Day: October 16, 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4677-18-3,2-(Tetrahydro-2H-pyran-4-yl)ethanol,as a common compound, the synthetic route is as follows.

To a solution of 2-(tetrahydro-2H-pyran-4-yl)ethan-l-ol (300 mg, 2.304 mmol) and TEA (0.964 mL, 6.91 mmol) in THF (10 mL) was added dropwise Ms-Cl (0.269 mL, 3.46 mmol) at 0 C. The reaction mixture was stirred for 20 hours at 25 C. The reaction mixture was poured into water (20 mL), extracted by EtOAc (30 mL), washed with 1M HC1 (5 ml), sat NaHCCh, (10 ml) and brine (10 ml). The organic layer was dried over Na2S04, filtered and concentrated to give 2-(tetrahydro-2H-pyran-4-yl)ethyl methanesulfonate (300 mg, 1.329 mmol, 57.7 % yield) as a brown oil which was used in the next step without purification.

4677-18-3, As the paragraph descriping shows that 4677-18-3 is playing an increasingly important role.

Reference£º
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; EASTMAN, Kyle J.; KADOW, John F.; GILLIS, Eric P.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; (0 pag.)WO2020/3093; (2020); 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.14774-36-8,(Tetrahydropyran-3-yl)methanol,as a common compound, the synthetic route is as follows.

14774-36-8, To a solution of Compound 29 (100 mg, 0.34 mmol) in THF (4 mL) was added (0759) tetrahydropyran-3-ylmethanol (117.65 mg, 1.01 mmol), PPli3 (177.1 mg, 0.68 mmol) and then DIAD (136.54 mg, 0.68 mmol). The resulting mixture was stirred at 20 C under N2 for 16 hours . The reaction solution was concentrated to give the crude product, which was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 10% to 20%) and Prep- TLC (silica gel, PE: EtOAc = 4: 1) to afford A-58 (50 mg) as a solid. A-58 was purified by SFC (Chiralcel AD (250 mm x 30 mm, 5 muiotaeta); A = C02 and B = EtOH (0.1% NH3H20); 38C; 50 mL/min; 30% B over 11 minutes; multiple injections) to afford Enantiomer 1, randomly assigned as Compound 66 (Rt = 6.8 min) and Enantiomer 2, randomly assigned as Compound 67 (Rt = 9.2 min). Compound 66 (14.37 mg, 0.04 mmol) 1H NMR (CDCI3 400MHz) deltaEta = 8.00 (d, 2H), 7.48 (s, 2H), 7.33 (d, 2H), 4.01 – 3.80 (m, 4H), 3.56 – 3.35 (m, 2H), 2.43 – 2.30 (m, 1H), 1.96 – 1.85 (m, 1H), 1.82 – 1.72 (m, 1H), 1.69 – 1.59 (m, 1H), 1.49 – 1.37 (m, 1H). LCMS Rt = 1.32 min using Method A, MS ESI calcd. for Ci9Hi8F3N204 (0760) [M+H]+ 395.1, found 395.0. Compound 67 (15.66 mg, 0.04 mmol) 1H NMR (CDC13, 400MHz) deltaEta = 8.00 (d, 2H), 7.48 (s, 2H), 7.33 (d, 2H), 4.00 – 3.81 (m, 4H), 3.55 – 3.46 (m, 1H), 3.41 (dd, 1H), 2.43 – 2.31 (m, 1H), 1.96 – 1.86 (m, 1H), 1.82 – 1.72 (m, 1H), 1.69 – 1.59 (m, 1H), 1.49 – 1.37 (m, 1H). LCMS Rt = 1.33 min using Method A, MS ESI calcd. for Ci9Hi8F3N204 [M+H]+ 395.1, found 395.1.

14774-36-8 (Tetrahydropyran-3-yl)methanol 85769, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); 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.873397-34-3,Tetrahydro-2H-pyran-3-carboxylic acid,as a common compound, the synthetic route is as follows.,873397-34-3

A mixture of methyl 2,3,4,5-tetrahydro-1,4-benzoxazepine-8-carboxylate (250 mg, 1.21 mmol, 1 equiv), tetrahydro-2H-pyran-3-carboxylic acid (157 mg, 1.21 mmol, 1 equiv), DIEA (469 mg, 3.63 mmol, 3 equiv), and HATU (552 mg, 1.45 mmol, 1.2 equiv) and in DMF (4 mL) was stirred overnight at room temperature. The reaction was then quenched by the addition of water (2 mL). The resulting solution was extracted with CH2Cl2 (3¡Á10 mL) and washed with brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under vacuum. The crude racemic mixture was purified by chiral Prep-HPLC (Column: Chiralpak IA 2¡Á25 cm, 5 m; Mobile Phase A: hexanes; Mobile Phase B: EtOH; Flow rate: 20 mL/min; Gradient: 30percent B for 26 min; Detector, UV 254, 220 nm) to afford single isomers of the title compound. The first eluting isomer was isolated as a white solid (55 mg, 14percent yield). MS: (ES, m/z): 320 [M+H]+. The second eluting isomer was isolated as a white solid (55 mg, 14percent yield). MS: (ES, m/z): 320 [M+H]+.

The synthetic route of 873397-34-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Forma Therapeutics, Inc.; Zheng, Xiaozhang; Ng, Pui Yee; Han, Bingsong; Thomason, Jennifer R.; Zablocki, Mary-Margaret; Liu, Cuixian; Davis, Heather; Rudnitskaya, Aleksandra; Lancia, JR., David; Bair, Kenneth W.; Millan, David S.; Martin, Matthew W.; (190 pag.)US2016/222028; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

624734-17-4, 3-Methoxydihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

624734-17-4, Intermediate 18a 3-Methoxy-tetrahydro-pyran-4-one* (1 g, 7.68 mmol), commercially available (R)-(+)-1-phenylethylamine (0.99 ml, 7.68 mmol) and Raney-Nickel (200 mg) in 10 ml of dry ethanol were stirred under a hydrogen atmosphere (5 bar) for 15 days. The reaction mixture was diluted with 20 ml of methanol and 20 ml of tetrahydrofurane, stirred for 15 minutes, filtered on a celite pad and concentrated under vacuum. The crude product was loaded on a SCX cartridge (50 g). The cartridge was washed with methanol and the desired product was eluted with a 7 M solution of ammonia in methanol. The basic organic phase was concentrated under vacuum and the crude product was purified by flash chromatography (dichloromethane/methanol=98/2%) to obtain 710 mg (3.02 mmol) of the desired product as single stereoisomer (diastereoisomeric purity confirmed and relative cis stereochemistry assigned by NMR).GC/MS (method 3B) Rt=35.04 min

The synthetic route of 624734-17-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/4252; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

62071-40-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.62071-40-3,4-(Tetrahydropyran-4-yl)phenylamine,as a common compound, the synthetic route is as follows.

To a solution of 2,4-dichloro-i,3,5-triazine (0.93 g, 6.2 mmol) in N,Ndimethylformamide (DMF, 10 mE) at 0 C. were added sequentially N,N-diisopropylethylamine (DIEA, 1.1 mE, 6.5 mmol) and a solution of 4-(oxan-4-yl)aniline (CombiBlocks, 1.0 g, 5.6 mmol) in DMF (5 mE). The mixture was stirred at 0 C. for 30 minutes and then allowed to warm to room temperature overnight. The mixture was diluted with first with toluene and half-saturated aqueous sodium hydrogen carbonate solution and then with ethyl acetate and water. The mixture was filtered through a pad of Celite diatomaceous earth. The aqueous phase was extracted thrice with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel) to provide 4-chloro-N-(4-(tetrahydro- 2H-pyran-4-yl)phenyl)-i ,3,5-triazin-2-amine.11026] ECMS-ESI (mlz): [M+H] calcd for C,4H,5C1N40: 291.1. found: 291.2

The synthetic route of 62071-40-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Gilead Sciences, Inc.; Du, Zhimin; Guerrero, Juan A.; Kaplan, Joshua A.; Knox, JR., John E.; Lo, Jennifer R.; Mitchell, Scott A.; Naduthambi, Devan; Phillips, Barton W.; Venkataramani, Chandrasekar; Wang, Peiyuan; Watkins, William J.; Zhao, Zhongdong; (593 pag.)US2016/96827; (2016); 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.14774-36-8,(Tetrahydropyran-3-yl)methanol,as a common compound, the synthetic route is as follows.

[00175] At rt, to a suspension of 4,5-dichloro-3,6-dioxocyclohexa-1 ,4-diene-1 ,2- dicarbonitrile (1 .216 g, 5.356 mmol), TBAB (1 .727 mg, 5.356 mmol) and PPh3 (1 .405 g, 5.356 mmol) in DCM (15 mL) was added a solution of 15.1 (360 mg, 3.151 mmol) in DCM (10 mL) dropwise quickly. After addition, the reaction mixture turned to a brown solution and was stirred at rt for another 1 h. Then it was purified by column chromatography on silica gel (pH=8~9, eluent: PE/EA=10:1) directly to give crude title compound (140 mg, 25%) as a colorless oil.

14774-36-8, As the paragraph descriping shows that 14774-36-8 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; HE, Feng; DU-CUNY, Lei; XIAO, Qitao; XUN, Guoliang; ZHENG, Qiangang; (152 pag.)WO2017/149463; (2017); 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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Step 1: Preparation of ethyl 6-ethy 1-10-methoxy-2-oxo-9-(tetrahy dropy ran-4- ylmethoxy)-6,7-dihydrobenzo [a] quinolizine-3-carboxylate To a solution of ethyl 6-ethyl-9-hydroxy-10-methoxy-2-oxo-6,7- dihydrobenzo[a]quinolizine-3-carboxylate ( 100 mg, 0.29 mmol ) in DMF was added 4- (iodomethyi)tetrahydropyran ( 196.7 mg, 0.87 mmol ) and K >C() ; (80 mg, 0.58 mmol ). The mixture was stirred for 2 hours at 80 C, and then cooled to room temperature and filtered. The filtrate was concentrated in vacuo to give crude ethyl 6-ethyl- 10-methoxy-2-oxo-9- (tetrahydropyran-4-ylmethoxy)-6,7-dihydrobenzo[a]quinolizine-3-carboxylate which was used for the next step without further purification., 101691-94-5

101691-94-5 4-(Iodomethyl)tetrahydro-2H-pyran 2795507, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAN, Xingchun; JAVANBAKHT, Hassan; JIANG, Min; LIANG, Chungen; WANG, Jianping; WANG, Yongguang; WANG, Zhanguo; WEIKERT, Robert James; YANG, Song; ZHOU, Chengang; WO2015/113990; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

65412-03-5, 4-(2-Aminoethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

65412-03-5, Place 5- (4-FORMYLPHENOXY) THIOPHENE-2-CARBOXAMIDE (Example 10, Part C) (0.235 g, 0.948 mmol), 2- (TETRAHYDROPYRAN-4-YL) ETHYLAMINE (0.122 g, 0.996 mmol) and 3A molecular sieves in a vial. Add methanol (4.7 mL), cap and stir overnight. Add NaBH4 (0.0359 g, 0.948 mmol) and stir until the gasses stop evolving. Load the reaction mixture directly onto a 25 g ISCO pre-load column. Dry the column in a vacuum oven at room temperature. Purify by eluting through a 40 g ISCOO column with 5% to 30% (2.0 M NH3 in methanol) in ethyl acetate over 45 minutes to give the title compound : TOF MS ES+ 361.2 (M+H) +, HRMS calcd for CL9H25N203S 361.1586 (M+H) +, found 361.1604, time 0.36 min; HPLC [YMC-Pro pack C-18 (150 x 4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18], TR = 9. 4 min, 100% purity

The synthetic route of 65412-03-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2004/80996; (2004); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

5631-96-9, 2-(2-Chloroethoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5631-96-9, In a 2 L round bottom flask with magnetic stirrer, add 2-(2-chloroethoxy)tetrahydro-2H-pyran (29.5 mL, 0.200 mol, 1.5 equivalents) to a solution oftert-butyl 4-(4-(4-fluorophenyl)- 1 H-imidazol-2-yl)piperidine- 1 -carboxylate (46.0 g, 0.133mol, 1 equivalent) in dimethyl sulfoxide (DMSO; 460 mL) and KOH pellets (22.4 g, 0.400 mol, 3 equivalents) and heat the mixture at 60C for 18 hours. Add additional 2-(2- chloroethoxy)tetrahydro-2H-pyran (10 mL, 0.067 mol, 0.5 equivalents) and continue heating at 60C for an additional 20 hours. Cool to room temperature and pour thereaction mixture onto ice/water (1.0 L) and extract with EtOAc (2 x 250 mL). Combine the organic layers, wash with water (2 x 750 mL) and saturated aqueous sodium chloride (500 mL), dry over sodium sulphate, filter, and concentrate to an orange oil. Triturate the residue with 1:1 diethyl ether (Et20)/heptane (250 mL), filter the solids and dry under vacuum to give the title compound (47.0 g, 75% yield) as a cream solid; mass spectrum(mlz): 474(M+1).

The synthetic route of 5631-96-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; COATES, David Andrew; JOSEPH, Sajan; WOLFANGEL, Craig Daniel; (28 pag.)WO2016/40078; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125995-03-1, Atorvastatin lactone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The lactone (V) ( 100.0 g, 0.185 mol) was dissolved in THF (500 ml) and reacted with the suspension of calcium hydroxide ( 18.68 g, 0.185 mol) in water ( 100 ml) and stirred at 45 to 5O0C. After the reaction was(2 hrs), the mixture was poured into water (1.0 It), extracted twice with dichloromethane (3.0 It and 1.0 It each), the combined organic layer was optionally washed with water( 250 ml and concentrated to approx 700 ml at 40 to 420C. The concentrated layer was fine filtered through Whatman paper, cooled to 10 to 150C and diisopropyl ether (3.0 It) was then added to the mixture keeping the temperature below 150C. After stirring for 15 min, the precipitated solid was filtered, washed with cold diisopropyl ether and dried at 55 to 600C under vacuum for 24 hrs. Yield: 101.8 g (95.1 %); Purity (HPLC): 99.55 %, Assay (HPLC): 99.21 %: Calcium content: 3.33%; Moisture content (by K. F): 1.81 %;Residual solvents: Methanol < 0.05 %, THF < 0.05 %, Dichloromethane < 0.02 %, Diisopropyl ether < 0.01 %. 125995-03-1, As the paragraph descriping shows that 125995-03-1 is playing an increasingly important role.

Reference£º
Patent; MOREPEN LABORATORIES LIMITED; WO2006/48893; (2006); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics