Heterocyclic Building Blocks-Tetrahydropyrans

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

[00660] Synthesis of compound 112.2. Into a 100-mL 3-necked round-bottom flask under nitrogen were added compound 112.1 (3 g, 23.41 mmol, 1.00 equiv), ethyl 2-cyanoacetate (2.9 g, 25.64 mmol, 1.10 equiv), S (3.0 g) and morpholine (0.75 g) in 50 mL of dry ethanol. The resulting mixture was stirred overnight at 50 C. Upon completion of the reaction solvent was removed under vacuum and crude was purified via flash column chromatography to afford 5.6 g (94%) of compound 112.2 as a yellow solid., 1194-16-7

The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NIMBUS IRIS, INC.; CHAUDHARY, Divya; KAPELLER-LIBERMANN, Rosana; WO2014/194242; (2014); A2;,
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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Step 3 [0341] 4-(Iodomethyl)tetrahydro-2H-pyran obtained in Step 2 (0.940 g, 4.16 mmol) was dissolved in acetonitrile (10 mL), triphenylphosphine (1.09 g, 4.16 mmol) was added thereto, and the mixture was stirred for 13 hours under reflux with heating. The solvent in the reaction mixture was evaporated under reduced pressure, diethyl ether was added to the residue, and the precipitated crystal was collected by filtration, whereby triphenyl[(tetrahydro-2H-pyran-4-yl)methyl]phosphonium iodide (0.600 g, 30%) was obtained. 1H NMR (300 MHz, DMSO-d6, delta): 7.90-7.74 (m, 15H), 3.68-3.61 (m, 4H), 3.16-3.13 (m, 2H), 2.02-1.91 (m, 1H), 1.41-1.31 (m, 4H)., 101691-94-5

The synthetic route of 101691-94-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kyowa Hakko Kirin Co., Ltd.; FURUTA, Takayuki; SAWADA, Takashi; DANJO, Tomohiro; NAKAJIMA, Takahiro; UESAKA, Noriaki; EP2881394; (2015); 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.156002-64-1,Methyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

Sodium hydroxide (16 g) in water (400 mi) was added to a solution of Intermediate 27 (13 g) in MeOH (60 ML). The mixture was stirred overnight at room temperature, then evaporated in vacuo. The solution was washed with Et2O (50 ml), acidified with concentrated hydrochloric acid to pH 2 and extracted with EtOAc (100 ML), the solvent washed with brine (50 ML), dried (MGS04) and evaporated to give the title compound as a colourless solid (10.2 g). MS 144 (M), 156002-64-1

As the paragraph descriping shows that 156002-64-1 is playing an increasingly important role.

Reference£º
Patent; CELLTECH R & D LIMITED; WO2004/113298; (2004); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics