Category: isoquinoline

51206-40-7, 1,4-Dibromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,51206-40-7

A mixture of 1.00 g, 3.49 mMol of 1,4-dibromoisoquinoline (Intermediate A) from step 1 and 4-chloroaniline were melted together at 140. The reaction mixture turned into a deep red liquid and after about 10 minutes the reaction mixture solidified and was done. The reaction mixture was broken up and triturated with a 50/50 methanol/THF mixture then filtered and air dried without further purification. wt. 0.75 g, 64.4%, mp.=260-263. Rf=0.58 in 40% ethyl acetate in hexanes.

As the paragraph descriping shows that 51206-40-7 is playing an increasingly important role.

Reference£º
Patent; BAYER CORPORATION; EP1228063; (2009); B1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1350643-72-9,(S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

To a suspension of 6-chloro-5-(2-methyl-2H-tetrazol-5-yl)pyrimidin-4-amine (30 mg, 0.142 mmol) and (S)-3-(1-aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one (44 mg, 0.149 mmol) in n-BuOH (3 mL) was added DIPEA (37 mg, 0.284 mmol). The resulted mixture was heated at reflux for 42 hours and monitored by TLC (PE/EtOAc, v/v, 1/3). The mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with EtOAc (15 mL), washed with water (15 mL) and brine (10 mL). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a preparative TLC (PE/EtOAc (v/v)=1/4) to give the title compound as a pale yellow solid (35 mg, 52.1%). [0633] MS (ESI, pos, ion): 474.1 [M+H]+; HPLC: 91.4%; [0634] 1H NMR (400 MHz, CDCl3) delta (ppm): 8.79 (d, J=6.8 Hz, 1H), 8.01 (s, 1H), 7.56-7.32 (m, 8H), 6.58 (s, 1H), 5.11 (d, J=6.9 Hz, 1H), 4.52 (s, 3H), 1.53 (d, J=6.8 Hz, 3H)., 1350643-72-9

1350643-72-9 (S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one 66607319, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; Xi, Ning; Wang, Liang; Wang, Tingjin; US2015/87658; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.394-67-2,4-Fluoroisoquinoline,as a common compound, the synthetic route is as follows.

4-Fluoroisoquinoline (3.6 g) obtained in Reference Example 1 was dissolved in concentrated sulfuric acid (20 ml), and the solution was added dropwise with a solution of potassium nitrate (3.25 g, Wako Pure Chemical Industries) in concentrated sulfuric acid (28 ml) under cooling at -5¡ã C. so that the temperature of the reaction mixture should not exceed 5¡ã C. The reaction mixture was stirred at 0¡ã C. for 1 hour, poured into ice water, neutralized with 28percent aqueous ammonia (pH 8), and extracted 3 times with ethyl acetate (150 ml for each time). The combined organic layer was washed with saturated aqueous sodium hydrogencarbonate (300 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (2.2 g)., 394-67-2

The synthetic route of 394-67-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Asahi Kasei Pharma Corporation; US2009/48223; (2009); A1;,
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201150-73-4, tert-Butyl 5-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step-1: Synthesis of tert-butyl 5-(2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate To a stirred solution of 2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (200 mg, 0.58 mmol, 1.0 eq) in 5 mL of Toluene was added m-CPBA (250 mg, 1.45 mmol, 2.5 eq.) and allowed to stir at rt for 30 minutes. tert-butyl 5-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (140 mg, 0.58 mmol, 1.0 eq) and DIPEA (300 mg, 2.32 mmol, 4.0 eq) were added and allowed to stir at rt for 1 h. Progress of reaction was monitored by LCMS. After completion of reaction solvent was removed under reduced pressure, residue was diluted with 20 ml of water and extracted with ethyl acetate (50 mL*3). Combined organic layer was washed with water (20 ml*3), dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crude was purified by flash chromatography to obtain 170 mg (53.79%) of tert-butyl 5-(2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate., 201150-73-4

The synthetic route of 201150-73-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
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26947-41-1, 3-Isoquinolinecarbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,26947-41-1

a) Isoquinoline-3-amidoxime The title compound was prepared from isoquinoline-3-carbonitrile (364 mg, 2.36 mmol) and 50 wt percent hydroxylamine (160 muL, 2.61 mmol) similar to Example 36c, and yielded 439 mg (99percent) of light yellow solid. 1H NMR (DMSO-d6): 9.81 (s, 1H), 9.35 (s, 1H), 8.31 (s, 1H), 8.16 (dd, J=8.17, 0.75 Hz, 1H), 8.06 (d, J=7.97 Hz, 1H), 7.80 (ddd, J=8.24, 6.87, 1.37 Hz, 1H), 7.70 (ddd, J=8.11, 6.87, 1.24 Hz, 1H), 5.97 (s, 2H).

26947-41-1 3-Isoquinolinecarbonitrile 5076808, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Cai, Sui Xiong; Zhang, Han-Zhong; Drewe, John A.; Reddy, P. Sanjeeva; Kasibhatla, Shailaja; Kuemmerle, Jared Daniel; Ollis, Kristin P.; US2003/45546; (2003); A1;,
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80278-67-7, Isoquinoline-5-carbaldehyde is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

80278-67-7, Isoquinolin-5-ylmethanol MDE 32040To a solution of isoquinoline-5-carboxaldehyde (0.65 g, 4.14 mmol) in absolute EtOH (20 mL) at 0¡ã C. in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (156 mg, 4.14 mmol) and the mixture was stirred overnight at RT.The solution was then cooled down to 0¡ã C. before quenching with 2.8 mL of a 6 N aq. HCl solution.The reaction mixture was stirred at RT for 15 min then basified with a 2 N aq. NaOH solution (8.3 mL).EtOH was removed at 40¡ã C. under vacuum and the residue was extracted with CH2Cl2 (2*50 mL).The organic phase was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40¡ã C. under vacuum.Purification by column chromatography (SiO2, eluent cyclohexane_EtOAc=100:0 to 75:25) gave, after evaporation and drying, isoquinolin-5-ylmethanol MDE 32040 as an off-white solid (536 mg, 81percent yield).MW: 159.19; Yield: 81percent; Off-white solid; Mp (¡ã C.): 101.2Rf: 0.25 (cyclohexane:EtOAc=75:25).1H-NMR (CDCl3, delta): 3.23 (broad s, 1H, OH), 5.13 (s, 2H, OCH2), 7.55 (dd, 1H, J=7.7 Hz, ArH), 7.76 (d, 1H, J=7.0 Hz, ArH), 7.86-7.88 (m, 2H, 2*ArH), 8.48 (d, 1H, J=6.0 Hz, ArH), 9.17 (s, 1H, ArH).13C-NMR (CDCl3, delta): 62.5, 116.8, 126.9, 127.7, 128.8, 129.2, 134.0, 136.0, 143.1, 152.9.MS-ESI m/z (percent rel. Int.): 160 ([MH]+, 100).

The synthetic route of 80278-67-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ExonHit Therapeutics SA; ALLERGAN, INC.; US2012/214837; (2012); A1;,
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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;,
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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;,
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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;,
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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;,
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