Heterocyclic Building Blocks-Isoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.105627-79-0,Isoquinoline-5-sulfonyl chloride hydrochloride,as a common compound, the synthetic route is as follows.

2) In 1000 L in the reactor are separately put into dichloromethane 500 L, homopiperazine 50 kg and liquid ammonia 33 kg, stirring solution cleaning, adding step 1) obtained FZ010 – 1. In the 10 C insulation reaction to the TLC detection without FZ010 – 1 residue when the end of the reaction, the reaction time is 2 – 4 H-. The reaction […] purified water 300 L, stir, fully after standing, divide the methylene chloride level. The aqueous layer then 100 L methylene chloride extraction, repeating the extraction of two, then the collection of methylene chloride level; to-methylene chloride layer in purified water 300 L, dropwise 4 mol/L hydrochloric acid solution to adjust system for pH 4.5 – 5.0, during the dropping temperature of not higher than 40 C, layered; collecting water layer, mass fraction of 20% NaOH solution to adjust the pH of the aqueous layer to 8.0, during the dropping temperature of not higher than 40 C. For 200 L methylene chloride extraction, repeating the extraction of 3 times, then the collection of methylene chloride level, vacuum distillation, to obtain yellowish sticks the thick oil objects, about 21.8 kg, is the intermediate hexahydro -1 – (5 – isoquinoline sulfonyl) – 1 H – 1, 4 – benzodiazepine salt (formula (I) in the FZ010 – 2), yield is 54.5%.

105627-79-0, As the paragraph descriping shows that 105627-79-0 is playing an increasingly important role.

Reference£º
Patent; Henan Runhong Pharmaceutical Co., Ltd.; Cui Hailong; Ma Liyan; Wang Xiaoxue; Shi Yongzhi; An Xiaomin; Shi Huifeng; Zhang Wei; (8 pag.)CN109574992; (2019); A;,
Isoquinoline – Wikipedia
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925672-85-1, 1,6-Dibromoisoquinolin-3-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,925672-85-1

Step 1 To a mixture of 1,6-dibromoisoquinolin-3-amine (XVIII)(0.5 g, 1.66 mmol), ammonium formate-d5 (0.56 g, 8.28 mmol)and Pd(PPh3)4 (191.3 mg, 0.170 mmol)in DMF (5 mL)was heated to 50 C. for 48 h. The solvents were concentrated and the residue was suspended in chloroform. The solid was collected by filtration and washed with water and EtOAc. The solid were dried under high vacuo to obtain 6-bromo-1-deuterio-isoquinolin-3-amine (XIX)(115 mg,0.513 mmol, 31.0% yield)as a pale yellow solid. 1H NMR (500 MHz, DMSO-d6)delta ppm 6.11 (2H, s), 6.55 (1H, s), 7.22 (1H, dd, J=8.78, 1.92 Hz), 7.73 (1H, d, J=8.51 Hz), 7.79 (1H, d, J=1.92 Hz); ESIMS found for C9H6DBrN2 m/z 224.0 (79BrM+H).

As the paragraph descriping shows that 925672-85-1 is playing an increasingly important role.

Reference£º
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Eastman, Brian Walter; Cao, Jianguo; Bollu, Venkataiah; Mittapalli, Gopi Kumar; Chiruta, Chandramouli; (218 pag.)US2017/313682; (2017); A1;,
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Isoquinoline | C9H7N – PubChem

1109230-25-2, 5-Bromo-3,4-dihydroisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 0.15 g of 5-bromo-3,4-dihydroisoquinolin-1(2H)-one in 5 cm3 of dimethylformamide is poured into a mixture containing 31 mg of sodium hydride (60% in oil) and 10 cm3 of dimethylformamide at a temperature close to 20 C. under an inert atmosphere. Then a solution of 0.2 g of 1-(1-bromoethyl)-4-fluorobenzene in 5 cm3 of dimethylformamide is poured into the reaction mixture. The latter is stirred for 20 h at a temperature close to 20 C. Water and ethyl acetate are added to the reaction mixture. After decanting, the organic phase is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered then concentrated using a rotary evaporator under reduced pressure (5 kPa). The 325 mg of crude product obtained are purified by filtration through a silica pellet (eluent: 20% ethyl acetate/80% cyclohexane). After concentrating the fractions under reduced pressure, 146 mg of 5-bromo-2-[1-(4-fluorophenyl)ethyl]-3,4-dihydroisoquinolin-1(2H)-one are obtained in the form of a thick pale yellow oil.NMR: ppm: 1.54 (d, J=7.3 Hz, 3H) 2.85 (m, 1H) 2.97 (m, 1H) 3.10 (m, 1H) 3.47 (m, 1H) 5.92 (q, J=7.3 Hz, 1H) 7.18 (t, J=8.8 Hz, 2H) 7.33 (t, J=8.1 Hz, 1H) 7.41 (dd, J=8.8, 5.9 Hz, 2H) 7.78 (dd, J=8.1, 1.4 Hz, 1H) 7.98 (dd, J=8.1, 1.4 Hz, 1H)LC-MS-DAD-ELSD: [M+H]+ m/z=348, 1109230-25-2

1109230-25-2 5-Bromo-3,4-dihydroisoquinolin-1(2H)-one 21865472, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; SANOFI-AVENTIS; US2010/197725; (2010); 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.1165923-89-6,tert-Butyl 6-hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.

1165923-89-6, To a solution of 1 ,1-dimethylethyl 6-hydroxy-5-methyl-3,4-dihydro-2(1 H)- isoquinolinecarboxylate (Preparation 168) (3.16g, 12 mmol) in DCM (50ml) at room temperature under nitrogen was added pyridine (1.94ml, 24 mmol) and the resulting solution was cooled to -300C before trifluoromethanesulfonic anhydride (2.23ml, 13.20 mmol) was added dropwise. The resulting mixture was stirred for 40min at this temperature, warmed to room temperature and concentrated. The residue was diluted with ethyl acetate and washed sequentially with a hydrochloric acid (1 N), saturated sodium hydrogen carbonate and brine. The solution was dried (MgSO4) and concentrated in vacuo to give 1 ,1-dimethylethyl 5-methyl-6- {[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2(1 H)-isoquinolinecarboxylate (4.85g, 102%) as a red oil which was used in the next step (Preparation 22) without further purification. LCMS (Method HpH): Retention time 1.46min, [M-H]” = 3941 H NMR (CDCI3): deltaH 7.10(1 H, d), 7.02(1 H, d), 4.58(2H, s), 3.68(2H, t), 2.76(2H, t), 2.25(3H, s), 1.49(9H, s).

1165923-89-6 tert-Butyl 6-hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 54756910, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXO GROUP LIMITED; BAILEY, James, Matthew; BIT, Rino, Antonio; DEMONT, Emmanuel, Hubert; HARRISON, Lee, Andrew; JONES, Katherine, Louise; SMETHURST, Christian, Alan, Paul; WITHERINGTON, Jason; WO2010/146105; (2010); A1;,
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23707-37-1, Isoquinolin-7-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of 7-[(2-chloro-pyridine-3-carbonyl)-amino]-4,4-dimethyl-3,4-dihydro-lH-isoquinoline-2-carboxylicacid tert-butyl ester (20.8 g, 50 mmol, 1.0 eq.), 7-aminoisoquinoline (7.2 g, 50 mmol, 1.0 eq.), Pd2(dba)3 (915mg, lmmol,0.02 eq), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (CASNo. 213697-53-1, Strem Chemicalscat no. 15-1145; 785 mg, 2 mmol, 0.04 eq) under N2 in a 250mL pressure reaction vessel was added 1.0 M LiNTMS2 THFsolution (120 mL, 120 mmol, 2.4 eq.). The reaction vesselwas sealed with a Teflon screwcap and the mixture wasstirred at 70 SC for 17 h. The mixture was then cooled toRT. 100 mL of water was added to the mixture and the mixturewas extracted with 500 mL of EtOAc. The organic layer waswashed with sat. NH4C1 solution, 1M NaHP04 solution (4x200mL) then dried over MgS04. After filtration andconcentration, the crude was purified through a silica gelcolumn chroma tography, eluting with CH2Cl2/EtOAc. Thedesired title compound was obtained as a yellow solid. MS(ES+) : 524 (M+H) + . Calc’d for CsiHssNsOs- 523.26, 23707-37-1

As the paragraph descriping shows that 23707-37-1 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; WO2006/12374; (2006); A1;,
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Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.

18881-17-9, EXAMPLE 1 STR12 (S-N-benzyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline To a stirred mixture of (S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (10 g) and sodium bicarbonate (15.5 g) in tetrahydrofuran (50 mL) was added dropwise benzyl chloroformate (9.7 mL) at 5 C. The reaction was stirred for 2 hours at room temperature, and worked up by adding ethyl acetate, washing with brine and concentrating in vacuo. The resulting concentrate was purified by flash chromatography to yield the product (17.9 g) as an oil. 1 H-NMR (300 Mhz, CDCl3) delta: 2.48 (OH), 2.85 & 3.05 (m, 2H), 3.58 (m, 2H), 4.30-4.85 (m, 3H), 5.22 (s, 2H), 7.05-7.50 (m, 9H).

The synthetic route of 18881-17-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SK Corporation; US5955471; (1999); A;,
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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

34784-05-9, 6-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[00211] 6-Vinylisoquinoline: In a 250 mL round bottom flask, 6- bromoisoquinoline (5 g, 24 mmol)(commercially available from Kalexsyn Product List Order Number 2003-005) was dissolved in dioxane (50 ml). Vinyltributylstannane (9 mL, 29 mmol) was added and the solution was degassed with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium (3 g, 2 mmol) was added in one portion. The reaction mixture was stirred for 3 hours at 1000C. The reaction mixture was adsorbed onto silica gel, and purified by flash chromatography (5-30 %, EtOAc in hexane) to provide the product (3.0 g, 80 %). LCMS (API-ES) m/z (%): 156 (M+H+).

34784-05-9, 34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; WO2009/11880; (2009); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

891782-60-8,891782-60-8, 7-Bromo-3,4-dihydro-2H-isoquinolin-1-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7-bromo-3,4-dihydro-2H-isoquinolin-1-one (1.09 g) and tertbutyl 5-hydroxy-4-methyl-2,3-dihydro-1H-indole-1-carboxylate (1.00 g) in 1,4-dioxane (15mL) solution of copper iodide (I) (0.153 g), N,N-dimethylglycine (0.166 g) and cesium carbonate (2.61 g), and the mixture was stirred for 12 hours at 95 C. After cooling, the ethyl acetate was added to the reaction mixture, and the insoluble material was removed by filtration. The solvent was distilled off under reduced pressure, the residue was purified by column chromatography (ethyl acetate/hexane) to give the title compound (0.960 g) as a white solid.

The synthetic route of 891782-60-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DAIICHI SANKYO COMPANY LIMITED; NAGAMOCHI, MASATOSHI; GOTANDA, KENTOKU; NOGUCHI, TETSUJI; GOTO, TAIJI; SASAKI, JUNKO; TORIHATA, MUNEFUMI; YOSHINO, TOSHIHARU; ISOBE, TAKASHI; (97 pag.)JP2016/108257; (2016); A;,
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Isoquinoline | C9H7N – PubChem

3336-43-4, 1-Chloroisoquinolin-4-ol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 1-chloroisoquinolin-4-ol (0.5 g, 2.78 mmol), 1-bromo-2-methoxyethane (0.318 mL, 3.34 mmol), and potassium carbonate (0.539 g, 3.90 mmol) were added to a solution of DMF (10 mL) and heated to 45 C. for 1 hr. Ater 45 min, the temp was raised to 55 C. for 45 min. One half of an equivalent of 1-bromo-2-methoxyethane (0.318 mL, 3.34 mmol) was then added and then stirred at 40 C. for overnight. The reaction was diluted with water and extracted with EtOAc. The organic layer was washed with brine, collected, dried over MgSO4, filtered and evaporated to give the crude product. Crude material purified via silica gel chromatography (10-60% EtOAc:Hex) to give the desired product 1-chloro-4-(2-methoxyethoxy)isoquinoline (368 mg, 1.548 mmol, 55.6% yield) as an orange solid. 1H NMR (400 MHz, CHLOROFORM-d) delta 8.33-8.24 (m, 2H), 7.83 (s, 1H), 7.81-7.68 (m, 2H), 4.40-4.32 (m, 2H), 3.95-3.84 (m, 2H), 3.52 (s, 3H). MS: MS m/z 238.15 (M++1).

3336-43-4, As the paragraph descriping shows that 3336-43-4 is playing an increasingly important role.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem