the appropriate amine (5.45mmol) and triethylamine (0.276g, 2.72mmol) in dry THF (10mL). After 30min at 0 and 30min at room temperature the reaction mixture was quenched by the addition of 50ml of H2O and extracted with dichloromethane (3¡Á50ml). The combined organic extracts were washed with saturated NaHCO3 and brine, and then dried over anhydrous Na2SO4. Evaporation under reduced pressure gave the crude 3-bromopropanamide derivatives (1-3) which were purified by flash chromatography on silica gel, using CH2Cl2 and cyclohexane as eluent.

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

Reference£º
Article; Ronsisvalle, Simone; Arico, Giuseppina; Panarello, Federica; Spadaro, Angelo; Pasquinucci, Lorella; Pappalardo, Maria S.; Parenti, Carmela; Ronsisvalle, Nicole; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5280 – 5290;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem