164148-92-9| Page 4 of 4 | Heterocyclic Building Blocks-Isoquinoline

Downstream synthetic route of 164148-92-9

164148-92-9, 164148-92-9 tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate 2756371, aisoquinoline compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.164148-92-9,tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.

Step 2: Synthesis of tert-butyl 6-((1-(2-(tert-butyl)pyrimidin-4-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate To a stirred solution of 1-(2-(tert-butyl)pyrimidin-4-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (176 mg, 0.49 mmol, 1.0 eq.) in 3 mL of toluene was added m-CPBA (169 mg, 0.98 mmol, 2 eq.) and allowed to stir at rt for 1 h. Further, tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (146 mg, 0.58 mmol, 1.2 eq.) and DIPEA (0.33 mL, 1.96 mmol, 4 eq.) were added and allowed to stir at rt for overnight. After completion of reaction, solvent was removed under reduced pressure; residue was diluted with water and extracted with ethyl acetate (50 mL*3). The combined organic layer was washed with brine solution (10 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford crude product which was purified by flash chromatography to afford tert-butyl 6-((1-(2-(tert-butyl)pyrimidin-4-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate (120 mg, 43.74%) as yellow solid.

164148-92-9, 164148-92-9 tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate 2756371, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

Brief introduction of 164148-92-9

164148-92-9, As the paragraph descriping shows that 164148-92-9 is playing an increasingly important role.

Intermediate 91 : 1 ,1-Dimethylethyl 6-ralphai-r(3.4-dichlorophenyl)methyll-1 H-1 ,2,3-triazol-4- yl}carbonyl)amino1-3,4-dihvdro-2(1 /-/)-isoquinolinecarboxylate; A mixture of 1-[(3,4-dichlorophenyl)methyl]-1 H-1,2,3-triazole-4-carboxylic acid (Intermediate 65) (0.1g, 0.37mmol), 1 ,1-dimethylethyl 6-amino-3,4-dihydro-2(1 H)-isoquinolinecarboxylate (91 mg, 0.37mmol), HATU (0.182g, 0.48mmol) and DIPEA (83muL, 0.48mmol) in DMF (5mL) was stirred at room temperature overnight. The mixture was evaporated and the residue was washed with water (2OmL) and extracted with DCM (2OmL). The organic phase was dried over Na2SO4, filtered and concentrated to give the title compound as a brown oil (1 18mg, 64%).LC/MS: m/z 500 (M-H)+, Rt: 3.80 min.

164148-92-9, As the paragraph descriping shows that 164148-92-9 is playing an increasingly important role.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/16216; (2009); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

Analyzing the synthesis route of 164148-92-9

164148-92-9, As the paragraph descriping shows that 164148-92-9 is playing an increasingly important role.

164148-92-9, tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

First 1,2,3,4- tetrahydroisoquinolin-6-amine bis hydrochloride was prepared from tert-butyl 6-amino-3,4- dihydroisoquinoline-2(1H)-carboxylate. A suspension of tert-butyl 6-amino-3,4- dihydroisoquinoline-2(1H)-carboxylate (200 mg, 0.81 mmol) in HCl (2 mL, 4 M, in dioxane, 8 mmol) was stirred at room temperature for 15 h. The mixture was concentrated and residual HCl removed by co-evaporation ethyl acetate (2 ¡Á 4 mL) to provide 1,2,3,4-tetrahydroisoquinolin-6- amine bis-hydrochloride as a pale yellow solid (176 mg, 99%) and used without further purification.

164148-92-9, As the paragraph descriping shows that 164148-92-9 is playing an increasingly important role.

Reference£º
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; BURNETTE, Pearlie; LAWRENCE, Harshani; LAWRENCE, Nicholas J.; (285 pag.)WO2017/161119; (2017); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

Simple exploration of 164148-92-9

164148-92-9, The synthetic route of 164148-92-9 has been constantly updated, and we look forward to future research findings.

To a dichloromethane (10 mL) solution of 4-nitrophenyl chloroformate (812 mg), a dichloromethane (10 mL) solution of 6-amino-2N-Boc-1,2,3,4-tetrahydroisoquinoline (1.00 g) and pyridine (0.33 mL) was gradually added at 0C. The reaction mixture was stirred at 0C for 1 hour and at room temperature for 2 hours and then concentrated. The residue was vigorously stirred in a mixed solution of diisopropyl ether and water (diisopropyl ether/water). The precipitate was collected by filtration and dried under reduced pressure to obtain the title compound (1.46 g, 88%) as a yellow solid. 1H NMR (400 MHz, CDCl3): delta (ppm) = 8.40-8.24 (3H, m), 7.50-6.99 (4H, m), 5.33 (1H, brs), 4.67-4.49 (2H, m), 4.67-4.49 (2H, m), 2.97-2.79 (2H, m), 1.50 (9H, s).

164148-92-9, The synthetic route of 164148-92-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Daiichi Sankyo Company, Limited; EP2256105; (2010); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

Some tips on 164148-92-9

164148-92-9, The synthetic route of 164148-92-9 has been constantly updated, and we look forward to future research findings.

164148-92-9, tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step-2: Synthesis of tert-butyl 7-((1-(2-(tert-butyl)pyridin-4-yl)-2-cyclopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate To a stirred solution of 1-(2-(tert-butyl)pyridin-4-yl)-2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (196 mg, 0.548 mmol, 1.0 eq) in (6.0 mL) of toluene was added m-CPBA (189 mg, 1.096 mmol, 2.0 eq) and allowed to stir at rt for 1 h. tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (163 mg, 0.657 mmol, 1.2 eq) and DIPEA (0.37 mL, 2.192 mmol, 4.0 eq) were added and allowed to stir at rt for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography [silica gel 100-200 mesh; elution 0-50% EtOAc in hexane] to afford the desired compound, tert-butyl 7-((1-(2-(tert-butyl)pyridin-4-yl)-2-cyclopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate (100 mg, 32.63%) as an off white solid.

164148-92-9, The synthetic route of 164148-92-9 has been constantly updated, and we look forward to future research findings.

Downstream synthetic route of 164148-92-9

164148-92-9, 164148-92-9 tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate 2756371, aisoquinoline compound, is more and more widely used in various.

Step-3: Synthesis of tert-butyl 6-((2-cyclopropyl-1-(6-(2-fluoropropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate To a stirred solution of 1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (260 mg, 0.722 mmol, 1.0 eq) in (5.0 mL) of toluene was added m-CPBA (249 mg, 1.444 mmol, 2.0 eq) and allowed to stir at rt for 30 minutes. tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (358 mg, 1.444 mmol, 2.0 eq) and DIPEA (0.5 mL, 2.888 mmol, 4.0 eq) were added and allowed to stir at rt for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography [silica gel 100-200 mesh; elution 0-50% EtOAc in hexane] to afford the desired compound, tert-butyl 6-((2-cyclopropyl-1-(6-(2-fluoropropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate (100 mg, 24.75%) as an off white solid.

164148-92-9, 164148-92-9 tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate 2756371, aisoquinoline compound, is more and more widely used in various.