Heterocyclic Building Blocks-Isoquinoline

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;,
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 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;,
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

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.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

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

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

147497-32-3, 6-Bromo-3,4-dihydroisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

REFERENCE EXAMPLE 20; 6-Amino-2-isopropyl-3,4-dihydroisoqui?oli?-1(2H)-one; a) 6-Bromo-2-isopropyl”3s4-dihydroisoquinoSin-1 (2H)-one; 0.26 mL (2.76 mmoi) of 2-bromopropane, and 88 mg (2.2 mmol) of NaH were added to a solution of 6-bromo-3,4-dihydroisoquinoiin-1 (2H)-one (250 mg, 1.10 mmol) in DMF (2 mL). The reaction mixture was stirred at 100 0C overnight. The crude product was diluted with H2O and extracted thrice with EtOAc. The combined organic phases were separated, dried over Na2SO4 and the solvent was evaporated. The crude product thus obtained was purified by column chromatography over silica gel, using hexane/EtOAc mixtures of increasing polarity as eluent, and 87 mg of the desired compound were obtained (yield: 29%).

As the paragraph descriping shows that 147497-32-3 is playing an increasingly important role.

Reference£º
Patent; PALAU PHARMA, S.A.; SALAS SOLANA, Jorge; ALMANSA ROSALES, Carmen; SOLIVA SOLIVA, Robert; FONTES USTRELL, Montserrat; COMELLES ESPUGA, Josep; WO2010/34740; (2010); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

34784-05-9, 6-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a degassed solution of 2-(4-fluorophenyl)-N-methyl-6-(N- methylmethylsulfonamido)-5-(3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)benzofuran-3-carboxamide (90 mg, 0.189 mmol) and 6-bromo-isoquinoline (51 mg, 0.246 mmol) in dry DMF (1.5 mL) was added Pd(dppf)Cl2 (20 mg) and K3P04 (81 mg, 0.381 mmol) under N2. The mixture was heated to 100 C for about 15 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was washed with H20, brine, dried over Na2S04, filtered and concentrated in vacuo. The residue obtained was purified using prep- TLC (PE : EtOAc = 2 : 1) to provide 2-(4-fluorophenyl)-5-(3-(isoquinolin-6-yl)phenyl)-N- methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (Compound 210, 85 mg, 93%). 1H- MR (CDC13, 400 MHz) delta 9.62 (s, 1H), 8.46 (d, J= 6.0 Hz, 1H), 8.38 (s, 1H), 8.31-8.33 (m, 1H), 8.21-8.23 (m, 1H), 8.15 (d, J= 6.0 Hz, 1H), 7.98 (s, 1H), 7.81-7.85 (m, 3H), 7.71-7.72 (m, 1H), 7.51-7.60 (m, 3H), 7.12-7.19 (m, 2H), 6.02-6.03 (m, 1H), 3.02 (s, 3H), 2.89-2.92 (m, 6H). MS (M+H)+: 580.

34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; MCCOMAS, Casey Cameron; LIVERTON, Nigel J.; SOLL, Richard; LI, Peng; PENG, Xuanjia; WU, Hao; WO2011/106986; (2011); 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.23687-25-4,Isoquinolin-4-amine,as a common compound, the synthetic route is as follows.

Example 1071-[(2-Chloro-4-fluorophenyl)methyl]-4-(4-isoquinolinyl)-2,3-piperazinedione(E107)Methyl [[(2-chloro-4-fluorophenyl)methyl](2-oxoethyl)amino](oxo)acetate (0.40 g, 1.39 mmol, prepared as described earlier), 4-aminoisoquinoline (0.40 g, 2.78 mmol) and acetic acid (0.08 ml, 1.39 mmol) were dissolved in 1 ,2-dichloroethane (20 ml) and stirred for 10 minutes. Polymer-supported cyanoborohydride (1.74 g, 6.95 mmol) was added and the reaction stirred at room temperature for approximately 64 hours. The reaction was then heated to reflux at 850C for 7 hours. The reaction mixture was then concentrated in vacuo and redissolved in 1-butanol (3 ml). The solution was heated to 16O0C for 1 hour in the microwave. The mixture was concentrated in vacuo and purified by flash-silica gel chromatography. The mixture was eluted with ethyl acetates followed by 5% methanol in dichloromethane and finally 10% methanol in dichloromethane. Clean product fractions were combined and concentrated in vacuo to give a brown oil, which was triturated with a mixture of diethyl ether (10 ml) and methanol (2 ml) to yield 1-[(2-chloro-4-fluorophenyl)methyl]-4-(4-isoquinolinyl)-2,3- piperazinedione (0.032 g) as a cream-coloured solid. LC/MS [M+H]+ = 384, retention time = 2.29 minutes.

As the paragraph descriping shows that 23687-25-4 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; CHAMBERS, Laura Jane; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; STEADMAN, Jon Graham Anthony; WALTER, Daryl Simon; WO2010/125103; (2010); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem