Heterocyclic Building Blocks-Isoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.622867-52-1,tert-Butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.,622867-52-1

[00357] A solution of BS (34.07 g, 191.39 mmol, 4 equiv) in THF (200 mL) was added in portions to a solution of tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(lH)- carboxylate (12.6 g, 47.85 mmol, 1.0 equiv) and triphenylphosphine (37.65 g, 143.55 mmol, 3.0 equiv) in THF (200 mL) at 0 C. After the addition was complete, the mixture was stirred for 1 h at room temperature. EtOAc (150 mL) was added and the mixture was washed with H2O (200 mL) and brine (150 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (100/1 to 10/1 petroleum ether/EtOAc) to afford tert-butyl 6-(bromomethyl)-3,4-dihydroisoquinoline-2(lH)- carboxylate (8.56 g, 54.8% yield) as a light yellow solid.

As the paragraph descriping shows that 622867-52-1 is playing an increasingly important role.

Reference£º
Patent; REVOLUTION MEDICINES, INC.; SEMKO, Christopher; PITZEN, Jennifer; WANG, Gang; TIBREWAL, Nidhi; AGGEN, James Bradley; THOTTUMKARA, Arun P.; BURNETT, G. Leslie; GLIEDT, Micah James Evans; KISS, Gert; WON, Walter; LEE, Julie Chu-li; GILL, Adrian Liam; (538 pag.)WO2018/204416; (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.1165923-89-6,tert-Butyl 6-hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.

1165923-89-6, RRN 34Example 5 Preparation of intermediate 6-bromomethyl-5-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (5-34) To a solution of compound 5-30 (100.0 g, 380 mmol) and Et3N (76.8 g, 760 mmol) in dichloromethane (1.5 L) cooled to 0 C. is added triflic anhydride (Tf2O) (107.0 g, 380 mmol) via addition funnel. Upon complete addition of Tf2O, the solution is warmed to room temperature for 5 h. The reaction mixture is then treated with H2O and dichloromethane, and the organic phase is separated, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is purified by silica gel chromatography (using 20:1 petroleum ether:EtOAc) to provide compound 5-31 (105.0 g).

As the paragraph descriping shows that 1165923-89-6 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BRENNEMAN, Jehrod Burnett; GINN, John; LOWE, Michael D.; SARKO, Christopher Ronald; TASBER, Edward S.; ZHANG, Zhonghua; US2014/73629; (2014); 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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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

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.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.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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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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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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4456-77-3, Isoquinoline-1,3(2H,4H)-dione is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4456-77-3

A mixture of homophthalimide (770 mg, 4.78 mmol), 4-pyridinecarboxaldehyde (0.469 mL, 4.78 mmol) and piperidine (0.5 mL) in acetic acid (25 mL) was heated at reflux for 1 h. The resultant solution was cooled to room temperature. The solid product was removed by filtration, washed by water (4¡Á10 mL) and dried under vacuum to afford 920 mg (3.67 mmol, 77% yield ) of a mixture of Z and E isomers of the above compound. 1H-NMR (DMSO-d6) complex proton signals shown in aromatic region due to existence of both E and Z isomers. MS ES 251 (M+H)+, 252 (M+2H)+.

The synthetic route of 4456-77-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bayer Pharmaceuticals Corporation; US6689883; (2004); B1;,
Isoquinoline – Wikipedia
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