Tag: M.W:200-300

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;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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.55270-27-4,4-Bromoisoquinolin-1-amine,as a common compound, the synthetic route is as follows.,55270-27-4

General procedure: To a solution of CuI (0.1 eq), Pd(PPh3)2Cl2 (0.05 eq) and compound7 (1 eq) in MeCN (5 mL) were added ArBr (Ar a, b, c, e, f, g,h, k, l) or ArI (Ar q, r, s, t) (3 eq) and trimethylamine (1.5 eq). Thereaction mixture was flushed with argon and sealed in a pressuretube. The reaction mixture was stirred at 80 C for 3-4 h. The reactionmixture was extracted with EtOAc, washed with water andbrine and concentrated in vacuo. The product was dissolved inMeOH (15 mL) at 60 C for 1 h. The organic solvent was removed invacuum. The crude mixture was purified by column chromatographyon silica gel to give 8a, 8b, 8c, 8e, 8f, 8g, 8h, 8k, 8l, 8q, 8r, 8s,8t.To a solution of ArI (Ar = n, p) (3 eq) in MeCN (5 mL) was addedtrimethylamine (5 mL). The mixture was stirred at room temperaturefor 1 h, after which time CuI (0.1 eq), Pd(PPh3)2Cl2 (0.05 eq)and compound 7 (1 eq) were added. The reaction mixture wasflushed with argon and sealed in a pressure tube. The reactionmixture was stirred at 50 C for 24 h. The reaction mixture wasextracted with EtOAc, washed with water and brine and concentratedin vacuum. The product was then dissolved in MeOH (15 mL)at 60 C for 1 h. The organic solvent was removed in vacuo. Thecrude mixturewas purified by column chromatography on silica gelto give 8n and 8p.

As the paragraph descriping shows that 55270-27-4 is playing an increasingly important role.

Reference£º
Article; Ma, Cong-Xuan; Lv, Wei; Li, Ya-Xin; Fan, Bing-Zhi; Han, Xu; Kong, Fan-Sheng; Tian, Jing-Chao; Cushman, Mark; Liang, Jian-Hua; European Journal of Medicinal Chemistry; vol. 169; (2019); p. 1 – 20;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

50458-79-2, Ethyl 3-isoquinolinecarboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,50458-79-2

General procedure: To the solution of ester (10 mmol) in THF (20 mL) and ethyl acetate (70 mmol), LiHMDS (30 mmol) was added very quickly at -40 C, and stirred at this temperature for 20 min. After completion of the reaction, reaction mixture was quenched with acetic acid (50 mmol) and then basified using 10% NaHCO3 solution, extracted with ethyl acetate (2¡Á100 mL), the combined organic layer was washed with water and brine solution and dried over Na2SO4. The specific purification procedure for each compound has been included along with their characterization data.

As the paragraph descriping shows that 50458-79-2 is playing an increasingly important role.

Reference£º
Article; Venkat Ragavan; Vijayakumar; Rajesh; Palakshi Reddy; Karthikeyan; Suchetha Kumari; Bioorganic and Medicinal Chemistry Letters; vol. 22; 12; (2012); p. 4193 – 4197;,
Isoquinoline – Wikipedia
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1350643-72-9, (S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 1 was prepared in 3 steps from compound A according to the following procedures:Compound A was coupled to 2-((tert-butoxycarbonyl)amino)pyrazolo [1,5 -ajpyrimidine-3-carboxylic acid according to the following procedure: Compound A (27.4 mmol, 1.0 equiv), HOBt hydrate (1.2 equiv), 2-((tert- butoxycarbonyl)amino)pyrazolo [1 ,5-a]pyrimidine-3-carboxylic acid (1.05 equiv) and EDCI (1.25 equiv) were added to a 200 mL round bottomed flask with a stir bar. N,N-Dimethylfonnamide (50 mL) was added and the suspension was stirred at RT for 2 mi Hunig?s base (4.0 equiv) was added and after which the suspension became homogeneous and was stirred for 22h resulting in the formation of a solid cake in the reaction flask. The solid mixture was added to water (600 mL) and stirred for 3h. The resulting cream colored solid was filtered and washed with water (2 x 100 mL) and dried. The solid was then dissolved in methylene chloride (40 mL) after which trifluoroacetic acid (10 equiv, 20 mL) was added and the reaction was stirred for 30 mm at RT after which there is no more starting material by LC/MS analysis. The solution was then concentrated and coevaporated with a mixture of methylene chloride/ethanol (1:1 v/v) and then dried under high vacuum ovemight. The resulting solid was triturated with 60 mL of ethanol for lh and then collected via vacuum filtration. The beige solid was then neutralized with sodium carbonate solution (100 mL) and then transferred to a separatory funnel with methylene chloride (350 mL). The water layer was extracted with an additional 100 mL of methylene chloride. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum to provide a pale yellow solid that was purified using flash silica gel chromatography (Combiflash, 24g column, gradient of 0- 5% methanol/methylene chloride) to provide amide B. ESI-MS m/z: 459.4 [M+Hj+., 1350643-72-9

As the paragraph descriping shows that 1350643-72-9 is playing an increasingly important role.

Reference£º
Patent; INFINITY PHARMACEUTICALS, INC.; CRENIER, Louis; LESCARBEAU, Andre; SHARMA, Praveen; GENOV, Daniel G.; (324 pag.)WO2017/48702; (2017); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

190777-77-6, 5-Bromoisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0461] To 5-bromoisoquinolin- 1 (2H)-one (40 mg, 0.18 mmol) in dioxane (1 mL) was added bis(pinacolato)diboron (63 mg, 0.25 mmol), and PdC12[P(Ph)3]2 (6 mg, 0.01 mmol). The reaction mixture sealed and heated to 100 C for lh. The reaction was cooled to room temperature and telescoped to the next reaction. MS (m/z) 272.3 [M+H]., 190777-77-6

As the paragraph descriping shows that 190777-77-6 is playing an increasingly important role.

Reference£º
Patent; GILEAD SCIENCES, INC.; BRIZGYS, Gediminas; CANALES, Eda; CHOU, Chien-hung; GRAUPE, Michael; HU, Yunfeng, Eric; LINK, John, O.; LIU, Qi; LU, Yafan; SAITO, Roland, D.; SCHROEDER, Scott, D.; SOMOZA, John, R.; TSE, Winston, C.; ZHANG, Jennifer, R.; WO2014/134566; (2014); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

1350643-72-9, (S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[001313] Compound 4 was prepared in 3 steps from compound A according to the following procedures: Compound A was prepared according to Method A. It was coupled to 2-((tert- butoxycarbonyl)amino)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid according to the following procedure: Compound A (27.4 mmol, 1.0 equiv), HOBt hydrate (1.2 equiv), 2-((tert- butoxycarbonyl)amino)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid (1.05 equiv) and EDC (1.25 equiv) were added to a 200 mL round bottomed flask with a stir bar. N,N-Dimethylformamide (50 mL) was added and the suspension was stirred at RT for 2 min. Hunig’s base (4.0 equiv) was added and after which the suspension became homogeneous and was stirred for 22h resulting in the formation of a solid cake in the reaction flask. The solid mixture was added to water (600 mL) and stirred for 3h. The resulting cream colored solid was filtered and washed with water (2 x 100 mL) and dried., 1350643-72-9

As the paragraph descriping shows that 1350643-72-9 is playing an increasingly important role.

Reference£º
Patent; INFINITY PHARMACEUTICALS, INC.; KUTOK, Jeffery, L.; WINKLER, David, G.; PALOMBELLA, Vito, J.; WO2015/143012; (2015); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

27655-40-9, Isoquinoline-5-sulfonic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Add 8L of thionyl chloride to the dry 20L glass reactor, add 2kg of 5-isoquinoline sulfonic acid, add 200ml of N,N-dimethylformamide (DMF) with stirring, and control the temperature of the reaction solution at 50 Below C, after the addition was completed, the temperature was raised to reflux and refluxed for 2 hours. Concentrated to dryness to give a white solid.Filtration gave a white solid which was re-slued twice and filtered to give a white-white 5-isoquinoline sulfonyl chloride hydrochloride solid.Into a 50 L glass reactor, 12 L of dichloromethane was added, and then 5-isoquinolinesulfonyl chloride hydrochloride was added to the front, and the temperature was lowered to -5 to 5 C, and a saturated aqueous solution of sodium hydrogencarbonate was added thereto with stirring to adjust the pH to 5 to. 6. Control the temperature of the reaction solution at -5 to 5 C, separate the dichloromethane phase, and extract the aqueous solution twice with dichloromethane (dichloromethane 4 L ¡Á 2), and combine the dichloromethane phase with anhydrous magnesium sulfate 0.5. ~ 1 kg of dry, filtered to give a pale yellow 5-isoquinoline sulfonyl chloride clear solution, to be used.

27655-40-9, As the paragraph descriping shows that 27655-40-9 is playing an increasingly important role.

Reference£º
Patent; Xuzhou Wan Bang Jinqiao Pharmaceutical Co., Ltd.; Jiangsu Wanbang Biochemical Pharmaceutical Group Co., Ltd.; Zhang Haifeng; Qiao Deshui; Gao Xueqin; (8 pag.)CN109970712; (2019); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

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;,
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.

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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