Category: 164148-92-9

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

To a mixture of 3-bromo-2-methylbiphenyl (Example 2, Step 1: 30 mg, 0.1 mmol), palladium acetate (2.7 mg, 0.012 mmol), (R)-(+)-2,2?-bis(diphenylphosphino)-1,1?-binaphthyl (7.6 mg, 0.012 mmol), and cesium carbonate (120 mg, 0.37 mmol) in 1,4-dioxane was added tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (Oakwood cat011348: 33 mg, 0.13 mmol) under N2. The reaction mixture was stirred at 120 C. overnight. The crude reaction mixture was cooled to room temperature, diluted with ethyl acetate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-20%) to afford the desired product. LC-MS calculated for C27H31N2O2 (M+H)+: m/z 415.2; found: 415.2.

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; Incyte Corporation; Wu, Liangxing; Qian, Ding-Quan; Lu, Liang; Lajkiewicz, Neil; Konkol, Leah C.; Li, Zhenwu; Zhang, Fenglei; Li, Jingwei; Wang, Haisheng; Xu, Meizhong; Xiao, Kaijiong; Yao, Wenqing; (101 pag.)US2018/177784; (2018); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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

ferf-Butyl 6-amino-3,4-dihydroisoquinoline-2(1 H)-carboxylate (0.500 g, 2.01 mmol), methyl 2-(2-(2-(2-(methylsulfonyl)-5-(trifluoromethyl)pyrimidin-4- yl)ethyl)phenyl)acetate (166) (0.675 g, 1.68 mmol), trifluoroethanol (3 mL), and TFA (0.3 mL) were loaded into a microwave tube, sonicated for two minutes, then heated under microwave irradiation at 100 C for 20 minutes. The cooled mixture was concentrated, co-evaporated with toluene (3x 20 mL) and loaded onto a 10 g SCX cartridge in methanol. The cartridge was eluted with methanol (200 mL), then with 1 % methanolic methylamine (200 mL). The methanolic methylamine eluent was concentrated to give a brown oil (0.850 g). The oil was dissolved in DCM (5 mL), and Boc anhydride (549 mg, 2.52 mmol) was added. The resulting mixture was stirred under an oil bubbler for 18 hours, then diluted with DCM (50 mL) and washed with water (50 mL). The aqueous layer was extracted with DCM (2x 50 mL), and the combined DCM phases dried (phase separation filter) and evaporated.Chromatography (Isolera, 40 g silica cartridge, 0-50% ethyl acetate/petroleum benzine 40-60 C) gave the title compound (180) (520 mg, 54%) as a yellow syrup; 1H NMR (400 MHz, CDCI3) delta 8.54 (s, 1 H), 7.45 (s, 2H), 7.38 (s, 1 H), 7.28 – 7.18 (m, overlaps with CDC ), 7.10 (d, J = 8.5 Hz, 1 H), 4.56 (s, 2H), 3.75 (s, 2H), 3.70 – 3.62 (m, 5H), 3.17 – 3.03 (m, 4H), 2.85 (t, J = 5.6 Hz, 2H), 1.50 (s, 9H). LCMS Method C: H 6.93 min; m/z 571 .1 {M+H] +, m/z 515.0 [M+tBu+2H] +.

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

Reference£º
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; HOLMES, Ian, Peter; BERGMAN, Ylva; LUNNISS, Gillian Elizabeth; NIKAC, Marica; CHOI, Neil; HEMLEY, Catherine Fae; WALKER, Scott Raymond; FOITZIK, Richard Charles; GANAME, Danny; LESSENE, Romina; WO2012/110773; (2012); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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.

A toluene solution of 6-amino-2N-Boc-1,2,3,4-tetrahydroisoquinoline (248 mg), 2-chlorobenzothiazole (186 mg), palladium acetate (22 mg), cesium carbonate (651 mg), and Xanphos (58 mg) was stirred at 120C for 1 hour under microwave irradiation. The reaction solution was purified by column chromatography to obtain the title compound (381 mg, quantitative yield). 1H NMR (400 MHz, CDCl3) : delta (ppm) = 7.77 (1H, d, J = 8.2 Hz), 7.69 (1H, d, J = 7.8 Hz), 7.40-7.29 (3H, m), 7.25-7.19 (2H, m), 4.69 (2H, s), 3.70 (2H, t, J = 5.3 Hz), 2.90 (2H, t, J = 5.7 Hz), 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

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

Preparation of intermediate 235 was performed via 2 reactions as reported below.Reaction 1: N-bromosuccinimide (716 mg; 4.03 mmol) was added portionwise at 0C to a solution of t-Butyl-6-amino-3,4-dihydroisoquinoline-2-carboxylate (1 g; 4.03 mmol) inDCM (20 mL). The reactiocn mixture was stirred at room temperature for 2 hours, poured onto a 10% aqueous solution of K2C03 and extracted with DCM.Reaction 2: N-bromosuccinimide (2.08 g; 11.68 mmol) was added portionwise at 0C to a solution of t-Butyl-6-amino-3,4-dihydroisoquinoline-2-carboxylate (2.9 g; 11.68 mmol) inC (60 mL). The reaction mixture was stirred at room temperature for 2 hours, poured onto a 10% aqueous solution of K2C03 and extracted with DCM.The two residues were combined and purified by chromatography over silica gel (irregular SiOH, 80g; mobile phase: gradient from 20% EtOAc, 80% heptane to 40% EtOAc, 60%hetptane). The pure fractions were collected and evaporated to dryness yielding 2.8 g (54%) of intermediate 235.

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; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (419 pag.)WO2018/2219; (2018); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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-3: Synthesis of tert-butyl 6-((1-(2-(2-fluoropropan-2-yl)pyridin-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-(2-fluoropropan-2-yl)pyridin-4-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (150 mg, 0.415 mmol, 1.0 eq) in (5 mL) of toluene was added m-CPBA (143.4 mg, 0.830 mmol, 2.0 eq) and allowed to stir at rt for 30 min. tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (123 mg, 0.498 mmol, 1.2 eq) and DIPEA (0.3 mL, 1.662 mmol, 4.0 eq) were added and allowed to stir at 80 C. for overnight. Solvent was evaporated and reaction mass was diluted with water and extracted with EtOAc (30 mL*2). The combined organic layer were dried over sodium sulphate, concentrated under reduced pressure purified by column chromatography (Combiflash, elution-0-70% EtOAc in Hexane) to afford the desired compound, tert-butyl 6-((1-(2-(2-fluoropropan-2-yl)pyridin-4-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate (52 mg, 22.30%) as yellow liquid.

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

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

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

To a solution of (2S,5R)-6-(phenylmethoxy)-7-oxo-l,6-diazabicyclo[3.2.1]octane- 2-carboxylic acid (53.3 mg, 0.193 ramol) in dry dichloromethane (2 mL) was added triethylamine (0.067 mL, 0.482 mmol), 2-chloro-l-methylpyridinium iodide (58.7 mg, 0.230 mmol), and 6-amino-2-N-BOC-ls23>4-tetrahydro-isoqumoline (54.8 mg, 0.221 mmol) sequentially at room temperature under nitrogen. The reaction mixture was then heated to 500C for 45 minutes then the reaction product was concentrated in vacuo. Attempts to dissolve the reaction product in eluant (2:1:1 CH3CN/DMSO/water) for HPLC were unsuccessful, so it was partitioned between aqueous layer and dichloromethane. The organic layer was collected, dried over sodium sulfate, concentrated in vacuo and set aside for separate purfcation. The aqueous layer was also collected and purified by HPLC (30X100 mm Waters Sunfire column; 5 micron; 35 mL/min.; 210 nM; 15% to 100% CH3CN + 0.05% TFA / water + 0.05% TFA over 15 minutes; the title compound eluted at 80% CH3CN + 0.05% TFA / water + 0.05% TFA).Fractions containing the title compound were lyophilized overnight to afford the title compound as a white sticky solid. The organic layer from partitioning the crude product was purified by preparative TLC (1000 micron silica gel plate eluted with 50% ethyl acetate/hexane) to afford the title compound. Both batches of the title compound were combined and used without further purification in the next step.

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; MERCK & CO., INC.; WO2009/91856; (2009); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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

Intermediate 34: 1 ,1-Dimethylethyl 6-r(1 H-pyrazol-4-ylcarbonyl)aminol-3,4-dihvdro- 2(1 HVisoalphauinolinecarboxylate; To a solution of 1 H-pyrazole-4-carboxylic acid (800 mg, 7.1 mmol), N-(3- dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (1.48 g, 7.74 mmol), 1- hydroxybenzotriazole hydrate (1.04 g, 7.74 mmol) and triethylamine (1.8 ml_, 12.9 mmol) in DCM was added 1 , 1 -dimethylethyl 6-amino-3,4-dihydro-2(1 /-/)- isoquinolinecarboxylate (1.6 g, 6.45 mmol) and the reaction mixture was stirred at room temperature for 9 days. The organic phase was washed with 1 N sodium hydroxide, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM/MeOH: 90/10 to give the title compound as a solid (580 mg, 24%). LC/MS: m/z 341 (M-H)+, Rt: 2.70 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; WO2008/74824; (2008); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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-1: Synthesis of tert-butyl 6-((1-(2-(2-hydroxypropan-2-yl)pyridin-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-(2-hydroxypropan-2-yl)pyridin-4-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (200 mg, 0.5571 mmol, 1.0 eq) in (3.0 mL) of toluene was added m-CPBA (270 mg, 1.1142 mmol, 2.0 eq) and allowed to stir at rt for 1 h. tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (166 mg, 0.6685 mmol, 1.2 eq) and DIPEA (0.4 mL, 2.2284 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-((1-(2-(2-hydroxypropan-2-yl)pyridin-4-yl)-2-isopropyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate (110 mg, 35.32%) 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.

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

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.

fe/f-Butyl 6-amino-3,4-dihydroisoquinoline-2(1 H)-carboxylate (0.500 g, 2.01 mmol), methyl 2-(2-(2-(2-(methylsulfonyl)-5-(trifiuoromethyl)pyrimidin-4- yi)ethyi)phenyl)acetate (166) (0.675 g, 1.68 mmol), trifiuoroethanol (3 mL), and TFA (0.3 mL) were loaded into a microwave tube, sonicated for two minutes, then heated under microwave irradiation at 100 C for 20 minutes. The cooled mixture was concentrated, co-evaporated with toluene (3x 20 mL) and loaded onto a 10 g SCX cartridge in methanol. The cartridge was eluted with methanol (200 mL), then with 1 % methanolic methyiamine (200 mL). The methanolic methylamine eluent was concentrated to give a brown oil (0.850 g). The oil was dissolved in DCM (5 mL), and Boc anhydride (549 mg, 2.52 mmoi) was added. The resulting mixture was stirred under an oil bubbler for 18 hours, then diluted with DCM (50 mL) and washed with water (50 mL). The aqueous layer was extracted with DCM (2x 50 mL), and the combined DCM phases dried (phase separation filter) and evaporated. Chromatography (isoiera, 40 g silica cartridge, 0-50% ethyl acetate/petroleum benzine 40-80 C) gave the title compound (/SO) (520 mg, 54%) as a yellow syrup; 1H NMR (400 MHz, CDCI3) delta 8.54 (s, 1 H), 7.45 (s, 2H), 7.38 (s, 1 H), 7.28 – 7.18 (m, overlaps with CDCI3), 7.10 (d, J = 8.5 Hz, 1 H), 4.56 (s, 2H), 3.75 (s, 2H), 3.70 – 3.62 (m, 5H), 3.17 – 3.03 (m, 4H), 2.85 (t, J = 5.6 Hz, 2H), 1.50 (s, 9H). LCMS Method C: rt 6.93 min; m/z 571.1 [M+H] +, m/z 515.0 [M+tBu+2H] +.

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

Reference£º
Patent; CANCER THERAPEUTICS CRC PTY LTD; DEVLIN, Mark Graeme; STREET, Ian Philip; TONG, Warwick Bonner; WO2014/27199; (2014); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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

A tetrahydrofuran (20 mL) solution of 5-fluoro-2-methoxybenzoic acid (1.00 g), DPPA (1.25 mL), and triethylamine (1.6 mL) was heated to reflux for 1 hour. A tetrahydrofuran (10 mL) solution of 6-amino-2N-Boc-1,2,3,4-tetrahydroisoquinoline (1.00 g) was added to the reaction solution. The reaction mixture was further heated to reflux for 5.5 hours, then cooled to room temperature, and then concentrated. The residue was purified by chromatography (dichloromethane/ethyl acetate=20:1?4:1) to obtain the title compound (1.51 g, 90%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta (ppm) = 9.33 (1H, s), 8.38 (1H, s), 8.05-7.97 (1H, m), 7.38-7.28 (1H, m), 7.24-7.16 (1H, m), 7.10-7.05 (1H, m), 7.02-6.97 (1H, m), 6.77-6.69 (1H, m), 4.41 (2H, s), 3.84 (3H, s), 3.51 (2H, t, J = 6.1 Hz), 2.73 (2H, t, J = 7.0 Hz), 1.41 (9H, s); MS (FAB) m/z: 416 (M + H)+.

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

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