Category: isoquinoline

106778-42-1, Isoquinoline-6-carbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation Example G-1. Isoquinoline-6-carboxylic acid A solution prepared by adding (4-bromobenzylydene)-(2,2-diethoxyethyl) amine (synthesized from 4-bromobenzaldehyde, according to the method described in J. Org. Chem., vol. 48, 3344-3346 (1983)) (51.4g, 0.189mmol) to an ice-cold concentrated sulfuric acid (20g) was added to a solution prepared by adding diphosphorus pentoxide (40g) to an ice-cold concentrated sulfuric acid (360g), and the solution was stirred at 160C for 2 hours. The reaction solution was gradually cooled to 0C, the solution was filtered through Celite pad, the filtrate was neutralized with sodium carbonate. This solution was further filtrated through Celite pad, this filtrate was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate), and 6-bromoisoquinoline (482mg, 1.2%) was obtained as an orange oil. Next, to a solution of 6-bromoisoquinoline (382mg, 1.84mmol) in N,N-dimethylformamide (3.8mL) were added zinc cyanide (431 mg, 3.67mmol) and tetrakis(triphenylphosphine)palladium(0) (42mg, 0.0367mmol) under nitrogen atmosphere, and the mixture was stirred at 100C for 1 hour. Tetrakis(triphenylphosphine)palladium(0) (42mg, 0.0367mmol) was further added, and the mixture was stirred for 2.5 hours at 100C. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for extraction, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (hexane : ethyl acetate), and isoquinoline-6-carbonitrile (234mg, 83%) was obtained as a yellow solid. Lastly, isoquinoline-6-carbonitrile (51mg, 0.331 mmol) was dissolved in diethyleneglycol (1.0mL), potassium hydroxide (9mg, 0.166mmol) was added thereto, followed by stirring at 160C for 3 hours. The reaction mixture was allowed to room temperature, neutralized using hydrochloric acid, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, then, the solvent was evaporated. Water was added to the residue, the precipitated solid was collected, washed with water, dried in vacuo, so as to obtain the title compound (12mg, 21 %) as a yellow solid.

As the paragraph descriping shows that 106778-42-1 is playing an increasingly important role.

Reference£º
Patent; Eisai R&D Management Co., Ltd.; EP1782811; (2007); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

34784-02-6, 3-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A suspension of 6-(l-cyclobutylpiperidin-4-yloxy)-3,4-dihydroquinolin-2(lH)-one synthesized in Example 4-(l) (0.10 g), 3-bromoisoquinoline (0.10 g), rac-trans-N,N’- dimethylcyclohexane-l,2-diamine (0.047 g), copper iodide (0.016 g) and cesium carbonate (0.22 g) in toluene (1 mL) was stirred at 1100C for 3 hours. The reaction mixture was cooled to room temperature, diluted with chloroform and filtered to remove insoluble materials. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: hexane/ethyl acetate = 4/1 to 1/4) and OH-type preparative TLC (on two plates of 1 mm thickness, developing solvent: chloroform/methanol = 4/1) to give the titled compound (0.061 g, 44%) as a colorless amorphous substance.1H NMR (600 MHz, CHLOROFORM-d) delta ppm 1.54-2.24 (m, 12 H), 2.54-2.80 (m, 3 H), 2.82-2.91 (m, 2 H), 3.04-3.12 (m, 2 H), 4.17-4.31 (m, 1 H), 6.30 (d, J=8.7 Hz, 1 H), 6.57 (dd, J=8.7, 2.8 Hz, 1 H), 6.83 (d, J=2.8 Hz, 1 H), 7.56-7.64 (m, 1 H), 7.74-7.81 (m, 1 H), 7.84 (d, J=8.3 Hz, 1 H), 8.10-8.22 (m, 2 H), 8.74 (d, J=2.3 Hz, 1 H)MS (ESVAPCI Dual) (Positive) m/z; 428(M+H)+

As the paragraph descriping shows that 34784-02-6 is playing an increasingly important role.

Reference£º
Patent; TAISHO PHARMACEUTICAL CO., LTD.; NAKAMURA, Toshio; MASUDA, Seiji; FUJINO, Aya; WO2010/90347; (2010); 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.90806-60-3,5-Methoxyisoquinoline-1-carbonitrile,as a common compound, the synthetic route is as follows.

[00244] Cap-138, Step c (0.45 g, 2.44 mmol) was treated with 5N sodium hydroxide solution (10 mL) and the resulting suspension was heated at 85 C for 4 h, cooled to 25 C, diluted with dichloromethane and acidified with IN hydrochloric acid. The organic phase was separated, washed with brine, dried over Na2S04, concentrated to ? volume and filtered to afford Cap-138 as a yellow solid (0.44g, 88.9%). XH NMR (DMSO-d6, 400 MHz) delta 13.6 (br s, 1H), 8.56 (d, J= 6.0 Hz, 1H), 8.16 (d, J = 6.0 Hz, 1H), 8.06 (d, J = 8.8 Hz, 1H), 7.71-7.67 (m, 1H), 7.30 (d, J= 8.0 Hz, 1H), 4.02 (s, 3H); Rt = 0.70 min (Cond.-Dl); 95% homogenity index; LC-MS: Anal. Calc. for [M+H]+ CnH10NO3:204.07; found: 204.05.

As the paragraph descriping shows that 90806-60-3 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BELEMA, Makonen; ROMINE, Jeffrey, Lee; NGUYEN, Van, N.; WANG, Gan; LOPEZ, Omar, D.; ST. LAURENT, Denis, R.; CHEN, Qi; BENDER, John, A.; YANG, Zhong; HEWAWASAM, Piyasena; XU, Ningning; MEANWELL, Nicholas, A.; EASTER, John, A.; SU, Bao-Ning; SMITH, Michael, J.; WO2011/75439; (2011); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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.

As the paragraph descriping shows that 105627-79-0 is playing an increasingly important role.

Reference£º
Patent; Asahi Kasei Pharma Corporation; EP1726306; (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.1196-38-9,3,4-Dihydroisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

3,4-Dihydroisoquinolin-1(2H)-one (190 mg, 1.28 mmol, 1.0 equiv) was dissolved in dry THF (15 mL) and POCl3 (0.15 mL, 1.54 mmol, 1.2 equiv) added at 60 ¡ãC. The mixture was stirred under Ar atmosphere for 40 min. Methyl 2-aminobenzoate (340 mg, 2.25 mmol, 1.8 equiv) was dissolved in dry THF (3 mL) and added dropwise to the reaction mixture over 5 min. The temperature was increased to 75 ¡ãC and the solution stirred for 113 h. The solution was cooled to rt and 25percent NH3 solution (6 mL) was added until the aqueous phase reached pH=9. The yellow mixture was stirred vigorously for 30 min. The mixture was extracted with CH2Cl2 (4*50 mL), washed with brine and the combined organic layers were dried over Na2SO4. Evaporation of solvent yielded 0.38 g of crude product. Parts of the crude product (220 mg) were purified by column chromatography (SiO2, 30*2 cm, petrolether/ethyl acetate 2:1, F 8-15) to yield off-white crystals (84.7 mg, 0.302 mmol, 24percent). Rf=0.50 (SiO2, petrolether/ethyl acetate 2:1). Mp=158.0-158.7 ¡ãC. 1H NMR (400 MHz, CDCl3, 300 K): delta=8.56-8.41 (m, 1H, Ar-HD-ring), 8.42-8.24 (m, 1H, Ar-HA-ring), 7.86-7.63 (m, 2H, Ar-HA-ring), 7.54-7.41 (m, 3H, Ar-HD-ring (2H) and Ar-HA-ring (1H)), 7.33-7.25 (m, 1H, Ar-HD-ring), 4.47-4.37 (m, 2H, NCH2CH2), 3.11 (t, J=6.4 Hz, 2H, NCH2CH2) ppm. 13C{1H} NMR (101 MHz, CDCl3, 300 K): delta=161.85 (s, C=O), 149.51 (s, Cquart.), 147.97 (s, C=N), 137.19 (s, Cquart.), 134.35 (Ar-CA-ring), 131.84 (Ar-CA-ring), 129.74 (s, Cquart.), 128.18 (Ar-CD-ring), 127.77 (2 Ar-CA-ring), 127.64 (Ar-CD-ring), 127.01 (Ar-CD-ring), 126.66 (Ar-CD-ring), 120.91 (s, Cquart.), 39.76 (s, NCH2CH2), 27.63 (s, NCH2CH2) ppm. IR: nu=3070w, 3031w, 2928w, 2901w, 2850w, 2359w, 2120w, 1921w, 1668s, 1608m, 1589s, 1557s, 1470s, 1457s, 1395s, 1334s, 1308m, 1265m, 1253m, 1173m, 1149s, 1108m, 1065w, 1030w, 1013w, 980m, 958w, 947m, 905m, 876m, 840m, 795w, 760s, 737s, 705s, 691s, 669m cm-1. HPLC: Synergi 4U fusion-RP (15*0.46 cm), water/methanol (30-95percent), 1.00 mL/min, 20 ¡ãC, tR=9.917 min, purity>99.99percent. Mass: calcd for [M+H]+ (C16H13N2O) requires m/z: 249.10; found: 249.05. Spectral data is in accordance with literature data. 24

1196-38-9 3,4-Dihydroisoquinolin-1(2H)-one 150896, aisoquinoline compound, is more and more widely used in various.

Reference£º
Article; Wehle, Sarah; Espargaro, Alba; Sabate, Raimon; Decker, Michael; Tetrahedron; vol. 72; 20; (2016); p. 2535 – 2543;,
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

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.80278-67-7,Isoquinoline-5-carbaldehyde,as a common compound, the synthetic route is as follows.

General procedure: To a dried two-neck round-bottom flask containing DMF (0.7mL for 1.10mmol of starting material) chilled in an ice bath, POCl3 (1.95 equiv) was added slowly. After stirring for 20min, a solution of an indole derivative (1.0 equiv) in DMF (3mL for 1.10mmol of starting material) was added dropwise. The reaction was allowed to warm to room temperature and allowed to stir for 1.5h. The reaction was quenched by adding ice followed by 1N NaOH (40mL) dropwise in an ice bath. The crude mixture was allowed to stand at room temperature and the precipitate formed was filtered to afford the 3-formyl-indole derivative product.

As the paragraph descriping shows that 80278-67-7 is playing an increasingly important role.

Reference£º
Article; See, Cheng Shang; Kitagawa, Mayumi; Liao, Pei-Ju; Lee, Kyung Hee; Wong, Jasmine; Lee, Sang Hyun; Dymock, Brian W.; European Journal of Medicinal Chemistry; vol. 156; (2018); p. 344 – 367;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

80278-67-7, Isoquinoline-5-carbaldehyde is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a dry sealed tube, intermediate 12e (92?mg, 0.530?mmol, 1.0 equiv) and isoquinoline-5-carboxaldehyde (83?mg, 0.530?mmol, 1.0 equiv) was dissolved in anhydrous acetonitrile (3?mL). Tributylphosphine (301?muL, 244?mg, 1.195?mmol, 2.25 equiv) was added and the sealed reaction was heated at 90?¡ãC in an oil bath for 22?h, protected from light. After the reaction was allowed to cool to room temperature, the solvent was removed under vacuum. The crude material was washed with methanol and diethyl ether to afford 21 as a yellow precipitate which was filtered and dried under vacuum (40?mg, 0.148?mmol). Yield 28percent. HPLC RT 12.20?min; HPLC purity 98.96percent. 1H NMR (400?MHz, Acetone-d6) delta: 10.57 (s, 1H), 9.28 (d, J?=?0.8?Hz, 1H), 8.56 (d, J?=?6.0?Hz, 1H), 8.22 (d, J?=?6.0?Hz, 1H), 8.17-8.11 (m, 2H), 7.98 (d, J?=?8.2?Hz, 1H), 7.90 (d, J?=?16.2?Hz, 1H), 7.78 (d, J?=?2.5?Hz, 1H), 7.69 (t, J?=?7.7?Hz, 1H), 7.62 (d, J?=?16.2?Hz, 1H), 7.53-7.47 (m, 1H), 7.29-7.14 (m, 2H). 13C NMR (100?MHz, Acetone-d6) delta: 154.07, 151.28, 147.70, 143.48, 138.48, 136.75, 129.59, 128.49, 127.67, 126.60, 124.40, 123.17, 121.19, 120.89, 116.74, 116.54, 115.67, 112.82. LC-MS (ESI): m/z 272.1 [M + H]+.

80278-67-7 Isoquinoline-5-carbaldehyde 7016853, aisoquinoline compound, is more and more widely used in various.

Reference£º
Article; See, Cheng Shang; Kitagawa, Mayumi; Liao, Pei-Ju; Lee, Kyung Hee; Wong, Jasmine; Lee, Sang Hyun; Dymock, Brian W.; European Journal of Medicinal Chemistry; vol. 156; (2018); p. 344 – 367;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

23707-37-1, Isoquinolin-7-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 117 [N-(4-TERT-BUTYL-PHENYL)-2-(ISOQUINOLIN-7-YLAMINO)-BENZAMIDE] Step A: Preparation of [2- (ISOQUINOLIN-7-YLAMINO)-BENZOIC] acid ethyl ester A mixture of 2-bromo-benzoic acid ethyl ester [(458] mg, 2.0 mmol), 7-aminoisoquinoline (144 mg, 1.0 mmol), Pd (OAc) [2] (11 mg), BINAP [(30] mg) and [K2CO3] (414 mg) in 1 mL of toluene was stirred in a sealed tube for 16 h at [105 C.] The reaction was cooled to RT, diluted with 20 mL of [CH2C12,] filtered through [CELITE] concentrated, and purified by flash column chromatography to obtain the titled compound as an oil. MS [(ES+)] : 293.3 (M+H) [+.] [CALC’D] for [C18HL6N202-292.]

The synthetic route of 23707-37-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMGEN INC.; WO2004/5279; (2004); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem