Category: isoquinoline

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-((benzyloxy)methyl)phenyl)cyclopropane-1-carboxylic acid (E256) in pyridine was added EDC, DMAP and 6-aminoisoquinoline and the solution was stirred at room temperature under N2 overnight. The mixture was poured into NaHC03 (sat) and EtOAc and further extracted with EtOAc, dried (Na2S04), filtered and evaporated. Colum chromatography 4percentMeOH-CH2CI2 gave pure 2-(4-((benzyloxy)methyl)phenyl)-N-(isoquinolin-6-yl)cyclopropane-1-carboxamide (E257).

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.; 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.19493-45-9,3-Chloroisoquinoline,as a common compound, the synthetic route is as follows.

EXAMPLE 1 This example illustrates the preparation of 3-chloro-5-nitro-isoquinoline having the formula: SPC6 3-chloro-isoquinoline (16.35 g., 0.1 mole) was dissolved in concentrated sulphuric acid (80 ml) and the solution was cooled to approximately 5C in an ice-water bath. Potassium nitrate (11 g. 0.11 mole) was dissolved in concentrated sulphuric acid (60 ml), the solution was cooled to approximately 5C and added dropwise, with stirring, over a period of 2 hours to the 3-chloro-isoquinoline solution, the temperature of the reaction mixture being maintained in the region of from 3 to 8C by means of the ice-water bath. The bath was then removed and the mixture stirred for a further 2 hours, and allowed to stand overnight. Next day the reaction mixture was poured into a water (800 ml)-ice (800 g.) mixture, and 3-chloro-5-nitro-isoquinoline precipitated as fine white crystals. The precipitate was filtered off, slurried with water, filtered again, washed thoroughly with water, and then recrystallized from a 3:1 v/v mixture of ethanol/acetone to yield 16.33 g. of 3-chloro-5 -nitro-isoquinoline of melting point 163 – 164C., 19493-45-9

19493-45-9 3-Chloroisoquinoline 640968, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; ICI Australia Limited; US3930837; (1976); A;,
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Isoquinoline | C9H7N – PubChem

90806-60-3, 5-Methoxyisoquinoline-1-carbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,90806-60-3

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 to 85 0C for 4 h, cooled to 25 0C, diluted with dichloromethane and acidified with IN hydrochloric acid. The organic phase was separated,169 washed with brine, dried, concentrated to 1A volume and filtered to afford Cap-138 as a yellow solid (0.44 g, 88.9%) . 1H NMR (DMSO-d6, 400 MHz) delta 13.6 (br s, IH), 8.56 (d, J” = 6.0 Hz, IH), 8.16 (d, J = 6.0 Hz, IH), 8.06 (d, J = 8.8 Hz, IH), 7.71-7.67 (m, IH), 7.30 (d, J = 8.0 Hz, IH) , 4.02 {s, 3H) ; Rt = 0.70 min (Cond.-Dl); 95% homogenity index; LCMS: Anal. CaIc. for [M+H] + CnHi0N03 : 204.07; found: 204.05.Synthetic Strategy. Method B (derived from Tetrahedron Letters, 2001, 42, 6707) .

The synthetic route of 90806-60-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAVOIE, Rico; BENDER, John A.; BACHAND, Carol; RUEDIGER, Edward H.; KADOW, John F.; WO2010/120621; (2010); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

630421-73-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.630421-73-7,1,6-Dichloroisoquinoline,as a common compound, the synthetic route is as follows.

The following compounds were dissolved in a mixed solution of 100 ml of toluene, 50 ml of ethanol, and 50 ml of a 2-normal aqueous sodium carbonate solution. Compound 3-1: 4.0 g (20.2 mmol)Compound B3-1: 3.96 g (22.2 mmol)In the resulting reaction solution, 1.17 g (1.01 mmol) of tetrakis(triphenylphosphine)palladium(0) was added while the reaction solution was stilTed in a nitrogen atmosphere at a room temperature. The reaction solution was heated to 60 degrees Celsius and then stilTed for 6 hours. After the reaction was completed, water was added in the reaction solution. The organic layer was extracted with toluene and dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off under reduced pressure. The residue was partially purified by column chromatography (gel used in chromatography: BW300 (produced by Fuji Silysia Chemical Ltd.), developing solvent: ethyl acetate/heptane = 1/3) and washed with methanol. Thus, 5.98 g (yield 100%) of a crude product of Compound 3-2 was prepared.

630421-73-7 1,6-Dichloroisoquinoline 23595199, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; CANON KABUSHIKI KAISHA; ABE, Shigemoto; KAMATANI, Jun; KISHINO, Kengo; SAITOH, Akihito; YAMADA, Naoki; KOSUGE, Tetsuya; HORIUCHI, Takayuki; NISHIDE, Yosuke; MIYASHITA, Hirokazu; WO2014/115528; (2014); 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.6624-49-3,Isoquinoline-3-carboxylic acid,as a common compound, the synthetic route is as follows.,6624-49-3

General procedure: Mixtures of 4-(di-tert-butoxycarbonylamino)-6-amino-2-methylquinoline (100mg, 0.27mmol), the respective carboxylic acid (0.53mmol, 2equiv), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU; 190mg, 0.500mmol, 2.0equiv) and di-iso-propylethylamine (0.5mL, 2.9mmol, 10equiv) in DMF (5mL) were stirred at room temperature for 16h. The mixtures were poured into 50mL of 5percent aq Na2CO3 and extracted with EtOAc (3¡Á50mL). The combined organic layers were washed with 5percent aq Na2CO3 (1¡Á50mL), brine (1¡Á50mL), dried (MgSO4), and evaporated. The residual materials were co-evaporated with diethyl ether and treated without further purification with 1:1 TFA/DCM (5mL) for 30min?2h. Removal of solvents gave crude materials as solids or oils that were triturated with diethyl ether and recrystallized from CH3CN/MeOH) to yield the final product as a TFA salt or purified using prep TLC (80:18:2 CHCl3/MeOH/aq CH3NH2) to provide the free base. Some of the free bases were further reacted with a slight excess of p-toluenesulfonic acid in diethyl ether to provide the corresponding p-TsOH salts.

As the paragraph descriping shows that 6624-49-3 is playing an increasingly important role.

Reference£º
Article; Williams, John D.; Khan, Atiyya R.; Cardinale, Steven C.; Butler, Michelle M.; Bowlin, Terry L.; Peet, Norton P.; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 419 – 434;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.205055-63-6,6-Bromo-1-chloroisoquinoline,as a common compound, the synthetic route is as follows.

Step 3. R-[4-Chloro-3-(5-phenyl-lH-imidazol-2-yl)-phenyl]-[6-(2-methyl- morpholin-4-yl)-isoquinolin-l-yl] -amine [0067] A mixture of l-chloro-6-bromo-isoquinoline (242 mg, 1.00 mmol), which is prepared according to literature procedure [1], R-2-methylmorpholine hydrochloride (138 mg, 1.00 mmol), Pd2(dba)3 (18.3 mg, 0.02 mmol), xantphos 34.7 mg, 0.06 mmol), and ?-BuONa (288 mg, 3.00 mmol) is subject to vacuo and backfilled with argon. Toluene (1.8 mL) is then added and the mixture was heated at 100 0C for 2 hours. After the reaction mixture is cooled to room temperature, it is directly loaded to a silica gel column and is chromatographed (DCM: EtOAC = 100 : 3) to give l-chloro-6-(2-R- methyl-morpholin-4-yl)-isoquinoline as an oil.[0068] A mixture of l-chloro-6-(2-R-methyl-morpholin-4-yl)-isoquinoline (26.3 mg, 0.1 mmol), 4-chloro-3-(5-phenyl-l//-imidazol-2-yl)-phenylamine (27.0 mg, 0.1 mmol), Pd2(dba)3 (9 mg, 0.01 mmol), xantphos 17 mg, 0.03 mmol), and K3PO4 (64 mg, 0.3 mmol) is subject to vacuo and backfilled with argon. 1,4-Dioxane (0.4 mL) is then added and the mixture is heated under stirring at 96 0C overnight. After it is cooled to room temperature, the reaction mixture is redistributed between ethyl acetate (30 mL) and saturated solution of ammonium chloride (30 mL). The organic phase is separated, dried with Na2SO4, and evaporated to give a residue which is subject to reverse -phase preparative LC-MS (acetonitrile/water/TFA gradient 10-90 % CH3CN in 7.5 min, Ultro 120 5uM C18Q, 75x30mmID). The collected water/MeCN solution of the TFA salt of the product is evaporated to remove the acetonitrile. A saturated aqueous solution of NaHCO3 is added to raise the pH to 8-9. Then ethyl acetate is used to extract the product and the organic phase is dried with Na2SO4. Evaporation of the solvent yields the free- based R-[4-chloro-3-(5-phenyl-lH-imidazol-2-yl)-phenyl]-[6-(2-methyl-mophiholin-4-yl)- isoquinolin-l-yl]-amine. 1H NMR 400 MHz (MeOD) delta 8.19 (d, / = 9.2 Hz, IH), 7.97- 7.91 (m, IH), 7.79-7.71 (m, IH), 7.50 (s, IH), 7.44 (d, J = 8.8 Hz, IH), 7.40-7.31 (m, IH), 7.26-7.18 (m, IH), 7.05-7.01 (m, IH), 4.03-3.97 (m, IH), 3.90-3.64 (m, 4H), 2.92- 2.81 (m, IH), 2.58-2.50 (m, IH), 1.24 (d, J= 6.0 Hz, 3H). LRMS m/z 496.3 (MH+).

205055-63-6, As the paragraph descriping shows that 205055-63-6 is playing an increasingly important role.

Reference£º
Patent; IRM LLC; CHENG, Dai; HAN, Dong; GAO, Wenqi; JIANG, Jiqing; PAN, Shifeng; WAN, Yongqin; WO2008/14291; (2008); A2;,
Isoquinoline – Wikipedia
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1532-97-4, 4-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 1654-[5-(4-Dimethylamino-piperidin-1-yl)-3H-imidazo[4,5-b]pyridine-2-carbonyl]-2- isoquinolin-4-yl-benzonitrileSynthetic scheme Step i4-Cyano-3-isoquinolin-4-yl-benzoic acid methyl esterThe mixture of 4-cyano-3-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (100 mg, 0.348 mmole), 4-bromo-isoquinoline (80 mg, 0.383 mmole), Pd2(dba)3 (31.9 mg, 0.035 mmole), Sphos (28.6 mg, 0.070 mmole), 2 molar K3PO4 aqueous (0.4 ml, 0.8 mmole) and dioxane (5 ml) was degassed and heated to 1200C for 40 minutes in microwave. Reaction solution was diluted with water and extracted with EtOAc. EtOAc layer was concentrated. Residue was purified by using silica gel chromatography, eluting with EtOAc/ heptane to afford 4-cyano-3-isoquinolin-4-yl-benzoic acid methyl ester (60 mg, 60 percent). 1 H NMR (400MHz, CD2CI2) delta 3.88 (s, 3H), 7.45 (d, J=8.03 Hz, 1 H), 7.65 (m, 2H), 7.90 (m, 1 H), 8.06 (d, J=8.53 Hz, 1 H), 8.15 (m, 2H), 8.42 (s, 1 H), 9.29 (s, 1 H). HR-MS m/z 289.0979 [M+1]., 1532-97-4

The synthetic route of 1532-97-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; ASTEX THERAPEUTICS LIMITED; HOWARD, Steven; MORTENSON, Paul Neil; HISCOCK, Steven Douglas; WOOLFORD, Alison Jo-Anne; WOODHEAD, Andrew James; CHESSARI, Gianni; O’REILLY, Marc; CONGREVE, Miles Stuart; DAGOSTIN, Claudio; CHO, Young Shin; YANG, Fan; CHEN, Christine Hiu-Tung; BRAIN, Christopher Thomas; LAGU, Bharat; WANG, Yaping; KIM, Sunkyu; GRIALDES, John; LUZZIO, Michael Joseph; PEREZ, Lawrence Blas; WO2010/125402; (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.105627-79-0,Isoquinoline-5-sulfonyl chloride hydrochloride,as a common compound, the synthetic route is as follows.

Powdered isoquinoline-5-sulfonyl chloride hydrochloride (1.00 g, 3.79 mmol) is added in small portions to a stirred solution of tert-butylamine (2.00 mL, 18.9 mmol) in CHIC12 (10 mL) at 0 C under nitrogen. The resultant mixture is allowed to stir at ambient temperature for 1 hour. Ethyl acetate (50 mL) is added to the mixture and the mixture is washed with saturated aqueous NAHCO3 (20 mL). The organic layer is dried over MGS04, filtered and concentrated. The crude product is chromatographed on silica (gradient 0-2% CH30H in CH2C12) to give 857 mg (3.24 mmol, 86% yield) of the title compound as a white solid. ESIMS : m/z 265 (M+H) +. Analysis for C13HL6N202S : calcd : C, 59.07 ; H, 6.10 ; N, 10.60 ; found: C, 59.21 ; H, 6.01 ; N, 10.67.

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

Reference£º
Patent; ELI LILLY AND COMPANY; WO2004/94386; (2004); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

347146-33-2, 1-Chloroisoquinolin-6-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 63 1-Chloro-6-(4-(pyrrolidin-1 ylsulfonyl)benzenesulfonylamino)isoquinoline The title compound was obtained by the procedure of Example 1, except using 6-amino-1-chloroisoquinoline (Preparation Example 23) and 4-(pyrrolidin-1-ylsulfonyl)benzenesulfonyl chloride. 1H-NMR (CDCl3) delta (ppm): 1.71 (4H, m), 3.20 (4H, t, J=7.0 Hz), 7.46 (1H, d, J=5.4 Hz), 7.49 (1H, dd, J=2.0, 9.2 Hz), 7.61 (1H, d, J=2.0 Hz), 7.87 (2H, d, J=8.8 Hz), 8.02 (2H, d, J=8.8 Hz), 8.19 (1H, d, J=9.2 Hz), 8.20 (1H, d, J=5.4 Hz), 9.72 (1H, s)., 347146-33-2

347146-33-2 1-Chloroisoquinolin-6-amine 22674114, aisoquinoline compound, is more and more widely used in various fields.

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.1075-11-2,6-Fluoroisoquinoline,as a common compound, the synthetic route is as follows.

7.49 g of 4-hydroxy-piperidine-1-carboxylic acid-tert-butylester were dissolved in 20 ml_ of dry dimethyl acetamide. 1.49 g of sodium hydride (60%) were added. Then a solution of 3.65 g of 6-fluoroisoquinoline (3) in dimethyl acetamide was added dropwise. The solution was heated at 80 0C for 2 hours, then the solvent was removed and the residue was taken up in dichloromethane. The organic layer was extracted twice with water and then with brine, dried over magnesium sulfate and evaporated to dryness. The crude product was purified by silica gel chromatography to yield 6.22 g of 4-(isoquinolin-6-yloxy)-piperidine-1-carboxylic acid-tert-butylester (7). Rt = 1.32 min (Method B). Detected mass: 329.1 (M+H+).

1075-11-2, The synthetic route of 1075-11-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SANOFI-AVENTIS DEUTSCHLAND GMBH; WO2007/12421; (2007); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem