Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.,18881-17-9

Step 2: Compound A2 (5.3 g, 16.47 mmol) and (S)-(1,2,3,4-tetrahydroisoquinolin-3- yl)methanol (2.96 g, 18.12 mmol) were dissolved in DCM (47.1 mL). The reaction mixture was cooled to 0 C and TEA (3.44 mL, 24.71 mmol) was added dropwise under Ar. The reaction mixture was then warmed to rt and was stirred overnight. The solution was concentrated and the crude product was purified by silica gel chromatography (EtOAc/hexanes, gradient, 0% to 80%) to obtain compound A3 (7.22 g, 16.10 mmol, 98% yield). LCMS = 5.482 mm (8 mm method). Mass observed (ESI): 449.25 (M+H).

18881-17-9 (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol 776757, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; IMMUNOGEN, INC.; MILLER, Michael, Louis; SHIZUKA, Manami; CHARI, Ravi, V.J.; (312 pag.)WO2019/133652; (2019); 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.23687-26-5,6-Aminoisoquinoline,as a common compound, the synthetic route is as follows.

A mixture of 2 (340.41 g assay-corrected, 1.0 equiv.), collidine (1.3 equiv.) and 6-aminoisoquinoline (1.3 equiv.) in DMF at 0¡ã C. in a 50 L reactor was treated rapidly with a solution of 2,2,2-trichloro-1 , 1 -dimethylethyl chloroformate (1.3 equiv.) in DMF in a single portion. The reaction was exothermic, with a rise in temperature to about 10¡ã C. Upon stirring for a minimum of 60 minutes, the reaction was assayed by TLC and deemed complete when two samples taken one hour apart showed no further conversion. Thereaction was quenched by the addition of 10percent KHCO3 (aq.), followed by diluting with ethyl acetate, washing with citric acid, a final 10percent KHCO3 (aq.) wash and concentrating to near dryness to afford a crude residue.The crude residue was dissolved in dichloromethane/ethylacetate (1:1) and the resulting solution returned to the 50 Lreactor, where it was stirred for 4.5 h. The resulting solution was filtered through a 10 jim Teflon filter to remove a colloidal solid. The selection of a 10 jim Teflon filter was based on the filter having enough surface area and beingchemically compatible with the dichloromethane/ethyl acetate (1:1) solvent mixture. Concentration of the filtrate in vacuo yielded 666.3 g of crude material.The resulting crude product was diluted with dichloromethane to give a solution that was divided into two portions for silica gel chromatography. The splitting of the dichloromethane solution maintained a 25:1 ratio of silicagel to crude product found to be useful for successful 41Fractions containing a high concentration of the desired material, irrespective of the impurities content, were combined and concentrated to afford 363.3 g of an off-white solid.The off-white solid was dissolved in dichloromethane and filtered through a 10 tm Teflon filter. The bulk of the solvent was then distilled off and the remainder gradually switched to acetonitrile via chase distillation. At this point, a white solid crystallized and the mixture was cooled to 0¡À5¡ã C. Thesolid was isolated by filtration and dried to obtain 333.7 g ofa white solid. A sample of the solid was subjected to TLCand HPLC purity analyses. No impurities could be detected by TLC, but the HPLC analysis showed the presence of an unspecified impurity at a level of 0.4 6percent while all identified impurities were below In-Process Action Levels.A first recrystallization from dichloromethane/heptane was then implemented. Afier dissolving the solid in dichloromethane, heptane was added and the resulting mixture stirred for 4 hat room temperature. A white solid crystallized out. The solid was filtered and dried to obtain 307.0 g of the solid. A sample of the solid was taken and subjected to TLC and HPLC purity analyses. No impurities could be detected by TLC, but the HPLC analysis showed the presence of the same unspecified impurity, but was reduced to a level of0.28percent.2025purification. The two portions of dichloromethane solution represented 166.5 g and 170.2 g of the crude product respectively. The purifications were achieved through theuse of two 5 kg silica gel colunms eluting with ethyl acetate/heptane (60:40) until the desired product had eluted.white solid was filtered and dried to obtain the title compound as a white solid (272.1 g; 60.5percent assay-correctedA fourth recrystallization from dichloromethane/heptane was utilized. After dissolving the solid in dichloromethane, heptane was added and the resulting mixture stirred for 4 h at room temperature during which time a white solid crystallized out. The white solid was filtered, dried, and sub-jected to HPLC purity testing. The impurity was detected at less than 0.05percent. The fourth recrystallization from dichloromethane/heptane yielded 250.9 g (55.3percent assay corrected yield) of the title compound as a white solid.To achieve even higher purities of the desired product, it may be useful to implement additional recrystallizations. ?H NMR (500 MHz, d5-DMSO) oe 1.32 (s, 9H), 2.29 (s, 3H), 2.49 (s, 3H), 3.3 (m, 1H), 3.56 (m, 1H), 4.11 (m, 1H), 5.25 (s, 2H), 7.02 (bt, J=5.4 Hz, 1H), 7.07 (d, J=8.4H, 1H), 7.11(s, 1H), 7.43 (s, 4H), 7.68 (m, 2H), 7.75 (d, J=7.9 Hz, 1H),8.02 (d, J=8.7 Hz, 1H), 8.38 (s, 1H), 8.39 (d, J=5.7 Hz, 1H),9.14 (s, 1H). 13C NMR (125 MHz, d5-DMSO) oe 20.8, 21.2,28.2, 42.9, 51.7, 65.6, 77.8, 113.1, 120.0, 121.0, 125.0,126.1, 126.6, 128.0, 128.1, 128.5, 130.4, 132.3, 135.2,136.1, 137.8, 139.5, 140.4, 142.4, 143.2, 151.5, 155.8,166.4, 171.0. LC-MS (ES+): mlz=554 (M+1), 576 (M+23).yield).

23687-26-5, As the paragraph descriping shows that 23687-26-5 is playing an increasingly important role.

Reference£º
Patent; Aerie Pharmaceuticals, Inc.; Sturdivant, Jill M.; deLong, Mitchell A.; Chambournier, Gilles; Pamment, Michael G.; Fedij, Victor; (31 pag.)US9643927; (2017); B1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23687-25-4,Isoquinolin-4-amine,as a common compound, the synthetic route is as follows.

Example 17 N-(1-Methyl-5-indolyl)-N’-(4-isoquinolyl) urea (E17) The title compound was prepared from 4-aminoisoquinoline, 1,1′-carbonyl diimidazole and 5-amino-1-methyl-indole using a procedure similar to that described for Example 1, and then converted to the hydrochloride salt using hydrogen chloride in ether/ethanol, in 26% overall yield, m.p. 195-197 C., 23687-25-4

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

Reference£º
Patent; SmithKline Beecham, p.l.c.; US5508288; (1996); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

22245-98-3, 6-Hydroxy-3,4-dihydroisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one (0.400 g, 2.44 mmol), 3-fluorobenzyl bromide (0.509 g, 2.69 mmol), potassium carbonate (0.372 g, 2.69 mmol) and N,N-dimethylformamide (5 ml) was heated to 90 C. for 8 h. Water was added and the resulting precipitate was washed with diethylether and then dried under high vacuum to afford the title compound (0.580 g, 87%). MS: m/e=272.3 (M+H+)., 22245-98-3

As the paragraph descriping shows that 22245-98-3 is playing an increasingly important role.

Reference£º
Patent; Cesura, Andrea; Rodriquez Sarmiento, Rosa Maria; Scalone, Michelangelo; Thomas, Andrew William; Wyler, Rene; US2003/225122; (2003); 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.119-65-3,Isoquinoline,as a common compound, the synthetic route is as follows.

Add 20g isoquinoline to 300ml fuming sulfuric acid, heat to 120C, stir for 5 hours, cool to room temperature,Pour slowly into ice water to precipitate a white solid which was filtered, washed with water and dried to give 24 g of 5-sulfonic acid isoquinoline.

119-65-3, 119-65-3 Isoquinoline 8405, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Bu Gonggaofamingren; (5 pag.)CN107778231; (2018); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

6624-49-3, Isoquinoline-3-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6624-49-3, The compound 3-isoquinolinecarboxylic acid (0801-132) (1.0 g, 5.78 mmol, 1.0 eq.)Dissolved in 30 ml of methanol,Sulfuric acid (0.5 ml) was then added and the reaction was refluxed overnight.After the reaction is finished, add sodium bicarbonate solutionpH to 8, extracted with dichloromethane, liquid-separated, and the organic phase dried over anhydrous sodium sulfate.Spin-drying afforded the compound 3-isoquinolinecarboxylic acid methyl ester (810 mg, 75%).

The synthetic route of 6624-49-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.,18881-17-9

To 50 mL dichloromethane solution containing (S)-3-hydroxymethy-1,2,3,4-tetrahydroisoquinoline (4.53 g, 27.75 mmol) was added di-tert-butyl dicarbonate (5.45 g, 25.0 mmol, 0.9 eq) and the reaction mixture was stirred for 2 hours until no gas bubbling was observed. The reaction mixture was washed with 0.5 N HCl (50 mL) followed by brine (50 mL) to remove the residual starting material. After drying wth MgSO4 and filtration , dichloromethane mixture was evaporated to yield crude (S)-N-tert-Butyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline. The crude N-tert-Butyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline was redissolved in 100 mL tetrahydrofuran. NaH (60%, 1.22 g) was added portion by portion to the solution at 0C and after 30 min stirring at room temperature, MeNCS (2.23 g) was added and the mixture was stirred for 2 h at rt. Brine (50 mL) was added to the mixture to quench the reaction and after evaporation of volatile in vacuo, it was extracted with dichloromethane (50mLx 2) and combined layer was dried (MgSO4), filtered, evaporated. The resulting material was chromatographed with hexane-EtOAc (4:1) mixture over SiO2 to provide 7.07 g-(81.8 %) of (S)-N-tert-butyloxycarbonyl-3-(N-Methyl-thiocarbamoyloxymethyl)-1,2,3,4-tetrahydroisoquinoline. This material was dissolved in THF(30 mL) and 10 mL conc. HCl was added to the solution. One hour later, 5 mL of conc, HCl was added and stirred another 1 h until the reaction is finished. The reaction mixture was diluted with 30 mL of water and volatile were evaporated. During the evaporation, desired product was precipitated as white solid. The solid was filtered and dried to yield the product as the hydrochloride salt (4.8 g). 1H-NMR (200 MHz, DMSO-d6) delta: 10.5-9.7 (m, 2H), 9.30 (s, 1H), 7.23 (s, 4H), 4.90 (m, 2H), 4.38 (s, 2H), 3.15-3.00 (m, 2H), 2.95 (d, 2H), 2.80 (1H)

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

Reference£º
Patent; SK Corporation; EP1149079; (2004); B1;,
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

To an ice cooled solution of 5-bromo-2-(3-(ethoxycarbonyl)-5-methyl-lH-pyrazol-l-yl)benzoic acid (45.0 g, 127.8 mmol) in DCM (450 mL) were added (5)-(l ,2,3,4-tetrahydroisoquinolin-3-yl)methanol (20.8 g, 102.27 mmol), HATU (72.7 g, 191.2 mmol), DIPEA (55.7 mL, 319.6 mmol) followed by stirring at RT for 12h. The reaction mixture was diluted with DCM (750 mL), washed with water (500 mL), brine (100 mL), dried over sodium sulphate and concentrated invacuo. The residue was purified on silica gel (100-200 mesh) to afford the the title compound as a liquid 50 g (79%). Rf = 0.44 (55 % EtOAc in hexane); NMR (400 MHz, DMSO-d6): delta 8.00 – 7.40 (m, 3H), 7.30 – 7.00 (m, 4H), 6.80 – 6.40 (m, 1H), 5.10 – 3.80 (m, 7H), 3.50 – 2.40 (m, 3H), 2.40 – 2.10 (m, 3H), 1.30 – 1.00 (m, 3H); ES-MS: m/z 498.2 (M+H).

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

Reference£º
Patent; NOVARTIS AG; VISSER, Michael Scott; YUSUFF, Naeem; WO2013/96055; (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.3336-43-4,1-Chloroisoquinolin-4-ol,as a common compound, the synthetic route is as follows.

To a solution of 1-chloroisoquinolin-4-ol (5.0 g, 27.8 mmol) in acetonitrile (50 mL) was added TMS-diazomethane (12.73 g, 111.2 mmol) at 0¡ã C. The reaction mixture was allowed to come to room temperature and stirred for 2 h. Solvent was evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-4-methoxyisoquinoline (2.5 g, 46.4percent) as off-white solid.1H NMR (400 MHz, CD3OD): delta ppm 8.29-8.17 (m, 2H), 7.97 (s, 1H), 7.91-7.82 (m, 2H), 4.05 (s, 3H); MS: MS m/z 194.7 (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; (403 pag.)US9527885; (2016); B2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

3482-14-2, Isoquinolin-8-ol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Isoquinoline-8-ol (3.64 g, 25.08 mmol) was added to the vessel.A solution of potassium tert-butoxide (25.03 mmol) in THF was then added to the vessel.Rinse using less than 100 mL of DMF and stir the solution for about 15 minutes to ensure complete deprotonation of the isoquinoline-8-ol.Compound 5 (7.59 g, 22.39 mmol) obtained in the synthesis of Step 1-3 was added to a replenishing tank.Transfer the material to a reaction vessel (containing deprotonated isoquinoline-8-ol) with no more than 100-500 mL of DMF.It is then transferred to a reaction vessel.The solution of the rinse vessel was also transferred to the reactor using DMF.The reactor was heated to 50 C and aged at 50 C for 4 hours, or until the end of the reaction.No more compound 5 was shown to be converted to methyl 2-isoquinolin-8-yloxy-1-oxobenzo[b]thiophene-6-yl-isoxazole-5-carboxylate,The solution was used directly in the next step., 3482-14-2

As the paragraph descriping shows that 3482-14-2 is playing an increasingly important role.

Reference£º
Patent; Wang Liping; (11 pag.)CN108558852; (2018); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem