Category: isoquinoline

1350643-72-9, (S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[00721] To a mixture of amine (D-i) (1.0 eq, e.g., 0.5 mmol), Wd-COOH carboxylic acid (1.1 eq, e.g., 0.55 mmol), and N,N-diisopropylethylamine (2.0 eq, e.g., 0.17 mL, 1.0 mmol) in anhydrous DMF (e.g., 5 mL), 1- hydroxybenzotriazole hydrate (1.3 eq, e.g., 0.65 mmol) and EDC hydrochloride (1.3 eq, e.g., 0.65 mmol,) are added sequentially and the resulting mixture is stirred at RT for 2-i 6 h. Ice-water or saturated sodium carbonate solution is added to the reaction mixture and then stirred for 10 mm. The precipitate is collected by filtration, rinsed with water and dried in vacuo. The solid collected is further purified by flash column chromatography on silica gel (e.g., 0-i 0% MeOH-DCM) to afford the product amide (D-2). [00748] Compound 1 was prepared according to Method A. It was then coupled to 3-amino-6- bromopyrazine-2-carboxylic acid using Method D to provide compound 2 which was converted to compound 3 according to the following procedure: A 25 mL microwave tube was charged with compound 2 (0.35 mmol, 1.0 equiv), potassium cyclpropyltrifluoroborate (2 equiv) and sodium carbonate (3 equiv) and placed under Ar. A solution of dioxane/water (5 mL, 4:1 v/v) was added and the mixture was bubbled with Argon for 5 mm. PdC12(amphos)2 (10 mol%) was then added and bubbled with Ar for an additional 5 mm. The reaction was then sealed and heated to 90 oC for 3h after which there was no more SM by LC/MS analysis. The reaction was then partionned between methylene chlroide and water. The aqeuous layer was extracted with methylene chloride (2x). The organic layers were combined, dried over Na2504 and concentrated. This material was further purified by HPLC (10-60% methanol/0.1% trifluoroacetic acid in water) to provide compound 3. ESI-MS m/z: 460.4 [M+H]t

1350643-72-9 (S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one 66607319, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo, C.; EVANS, Catherine, A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; TREMBLAY, Martin, R.; WO2015/51241; (2015); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

18881-17-9, (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

This compound is obtained using a protocol from the literature (R. B. Kawthekar et al. South Africa Journal of Chemistry 63, 195, 2009) starting from 15 g of (3S)-1,2,3,4-tetrahydroisoquinolin-3-ylmethanol (91.9 mmol) in the presence of benzyl chloroformate and triethylamine in solution in dichloromethane. After purification over silica gel (petroleum ether/AcOEt gradient), the title compound is obtained in the form of an oil. (0132) 1H NMR: delta (300 MHz; DMSO-d6; 300K): 7.33 (m, 5H, aromatic Hs, O-benzyl); 7.15 (s, 4H, aromatic Hs, H tetrahydroisoquinoline); 5.13 (s, 2H, CH2-Ph); 4.73 (d, 1H, H tetrahydroisoquinoline); 4.47 (m, H, CH2OH); 4.36 (m, 1H, H tetrahydroisoquinoline); 4.28 (d, 1H, H tetrahydroisoquinoline); 3.39 (dd, 1H, CH2OH); 3.23 (dd, 1H, CH2OH); 2.93 (dd, 1H, H tetrahydroisoquinoline); 2.86 (dd, 1H, H tetrahydroisoquinoline) (0133) IR: nu: OH: 3416 cm-1; nu: C-H: 754 cm-1

As the paragraph descriping shows that 18881-17-9 is playing an increasingly important role.

Reference£º
Patent; Les Laboratoires Servier; Vernails (R&D) Limited; CASARA, Patrick; LE DIGUARHER, Thierry; HENLIN, Jean-Michel; STARCK, Jeroeme-Benoit; LE TIRAN, Arnaud; DE NANTEUIL, Guillaume; GENESTE, Olivier; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; WALMSLEY, Claire; GRAHAM, Christopher John; RAY, Stuart; MADDOX, Daniel; BEDFORD, Simon; (72 pag.)US2016/152599; (2016); 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.1350643-72-9,(S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

To a solution of 60 mg (0.221 mmol) of tert-butyl 4-chloro-6,7-dihydro-8H-pyrimido [5,4- b] [1,4] oxazine-8-carboxylate in a 5 mL microwave vial, 73 mg (0.243 mmol) of (S) -3- (1-aminoethyl) -8-chloro-2-phenylisoquinoline-1 (2H) -one obtained in Preparation Example 3 was dissolved in 3 mL of anhydrous toluene , 1.5 mg (0.007 mmol) of palladium (II) acetate (Pd (OAc) 2) 2,2′-bis (diphenylphosphino) -1,1′-binaphthalene ((+ -) – BINAP) 12 mg (0.020 mmol), 101 mg (0.309 mmol) of cesium carbonate (Cs2CO3) was added and the degassing was performed three times using argon gas. Followed by stirring at 80 C for 24 hours. The reaction mixture was filtered under reduced pressure, and the organic layer was extracted with ethyl acetate and water. The organic layer was dried (Na2SO4), filtered and concentrated. The crude product was dissolved in dichloromethane and purified by column chromatography (SiO2, eluent: hexane (20% ethyl acetate in hexane) to give tert-butyl (S)-4-((1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)amino)6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazine-8-carboxylate 50 mg (0.094 mmol, 42% yield) was obtained as a pale yellow solid.

1350643-72-9 (S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one 66607319, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; Korea Research Institute of Chemical Technology; Lee, Gay Hyung; Lim, Hee Jong; Cho, Hee Young; Park, Woo Kyu; Jung, Dae Young; (40 pag.)KR2017/74381; (2017); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

34551-41-2, 5-Bromo-1-chloroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 35:5-romoisoquinolin-l-amine. Acetamide (4.9 g, 82 mmol), 5-bromo-l- chloroisoquinoline (1.00 g, 4.1 mmol) and K2CO3 (2.8 g, 21 mmol) were combined in a sealaed tube and the mixture heated at 200 C for 1.5 h. The mixture was allowed to cool to rt and the solid residue suspended in 400 mL water. The brown solid was collected as the title compound (750 mg). MS (ESI pos. ion) m/z: 223 (MH+). Calc’d exact mass for C9H7BrN2 : 223.

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Reference£º
Patent; AMGEN INC.; WO2008/86014; (2008); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

4494-18-2, 1-Isoquinolinecarboxaldehyde is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

During DCE (50mL) 4-(2-aminoethyl) benzenesulfonamide(1.0g, 5.0mmol), AcOH and (1.0 mL) and isoquinoline-1-carbaldehyde(2.09 g, 13.3 mmol) the solution containing the mixture was stirredfor 30 minutes at under 75 C. nitrogen. The reaction mixture was cooled to 0 , and treated with NaBH (OAc) 3 (3.165g,15mmol). The reaction mixture was stirred at room temperature overnight anddecomposed with water. The reaction mixture was extracted with DCM.The organic layer was dried and concentrated in vacuo.The residue was purified by flash chromatography on silica gel to yield 4- (2-(bis (isoquinolin-1-ylmethyl) amino) ethyl) benzenesulfonamide (1.86 g, 77%).

4494-18-2 1-Isoquinolinecarboxaldehyde 265306, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; MOLECULAR INSIGHT PHARMACEUTICALS INCORPORATED; BABICH, JOHN W; (133 pag.)JP5856247; (2016); B2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem