Category: 23687-26-5

23687-26-5, 6-Aminoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 41 – Synthesis of Compound 62; 1. 200 mg (1.35 mmol) of 6-aminoisoquinoline were disolved in 20 ml ofacetonitrile. 239,568 mg (1 ,35 mmol) of N-bromsuccinimide was added. The reaction mixture was stirred for 4 h at room temperature. The reaction mixture was evaporated and dichloromethane was added. The organic phase was washed with water and dried. 224 mg of 5-brromo-isoquinolin-6-ylamine were obtained; HPLC/MS (B) 1.00 min, [M+H] 224.

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

Reference£º
Patent; MERCK PATENT GMBH; DORSCH, Dieter; JONCZYK, Alfred; HOELZEMANN, Guenter; AMENDT, Christiane; ZENKE, Frank; WO2012/595; (2012); A1;,
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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

Reference Example 2Synthesis of 6-chlorosulfonylisoquinoline (Reference Compound 2)4.0 g of 6-aminoisoquinoline (Reference Compound 1) was suspended at 0¡ã C. in 40 mL of concentrated hydrochloric acid (35percent).To the suspension, 4.0 g of sodium nitrite was added in small portions, and the mixture was stirred for 30 minutes.This reaction solution was added dropwise at 0¡ã C. to a mixed solution of 20 mL of acetic acid saturated with sulfite gas generated from sodium bisulfite and sulfuric acid, and 298 mg of copper chloride, and the mixture was stirred for 1 hour.The mixture was neutralized by the addition of a saturated aqueous solution of sodium bicarbonate, followed by extraction with dichloromethane (100 mL*2).The organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate.The obtained dichloromethane solution was used in the next reaction without being further purified because the compound of interest was unstable., 23687-26-5

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

Reference£º
Patent; D. WESTERN THERAPEUTICS INSTITUTE, INC; US2012/35159; (2012); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

23687-26-5, 6-Aminoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

K3P04 (0.481 g, 2.264 mmol), Pd2(dba)3 (0.043 g, 0.0472 mmol) and Xantphos (0.045 g, 0.0786 mmol) were added to a solution of intermediate 6 (0.127 g, 0.786 mmol) in THF (6 mL) while nitrogen was bubbling. After 10 min, isoquinolin-6-amine (0.125 g, 0.865 mmol, CAS 23687-26-5) was added and the mixture was stirred at rt for 10 min. Then, the mixture was heated at 90 ¡ãC for 16 h. After cooling to rt, the mixture was washed with sat. NaHC03 and extracted with EtOAc. The organic layer was dried over MgS04, filtered and the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in heptane from 5/95 to 100/0). The desired fractions were collected and concentrated in vacuo. The product was purified by preparative HPLC ((from 59percent H20 (25 mM NH4HC03) – 41 percent MeCN- MeOH to 17percent H20 (25 mM NH4HC03) – 83percent MeCN-MeOH). The desired fractions were collected and concentrated in vacuo. The product was triturated with n-pentane to yield compound 4 as a beige solid (0.075 g, 34percent). NMR (300 MHz, (0207) CHLOROFORM- ) delta ppm 5.69 (d, J=54.6 Hz, 2 H) 6.80 (br s, 1 H) 7.00 (d, J=8.9 Hz, 1 H) 7.39 – 7.47 (m, 1 H) 7.54 (d, J=5.8 Hz, 1 H) 7.89 (d, J=8.8 Hz, 1 H) 7.97 (s, 1 H) 8.22 (d, J=2.1 Hz, 1 H) 8.43 (d, J=5.8 Hz, 1 H) 9.09 (s, 1 H)

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

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; ANDRES-GIL, Jose, Ignacio; BORMANS, Guy, Maurits, R.; DECLERCQ, Lieven, Denis, Herwig; FIERENS, Katleen; LEENAERTS, Joseph, Elisabeth; MOECHARS, Diederik, Willem, Elisabeth; ROMBOUTS, Frederik, Jan, Rita; KOLB, Hartmuth; ZHANG, Wei; (67 pag.)WO2018/15307; (2018); A1;,
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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

A 5 mL microwave reaction vial was charged with methyl 2-(4-ethynylphenoxy)acetate, 1-(azidomethyl)-4-chlorobenzene, t-BuOH, copper turnings and copper sulfate. The reaction was heated under microwave conditions at 125¡ã C. for 25 minutes. The reaction was cooled to room temperature and poured into water. The reaction was extracted with CH2Cl2. The combined organic layers were washed with water, dried (Na2SO4), filtered and concentrated. Flash chromatography (SiO2, Hexanes/EtOAc) gave 2-(4-(1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)phenoxy)-N-(isoquinolin-6-yl)-acetamide (E148).

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

Reference£º
Patent; AERIE PHARMACEUTICALS, INC.; US2008/167340; (2008); 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.

Preparation Example 21 6-(4-Toluenesulfonylamino) isoquinoline In pyridine (30 ml) was dissolved 6-aminoisoquinoline (3.348 g, Synthesis, 733 (1975), and 4-toluenesulfonyl chloride (5.13 g) was added thereto, followed by stirring at room temperature overnight. Water was added thereto, followed by extracting with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was recrystallized from ethanol, to give the title compound (5.958 g, 85%) as pale yellow crystals. 1H-NMR (DMSO-d6) delta (ppm): 2.28 (3H, s), 7.32 (2H, d, J=8.2 Hz), 7.40 (1H, dd, J=1.6, 9.2 Hz), 7.55 (1H, brs), 7.67 (1H, d, J=5.6 Hz), 7.74 (2H, d, J=8.2 Hz), 7.97 (1H, d, J=9.2 Hz), 8.36 (1H, d, J=5.6 Hz), 9.10 (1H, s)., 23687-26-5

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

Reference£º
Patent; Haneda, Toru; Tsuruoka, Akihiko; Kamata, Junichi; Okabe, Tadashi; Takahashi, Keiko; Nara, Kazumasa; Hamaoka, Shinichi; Ueda, Norihiro; Wakabayashi, Toshiaki; Funahashi, Yasuhiro; Semba, Taro; Hata, Naoko; Yamamoto, Yuji; Ozawa, Yoichi; Tsukahara, Naoko; Owa, Takashi; US2003/144507; (2003); 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.23687-26-5,6-Aminoisoquinoline,as a common compound, the synthetic route is as follows.

To 6-aminoisoquinoline in DMF at 0¡ã C. is added NaH. After 30 min, chlorosulfonyl chloride is added to the reaction. After 2-4 hours at rt or when TLC indicates completion, the reaction is quenched by the addition of water and extracted with EtOAc. The combined organics are washed with brine and dried (Na2SO4), filtered and evaporated. Column chromatography (SiO2, 5percent MeOH/CH2Cl2) gives 1-chloro-N-(isoquinolin-6-yl) methanesulfonamide., 23687-26-5

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

Reference£º
Patent; AERIE PHARMACEUTICALS, INC.; US2008/167340; (2008); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

23687-26-5, 6-Aminoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 6 (50 mg, 0.148 mmol), Isoquinolin-6-ylamine (26 mg, 0.178 mmol), tris(dibenzylideneacetone)dipalladium(0) (8 mg, 0.009 mmol), xantphos (7 mg, 0.012 mmol) and sodium tert-butoxide (43 mg, 0.44 mmol) were combined with dioxane (3 ml), sealed and then purged with nitrogen gas. The reaction mixture was heated at 1050C for 18 h, evaporated and purified through a silica plug, eluting with 0 to 10percent methanol/DCM. Further purification by preparative LCMS (high pH buffer) gave the desired product as a white solid (15 mg, 23percent). 1H NMR (400 MHz, DMSO-^6) delta ppm 0.42 – 0.50 (m, 2 H), 0.78 – 0.86 (m, 2 H), 1.41 – 1.52 (m, 1 H), 1.71 – 1.81 (m, 2 H), 3.24 – 3.31 (m, 2 H), 3.36 – 3.45 (m, 2 H), 6.81 – 6.89 (m, 1 H), 7.13 (dd, 7=4.8, 3.9 Hz, 1 H), 7.54 – 7.63 (m, 2 H), 7.70 – 7.76 (m, 3 H), 8.02 (d, /=6.4 Hz, 1 H), 8.24 (dd, /=7.8, 0.9 Hz, 1 H), 8.43 (d, /=6.0 Hz, 1 H), 8.48 – 8.55 (m, 1 H), 8.90 (s, 1 H), 9.23 (s, 1 H); m/z (ES+APCI)+: 445 [M+H]+.

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

Reference£º
Patent; MEDICAL RESEARCH COUNCIL; WO2009/122180; (2009); 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.23687-26-5,6-Aminoisoquinoline,as a common compound, the synthetic route is as follows.

EXAMPLE II N-(2-Hydroxyethyl)-N’-(isoquinolin-6-yl)-N-[4-[2-(methoxycarbonyl)ethyl]phenyl]-urea To 7.2 g of imidazole and 10.1 g of N,N’-carbonyldiimidazole in 100 ml of dimethylformamide are added dropwise, at a temperature of 0¡ã to 10¡ã C., 9.0 g of 6-aminoisoquinoline in 70 ml of dimethylformamide. After 2 hours stirring at ambient temperature, 15.3 g of N-(2-hydroxyethyl)-4-[2-(methoxycarbonyl)ethyl]aniline in 20 ml of dimethylformamide are added dropwise and the mixture is stirred for 21/2 days at ambient temperature. The mixture is diluted with 750 ml of ethyl acetate and extracted twice with water and saturated saline solution. The organic phase is separated off, dried and evaporated down. The residue is purified by chromatography over a silica gel column using ethyl acetate/methylene chloride/methanol=70:30:10. Yield: 4.8 g (19percent of theory), Rf value: 0.48 (silica gel; methylene chloride/methanol/ethyl acetate=20:1:1), 23687-26-5

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

Reference£º
Patent; Karl Thomae GmbH; US5519036; (1996); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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.

A mixture of 2 (340.41 g assay-corrected, 1.0 equiv.), collidine (1.3 equiv.) and 6-aminoisoquinoline (1.3 equiv.) in DMF at 0¡ã C. in a 50 L reactor was treated rapidly with a solution of 2,2,2-trichloro-1 , 1 -dimethylethyl chloroformate (1.3 equiv.) in DMF in a single portion. The reaction was exothermic, with a rise in temperature to about 10¡ã C. Upon stirring for a minimum of 60 minutes, the reaction was assayed by TLC and deemed complete when two samples taken one hour apart showed no further conversion. Thereaction was quenched by the addition of 10percent KHCO3 (aq.), followed by diluting with ethyl acetate, washing with citric acid, a final 10percent KHCO3 (aq.) wash and concentrating to near dryness to afford a crude residue.The crude residue was dissolved in dichloromethane/ethylacetate (1:1) and the resulting solution returned to the 50 Lreactor, where it was stirred for 4.5 h. The resulting solution was filtered through a 10 jim Teflon filter to remove a colloidal solid. The selection of a 10 jim Teflon filter was based on the filter having enough surface area and beingchemically compatible with the dichloromethane/ethyl acetate (1:1) solvent mixture. Concentration of the filtrate in vacuo yielded 666.3 g of crude material.The resulting crude product was diluted with dichloromethane to give a solution that was divided into two portions for silica gel chromatography. The splitting of the dichloromethane solution maintained a 25:1 ratio of silicagel to crude product found to be useful for successful 41Fractions containing a high concentration of the desired material, irrespective of the impurities content, were combined and concentrated to afford 363.3 g of an off-white solid.The off-white solid was dissolved in dichloromethane and filtered through a 10 tm Teflon filter. The bulk of the solvent was then distilled off and the remainder gradually switched to acetonitrile via chase distillation. At this point, a white solid crystallized and the mixture was cooled to 0¡À5¡ã C. Thesolid was isolated by filtration and dried to obtain 333.7 g ofa white solid. A sample of the solid was subjected to TLCand HPLC purity analyses. No impurities could be detected by TLC, but the HPLC analysis showed the presence of an unspecified impurity at a level of 0.4 6percent while all identified impurities were below In-Process Action Levels.A first recrystallization from dichloromethane/heptane was then implemented. Afier dissolving the solid in dichloromethane, heptane was added and the resulting mixture stirred for 4 hat room temperature. A white solid crystallized out. The solid was filtered and dried to obtain 307.0 g of the solid. A sample of the solid was taken and subjected to TLC and HPLC purity analyses. No impurities could be detected by TLC, but the HPLC analysis showed the presence of the same unspecified impurity, but was reduced to a level of0.28percent.2025purification. The two portions of dichloromethane solution represented 166.5 g and 170.2 g of the crude product respectively. The purifications were achieved through theuse of two 5 kg silica gel colunms eluting with ethyl acetate/heptane (60:40) until the desired product had eluted.white solid was filtered and dried to obtain the title compound as a white solid (272.1 g; 60.5percent assay-correctedA fourth recrystallization from dichloromethane/heptane was utilized. After dissolving the solid in dichloromethane, heptane was added and the resulting mixture stirred for 4 h at room temperature during which time a white solid crystallized out. The white solid was filtered, dried, and sub-jected to HPLC purity testing. The impurity was detected at less than 0.05percent. The fourth recrystallization from dichloromethane/heptane yielded 250.9 g (55.3percent assay corrected yield) of the title compound as a white solid.To achieve even higher purities of the desired product, it may be useful to implement additional recrystallizations. ?H NMR (500 MHz, d5-DMSO) oe 1.32 (s, 9H), 2.29 (s, 3H), 2.49 (s, 3H), 3.3 (m, 1H), 3.56 (m, 1H), 4.11 (m, 1H), 5.25 (s, 2H), 7.02 (bt, J=5.4 Hz, 1H), 7.07 (d, J=8.4H, 1H), 7.11(s, 1H), 7.43 (s, 4H), 7.68 (m, 2H), 7.75 (d, J=7.9 Hz, 1H),8.02 (d, J=8.7 Hz, 1H), 8.38 (s, 1H), 8.39 (d, J=5.7 Hz, 1H),9.14 (s, 1H). 13C NMR (125 MHz, d5-DMSO) oe 20.8, 21.2,28.2, 42.9, 51.7, 65.6, 77.8, 113.1, 120.0, 121.0, 125.0,126.1, 126.6, 128.0, 128.1, 128.5, 130.4, 132.3, 135.2,136.1, 137.8, 139.5, 140.4, 142.4, 143.2, 151.5, 155.8,166.4, 171.0. LC-MS (ES+): mlz=554 (M+1), 576 (M+23).yield).

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

Reference£º
Patent; Aerie Pharmaceuticals, Inc.; Sturdivant, Jill M.; deLong, Mitchell A.; Chambournier, Gilles; Pamment, Michael G.; Fedij, Victor; (31 pag.)US9643927; (2017); B1;,
Isoquinoline – Wikipedia
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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

To (S)-3-[(tert-butoxycarbonyl)amino)]-2-(4-{[(2,4-dimethylbenzoyl) oxy]methyl}phenyl)propanoic acid (8) (2.3 g, 5.5 mmol) in DMF (33 mL) cooled to 0 ¡ãC was added 6-aminoisoquinoline (1.0 g, 7.1 mmol) and 2,4,6-trimethylpyridine (947 muL, 7.1 mmol). After 10 min at 0 ¡ãC, a solution of 2,2,2-trichloro-1,1-dimethylethyl chloroformate (1.7 g, 7.1 mmol) in DMF (8.6 mL) was added and the reaction stirred at 0 ¡ãC for 2 h. The mixture was poured into NaHCO3 (sat.)/EtOAc and extracted with EtOAc. The organic layers were then washed with NaCl (sat.), dried (Na2SO4) filtered and evaporated. Column chromatography (70percent EtOAc/hexanes) gave pure (S)-4-{3-[(tert-butoxycarbonyl) amino]-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl}benzyl 2,4-dimethylbenzoate (9) (1.93 g, 63percent, 98percent ee) as a off-white solid. Recrystallization from EtOAc/hexanes gave 9 (1.43 g, 47percent, 99.7percent ee, S,SWhelk-01) as a off-white crystalline solid. Mp 155-156 ¡ãC. IR (ATR): 1713, 1644, 1527 cm-1. 1H NMR (500 MHz, DMSO-d6): delta = 9.14 (s, 1H), 8.39 (d, J = 5.7 Hz, 1H), 8.38 (s, 1H), 8.02 (d, J = 8.7 Hz, 1H), 7.75 (d, J = 7.9 Hz, 1H), 7.69- 7.66 (m, 2 H), 7.43 (s, 4 H), 7.11 (s, 1H), 7.07 (d, J = 8.4 Hz, 1H), 7.02 (br t, J = 5.4 Hz, 1H), 5.25 (s, 2 H), 4.13-4.10 (m, 1H), 3.58-3.53 (m, 1H), 3.34-3.30 (m, 1H), 2.49 (s, 3 H), 2.29 (s, 3 H), 1.32 (s, 9 H). 13C NMR (125 MHz, DMSO-d6): delta = 171.0, 166.4, 155.8, 151.5, 143.2, 142.4, 140.4, 139.5, 137.8, 136.1, 135.2, 132.3, 130.4, 128.5, 128.1, 128.0, 126.6, 126.1, 125.0, 121.0, 120.0, 113.1, 77.8, 65.6, 51.7, 42.9, 28.2, 21.2, 20.8. LC-MS (ES+): m/z = 554 [M + 1]+, 576 [M + 23]+. Anal Calcd for C33H35N3O5: C, 71.59; H, 6.37; N, 7.59. Found: C, 71.54; H, 6.51; N, 7.58.

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

Reference£º
Article; Delong, Mitchell A.; Sturdivant, Jill M.; Synthesis; vol. 51; 4; (2019); p. 953 – 959;,
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