Category: isoquinoline

82827-09-6,82827-09-6, 6-Bromoisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 1666-{4-[l-{[(3S)-l-(Cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-5-(trifluoromethyl)- lH-benzimidazol-2-yl]phenyl}-l(2H)-isoquinolinone1 – { [(3 S)- 1 -(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl} -2-[4-(4,4,5 ,5-tetramethyl- 1 ,3 ,2- dioxaborolan-2-yl)phenyl]-5-(trifluoromethyl)-lH-benzimidazole (100 mg, 0.139 mmol) was dissolved in 1,4-dioxane in a 5 mL microwave vial. To this was added 6-bromo-l(2H)- isoquinolinone (31.2 mg, 0.139 mmol), PdC12(dppf)-CH2C12 adduct (5.68 mg, 6.95 muiotaetaomicron), and 2.0 M aqueous potassium carbonate (0.209 mL, 0.417 mmol) with stirring. The vial was purged with nitrogen, sealed and heated at 100 C for 2 hr. The reaction mixture was allowed to cool and the pH was adjusted to 7 with 1 N HC1. The reaction mixture was extracted with DCM (3 x 50 mL) and the combined extracts were dried over sodium sulfate, filtered and evaporated to dryness. The crude product was dissolved in DMSO (1.5 mL) and purified by preparative reverse phase HPLC using a gradient of 1% NH40H(aq)/acetonitrile. The appropriate fractions were combined and evaporated to dryness to afford 15 mg of the titled compound as an off- white solid. (LCMS m/z 556.9, M+H).

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

Reference£º
Patent; GLAXOSMITHKLINE LLC; HALLMAN, Jason; LAUDEMAN, Christopher; LIU, Ronggang; MILLER, Aaron; MOORE, Michael, Lee; DOCK, Steven; MUSSO, David; PARRISH, Cynthia; WO2011/56635; (2011); A1;,
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66491-03-0,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.66491-03-0,7-Amino-3,4-dihydroisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

7-(Piperazin-1-yl)-3,4-dihydro-1(1H)-isoquinolinone (1-2) A solution of 7-amino-3,4-dihydro-1(1H)-isoquinolone (1-1)(Girard et al, J. Org. Chem., 1983, vol. 48, p. 3220; 5.0 g, 30.8 mmol) and bis(2-chloroethyl)amine hydrochloride (6.3 g, 33.9 mmol) in n-butanol (250 mL) was stirred at 110 C. for 3 days. The precipitate was removed by filtration to provide the starting amine as the HCl salt (3.6 g). Evaporation of the n-butanol under reduced pressure afforded a dark oil which was purified by column chromatography (silica gel; EtOH/H2 O/NH4 OH 10:0.5:0.5) to give 1-2. 1 H NMR (CD3 OD); delta2.86 (2H, t), 3.10 (4H, m), 3.22 (4H, m), 3.44 (2H, t), 7.18 (2H, m), 7.55 (1H, m).

As the paragraph descriping shows that 66491-03-0 is playing an increasingly important role.

Reference£º
Patent; Merck & Co., Inc.; US5665723; (1997); A;,
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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.

fe/f-Butyl 6-amino-3,4-dihydroisoquinoline-2(1 H)-carboxylate (0.500 g, 2.01 mmol), methyl 2-(2-(2-(2-(methylsulfonyl)-5-(trifiuoromethyl)pyrimidin-4- yi)ethyi)phenyl)acetate (166) (0.675 g, 1.68 mmol), trifiuoroethanol (3 mL), and TFA (0.3 mL) were loaded into a microwave tube, sonicated for two minutes, then heated under microwave irradiation at 100 C for 20 minutes. The cooled mixture was concentrated, co-evaporated with toluene (3x 20 mL) and loaded onto a 10 g SCX cartridge in methanol. The cartridge was eluted with methanol (200 mL), then with 1 % methanolic methyiamine (200 mL). The methanolic methylamine eluent was concentrated to give a brown oil (0.850 g). The oil was dissolved in DCM (5 mL), and Boc anhydride (549 mg, 2.52 mmoi) was added. The resulting mixture was stirred under an oil bubbler for 18 hours, then diluted with DCM (50 mL) and washed with water (50 mL). The aqueous layer was extracted with DCM (2x 50 mL), and the combined DCM phases dried (phase separation filter) and evaporated. Chromatography (isoiera, 40 g silica cartridge, 0-50% ethyl acetate/petroleum benzine 40-80 C) gave the title compound (/SO) (520 mg, 54%) as a yellow syrup; 1H NMR (400 MHz, CDCI3) delta 8.54 (s, 1 H), 7.45 (s, 2H), 7.38 (s, 1 H), 7.28 – 7.18 (m, overlaps with CDCI3), 7.10 (d, J = 8.5 Hz, 1 H), 4.56 (s, 2H), 3.75 (s, 2H), 3.70 – 3.62 (m, 5H), 3.17 – 3.03 (m, 4H), 2.85 (t, J = 5.6 Hz, 2H), 1.50 (s, 9H). LCMS Method C: rt 6.93 min; m/z 571.1 [M+H] +, m/z 515.0 [M+tBu+2H] +.

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

Reference£º
Patent; CANCER THERAPEUTICS CRC PTY LTD; DEVLIN, Mark Graeme; STREET, Ian Philip; TONG, Warwick Bonner; WO2014/27199; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7651-81-2,Isoquinolin-3(2H)-one,as a common compound, the synthetic route is as follows.

Isoquinolin-3-ol was reacted with 2,3-dichloro-5-nitro pyridine in dry DMF and CS2CO3as base at room temperature to obtain 3-(3-chloro-5-nitropyridin-2-yloxy)isoquinoline which was further converted to 5-chloro-6-(isoquinolin-3-yloxy)pyridin-3-amine by reaction with stannous chloride dehydrate as reducing agent at room temperature to obtain 5-chloro-6- (isoquinolin-3-yloxy)pyridin-3-amine., 7651-81-2

Big data shows that 7651-81-2 is playing an increasingly important role.

Reference£º
Patent; PIRAMAL ENTERPRISES LIMITED; ENOSE, Arno, Appavoo; WO2013/117963; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.27655-40-9,Isoquinoline-5-sulfonic acid,as a common compound, the synthetic route is as follows.

a 5-Isoquinolinesulfonyl chloride A mixture of 5-isoquinolinesulfonic acid (4.18 g, 20 mmol), and phosphorus pentachloride (6.24 g, 30 mmol) in phosphorus oxychloride (20 mL) was heated at 120 C. for two days. The reaction mixture was cooled to room temperature and diluted with dry chloroform (60 mL). The white precipitate was collected, washed with dry chloroform, and dried under high vacuum to give the title compound as a white solid (4.40 g, 83%) which was used for next step without further purification. 1H-NMR (300 MHz, CDCl3)delta9.95 (s, 1H), 9.16 (d, J=6.8 Hz, 1H), 8.74 (d, J=6.8 Hz, 1H), 8.52 (t, J=7.0 Hz, 2H), 7.99 (t, J=7.3 Hz, 1H).

27655-40-9, 27655-40-9 Isoquinoline-5-sulfonic acid 241599, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; 3-Dimensional Pharmaceuticals, Inc.; US6235778; (2001); B1;,
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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.1350643-72-9,(S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

A mixture of (S)-3-(l-aminoethyl)-8-chloro-2-phenylisoquinolin-l(2H)-one (23 mg, 0.077mmol), 2,4-diamino-6-chloropyrimidine-5-carbonitrile (13 mg, 0.08 mmol), N,N- diisopropylethylamine (0.1 mL) and potassium fluoride (21 mg) in DMSO (1 mL) was heated at 90 C overnight. The reaction mixture was cooled to room temperature and EtOAc (20 mL) was added. The solution was washed with 0 (3 x 5mL), and concentrated in vacuo. The crude product was purified via column chromatography on silica gel (EtOAc/MeOH 20: 1) to provide the desired product, DWL-PI3K-3, as a white solid (23 mg, yield 70%). MS: m/z = 432 (M+l)., 1350643-72-9

The synthetic route of 1350643-72-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; THE TRUSTEES OF COLUMBIA UNIVERISTY IN THE CITY OF NEW YORK; LANDRY, Donald W.; DENG, Shi-Xian; XU, Xiaoming; DIACOVO, Thomas; (97 pag.)WO2019/28055; (2019); A1;,
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Isoquinoline | C9H7N – PubChem

82827-09-6, 6-Bromoisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

82827-09-6, To a solution of 3.93 g (17.5 mmol) 6-Bromo-2H-isoquinolin-1-one (6) in 150 ml Toluene were added 12.13 g (44.0 mmol) silver carbonate and 3.60 g (21.1 mmol) of benzyl bromide. The reaction mixture was refluxed for 1.5 h and then cooled to room temperature. The solution was filtered. The filtrate was washed with water and the aqueous phase extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated. Final purification was achieved by preparative HPLC. Rt = 2.47 min (Method B). Detected mass: 314.1/316.5 (M+H+).

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

Reference£º
Patent; SANOFI-AVENTIS; WO2008/77552; (2008); 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 tetrahydrofuran (20 mL) solution of 5-fluoro-2-methoxybenzoic acid (1.00 g), DPPA (1.25 mL), and triethylamine (1.6 mL) was heated to reflux for 1 hour. A tetrahydrofuran (10 mL) solution of 6-amino-2N-Boc-1,2,3,4-tetrahydroisoquinoline (1.00 g) was added to the reaction solution. The reaction mixture was further heated to reflux for 5.5 hours, then cooled to room temperature, and then concentrated. The residue was purified by chromatography (dichloromethane/ethyl acetate=20:1?4:1) to obtain the title compound (1.51 g, 90%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta (ppm) = 9.33 (1H, s), 8.38 (1H, s), 8.05-7.97 (1H, m), 7.38-7.28 (1H, m), 7.24-7.16 (1H, m), 7.10-7.05 (1H, m), 7.02-6.97 (1H, m), 6.77-6.69 (1H, m), 4.41 (2H, s), 3.84 (3H, s), 3.51 (2H, t, J = 6.1 Hz), 2.73 (2H, t, J = 7.0 Hz), 1.41 (9H, s); MS (FAB) m/z: 416 (M + H)+.

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

Reference£º
Patent; Daiichi Sankyo Company, Limited; EP2256105; (2010); A1;,
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Isoquinoline | C9H7N – PubChem

4494-18-2,4494-18-2, 1-Isoquinolinecarboxaldehyde is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The general procedure for the synthesis of the 3-aminoindolizine derivatives 1a-e, 6a-g, and uncyclized product 8a-c is described below: To a reaction mixture of cyano substrate 3 (2.0 mmol), 2-carbonyl pyridine derivative (2.0 mmol), and piperidinium acetate (15 mg, 0.10 mmol) in toluene (6 ml), was added diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (9) (Hantzsch ester, 557 mg, 2.2 mmol) in one portion at room temperature. The resulting mixture was degassed with a stream of nitrogen and then stirred at 105 C for 3 h. After cooling to room temperature, a minimum amount (ca 0.3-0.5 mL) of DMSO was added to the reaction mixture and the resulting solution was directly loaded to a silica gel column and purified by column chromatography using Teledyne Isco Combiflash system.

As the paragraph descriping shows that 4494-18-2 is playing an increasingly important role.

Reference£º
Article; Li, Lianhai; Chua, Waepril Kimberly S.; Tetrahedron Letters; vol. 52; 12; (2011); p. 1392 – 1394;,
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90806-58-9, 5-Methoxyisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,90806-58-9

To a stirred solution of Cap 138, step a (2.34 g, 14.7 mmol) in anhydrous dichloromethane (50 mL) at roomtemperature was added meta-chloroperbenzoic acid (77%, 3.42 g, 19.8 mmol) in one portion. After being stirred for 20h, powdered potassium carbonate (2.0 g) was added and the mixture was stirred for 1h at room temperature before itwas filtered and concentrated in vacuo to afford Cap-138, step b (2.15 g, 83%) as a pale, yellow solid which wassufficiently pure to carry forward directly. 1H NMR (CDCl3, 400 MHz) delta 8.73 (d, J = 1.5 Hz, 1H), 8.11 (dd, J = 7.3, 1.7Hz, 1H), 8.04 (d, J=7.1 Hz, 1H), 7.52 (t, J = 8.1 Hz, 1H), 7.28 (d, J = 8.3 Hz, 1H), 6.91 (d, J = 7.8 Hz, 1H), 4.00 (s, 3H);Rt= 0.92 min, (Cond.-D1); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C10H10NO2: 176.07; found: 176.0.

The synthetic route of 90806-58-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bristol-Myers Squibb Company; BELEMA, Makonen; NGUYEN, Van N.; SERRANO-WU, Michael; ST. LAURENT, Denis R.; QIU, Yuping; DING, Min; MEANWELL, Nicholas A.; SNYDER, Lawrence B.; (149 pag.)EP2328865; (2017); B1;,
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