Downstream synthetic route of 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

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

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

Analyzing the synthesis route of 170097-67-3

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

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

Step 3: lambda/-({2-r(trifluoromethvnoxylphenyl}methylV1 ,2.3.4-tetrahvdro-6- isoquinolinecarboxamide; To a solution of aforementioned carboxylic acid (0.20 g, 0.72 mmol) in DMF (5 ml.) was added DMAP (24.0 mg, 0.22 mmol) followed by 2-(trifluoromethoxy)benzylamine (108 DL, 0.79 mmol) and EDCI (138 mg, 0.72 mmol). After stirring overnight, the reaction was poured into H2O (10 ml.) and extracted with EtOAc (2×10 ml_). The organics were dried (Na2SO4) and evacuated. The crude material was redissolved in CH2CI2 (2 ml.) and treated with TFA (2 ml_). After stirring for 30 minutes, the reaction was diluted with CH2CI2 (15 ml.) and poured into ice cold 1 N NaOH (20 ml_). The organics were extracted, dried (Na2SO4), and evacuated to afford the title compound (0.15 g, 59%), which was used without further purification. MS (ES+) m/e 335.0 [M+1]+

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; SMITHKLINE BEECHAM CORPORATION; WO2009/49154; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Some tips on 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

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

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

A solution of 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6- isoquinolinecarboxylic acid (296 mg, 1.07 mmol), HATU (406 mg, 1.07 mmol), DIPEA (0.41 ml_, 2.36 mmol ) and ethyl 2-amino-4-methyl-1 ,3-thiazole-5-carboxylate (199 mg, 1.07 mmol) in DMF (5 ml.) was stirred at 500C for 6 hours. The volatiles were removed under reduced pressure and the residue was dissolved in ethyl acetate. The organic phase was then washed with dilute HCI, with a solution of sodium bicarbonate, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was dissolved in a mixture of ethanol (1.5 ml.) and water (2 ml.) and sodium hydroxide was added (86 mg, 2.15 mmol) and the reaction mixture was heated at 500C for 4 hours. The reaction was then cooled, acidified with dilute HCI and the aqueous phase was extracted with ethyl acetate. The combined extracts were dried over MgSO4, filtered and evaporated under reduced pressure. The residue obtained was used directly in the next step without further purification.

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; WO2009/150196; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

The important role of 170097-67-3

With the complex challenges of chemical substances, we look forward to future research findings about 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

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

General procedure: To a solution of 15 6 (60mg, 0.2mmol) in 57 CH2Cl2 (4mL) were added EDCI (58mg, 0.3mmol) and 16 DMAP (4 mg, 0.03mmol). The solution was stirred at room temperature for 0.5h and compound 715 (97mg, 0.18mmol) was added. The resulting mixture was stirred for another 8h and 58 water was added. The layers were separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated under vacuo. The residue was prified by chromatography (CH2Cl2/CH3OH 40:1) to provide 17 8 as white solid (108mg, 73%).

With the complex challenges of chemical substances, we look forward to future research findings about 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

Reference£º
Article; Liu, Xiaohua; Zhang, Yu; Huang, Wenjing; Tan, Wenfu; Zhang, Ao; Bioorganic and Medicinal Chemistry; vol. 26; 2; (2018); p. 443 – 454;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Analyzing the synthesis route of 170097-67-3

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

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

Application of 170097-67-3

170097-67-3, As the rapid development of chemical substances, we look forward to future research findings about 170097-67-3

A common heterocyclic compound, the tetrahydroisoquinoline compound, name is 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid,cas is 170097-67-3, mainly used in chemical industry, its synthesis route is as follows.

Preparation of intermediate 6-bromomethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (4-19) Compound 4-17 (12.50 g, 45.08 mmol) is dissolved in dry THF (125.0 mL) under nitrogen at 25 C. Borane THF complex (99.17 mL, 99.17 mmol) is added via syringe and the mixture is stirred at 25 C. for 16 h. Water (10.0 mL) is slowly added and then 2.0 M Na2CO3 (15.0 mL). This mixture is stirred for 15 min and then is diluted with EtOAc and the organic layers are collected. The organics are rinsed with 1.0 M HCl, dried over MgSO4, and concentrated in vacuo to afford an oil. The oil is purified by silica gel chromatography using a gradient of 10-80% EtOAc in heptane to yield the desired product, 4-18 (11.78 g), as a white solid.

170097-67-3, As the rapid development of chemical substances, we look forward to future research findings about 170097-67-3

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BRENNEMAN, Jehrod Burnett; GINN, John; LOWE, Michael D.; SARKO, Christopher Ronald; TASBER, Edward S.; ZHANG, Zhonghua; US2014/73629; (2014); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Simple exploration of 170097-67-3

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

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,170097-67-3

General procedure: To a solution of corresponding acids (1.0mmol) in DCM (6mL) was added EDCI (1.5mmol), HOBt (1.5mmol), Et3N (3.0mmol) and corresponding amines (1.0mmol). The mixture was stirred at room temperature for 4h. The reaction mixture was diluted with saturated sodium bicarbonate aqueous solution (10mL) and extracted with DCM (3¡Á10mL). The combined organic layers were then dried and concentrated. The residue was purified by silica gel chromatography (dichloromethane/methanol, v/v, 90:10) to give the desired product.

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

Reference£º
Article; Shao, Jingwei; Zhu, Kongkai; Du, Daohai; Zhang, Yuanyuan; Tao, Hongrui; Chen, Zhifeng; Jiang, Hualiang; Chen, Kaixian; Luo, Cheng; Duan, Wenhu; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 317 – 333;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Simple exploration of 170097-67-3

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

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,170097-67-3

To a solution of 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6- isoquinolinecarboxylic acid (33 mg, 0.12 mmol), HOBt (19 mg, 0.14 mmol), EDCI (26 mg, 0.14 mmol) and triethylamine (14 mg, 14 mmol) in DCM (3 ml.) was added 4-[(3- nitrophenyl)methyl]-1 ,3-thiazol-2-amine (30 mg, 0.12 mmol) and the resulting mixture was stirred at room temperature for 2 days. The organic phase was washed successively with water, with a 1 N solution of sodium hydroxide, with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM / MeOH: 98 / 2 to give the title compound as a pale yellow oil (30 mg, 52%). LC/MS: m/z 495 (M+H)+, Rt : 3.68 min.

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

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/150196; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Extracurricular laboratory: Synthetic route of 170097-67-3

170097-67-3, As the rapid development of chemical substances, we look forward to future research findings about 170097-67-3

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

To a solution of 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6- isoquinolinecarboxylic acid (0.1 1 g, 0.4 mmol), HOBt (55 mg, 0.4 mmol), EDCI (77 mg, 0.4 mmol) and triethylamine (140 mul, 1 mmol) in DCM (5 ml.) was added 2-[(4- chlorophenyl)methyl]-4-methyl-1 ,3-thiazol-5-amine hydrochloride (80 mg, 0.33 mmol) and the resulting mixture was stirred at room temperature for 5 days. The organic phase was washed successively with a 1 N solution of hydrochloric acid, with a 1 N solution of sodium hydroxide, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM / EtOAc: 8 / 2 to give the title compound as a yellow oil (25 mg, 15%). LC/MS: m/z 498 (M+H)+, Rt : 3.83 min.

170097-67-3, As the rapid development of chemical substances, we look forward to future research findings about 170097-67-3

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/150196; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Some tips on 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

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

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