Category: isoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.39989-39-4,7-Methoxyisoquinoline,as a common compound, the synthetic route is as follows.

TMPMgCl¡¤LiCl (1.0 M in THF/toluene; 5.65 mL, 5.65 mmol) was added dropwise at roomtemperature to a solution of 7-methoxyisoquinoline (600 mg, 3.77 mmol) in dry THF (11 mL).After 4 h the reaction mixture was cooled to 0C, a solution of iodine (1.43 g, 5.65 mmol) indry THF (6.65 mL) was added dropwise and the resulting mixture stirred while warming to room temperature over 1 h. Sat. aq. NH4Cl (6 mL) and sat. aq. Na2S2O3 (6 mL) were addedand the organic materials extracted using DCM (3 x 50 mL). The combined organic layerswere dried over Na2SO4 and concentrated in vacuo. The resulting crude product was purifiedby flash column chromatography (EtOAc/hexanes 1:9) to give 1-iodo-7-methoxyisoquinoline(S1) (469 mg, 1.64 mmol, 44%) as a yellowish solid.

The synthetic route of 39989-39-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Kraus, Yvonne; Glas, Carina; Melzer, Benedikt; Gao, Li; Heise, Constanze; Preusse, Monique; Ahlfeld, Julia; Bracher, Franz; Thorn-Seshold, Oliver; European Journal of Medicinal Chemistry; vol. 186; (2020);,
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105627-79-0, Isoquinoline-5-sulfonyl chloride hydrochloride is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Preparation Example Homopiperazine (3.413 g) was dissolved in tetrahydrofuran (57 ml) with stirring. After cooling the solution to -5 C, 5-isoquinolinesulfonyl chloride hydrochloride (3.00 g) was added while maintaining the intemal temperature at 10 C or less. The mixture was stirred at 5 C or less for four hours. The reaction mixture was allowed to stand to reach room temperature and filtered to remove insoluble matter. The filtrate was concentrated under reduced pressure, followed by the addition of ethyl acetate (57 ml), water (17 ml), and 3 N hydrochloric acid aqueous solution (6.4 ml). The mixture was separated into layers to obtain a water layer. After washing the water layer with ethyl acetate (7 ml), water (6 ml), ethyl acetate (57 ml), and 6 N sodium hydroxide aqueous solution (3 ml) were added to separate the mixture into layers and obtain an organic layer. The organic layer was concentrated under reduced pressure and the residue was dried under reduced pressure to obtain fasudil (1.36 g). The yield was 41%. The fasudil is processed by the method described in JP-A-9-71582 to obtain fasudil hydrochloride. Fasudil can also be obtained in the same manner using the solvents listed below instead of tetrahydrofuran used in the Reference Preparation Example at yields described in the parentheses. Acetone (22%), acetonitrile (30%), 1,2-dimethoxyethane (31%), 2-butanone (24%), anisole (34%), isopropyl ether (10%), ethyl acetate (38%), toluene (18%), etc. Concentration of the filtrate was unnecessary when anisole, isopropyl ether, ethyl acetate, and toluene were used as the solvent.

The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Asahi Kasei Pharma Corporation; EP1726306; (2006); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23687-26-5,6-Aminoisoquinoline,as a common compound, the synthetic route is as follows.

Compound 7A (10.9 g, 25 mmol) at room temperature6-aminoisoquinoline (4.32 g, 30 mmol)And EDCI (6.68g, 35mmol)Add pyridine (100ml), nitrogen protection,Then DMAP (4-dimethylaminopyridine) (4.2 g, 35 mmol) was added,Reaction overnight,The reaction was monitored by TLC (DCM:MA=20:1) until the disappearance of starting compound 7A, evaporated to dryness under reduced pressure, 3 mol of acetic acid aqueous solution was adjusted to pH=4-5, extracted with DCM (100 ml*4), and combined to obtain compound 8. (11.02 g), yield 78percent; LC-MS (M+1) 566, purity: 97.4percent.

As the paragraph descriping shows that 23687-26-5 is playing an increasingly important role.

Reference£º
Patent; Shanghai Taoqin Bio-pharmaceutical Technology Co., Ltd.; Li Yu; (18 pag.)CN107434780; (2017); A;,
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23687-26-5, 6-Aminoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthetic Example 84b 6-(4-Chlorobenzenesulfonylamino)-1-cyanoisoquinoline The compound obtained using 6-aminoisoquinoline (0.5 g, Synthesis, 733 (1975)) and 4-chlorobenzenesulfonyl chloride (0.88 g) in the same method as in Synthetic Example 1b was dissolved in chloroform (150 ml). Under ice-cooling, m-chloroperbenzoicacid (0.9 g) was added theterto, followed by stirring at room temperature overnight. The solvent was evaporated, and the resulting crystals were washed with diethyl ether, collected by filtration and dried, to give 6-(4-chlorobenzenesulfonylamino)isoquinoline-N-oxide (1.072 g).

The synthetic route of 23687-26-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Eisai Co., Ltd.; EP1258252; (2002); A1;,
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486-73-7, Isoquinoline-1-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A. 1,2,3,4-Tetrahydro-1-isoquinolinecarboxylic acid A solution of 1-isoquinolinecarboxylic acid (1.67 g) in glacial acetic acid (25 ml,) was hydrogenated at 60 p.s.i. over PtO2 (270 mg). When the reaction was complete, the mixture was filtered through diatomaceous earth (Celite), washing the solid pad with MeOH, and the filtrate was concentrated to dryness. The resultant white solid was triturated with cold water and filtered to provide the title compound (775 mg).

486-73-7 Isoquinoline-1-carboxylic acid 68092, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; ProScript, Inc.; US5780454; (1998); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23687-26-5,6-Aminoisoquinoline,as a common compound, the synthetic route is as follows.

To trans-2-(4-((((3-fluorobenzyl)carbamoyl)oxy)methyl)phenyl)cyclopropane-1-carboxylic acid (E141) in pyridine were added EDC, DMAP and 6-aminoisoquinoline and the solution was stirred under N2, overnight at room temperature. The reaction mixture was poured into NaHC03 (saturated) and extracted with EtOAc, dried (Na2S04), filtered and evaporated. Column chromatography over silica gel eluting with 4percent MeOH-CH2CI2 gave pure trans-4-(2-(isoquinolin-6-ylcarbamoyl)cyclopropyl)benzyl (3-fluorobenzyl)carbamate (E142).

23687-26-5 6-Aminoisoquinoline 588991, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; AERIE PHARMACEUTICALS, INC.; DELONG, Mitchell, A.; STURDIVANT, Jill, M.; LICHOROWIC, Cynthia, L.; KORNILOV, Andriy; (186 pag.)WO2018/183911; (2018); A1;,
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27810-64-6, Isoquinoline-5-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A round bottom flask was charged with isoquinoline-5-carboxylic acid (50 mg, 0.29 mmol, 1.05 eq) suspended in SOCl2 (2 mL). After addition of 3 drops of DMF the reaction was heated to 70C for 60 min and excess SOCl2 was removed under reduced pressure. The resulting solid was re-dissolved in DCM (3 mL) and after addition of DiPEA (140 muL, 0.41 mmol, 3 eq) a solution of tert-butyl(E)-(2-aminoethyl)(3-(4-(pyridin-3-yl)phenyl) allyl) carbamate (63) (97 mg, 0.275 mmol, 1 eq) and DMAP (3 mg, 0.03 mmol, 0.1 eq) dissolved in DCM (5 mL) was added dropwise at 0C. The reaction mixture was allowed to warm up to RT. After 75 min half saturated aqueous NaHCO3 solution (10 mL) was added, the mixture was extracted with DCM (3×15 mL), the combined organic layers were washed with brine (1×40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified via flash-column-chromatography (SiO2, 0% to 15% MeOH in DCM) to yield the product (57 mg, 41%). 1H NMR (400 MHz, chloroform-d) delta 9.26 (s, 1H), 8.85 (s, 1H), 8.62 – 8.51 (m, 2H), 8.36 – 8.16 (m, 1H), 8.03 (d, J = 8.2 Hz, 1H), 7.88 (d, J = 7.7 Hz, 2H), 7.62 – 7.33 (m, 7H), 6.55 (d, J = 15.9 Hz, 1H), 6.32 – 6.19 (m, 1H), 4.09 (bs, 2H), 3.73 (d, J = 5.3 Hz, 2H), 3.62 (bs, 2H), 1.41 (s, 9H). 13C NMR (101 MHz, chloroform-d) delta 168.47, 157.28, 152.82, 148.61, 148.18, 144.24, 137.20, 136.37, 136.16, 134.26, 133.35, 132.83, 131.68, 130.61, 129.46, 128.84, 127.45, 127.21, 126.24, 125.80, 123.73, 118.58, 80.77, 50.08, 45.59, 40.30, 28.42. LCMS (ESI, Thermo, C18, linear gradient, 10% to 90% ACN in H2O, 0.1% TFA, 10.5 min): tR = 4.67 min; m/z : 509 [M+H]+.

The synthetic route of 27810-64-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Grimm, Sebastian H.; Gagestein, Berend; Keijzer, Jordi F.; Liu, Nora; Wijdeven, Ruud H.; Lenselink, Eelke B.; Tuin, Adriaan W.; van den Nieuwendijk, Adrianus M.C.H.; van Westen, Gerard J.P.; van Boeckel, Constant A.A.; Overkleeft, Herman S.; Neefjes, Jacques; van der Stelt, Mario; Bioorganic and Medicinal Chemistry; vol. 27; 5; (2019); p. 692 – 699;,
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58-74-2, 1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE II Preparation of 6,7-Dimethoxy-1-[(alpha-piperidinomethyl)-veratryl]isoquinoline dihydrochloride (P3138) A mixture of 10.2 g (0.03 mole) of papaverine, 1.2 g (0.04 mole) of paraformaldehyde, 4.9 g (0.04 mole) of piperidine hydrochloride and 150 ml of ethyl alcohol were heated at reflux for 7 hours. The solvent was removed from the reaction mixture by evaporation and the residue dissolved in 100 ml of water. The solution was made basic (pH of 10) by addition of 50 percent aqueous sodium hydroxide solution and the resulting mixture extracted with two 100 ml portions of benzene. The benzene extracts were combined and washed with two 100 ml portions of water and finally with 100 ml of aqueous saturated sodium chloride solution. The benzene layer was evaporated and the residue dissolved in 250 ml of acetone. The dihydrochloride salt of the product was precipitated by the addition of hydrogen chloride.

As the paragraph descriping shows that 58-74-2 is playing an increasingly important role.

Reference£º
Patent; Armour Pharmaceutical Company; US3966724; (1976); A;,
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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.

Step 1) (S)-3-(1-aminoethyl)-2-phenyl-8-(prop-1-yn-1-yl)isoquinolin-1(2H)-one To a mixture of (S)-3-(1-aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one (1.5 g, 5.0 mmol) (See the synthetic method of step 1-2 of example 8 in WO2015042078) in DMAC (10 mL) was added Cs2CO3 (2.5 g, 7.7 mmol), PdCl2(PCy3)2(0.38 g, 0.51 mmol). The mixture was purged with N2, then propyne (21 mL, 15 mmol, 3-6% in n-heptane) was added, and the mixture was sealed and heated at 110 C. for 5.5 h. Then the mixture was cooled down to room temperature, added EtOAc (150 mL) and water (30 mL). The organic layer was separated and washed with saturated brine (50 mL*5), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc/TEA (v/v/v)=1/10/0.5) to give the title compound as a yellow solid (0.81 g, 53%). MS (ESI, pos.ion) m/z: 303.2 [M+H]+; 1H NMR (600 MHz, CDCl3) delta (ppm): 7.60-7.58 (m, 4H), 7.48 (dd, J=15.3, 7.9 Hz, 2H), 7.42 (d, J=7.7 Hz, 1H), 7.34 (d, J=7.4 Hz, 1H), 6.76 (s, 1H), 3.76-3.70 (m, 1H), 2.13 (s, 3H), 1.30 (d, J=6.5 Hz, 3H). 13C NMR (151 MHz, CDCl3) delta (ppm): 162.5, 138.0, 134.1, 131.6, 129.8, 129.7, 129.4, 129.0, 128.9, 125.6, 125.1, 124.7, 102.3, 92.8, 79.9, 46.9, 23.0, 5.4.

As the paragraph descriping shows that 1350643-72-9 is playing an increasingly important role.

Reference£º
Patent; Sunshine Lake Pharma Co., Ltd.; Calitor Sciences, LLC; Xi, Ning; Wang, Liang; Feng, Xuejin; Liao, Min; (88 pag.)US2019/224197; (2019); A1;,
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66728-98-1, 4-Bromo-1-chloroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4a) 1-Chloro-[4,7′]biisoquinolinyl A solution of 4-BROMO-1-CHLOROISOQUINOLINE (see Example 2d) (5.0 g, 20.7 MMOL) in 150 mL THF is cooled TO-78C. A solution of n-BuLi (1.6 M in hexanes) (15 mL, 24 MMOL) is added dropwise and the reaction temperature is maintained AT-78C–68C. The reaction mixture is kept stirring AT-78C for 30 minutes. ZNBR2 (dried under vacuum at 80C) (6.5 g, 24.9 MMOL) is dissolved in 50 mL THF and is transferred to above mixture slowly AT-78C. The solution is stirred 40 minutes AT-78C, then warmed to room temperature by removing the cooling bath. Pd (PPh3) 4 (2.4 g, 2.1 mmol is added followed by TRIFLUOROMETHANESULFONIC acid ISOQUINOLIN-7-YL ESTER- (5.7 G, 20. 7 MMOL) in 50 mL THF. The reaction mixture is heated to 60C for 30 minutes and is then concentrated. The resulting oil is dissolved in dichloromethane and washed with saturated NAHCO3. ORGANIC phase is separated, dried (MgS04) and concentrated to give a yellow solid. The solid is collected by filtration, washed with ether then hexane and dried under vacuum. 5.68 G (94%) yellow solid is obtained. m. p. 169.0-169. 6C. H NMR (400 MHz, DMSO-d6) d 9.44 (s, 1 H) ; 8.61 (d, 1 H, J=5.6 Hz); 8.45-8. 43 (m, 1H) ; 8.40 (s, 1H) ; 8.34 (s, 1H) ; 8.18 (d, 1H, J=8.1 Hz); 7.97-7. 90 (m, 5H) ppm. API-MS, m/z 291. 14 ([M+H]+, calcd. 291.06).

66728-98-1 4-Bromo-1-chloroisoquinoline 459766, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/28444; (2005); A1;,
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