Month: September 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19752-84-2,Tetrahydro-2H-pyran-3-ol,as a common compound, the synthetic route is as follows.

Combine tetrahydropyran-3-ol (1.3 g. 13 mmoi), 1-(methyisuifoni)-3-nitro-1H- pyrazole (2.4 g, 1.0 eq), and cesium carbonate (4.8 g, 1.2 eq) in acetonitrile (40 mL). Stir at 90 ?C overnight. Concentrate the mixture in vacuo. Dilute with EtOAc and filter through a pad of diatomaceous earth. Concentrate the filtrate in vacuo to provide a i-esidue. Subject the residue to C- 18 reverse phase chromatography eluting with a gradient from 0% to 100% of (0. 1% formic acid in acetonitrile) in (0. 1% formic acid in water), to give the title compound (0.35 g, 14%). MS (ES) m/z = 198 (M¡ÀH)., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; BASTIAN, Jolie Anne; CLAYTON, Joshua Ryan; COATES, David Andrew; SALL, Daniel Jon; WOODS, Timothy Andrew; (58 pag.)WO2018/13486; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

130290-79-8, (Tetrahydro-2H-pyran-4-yl)methanamine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 500 mL three-neck RB flask equipped with a mechanical stirrer were charged the 4-chloro-3-nitrobenzenesulfonamide, Compound M (10.0 g), diisopropylethylamine (17.5 g), (tetrahydro-2H-pyran-4-yl)methanamine (7.0 g) and acetonitrile (150 mL). The reaction mixture was adjusted to an internal temperature of 80 C. and agitated for no less than 12 hours. The product solution was cooled down to 40 C. and agitated for no less than 1 hour until precipitation observed. The product slurry was further cooled to 20 C. Water (75 mL) was slowly charged over no less than 1 hour, and the mixture cooled to 10 C. and agitated for no less than 2 hours before collected by filtration. The wet cake was washed with 1:1 mix of acetonitrile:water (40 mL). The wet cake was then reslurried in water (80 mL) at 40 C. for no less than 1 hour before collected by filtration. The wet cake was rinsed with water (20 mL), and dried at 75 C. under vacuum to give 12.7 g of the desired product in 99.9% purity and in 91% weight-adjusted yield. 1H NMR (DMSO-d6): delta 1.25 (m, 2H), 1.60 (m, 2H), 1.89 (m, 1H), 3.25 (m, 2H), 3.33 (m, 2H), 3.83 (m, 2H), 7.27 (d, J=9.3 Hz, 1H), 7.32 (s, NH2, 2H), 7.81 (dd, J=9.1, 2.3 Hz, 1H), 8.45 (d, J=2.2 Hz, 1H), 8.54 (t, J=5.9 Hz, 1H, NH).

130290-79-8, As the paragraph descriping shows that 130290-79-8 is playing an increasingly important role.

Reference£º
Patent; ABBVIE INC.; Chan, Vincent S.; Christesen, Alan C.; Grieme, Timothy A.; Ku, Yi-Yin; Mulhern, Mathew M.; Pu, Yu-Ming M.; US2014/275540; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4677-20-7,4-(2-Bromoethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

Intermediate 17: 2-Butoxy-8-methoxy-9-r2-(tetrahvdro-2/-/-pyran-4-yl)ethyll-9/-/-purin- 6-amine2-Butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (0.2 g) in anhydrous N, N- dimethylformamide (5 ml.) was treated with anhydrous potassium carbonate (0.315 g) and then heated to 600C for 1 hour. On cooling to room temperature, to the above was added 4-(2-bromoethyl)tetrahydro-2H-pyran (0.110 g) and the reaction was warmed to 500C, overnight. The reaction mixture was quenched with water (5 ml.) and extracted into ethyl acetate (3 times, 100 ml. combined total volume). The separated organic layers were combined and passed through a hydrophobic frit to dry. The organic phase was stripped to give a gum which was purified by C-ibeta reverse phase chromatography using water (containing 0.1 % formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (20-60%) to afford the title compound as a white solid (11 1 mg). MS calcd for (Ci7H27N5Os)+ = 349 MS found (electrospray): (M+H)+ = 3501 H NMR (CDCI3): 5.20 (2H, s), 4.24 (2H, t), 4.10 (3H, s), 3.94 (4H, overlapping m), 3.31 (2H, m), 1.78-1.65 (6H, overlapping m), 1.52-1.39 (3H, overlapping m), 1.30 (2H, m), 0.95 (3H, t).

4677-20-7, 4677-20-7 4-(2-Bromoethyl)tetrahydropyran 22637012, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/101867; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

850429-50-4,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.850429-50-4,2-(Tetrahydro-2H-pyran-4-yl)acetonitrile,as a common compound, the synthetic route is as follows.

(Tetrahydro-4-pyranyl) -acetonitrile (75 g, 0.60 mol), Pd / C 2.5 g, 400 ml of ethanol was added to a hydrogenation vessel,Replacement 3 times,Hydrogenation,Keep the pressure IMPa,Temperature 25 C,Stirring reaction 12h,The reaction was filtered and the filtrate was transferred to the reactionAnd distilled under reduced pressure to give 65.8 g (0.5 lmo 1) of 4- (2-aminoethyl) tetrahydropyran oil.

The synthetic route of 850429-50-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shandong Chuancheng Pharmaceutical Co., Ltd.; Liu, Huaizhen; Han, Lixia; Bai, Tiankai; Guo, Ming; Ma, Juliang; (7 pag.)CN106083787; (2016); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5631-96-9,2-(2-Chloroethoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.,5631-96-9

Addition of diethanolamine to compound 3 (39.12 g, 0.24 mol)(25.23 g, 0.24 mol), Na2CO3 (31.80 g, 0.30 mol),NaI (2 g, 13.34 mmol), TBABr (0.3 g) and DMF (60 mL),It was then stirred at 140 C for 5 hours. The solvent DMF was evaporated in vacuo.Then ethyl acetate (100 mL) was added in sequence.10% NaCl aqueous solution (100 mL), stirring for 5 minutes,The aqueous phase was separated and the organic phase was washed with 100 mL of 10% aqueous NaCI.Dry anhydrous Na2SO4,After vacuum evaporation2,2′-((2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)amino)bis(ethane-1-ol) (Compound 4), pale yellow oil 50.39 g, yield 90%.It was used directly in the next synthesis without further purification.

5631-96-9 2-(2-Chloroethoxy)tetrahydro-2H-pyran 254951, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Zhai Xuexu; (9 pag.)CN108912116; (2018); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

Step 1: To 4-bromotetrahydro-2H-pyran (10 g) in round bottom flask was added 10 N NaOH (15 ml). After heated at 90 C for 24 h, the aqueous layer was separated out leaving 3,6- dihydro-2H-pyran as the crude material.

25637-16-5, The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong J.; KANE, Brian; XU, Qing; BAUER, Shawn M.; SONG, Yonghong; PANDEY, Anjali; DICK, Ryan; WO2013/78468; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

85064-61-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.85064-61-5,Tetrahydropyranyl-4-acetic acid,as a common compound, the synthetic route is as follows.

Dissolve the (+) product of Preparative Example 6, Step B, (0.1 g, 0.212 mmol) in 5 mL of DMF, stir at room temperature and add 0.043 g (0.424 mmol) of 4-methylmorpholine, 0.053 g (0.0276 mmol) of DEC, 0.037 g (0.276 mmol) of HOBT and 0.0397 g (0.276 mmole) of the product of Preparative Example 32. Stir the mixture at room temperature for 18 hours, then concentrate in vacuo to a residue and partition between methylene chloride and water. Wash the organic phase with aqueous sodium bicarbonate solution then brine. Dry the organic phase over magnesium sulfate, filter and concentrate in vacuo to a residue. Chromatograph the residue on a silica gel plate, eluting with methylene chloride – methanol (96percent – 4percent) to yield the product (0.13g) as a white solid. M.p. = 83.2-88.7¡ãC, Mass Spec.: MH+ = 597. [a]D23.2¡ãC = +55.5¡ã, c=0.2, methylene chloride.

85064-61-5 Tetrahydropyranyl-4-acetic acid 2773575, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; SCHERING CORPORATION; EP1019398; (2004); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 8-mL round-bottom flask, was placed 3-nitro-4-[[(oxan-4-yl)methyljaminojbenzene-i-sulfonamide (6.08 mg, 0.019 mmol, 1 equiv), 4-(4- [[2-(4-chlorophenyl)-4,4-dimethylcyclohex- i-en-i -ylj methyljpiperazin- 1 -yl)-2- [14,1 4-dioxo-l4lambda6-thia-2,4, 10-triazatricyclo [7.5 .0.0?[3,7jjtetradeca- 1 (9),2,5,7-tetraen- 10-yljbenzoic acid (13 mg, 0.019 mmol, 1 equiv), DCM (0.47 mL, 5.506 mmol, 381.56 equiv), DMAP (9.42 mg, 0.077 mmol, 4 equiv), EDCI (7.39 mg, 0.039 mmol, 2 equiv). The resulting solution was stirred for overnight at room temperature. The resulting mixture was concentrated. The crude product was further purified by Prep-HPLC with the following conditions (Waters I): Column, Xbridge Prep C18 OBD column, Sum, 19*150mm; mobile phase, Water (0.05% TFA) and CH3CN (46% CH3CN up to 51% in 7 mm); Detector, UV 220&254nm. This resulted in 2.5 mg (6.24%) of 4-(4- [[2-(4-chlorophenyl)-4,4-dimethylcyclohex- 1-en-i -ylj methyljpiperazin- 1 -yl)-2- [14, 14-dioxo- l4lambda6-thia-2,4, 10-triazatricyclo [7.5 .0.0?[3 ,7j jtetradeca- 1 (9),2,5,7-tetraen- 10- ylj -N-(3 -nitro-4- [[(oxan-4-yl)methylj aminoj benzenesulfonyl)benzamide as a yellow solid. LCMS-PH-PHNW-4-65-0: (ES, m/z): M+1=971.5, R,T= 3.243 mm. The measurements of the retention were done with a reversed phase column (C 18). Shimadzu LCMS 2020; 50*3.0 Kinetex 2.6u XB-C18, 2.6 microm; Eluent A: water (0.05 % TFA); Eluent B: Acetonitrile; linear gradient

1228779-96-1, The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; LOU, Yan; (108 pag.)WO2019/40550; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4295-99-2, 4-Cyanotetrahydro-4H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Comparative example 1 (Synthesis of 4-aminomethyltetrahydropyran) In an autoclave made of stainless equipped with a stirring device, a thermometer and a pressure gauge and having an inner volume of 200 ml were charged 10.0 g (90.0 mmol) of 4-cyanotetrahydropyran, 100 ml of methanol and 2.0 g (17.0 mmol in terms of a nickel atom) of developed Raney nickel (available from Nikki Chemical Co., Ltd.; sponge nickel N154D), and the mixture was reacted under hydrogen atmosphere (0.51 to 0.61 MPa) at 50 to 60C for 5 hours under stirring. After completion of the reaction, insoluble materials were filtered, the filtered material was washed with 30 ml of methanol, and the filtrate and the washed solution were combined. When this solution was analyzed by gas chromatography (Internal standard method), 7.19 g (Reaction yield: 52.7%) of the 4-aminomethyltetrahydropyran was found to be formed. Incidentally, 4.28 g of bis(4-tetrahydropyranylmethyl)amine which is a by-product was formed.

4295-99-2, The synthetic route of 4295-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ube Industries, Ltd.; EP1671937; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14774-37-9,Tetrahydropyran-4-methanol,as a common compound, the synthetic route is as follows.

To a solution of 57 (8.12g, 10mmol) and N-bromobutanimide (NBS) (13.71g, 248mmol) in 130 DCM (400mL) was added PPh3 (20.17g, 248mmol) at 0C. The reaction mixture was stirred at room temperature for 1-2h. The resulting mixture was washed with water (20mL) and brine (3¡Á20mL). The organic layer was concentrated and the residue was purified by silica gel flash chromatography (eluting with ethyl acetate in petroleum ether 2-5%) to give the product58 as a colorless oil (6.2g, yield=49%). 1H NMR (400MHz, CDCl3) delta 3.98 (dd, J=11.2Hz, 4.4Hz, 2H), 3.37 (td, J=12.0Hz, 1.6Hz, 2H), 3.28 (d, J=6.4Hz, 2H), 1.91-1.84 (m, 1H), 1.76 (d, J=13.2Hz, 2H), 1.35 (qd, J=12.4Hz, 4.4Hz, 2H); LC/MS (ESI, m/z) 179.01 [M+H]

14774-37-9, The synthetic route of 14774-37-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wang, Beilei; Wu, Jiaxin; Wu, Yun; Chen, Cheng; Zou, Fengming; Wang, Aoli; Wu, Hong; Hu, Zhenquan; Jiang, Zongru; Liu, Qingwang; Wang, Wei; Zhang, Yicong; Liu, Feiyang; Zhao, Ming; Hu, Jie; Huang, Tao; Ge, Juan; Wang, Li; Ren, Tao; Wang, Yuxin; Liu, Jing; Liu, Qingsong; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 896 – 916;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics