Tag: M.W:100-200

1198-30-7, 1-Isoquinolinecarbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1198-30-7, A solution of isoquinoline-1-carbonitrile (Intemediate H1) (commercially available from Aldrich) (4.40 g, 28.5 mmol) in THF at 0 C. was treated with methylmagnesium bromide (20 mL, of a 3M soln in ether) for 3 h. (see procedure found in Vacher, B. et al J. Med. Chem. 1998 41, 5070; incorporated herein by reference). The mixture was quenched with a sat. solution of NH4Cl and stirred for 3 h at rt. The aqueous layer was basified with NaOH and extracted with ethyl acetate. The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified by chromatography on silica gel with 10% ethyl acetate: hexane to give 1-isoquinolin-1-yl-ethanone (Intermediate H2) 3.65g (75%). A mixture of 4-iodo-1-tritylimidazole (commercially available) (15.5 g, 35.4 mmol) in dichloromethane (80 mL) at 20 C. was treated with ethyl magnesium bromide (12.0 mL, 36 mmol, 3M in ether) and allowed to react for 1 h. A solution of 1-isoquinolin-1-yl-ethanone (Intermediate H2) (3.65 g, 21.3 mmol) in dichloromethane (20 mL) was added via addition funnel at 20 C. and stirred for 16 h. The mixture was quenched with sat. ammonium chloride (100 mL) and diluted with dichloromethane. The residue was isolated in an aqueous workup. The product was extracted with CH2Cl2 and purified by chromatography on silica gel with 5% NH3-MeOH: CH2Cl2 to give 1-isoquinolin-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate H3) as a solid. 1-Isoquinolin-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate H3) was subjected to TFA: trifluoroacetic acid, Pd/C under hydrogen similar to the catalytic reduction procedure of Method D to remove the trityl group and produced 1-1H-imidazol-4-yl)-isoquinolin-1-yl ethanol (Intermediate H4). 1-1H-Imidazol-4-yl)-isoquinolin-1-yl ethanol (Intermediate H4). (21 mmol) in dichloromethane (100 mL) was treated with triethylamine (24.0 mL, 172 mmol) at 0 C. Methanesulfonyl chloride (6.1 mL, 75 mmol) was added via syringe and the mixture was stirred for 2 h. The mixture was subjected to an aqueous work-up. The crude material was purified by chromatography on silica gel with 20% EtOAc: hexane to 5% NH3-MeOH: dichloromethane to give 1-[1-(1-methanesulfonyl-1H-imidazol-4-yl)-vinyl]-isoquinoline (Intermediate H5) 3 g. 1-[1-(1-Methanesulfonyl-1H-imidazol-4-yl)-vinyl]-isoquinoline (Intermediate H5) was subjected to the catalytic reduction procedure found in Method D to produce 1-[1-(1-methanesulfonyl-1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H6). Methanesulfonyl-1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H6) in ethanol and 2M HCl was heated at reflux for 18 h. The mixture was cooled to rt and basified with NaOH solid. The aqueous layer was extracted with isopropanol:chloroform (3:1). The organic fractions were dried over MgSO4, filtered and concentrated onto silica gel. The product, 1-[1-(1H-imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H7) was eluted from a column of silica gel with 3 to 5% NH3-MeOH: CH2Cl2. 1-[1-(1H-Imidazol-4-yl)-ethyl]-isoquinoline (Intermediate H7) was subjected to the appropriate process steps in Method A to produce 4-(1-isoquinolin-1-yl-ethyl)-1,3-dihydro-imidazole-2-thione (Compound 13) 1H NMR (300 MHz, DMSO-d6): delta11.9 (s, 1H), 11.6 (s, 1H), 8.42 (dd, J=5.4, 2.7 Hz, 1H), 8.31 (d, J=8.1 Hz, 1H), 7.96 (d, J=8.1 Hz, 1H), 7.78-7.64 (m, 3H), 6.40 (s, 1H), 5.0 (q, J=6.9 Hz, 1H), 1.59 (d, J=6.9 Hz, 3H).

1198-30-7 1-Isoquinolinecarbonitrile 306057, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Allergan, Inc.; US2006/69143; (2006); 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.374554-54-8,5-Amino-1-chloroisoquinoline,as a common compound, the synthetic route is as follows.

EXAMPLE 64B N-[(4-bromophenyl)methyl]-N’-(1-chloroisoquinolin-5-yl)urea The product from Example 64A (520 mg, 2.91 mmol) in toluene (8 mL) was treated with 1-bromo-4-(isocyanatomethyl)benzene (0.41 mL, 2.93 mmol) with stirring and then the mixture was heated at 90 C. for 2 hours. The mixture was allowed to cool to room temperature, filtered, the filter cake washed with toluene, and air-dried to provide the title compound as an off-white solid (717 mg, 63%). 1H NMR (300 MHz, DMSO-d6) delta 8.89 (s, 1H), 8.34-8.37 (m, 2H), 8.00 (dd, J=6.1 Hz, 0.7 Hz, 1H), 7.92-7.95 (m, 1H), 7.73 (t, J=8.1, 1H), 7.53-7.56 (m, 2H), 7.30-7.33 (m, 2H), 7.12 (t, J=5.8 Hz, 1H), 4.35 (d, J=5.8 Hz, 2H); MS (ESI+) m/z 390/392 (M+H+, 35Cl/37Cl)., 374554-54-8

As the paragraph descriping shows that 374554-54-8 is playing an increasingly important role.

Reference£º
Patent; Abbott Laboratories; US6933311; (2005); B2;,
Isoquinoline – Wikipedia
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

Step A: Benzyl (3S)-3-(hydroxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate 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 by chromatography over silica gel using petroleum ether and ethyl acetate as eluants, the title product is obtained in the form of an oil. 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) IR: nu: OH: 3416 cm-1; nu: C-H: 754 cm-1

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

Reference£º
Patent; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; STARCK, Jerome-Benoit; HENLIN, Jean-Michel; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; GENESTE, Olivier; FEJES, Imre; TATAI, Janos; NYERGES, Miklos; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; DURAND, Didier; US2015/31673; (2015); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

36034-54-5, 4-Methoxyisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-Chloro-1, 3-Oxazino [5,6-c] isoquinoline was prepared by the procedure of Miyoko Toyama and Hirotaka Otomasu starting from1-chloro-4-hydroxy isoquinoline. The starting material: 1-chloro-4-hydroxy isoquinoline (Example 226c) was prepared by the synthetic sequence shown above. MCPBA oxidation of 4-methoxy isoquinoline (Example 222a) was carried as usual to give 79.1% of the corresponding N-oxide (Example 226a). The material was converted into the 1-chloro derivative immediately afterward in POCI3 to give the chloride (Example 226b) in essentially quantitative yield. The crudel-chloro-4-methoxy isoquinoline was de-methylated in BBr3 at room temperature to give the corresponding 1-chloro-4-hydroxy isoquinoline (Example 226c) after treating the crude BBr3 mixture with anhydrous methanol at room temperature, followed by evaporation to get rid of excess of borate residues. The reaction of Miyoko Toyama and Hirotaka Otomasu gave 266mg of 6-chloro-1, 3- oxazino [5,6-c] isoquinoline (Example 226d, 62.3%) overall yield from 300mg of 4- methoxy isoquinoline in 4 steps. LC/MS Rt-min([M-HCHO] H+) [method D]: 2.45(192).’H NMR (400 MHz, CHLOROFORM-D)8 ppm 5.02 (s, 2 H) 5.41 (s, 2 H) 7.68 (m, 1 H) 7.77 (ddd, J=8. 25,6. 91,1. 22 Hz, 1 H) 8.10 (d, J=8. 31 Hz, 1 H) 8.26 (d, J=8. 56 Hz,1 H). The chloride was found to be unreactive under the alkylation protocol of Example 184. The corresponding 6-fluoro-1, 3-oxazino [5,6-c] isoquinoline (Example 226) was prepared by the method of [Uchibori, Y.; Umeno, M.; Yoshiokai, H.; Heterocycles, 1992,34 (8),1507-1510] cited earlier. The reaction was not allowed to go to completion, and the crude reaction mixture was recovered as a mixture of ratio of 1: 2.4 (Cl : F). Without further purification, the chloride/fluoride mixture was alkylated with the tripeptide using the procedure of Example 184 to give 66mg (50.0%) of BOCNH-P3(L-t-BuGly)-P2 [ (4R)- ( 1, 3-oxazino [5,6-c] isoquinoline-6-oxo)-S-proline]-P1 (lR, 2S VinylAcca)-CONHSO2Cyclopropane after preparative HPLC purification. LC/MS Rt-min(MNa+) [method D]: 3.03(764).’H NMR (400 MHz, CD30D)8 ppm 1.01 (s, 9 H) 1.06 (dd, J=8. 07,1. 96 Hz, 2 H) 1.22 (s, 10 H) 1.34 (d, J=6. 11 Hz,1 H) 1.42 (m, 1 H) 1.86 (dd, J=8. 07,5. 38 Hz,1 H) 2.23 (m, 2 H) 2.59 (dd,J=13. 82,6. 97 Hz,1 H) 2.93 (m,1 H) 4.03 (dd,J=11. 86,3. 06 Hz,1 H) 4.23 (s, 1 H) 4.41 (d,J=11. 98 Hz,1 H) 4.50 (dd, J=9. 66,6. 97 Hz,1 H) 4.87 (m, 2 H) 5.11 (d, J=10. 52 Hz, 1 H) 5.28 (d,J=17. 12 Hz,1 H) 5.34 (s, 2 H) 5.74 (m, 2 H) 7.51 (t, J=7. 46 Hz,1 H) 7.70 (t, J=7. 58 Hz,1 H) 7.95 (d, J=8. 31 Hz, 1 H) 8.12 (d, J=8. 31 Hz,1 H)., 36034-54-5

The synthetic route of 36034-54-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99274; (2003); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

66491-03-0,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.66491-03-0,7-Amino-3,4-dihydroisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

(a) 7-Bromo-3,4-dihydro-1 (2H)-isoquinolinone; To a solution of 7-amino-3,4-dihydro-1 (2/-/)-isoquinolinone, (for a synthesis see Girard, Yves; Atkinson, Joseph G.; Belanger, Patrice C; Fuentes, Jose J.; Rokach, Joshua; Rooney, C. Stanley; Remy, David C; Hunt, Cecilia A J.Org.Chem. (1983), 48(19), 3220) (0.773 g, 4.772 mmol) in acetonitrile (10ml) at O0C was added 48% aqueous hydrobromic acid (10 ml, precooled to O0C). The mixture was stirred at O0C for 0.5h before addition of a solution of sodium nitrite (0.379g, 5.49 mmol) in water (2ml) over 0.4h. The reaction was then stirred at O0C for 0.5h and then copper(l) bromide (0.822g, 5.726 mmol) was added portionwise over 10 min. The reaction mixture was then warmed to room temperature, stirred at room temperature for 0.5h and then at 7O0C for 1 h. The reaction mixture was then cooled to O0C, water (60ml) was added and the mixture stirred at O0C for 1 h before filtering and drying in vacuo. The residue was dissolved in 10% methanol/dichloromethane, dried with magnesium sulphate and evaporated to give the desired product (0.679g, 63%). MS (+ve ion electrospray) m/z 227 (MH+).

The synthetic route of 66491-03-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/115947; (2007); 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,18881-17-9

To a stirred solution of 2-(4-chloro-3-dibutylcarbamoyl-5-methyl-pyrazol-l-yl)-5- methoxy-benzoic acid (0.35 g, 0.82 mmol) and (S)-(l,2,3,4-tetrahydroisoquinolin-3-yl)methanol (0.13 g, 0.82 mmol) in dichloromethane (8 mL) under nitrogen atmosphere was added l-ethyl-3- (3-dimethylaminopropyl)carbodiimide (0.16 g, 0.82 mmol) and hydroxybenzotriazole (0.13 g, 0.82 mmol). The mixture was stirred at ambient temperature for 5 minutes. Triethylamine (0.34 mL, 2.5 mmol) was added to the mixture. The reaction was stirred for 60 hours at ambient temperature. The mixture was washed with water and purified by eluting through a silica gel column with a 10 to 100% ethyl acetate / heptane gradient to afford the title compound (21 mg, 4.5% yield). MS (ESI) [m/e, (M+H)+] = 567.3. XH NMR (400 MHz, chloroform-d) delta ppm 6.75 – 7.36 (m, 7 H), 4.13 – 5.41 (m, 4 H), 3.80 – 3.96 (m, 3 H), 2.51 – 3.71 (m, 8 H), 2.17 – 2.32 (m, 3 H), 1.48 – 1.68 (m, 4 H), 1.19 – 1.44 (m, 4 H), 0.70 – 0.97 (m, 6 H).

18881-17-9 (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol 776757, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; FORD, Daniel; PORTER, John Robert; VISSER, Michael Scott; YUSUFF, Naeem; WO2013/96060; (2013); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

131002-09-0, 6-Chloroisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-chloroisoquinolin-1 (2Eta)-one (12mm0l), bis(4-methoxyphenyl)disulfide (10mmol), hexafluorofluoride was sequentially added to the pressure resistant reaction tube at room temperature. Place silver acid (10 mmol) and dichloroethene (6 mL). Then the reaction mixture is at 90 C Reaction for 10 hours. The reaction was quenched and concentrated under reduced pressure to give a crude material which was washed with a mixture of petroleum ether and ethyl acetate. Flash column chromatography gave the corresponding product 4-(4-methoxyphenylthio)-6-chloroisoquinolin-1 (2H)-one. Yield 87%;, 131002-09-0

The synthetic route of 131002-09-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nankai University; Zhu Youquan; He Jingli; Niu Yunxia; Han Tingfeng; Li Haoyu; (14 pag.)CN108822035; (2018); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

22246-04-4, 7-Methoxy-3,4-dihydroisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example IX: Synthesis of l-(7-butoxy-2-isopropyl-l,2,3,4-tetrahydro-isoquinoIin-4- yl)-cyclohexanol; Step 1: Synthesis of 2-isopropyl-7-methoxy-3,4-dihydro-2H-isoquinolin-l-one; To a slurry of sodium hydride (671 mg, 27.97 mmol) in tetrahydrofuran (5 mL) was added 7-methoxy-3,4-dihydro-2/J-isoquinolin-l-one, obtained in example IV (step 2), in tetrahydrofuran (5 ml) and isopropyl iodide (1.40 ml, 13.98 mmol). The reaction mixture was stirred for 1 h at 80 0C. The reaction mixture was quenched with water (15 mL) and extracted with EtOAc (3×30 mL). The combined organic layer was washed with water (2×30 mL) and brine (30 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude material which was purified by column chromatography (silica gel, 2:98 MeOH : CHCl3) to yield the title compound (1.62 g, 79 %) as viscous liquid.ESIMS (m/z): 219.3 (M+l), 22246-04-4

The synthetic route of 22246-04-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PANACEA BIOTEC LIMITED; WO2009/118765; (2009); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

486-73-7, Isoquinoline-1-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1-Hydroxybenzotriazole hydrate (1.47 equiv of acid), N-ethyl-N’-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.47 equiv of acid), N,N-diisopropylethylamine (3.45 equiv of acid), and corresponding acid were added to a solution of compound 10 (1.0 equiv of acid) in dichloromethane (0.1 M). The reaction mixture was stirred at room temperature for 12 h and then washed with water. The separated organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The concentrate was purified with silica gel column chromatography to afford compound 11., 486-73-7

The synthetic route of 486-73-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Lee, Seung Kyu; Choi, Kwang Hyun; Lee, Sang Jae; Lee, Jong Sun; Park, Ji Yun; Kim, B. Moon; Lee, Bong Jin; Bioorganic and Medicinal Chemistry Letters; vol. 21; 1; (2011); p. 133 – 136;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.394-67-2,4-Fluoroisoquinoline,as a common compound, the synthetic route is as follows.

4-Fluoroisoquinoline (3.6 g) obtained in Reference Example 1 was dissolved in concentrated sulfuric acid (20 ml), and the solution was added dropwise with a solution of potassium nitrate (3.25 g, Wako Pure Chemical Industries) in concentrated sulfuric acid (28 ml) under cooling at -5¡ã C. so that the temperature of the reaction mixture should not exceed 5¡ã C. The reaction mixture was stirred at 0¡ã C. for 1 hour, poured into ice water, neutralized with 28percent aqueous ammonia (pH 8), and extracted 3 times with ethyl acetate (150 ml for each time). The combined organic layer was washed with saturated aqueous sodium hydrogencarbonate (300 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (2.2 g)., 394-67-2

The synthetic route of 394-67-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Asahi Kasei Pharma Corporation; US2009/48223; (2009); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem