Heterocyclic Building Blocks-Isoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.62882-02-4,6-Chloroisoquinoline,as a common compound, the synthetic route is as follows.

General procedure: 1,2,3,4-Tetrahydro-isoquinoline(1g, 7.5 mmol) was dissolved in 5 mL of anhydrous acetonitrile. Then to thissolution was slowly added 2-chloro- or 2-bromo-benzyl compound (7.5 mmol) and the reaction was carried out overnight at room temperature. The solvent wasremoved under reduced pressure. The residue was resuspended in 1 ml of DMSO andpurified using C18 flash chromatography as described above.

As the paragraph descriping shows that 62882-02-4 is playing an increasingly important role.

Reference£º
Article; Farha, Maya A.; Koteva, Kalinka; Gale, Robert T.; Sewell, Edward W.; Wright, Gerard D.; Brown, Eric D.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 3; (2014); p. 905 – 910;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61563-43-7,Isoquinoline-8-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: To a suspension of the acid(0.25 mmol, 1.00 equiv) and N,N,N0 ,N0-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU) (0.25 mmol,1.00 equiv) in CH2Cl2 (2.5 mL), under an air atmosphere, at ambienttemperature, was added diisopropylethylamine (0.1 mL,0.58 mmol, 2.34 equiv) and the mixture was stirred for 25 min.2-((5-(Trifluoromethyl)pyridin-2-yl)sulfonyl)ethan-1-aminiumchloride(14) (0.26 mmol, 1.05 equiv) and CH2Cl2 (5 mL) were thenadded and the mixture was stirred for 48 h. The reaction wasquenched with aqueous HCl (1 M, 2 mL), followed by H2O(10 mL) and EtOAc (20 mL). The mixture was transferred to a separatoryfunnel and the flask rinsed with EtOAc (10 mL). The organicphase was separated, washed with saturated aqueous NaHCO3(15 mL) and dried over anhydrous Na2SO4. The solvent was thenremoved under reduced pressure, at or below 40 C, to afford thecrude product. Purification was performed as indicated for eachcompound below 5.3.6.12 N-(2-((5-(Trifluoromethyl)pyridin-2-yl)sulfonyl)ethyl)isoquinoline-8-carboxamide (42) The title compound was prepared from isoquinoline-8-carboxylic acid (0.043 g, 0.25 mmol). The crude product was purified by flash chromatography on silica gel (0:100-60:40/EtOAc:Heptane) affording a colourless solid (0.032 g, 0.08 mmol, 31%). 1H NMR (600 MHz, DMSO-d6) delta 9.58 (s, 1H), 9.18-9.15 (m, 1H), 8.71 (t, J = 5.4 Hz, 1H), 8.56 (dd, J = 8.2, 2.3 Hz, 1H), 8.54 (d, J = 5.7 Hz, 1H), 8.32 (d, J = 8.1 Hz, 1H), 8.05 (d, J = 8.2 Hz, 1H), 7.86 (d, J = 5.6 Hz, 1H), 7.76 (dd, J = 8.3, 7.1 Hz, 1H), 7.62 (dd, J = 7.2, 1.1 Hz, 1H), 3.93 (t, J = 6.5 Hz, 2H), 3.79 (q, J = 6.3 Hz, 2H). 13C NMR (151 MHz, DMSO-d6) delta 167.0, 159.9 (br s), 150.0, 147.0 (q, J = 3.9 Hz), 142.7, 136.8 (q, J = 3.6 Hz), 135.2, 133.7, 129.1, 128.6, 128.3 (q, J = 33.1, 32.7 Hz), 126.4, 124.6, 122.5 (q, J = 273.3 Hz), 122.1, 120.2, 50.5, 33.3 (q, J = 32.8 Hz). HRMS (ESI) Calcd for C18H14F3N3NaO3S [M+Na]+: 432.0600; found 432.0598 (0.5 ppm). HPLC (CH3OH:H2O/50:50, 1 mL/min, 254 nm) tr(minor) 4.41 min (<1%), tr(minor) 4.54 min (<1%), tr(minor) 8.00 min (<1%), tr(major) 9.23 min (99%). The synthetic route of 61563-43-7 has been constantly updated, and we look forward to future research findings. Reference£º
Article; Kaupang, Asmund; Kase, Eili Tranheim; Vo, Cecilie Xuan Trang; Amundsen, Marthe; Vik, Anders; Hansen, Trond Vidar; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 247 – 260;,
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

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.

#N/A

Reference£º
Patent; AMGEN INC.; WO2008/86014; (2008); A2;,
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;,
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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

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.216064-48-1,tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.

In aN2 blanketed flask, 19.7 g (79.0 mmol) of 5-hydroxy-3,4-dihydro-lH-isoquinoline-2-carboxylic acid tert-butyl ester is dissolved in 300 mL of DMF, and.4.1g(79.2 mmol) of N-bromosuccihimide is added in one portion. The solution is stirredovernight and quenched with 500 mL of HaO. The resulting mixture is partitionedbetween 500 mL of EtOAc and 500 mL of H^O. The aqueous layer is extracted twicewith 400 mL of EtOAc, and the combined organic layer is washed with 300 mL of brineand dried over Na2SO4. Solvent is removed to afford 39.8 g crude product includingresidual DMF. The crude 8-bromo-5-hydroxy-3,4-dihydro-lH-isoquinoline-2-carboxylicacid tert-butyl ester is dissolved in 390 mL of acetone, and then 12.5 g (90.4 mmol) ofK^COs is added followed by 10.3 mL (14.8 g, 86.6 mmol) of benzyl bromide. Themixture is stirred at reflux 20h, and then cooled to ambient temperature and filtered. Thefiltrate is evaporated, and the residue is partitioned between 50 mL of H^O and 100 mL ofEtOAc. The aqueous layer is extracted with EtOAc (2 X 100 mL). The combinedorganic layer is washed with brine and dried over Na2SO4. The solvent is removed toafford crude product as an orange-brown oil which is purified by silica gelchromatography to afford clean product of 8-bromo-5-benzyloxy-3,4-dihydro-lH-isoquinoline-2-carboxylic acid tert-butyl ester as 34.1 g of orange oil which crystallizedupon standing. 1H NMR (250 MHz, CDC13) 8 7.3-7.15 (6H, m), 6.56 (1H, d, J=7.5 Hz),4.94 (2H, s), 4.42 (2H, s), 3.53 (2H, t, J=5.7 Hz), 2.71 (2H, d, J=5.7 Hz), 1.42 (9H, s).

216064-48-1 tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 10538586, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/51945; (2005); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

82827-09-6, 6-Bromoisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Under nitrogen atmosphere, 22 mg of 60% sodium hydride was added at 0C to 3 ml solution of dimethylformamide with 100 mg of 6-bromo-2H-isoquinoline-1-one, and the mixture was stirred for 30 min. 0.04 ml of ethyl iodide was added at 0C, and the mixture was stirred at room temperature for 3 hours. Cold water was added to the reaction solution, extracted with chloroform. Chloroform layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by thin-layer chromatography (hexane/ethyl acetate=3/1) to obtain 30 mg of the above compound as a white solid. 1HNMR(400MHz,CDCl3.)delta.:1.38(3H,t,J=7.4Hz), 4.04(2H,q,J=7.2Hz), 6.41(1H,d,J=7.2Hz), 7.10(1H,d,J=7.6Hz), 7.56(1H,dd,J=1.8,8.6Hz), 7.67(1H,d,J=2.0Hz), 8.28(1H,d,J=8.4Hz) ESI-MS Found:m/z 253.9[M+H]+

The synthetic route of 82827-09-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1726585; (2006); A1;,
Isoquinoline – Wikipedia
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

Example 34:3-Amino-l-(3-bromo-4,5-dimethoxy-phenyl)-9-chloro-lH-4-oxa-10-aza-phenanthrene-2- carbonitrile (34)(34)l-Chloro-4-hydroxyisoquinone (790 mg, 4.4 mmol), 5-bromo-3,4-dimethoxy-benzaldehyde ( 1.077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 mu, 1.46 mmol) and then stirred at 80 C under LC-MS control for 24 h. The reaction mixture was cooled down to room temperature, diluted with water to about 100 ml and the precipitates were collected by filtration, washed well with 50 % aqueous ethanol and dried under vacuum to yield the title compound (1.7 g, 3.6 mmol, 82 %).

3336-43-4 1-Chloroisoquinolin-4-ol 4281882, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; Deutsches Krebsforschungszentrum (DKFZ); Ruprechts-Karls-Universitaet Heidelberg; BOUTROS, Michael; MASKEY, Rajendra-Prasad; KOCH, Corinna; FUCHS, Florian; STEINBRINK, Sandra; GILBERT, Daniel; WO2012/62901; (2012); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem