Tag: 170097-67-3

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.

29a 6-(Methoxy-methyl-carbamoyl)-3,4-dihydro-1/-/-isoquinoline-2-carboxylic acid te/f-butyl esterTo 2.00 g (7.21 mmol) 3,4-dihydro-1 /-/-isoquinoline-2,6-dicarboxylic acid 2-te/f-butyl ester in 70 mL MeOH is added at RT 844 mg (8.65 mmol) O,lambda/-dimethyl-hydroxylamine and 1.59 mL (14.4 mmol) 4-methyl-morpholine. The mixture is stirred at RT and then 2.10 g (7.57 mmol) 4- (4,6-dimethoxy-1 ,3,5-triazin-2-yl)-4-methyl-morpholin-4-ium chloride hydrate is added and the mixture is stirred overnight at RT. The residue is directly purified via reverse HPLC chromatography (Waters XBridge, C18; water (0.3 % NH4OH)/acetonitrile (0.3 % NH4OH) 90:10 to 10:90). Yield: 2.30 g (100% of theory) ESI Mass spectrum: [M+H]+ = 321Retention time HPLC: 1.7 min (method K).

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/22979; (2008); 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

Intermediate 94: 1.1-dimethylethyl 6-r({1-r(3.4-dichlorophenyl)methyll-5-methyl-1 H-1.2.3- triazol-4-yl}amino)carbonyl1-3,4-dihvdro-2(1 H)-isoquinolinecarboxylate; A mixture of 1-[(3,4-dichlorophenyl)methyl]-5-methyl-1 H-1 ,2,3-triazol-4-amine (Intermediate 69) (0.1g, 0.39mmol), 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6- isoquinolinecarboxylic acid (0.1 1g, 0.37mmol), HATU (0.19g, O.deltammol) and DIPEA (88mul_, O.deltammol) in DMF (5mL) was stirred at room temperature overnight. The mixture was evaporated. The residue was washed with water and extracted with DCM. The organic phase was dried over Na2SO4, filtered and concentrated. The title compound was obtained as a white solid after purification by flash column chromatography eluting with DCM/MeOH: 98//2 and crystallisation from isopropyl ether (86mg, 43 %). HRMS calculated for C25H27CI2N5O3 (M+H)+ 516.1569, found: 516.1591 , Rt: 3.13 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; WO2009/16216; (2009); 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

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.

#N/A

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

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.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.

#N/A

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

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.

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).

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

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

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.

Intermediate 6: 1 ,1-Dimethylethyl 6-({ri-({5-chloro-2-r(cvclopropylmethyl)oxyl phenyllmethyl)- 5-methyl-1 /-/-pyrazol-3-yl1amino}carbonyl)-3,4-dihvdro-2(1 H)-isoquinolinecarboxylateTo a solution of 2-{[(1 ,1-dimethylethyl)oxy]carbonyl}-1 ,2,3,4-tetrahydro-6- isoquinolinecarboxylic acid (200 mg, 0.72 mmol), N-(3-dimethylaminopropyl)-N’- ethylcarbodiimide hydrochloride (158 mg, 0.82 mmol), 1-hydroxybenzotriazole hydrate (1 11 mg, 0.82 mmol) and diisopropylethylamine (1 15 mg, 0.89 mmol) in DCM (15 ml.) was added Intermediate 4 (200 mg, 0.69 mmol) and the mixture was stirred at room temperature for 4 days. The organic phase was then washed with HCI (1 N), NaOH (1 N) and brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM/EtOAc: 90/10 to give the title compound as yellow oil (316 mg, 84%). LC/MS: m/z 551 (M+H)+, Rt: 4.15 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; WO2009/10560; (2009); 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

Example 16 Preparation of intermediate 6-bromomethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (D-1) To a solution of 3,4-dihydro-1H-isoquinoline-2,6-dicarboxylic acid 2-tert-butyl ester (12.50 g, 45.08 mmol) in dry THF (125.0 mL), under nitrogen at 25 C., is added via syringe borane THF complex (99.17 mL, 99.17 mmol) The mixture is stirred at 25 C. for 16 h then water (10.0 mL) is slowly added followed by 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 1M HCl, dried over MgSO4, and concentrated under reduced pressure to afford an oil. The oil is purified by silica gel chromatography to yield D-1-1 (11.8 g, 99.3% yield), as a white solid. To a solution of alcohol, D-1-1, (9.50 g, 36.1 mmol) and N,N-diisopropylethylamine (9.43 mL, 54.1 mmol) in dichloromethane (200.0 mL) is added triphenylphosphine dibromide (23.79 g, 54.11 mmol) at 0 C. The reaction is stirred for 1 h then concentrated under reduced pressure. The resulting residue is purified by silica gel chromatography to yield D-1 (8.74 g, 74% yield), as a white solid.

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

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

Example 24: 1 ,1-Dimethylethyl 6-r({1-r(3,4-dichlorophenyl)methvH-1 /-/-pyrazol-4- yl}amino)carbonyll-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-[(3,4- dichlorophenyl)methyl]-1 H-pyrazol-4-amine (Intermediate 7) (120 mg, 0.5 mmol) and the reaction mixture was stirred at room temperature overnight. The organic phase was then washed with a 1 N sodium hydroxide solution, with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM/MeOH: 95/5 to give the title compound as a white solid (190 mg, 77%) after recrystallization from CH3CN. LC/MS: m/z 501 (M+H)+, Rt: 3.65 min.

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

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