Day: November 11, 2020

3336-43-4, 1-Chloroisoquinolin-4-ol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: Preparation of 1-chloro-4-ethoxyisoquinoline To a solution of 1-chloroisoquinolin-4-ol (1.0 g, 5.5 mmol) in acetonitrile (10 mL) was added K2CO3 (2.3 g, 16.7 mmol) followed by ethyl iodide (0.87 ml, 11.0 mmol) at room temperature. The reaction mixture was stirred at room temperature for overnight. The solvent was evaporated under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-4-ethoxyisoquinoline (0.7 g, 62%) as off-white solid. 1H NMR (400 MHz, CD3OD): delta ppm 8.26-8.24 (m, 2H), 7.79 (s, 1H), 7.76-7.26 (m, 2H), 4.29-4.24 (q, J=6.8 Hz, 2H), 1.58-1.54 (t, J=6.8 Hz, 3H); MS: MS m/z 207.7 (M++1).

3336-43-4, 3336-43-4 1-Chloroisoquinolin-4-ol 4281882, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); 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.164148-92-9,tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of tert-butyl 6-amino-3,4-dihydroisoquinoline-2(lH)-carboxylate (3 g, 12mmol), 3,5-dibromo-l-methylpyrazin-2(lH)-one (2.68 g, lOmmol), and triethylamine (1.5 g, 15mmol) in IPA (50 mL) was heated at 70C for 15 h. The mixture was cooled to room temperature. The resulting yellow solids were collected by filtration and dried in vacuum to afford 120a as a yellow solid (2.83 g, 65 ).MS: [M+H]+ 435.

164148-92-9, 164148-92-9 tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate 2756371, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
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Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.82827-09-6,6-Bromoisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

82827-09-6, To an ice-cooling solution of 6-bromoisoquinolin-1(2H)-one (800 mg, 3.57 mmol) in DMF (8 mL) was added sodium hydride (160 mg, 3.93 mmol, 60%) in small portions, after the addition, the reaction system was warmed up to room temperature and stirred for 20min, iodoethane (800 mg, 5.36 mmol) was added. After the addition, the reaction system was stirred at room temperature for 2h, the reaction was quenched by addition of water (20 mL), extracted with ethyl acetate (20 mL ¡Á 2), the combined organic layers were washed with brine, dried over sodium sulfate, separation of organic phase, dried over anhydrous sodium sulfate, filtered and concentrated, the residue was purified by column chromatography on silica gel (ethyl acetate: petroleum ether = 1:4) to afford compound 15.1 (800 mg, yield: 91%) as a white solid

As the paragraph descriping shows that 82827-09-6 is playing an increasingly important role.

Reference£º
Patent; Shanghai de Novo Pharmatech Co., Ltd.; GAO, Daxin; WANG, Yuxun; CHEN, Shoujun; YANG, Heping; (101 pag.)EP3453707; (2019); A1;,
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Isoquinoline | C9H7N – PubChem

164148-92-9, tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A. 6-(Toluene-4-sulfonylamino)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert butyl ester To a mixture of 275 mg (1.10 mmol) of 6-amino-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester, 134 mg (1.33 mmol) of triethylamine in 6 mL of methylene chloride at 00C was added 233 mg (1.2 mmol) of toluenesulfonyl chloride in one portion. The mixture was allowed to warm to room temperature and was stirred overnight. An additional 62 mg (0.61 mmol) of triethylamine and 105 mg (0.55 mmol) of toluenesulfonylchloride was added and stirring was continued for an additional 4 h. The mixture was concentrated and the residue dissolved in ethyl acetate. The organic portion was washed twice each with 1 N NaOH and brine, dried over Na2 SO4 and the product was purified by silica gel chromatography (1:3 v/v ethyl acetate:hexane) to give 274 mg of 20A as a foam.

164148-92-9, As the paragraph descriping shows that 164148-92-9 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc; US5936089; (1999); A;,
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Isoquinoline | C9H7N – PubChem

74417-44-0, 1-(Bromomethyl)isoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,74417-44-0

1-(bromomethyl)isoquinoline (150 mg, 0.675 mmol) was dissolved in chloroform (15 mL) and cooled in water-ice bath m-chloroperoxobenzoic acid (77%, 0.230 g, 1.03 mmol) was added while stirring. The reaction mixture was let to gradually warm up to room temperature and stirred for 24 hours. The solvent was evaporated and the residue was purified by column chromatography on silica in methanol/ethyl acetate mixture. Fractions containing the product were evaporated to give 102 mg of product as pale yellow solid (0.430 mmol, 64 % yield relative to l-(bromomethyl)isoquinoline).’H NMR (CDC13, 25 C, 500 MHz): 5.17 (C//2-arom.. s, 2H); 7.61 ( arom ., ddd,1H,3/HH= 8 Hz,3/HH= 7 Hz,4/HH= 1 Hz); 7.64 (arom., d, 1H,3/HH = 7 Hz); 7.73(arom., ddd, 1H,3/HH = 9 Hz,3/HH = 7 Hz,4/HH = 1 Hz); 7.80-7.83 (arom., m, 1H);7.95 (arom., ddd, 1H,3/HH= 9 Hz,4/HH= 2 Hz,4/HH= 1 Hz); 8.19 (arom., d, 1H,3/HHNMR (CDC13, 25 C, 125 MHz): 5C20.9 (C//2-arom., s); 122.9 (arom., s); 124.0 (arom., s); 127.6 (arom., s); 127.8 (arom., s); 128.6 (arom., s); 128.8 (arom., s); 129.9 (arom., s); 136.9 (arom., s); 143.1 (arom., s).HRMS (ESI) m/z: [(M + H)+] (Ci0H9BrNO) calculated: 237.9862, found: 237.9863

74417-44-0 1-(Bromomethyl)isoquinoline 2776246, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, V.V.I.; POLASEK, Miloslav; (102 pag.)WO2019/106182; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4721-98-6,6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline,as a common compound, the synthetic route is as follows.

EXAMPLE 6 Preparation of 1-[bis(hydroxymethyl)-methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline To 1 mole (205.3 g) of 1-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline 100 ml of a 30% aqueous formaldehyde solution and then freshly prepared sodium methylate (1 g of sodium+50 ml of methanol) are added. The mixture is then slightly refluxed in 500 ml of methanol for 2 hours. The reaction mixture is evaporated under reduced pressure and the obtained crystalline product is recrystallized from a mixture of acetone and ether. The aimed compound is obtained with the same melting point as the product of Example 1.

4721-98-6, 4721-98-6 6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline 22652, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Richter Gedeon Vegyeszeti Gyar R.T.; US4656179; (1987); A;,
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23687-25-4, Isoquinolin-4-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

23687-25-4, General procedure: To a solution of 3 (100 mg, 0.18 mmol) in dry DCM (10 mL), oxalyl chloride (70 mg, 0.55 mmol), triethylamine (3 mg, 0.03 mmol) and DMF (2 mg, 0.03 mmol) were added, and the mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure, the residue was dissolved in dry THF (1 * 10 mL), the solvent was removed, and the residue was immediately dissolved in dry DCM (10 mL). The solution was cooled to 0 C and triethylamine (24 mg, 0.24 mmol), DMAP (2 mg, 0.02 mmol) as well as 3-aminopyridine (52 mg, 0.55 mmol) were added. After 2 days of stirring, Et2O (100 mL) was added, the organic was washed with diluted HCl (0.1 m, 1 * 100 mL), water (2 * 100 mL) and brine (1 * 50 mL), dried (MgSO4), filtrated and evaporated to dryness. Column chromatography (silica gel, hexane/ethyl acetate, 7:3) afforded 5 (85 mg, 75%) as a white solid; 4.2.242alpha, 3beta, 24-Triacetyloxy-ursan-12-en-28-oic acid 4-isoquinolinyl amide (28) As described for 5, compound 28 (53 mg, 44%) was obtained from 25 and 4-aminoisoquinoline as a white solid; m. p. 173-177 C; RF = 0.40 (silica gel, chloroform/ethyl acetate, 1:1); [alpha]D = -0.85 (c = 0.33, CHCl3); UV-vis (CHCl3): lambdamax (log epsilon) = 289 nm (3.68), 301 nm (3.67), 324 nm (3.72); IR (KBr): nu = 3396 m, 2948 m, 2926 m, 2870 m, 1746vs, 1684 m, 1626w, 1586w, 1522 m, 1488 m, 1456 m, 1370s, 1252vs, 1044 s cm-1; 1H NMR (500 MHz, CDCl3): delta = 9.08 (s, 1 H, H-38), 9.03 (s, 1 H, H-39), 8.00 (d, J = 8.2 Hz, 1 H, H-41), 7.91 (m, 1 H, NH), 7.77-7.72 (m, 2 H, H-44 + H-42), 7.63 (ddd, J = 8.0, 5.9, 2.0 Hz, 1 H, H-43), 5.56 (dd, J = 3.4, 3.4 Hz, 1 H, H-12), 5.14 (ddd, J = 10.5, 10.5, 4.5 Hz, 1 H, H-2), 5.07 (d, J = 10.3 Hz, 1 H, H-3), 3.82 (d, J = 11.8 Hz, 1 H, H-24a), 3.57 (d, J = 11.8 Hz, 1 H, H-24b), 2.22 (d, J = 10.1 Hz, 1 H, H-18), 2.15 (ddd, J = 13.6, 13.6, 4.2 Hz, 1 H, H-16a), 2.10-1.91 (m, 5 H, H-1a + H-11a + H-11b + H-22a + H-16b), 2.08 (s, 3 H, H-36), 2.01 (s, 3 H, H-34), 1.98 (s, 3 H, H-32), 1.86 (ddd, J = 14.4, 14.4, 4.4 Hz, 1 H, H-15a), 1.77 (ddd, J = 13.6, 13.6, 4.3 Hz, 1 H, H-22b), 1.69 (dd, J = 11.0, 6.6 Hz, 1 H, H-9), 1.62 (ddd, J = 13.3, 6.6, 3.2 Hz, 1 H, H-21a), 1.59-1.52 (m, 1 H, H-19), 1.50-1.28 (m, 6 H, H-7a + H-7b + H-21b + H-6a + H-6b + H-5), 1.20-1.04 (m, 3 H, H-15b + H-1b + H-20), 1.17 (s, 3 H, H-27), 1.02 (d, J = 6.3 Hz, 3 H, H-30), 1.00 (s, 3 H, H-25), 0.97 (d, J = 6.5 Hz, 3 H, H-29), 0.85 (s, 3 H, H-23), 0.73 (s, 3 H, H-26) ppm; 13C NMR (125 MHz, CDCl3): delta = 176.8 (C-28), 170.9 (C-35), 170.6 (C-31), 170.5 (C-33), 149.5 (C-39), 140.2 (C-13), 137.6 (C-38), 130.5 (C-42), 130.0 (C-37), 128.9 (C-40), 128.5 (C-41), 128.3 (C-45), 127.4 (C-43), 126.0 (C-12), 120.1 (C-44), 74.9 (C-3), 70.0 (C-2), 65.4 (C-24), 54.7 (C-18), 49.5 (C-17), 47.7 (C-5), 47.7 (C-9), 43.9 (C-1), 42.8 (C-14), 42.1 (C-4), 40.1 (C-19), 39.8 (C-8), 39.3 (C-20), 37.9 (C-10), 37.8 (C-22), 32.5 (C-7), 31.0 (C-21), 28.0 (C-15), 25.2 (C-16), 23.6 (C-11), 23.5 (C-27), 21.3 (C-30), 21.2 (C-32), 21.0 (C-36), 20.9 (C-34), 17.9 (C-6), 17.4 (C-26), 17.4 (C-29), 17.2 (C-25), 14.0 (C-23) ppm; MS (ESI): m/z (%) = 741.5 ([M+H]+, 100), 763.3 ([M+Na]+, 4), 1482.3 ([2 M + H]+, 92); analysis calculated for C45H60N2O7 (740.97): C 72.94, H 8.16, N 3.78; found: C 72.75, H 8.33, N 3.52.

The synthetic route of 23687-25-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Sommerwerk, Sven; Heller, Lucie; Kuhfs, Julia; Csuk, Rene; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 452 – 464;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

18881-17-9, (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,18881-17-9

Then, 2,4-dichloro-6-mophiholin-4-yl-[l,3,5]triazine (3.0 g, 12.8 mmol) thus obtained was dissolved in acetonitrile (50 ml), mixed with diisopropylethylamine (71.7 g, 12.8 mmol) and (_S)-l,2,3,4-tetrahydro-3- isoquinolinemethanol (2.1 g, 12.8 mmol) at room temperature, and stirred for 24 hours. The resulting mixture was diluted with ethyl acetate, and washed successively with water and saturated NaCl. The resulting organic layer was dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure. The resulting residue was purified by column chromatography to obtain [2-(4-chloro-6-morpholin-4-yl-[l,3,5]triazin-2-yl)-l,2,3,4- tetrahydroisoqumolin-(35)-yl]-methanol (4.4 g, 95%).1H NMR (300 MHz, CDCl3) delta: 7.25-7.15 (4H, m), 5.13-5.01 (2H, m), 4.52 (IH, t, J=17.7Hz), 3.85 (4H, br), 3.73 (4H, br), 3.65-3.50 (2H, m), 3.09 (IH, dd, J=15.9Hz, 6.0Hz), 2.89 (IH, dt, J=13.1Hz 3.3Hz), 2.55 (IH, br).

As the paragraph descriping shows that 18881-17-9 is playing an increasingly important role.

Reference£º
Patent; AMOREPACIFIC CORPORATION; CRYSTALGENOMICS, INC.; INDUSTRY-ACADEMIC COOPERATION FOUNDATION, YONSEI UNIVERSITY of Yonsei University; WO2008/72850; (2008); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

34784-04-8, 5-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N-Bromosuccinimide (17.8 g, 10 mmol) was added in portions to a solution of isoquinoline 1 (10.1 mL, 8.5 mmol) in concentrated H2SO4 (100 mL) at -10 C. The mixture was stirred for 2 h at 20 C, followed by the addition of KNO3 (11.2 g, 11.1 mmol) and standing at room temperature for 48 h. Then, the mixture was poured in ice and neutralized with saturated aqueous NH3, the precipitate formed was collected by filtration and recrystallized from MeOH. The yield was 14.2 g (65%).

34784-04-8, The synthetic route of 34784-04-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Bastrakov; Starosotnikov; Russian Chemical Bulletin; vol. 68; 9; (2019); p. 1729 – 1734; Izv. Akad. Nauk, Ser. Khim.; 9; (2019); p. 1729 – 1734,6;,
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

Example 29 Preparation of 2-(2-(1,3-dioxan-2-yl)ethyl)-6-bromo-3,4-dihydroisoquinolin-1(2H)-one A suspension of sodium hydride (60% dispersion in mineral oil, 0.54 g, 13.6 mmol) in DMF at room temperature, under nitrogen, was treated dropwise over 15 min with a solution of 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (2.05 g, 9.1 mmol) in DMF, stirred at room temperature for 20 min, treated with 2-(2-bromoethyl)-1,3-dioxane (1.84 mL, 13.6 mmol), stirred for 16 h and partitioned between water and CH2Cl2. The aqueous phase was extracted with CH2Cl2. The combined organic phase and extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by ISCO CombiFlash chromatography (silica, 0-100% ethyl acetate in hexanes) to afford the title compound as a light yellow oil, 3.0 g (97%), MS (ES) m/z 340.1 [M+H]+., 147497-32-3

The synthetic route of 147497-32-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wyeth; US2009/69300; (2009); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem