Analyzing the synthesis route of 135643-82-2

135643-82-2, As the paragraph descriping shows that 135643-82-2 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.135643-82-2,Methyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetate,as a common compound, the synthetic route is as follows.

A. Under nitrogen with stirring at room temperature solution of 17beta-hydroxy-5alpha-androstan-3-one (the compound of Formula VII wherein X-Y is STR14 and Z is H, 145.2 g.) in dry dimethylformamide (500 ml.) was added slowly to a suspension of sodium hydride (60%, 48 g.) in dry dimethylformamide (100 ml.). A solution of methyl glycolate tetrahydropyranyl ether (130.5 g.) in dry dimethylformamide (100 ml.) was then slowly added. After continued stirring overnight methanol (50 ml.) was added slowly. The resulting mixture was poured into ice-water (4 1.). The resulting solution was filtered and the filter pad was washed with water. Neutralization of the filtrate with hydrochloric acid (6N) gave a white crystalline solid, which was collected by filtration, washed with water and dried, affording 17beta-hydroxy-2alpha-{[(tetrahydro-2H-pyran-2-yl)oxy]acetyl}-5alpha-androstan-3-one (the compound of Formula VI wherein Q’ is tetrahydropyranyl, X-Y is STR15 and Z is H; 206 g, 96% yield). Recrystallization of part (15.0 g.) of the product from cyclohexane gave a white crystalline solid (12.0 g.) having m.r. 128-131 C.

135643-82-2, As the paragraph descriping shows that 135643-82-2 is playing an increasingly important role.

Reference£º
Patent; Sterling Drug Inc.; US5100882; (1992); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 220641-87-2

The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

To a solution of 2-bromo-4-isopropyl-thiazole-5-carboxylic acid ethyl ester (0.50 g, 1.80 mmol) in 1-methyl-2-pyrrolidone (10 ml) are added potassium carbonate (0.37 g, 2.70 mmol) and N-methyltetrahydro-2H-pyran-4-amine (0.62 g, 5.40 mmol) at RT and the reaction mixture is heated at 150C for 16 h. After completion of the reaction, the mixture is diluted with methyl tert-butyl ether (20 ml) and washed with water (3 x 20 ml) and brine (3 x 20 ml). The organic layer is dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel,10% EtOAc/hexane) to yield 4-isopropyl-2-(methyl-tetrahydro-pyran-4-yl-amino)-thiazole-5-carboxylic acidethyl ester (0.56 g, 1.92 mmol, 99%)., 220641-87-2

The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GRUeNENTHAL GMBH; LUCAS, Simon; KUHNERT, Sven; BAHRENBERG, Gregor; SCHROeDER, Wolfgang; WO2014/82739; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 116131-44-3

As the paragraph descriping shows that 116131-44-3 is playing an increasingly important role.

116131-44-3, 3-(Bromomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2,4-dimethyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide (0.050 g, 0.136 mmol) in anhydrous dimethylformamide (3 mL) in a flamed dried flask under argon atmosphere at 0 C. was added sodium hydride (60% in mineral oil, 0.014 g, 0.339 mmol) was added in one portion. The reaction was stirred for 10 min at 0 C. then 3-(bromomethyl)tetrahydro-2H-pyran (0.024 g, 0.136 mmol) was added via syringe. The mixture was then stirred for 24 hours at room temperature. After consumption of starting material, the reaction mixture was quenched with saturated ammonium chloride (25 mL) and extracted with ethyl acetate (2*25 mL). The combined organics were washed once with saturated sodium bicarbonate (50 mL) and dried over anhydrous sodium sulfate. The concentrated residue was purified by flash chromatography over silica gel using 95:5 dichloromethane/methanol to give 2,4-dimethyl-N-(4-(2-oxo-1-((tetrahydro-2H-pyran-3-yl)methyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)oxazole-5-carboxamide (0.062 g, 97%) as a white solid. 1H NMR (400 MHz, DMSO-d): delta 12.53 (s, 1H), 7.80 (m, 2H), 7.61 (s, 1H), 7.24 (d, 1H, J=8.4 Hz), 3.87 (d, 2H, J=7.2 Hz), 3.68 (m, 2H), 3.32 (m, 1H), 3.17 (dd, 1H, J=11.6, 9.6 Hz), 2.92 (m, 2H), 2.59 (m, 2H), 2.41 (s, 3H), 1.87 (m, 1H), 1.72 (m, 1H), 1.58 (m, 1H). MS (ESI): Calcd. for C24H26N4O4S: 466, found 467 (M+1)+., 116131-44-3

As the paragraph descriping shows that 116131-44-3 is playing an increasingly important role.

Reference£º
Patent; Nantbio, Inc.; Tao, Chunlin; Nallan, Laxman; Ho, David G.; Wang, Qinwei; Weingarten, Paul; Juncker-Jensen, Anna B.; (121 pag.)US2018/201610; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 29943-42-8

29943-42-8, As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

To a solution of tetrahydropyran-4-one (71.6 g, 715 mmol) in methanol (2 L) was added tert-butylcarbazate (100 g, 758 mmol) at ambient temp. The mixture was stirred at ambient temp for 20 h. The reaction mixture was concentrated under reduced pressure to dryness to afford a white solid (154 g). To a suspension of the white solid (154 g, 715 mmol) in water (1 L) was added acetic acid (500 mL, 8.73 mol) and the mixture was stirred for 30 min to get a clear solution. To this solution, solid NaCNBH3 (44.5 g, 708 mmol) was added portion-wise. The mixture was stirred at ambient temp for 2 h. The mixture was then transferred to a 12 L flask, cooled to 0 C., and quenched with 1N NaOH (8.73 L, 8.73 mol). The mixture was extracted with CH2Cl2 (3*3 L) and dried over Na2SO4. The organic layer was filtered and concentrated to afford a white solid (164 g, contains ~15% of N-acetyl-N’-Boc-hydrazine derivative). Chromatography [silica, ethyl acetate/MeOH (95:5] gave 94 g of 90% pure boc-hydrazine. A solution of boc-hydrazine (50 g, 231 mmol) in methanol (500 mL) was added a solution of HCl in dioxane (462 mL, 1.85 mol, 4.0 M). The mixture was stirred at ambient temp overnight. Concentration of the reaction mixture under reduced pressure afforded the title compound as a white solid (43 g, 98%). 400 MHz 1H NMR (DMSO) delta 3.85-3.82 (m, 2H), 3.27-3.21 (m, 2H), 3.13-3.05 (m, 1H), 1.88-1.84 (m, 2H), 1.48-1.38 (m, 2H). MS: (M+H m/z=117.2).

29943-42-8, As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc; US2009/30003; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 624734-17-4

As the paragraph descriping shows that 624734-17-4 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.624734-17-4,3-Methoxydihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

624734-17-4, Intermediate 21b3-Methoxy-tetrahydro-pyran-4-one* (1 g, 7.68 mmol), commercially available (R)-(+)-l- 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 (50g). 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 configuration assigned by NMR). GC/MS (method 3B) Rt = 35.04 min.

As the paragraph descriping shows that 624734-17-4 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; EBEL, Heiner; FRATTINI, Sara; GIOVANNINI, Riccardo; HOENKE, Christoph; SCHEUERER, Stefan; WO2011/147772; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 29943-42-8

29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various fields.

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

29943-42-8, A mixture of tetrahydro-4H-pyran-4-one (31.7mL, 0.34mol) and tert-butylcarbazate (47.7g, 0.36mol) in EtOH (50OmL) was stirred at ambient temperature overnight. The reaction mixture was evapotrated and the reisdue suspended in HOAc-H2O (1:1 / 50OmL). NaCNBH3 (22.64g,0.36mol) was added and the mixture was stirred at ambient temperature for 2.5hr. The reaction mixture was suspended in EtOAc-10% K2CO3 (2:1 / 75OmL). The organic layer was separated, washed with brine (2 x 40OmL) and dried (MgSO4). Filtration and evaporation of the solvent and trituration of the residue with hexane afforded the product as a white amorphous solid(47.5g, 64%). 1H NMR (CDCl3) 6.10 (IH, br s), 3.99-3.35 (5H, m), 3.06 (IH, m), 1.79-1.35(4H, m), 1.46 (9H, s)

29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; JAMES BLACK FOUNDATION; WO2007/135350; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 61363-56-2

As the paragraph descriping shows that 61363-56-2 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61363-56-2,2H-Pyran-3,5(4H,6H)-dione,as a common compound, the synthetic route is as follows.

EXAMPLE 57 1-methyl-4-(5-nitro-3-thienyl)-4,9-dihydro-1H-isoxazolo[3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione The product from Example 45A (0.086 g, 0.75 mmol), nitro-3-thiophenecarbaldehyde (0.12 g, 0.75 mmol) and 2H-pyran-3,5(4H,6H)-dione (0.085 g, 0.75 mmol) in ethyl alcohol (2 mL) were heated at 80 C. for 2 days in a sealed tube. The reaction mixture was allowed to cool to ambient temperature and was evaporated under reduced pressure. The residue was crystallized from methylene chloride/ethanol to provide the title product. 1H NMR (300 MHz, DMSO-d6) delta 3.23 (s, 3H), 4.1 (q, 2H), 4.53 (s, 2H), 4.88 (s, 1H), 7.7 (d, 1H), 7.92 (d, 1H), 10.8 (s, 1H); MS (ESI) m/z 348 (M+H)-; Anal. Calcd for C14H11N3O6S: C, 48.13;H, 3.15; N, 12.03. Found: C, 47.76;H, 3.25; N, 11.78., 61363-56-2

As the paragraph descriping shows that 61363-56-2 is playing an increasingly important role.

Reference£º
Patent; Drizin, Irene; Altenbach, Robert J.; Carroll, William A.; US2002/7059; (2002); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 25637-16-5

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

25637-16-5, Step 1: To a solution of Core B (700.00 mg, 2.84 mmol, 1.00 eq) in MeCN (14 mL) was added CS2CO3 (1.85 g, 5.68 mmol, 2.00 eq) at 0C. After 30 min, 4- 0242952445-01 bromotetrahydropyran (703.03 mg, 4.26 mmol, 1.50 eq) was added. The mixture was stirred at 100C for 16 h in a sealed tube. The reaction mixture was filtered and the filtrate was concentrated. The crude product was purified by prep-HPLC (TFA) to give compound 39_6 (45.0 mg, 136.18 mupiiotaomicron, 4.8% yield) as a yellow solid. LCMS: RT = 0.702 min, mlz 331.1 [M+H]+ NMR (CDCb, 400 MHz) delta 8.42-8.40 (d, / = 5.6 Hz, 1H), 7.94 (s, 1H), 7.11- 7.10 (d, / = 5.2 Hz, 1H), 4.37-4.33 (m, 1H), 4.19-4.15 (m, 1H), 3.59-3.54 (m, 2H), 3.28- 3.26 (d, / = 6.4 Hz, 2H), 2.6 (s, 3H), 2.44-2.40 (m, 2H), 1.87-1.84 (m, 2H), 1.05-1.02 (m, 1H), 0.55-0.50 (m, 2H), 0.33-0.30 (m, 2H).

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

Reference£º
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BEN NERIAH, Yinon; BRACHYA, Guy; BURSTAIN, Ido; MINZEL, Waleed; SNIR-ALKALAY, Irit; VACCA, Joseph; LI, Dansu; (129 pag.)WO2017/21969; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 1194-16-7

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

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.

To a solution of 2,2-dimethyltetrahydropyran-4-one (10.4 g, 81.14 mmol) in dichloromethane (40 mL) and boron fluoride ethyl ether (11.2 m1,48% ethyl ether) was added (diazomethyl)trimethylSilane (48.0 mL, 96.0 mmol, 2 M in hexane) dropwise at -30 C. After addition, the resulting solution was stirred for 1H at -30 C and then quenched by addition of saturated sodium bicarbonate (30 mL). The resulting mixture was extracted with dichloromethane (3 x 100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 18% ethyl acetate in petroleum ether) to afford a mixture of 7,7-dimethyloxepan-4-one and 2,2-dimethyloxepan-4-one (2.6 g, 22.5% yield, ratiol : 1) as a pale yellow oil., 1194-16-7

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; HAMILTON, Gregory; STIVALA, Craig; CHEN, Huifen; ZHAO, Guiling; (1236 pag.)WO2017/4500; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 14774-37-9

14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various fields.

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.

Step 1 a Synthesis of Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate To a stirred solution of (tetrahydro-2H-pyran-4-yl)methanol (300 mg, 2.58 mM) in DCM (5 ml), triethyl amine (784 mg, 7.75 mM) was added. The reaction mixture was stirred for 5 min at 0 QC followed by the addition of 4-methylbenzene-1 -sulfonyl chloride (542 mg, 2.84 mM). The reaction mixture was further stirred for 2h. RM, concentrated and purified by column chromatography to afford the title compound tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (634 mg). Yield: 91 %; 1 H NMR (CDCI3, 300 MHz): delta 7.81 (d, J=8.1 Hz, 2H), 7.38 (d, J=8.1 Hz, 2H), 3.97-3.86 (m, 4H), 3.36 (t, J=6.5 Hz, 2H), 2.47 (s, 3H), 1 .97-1 .94 (m, 1 H), 1 .62 (d, J=12 Hz, 2H), 1 .35-1 .23 (m, 2H), MS: m/z 293 (M+Na)., 14774-37-9

14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PIRAMAL ENTERPRISES LIMITED; KUMAR, Sanjay; SHARMA, Rajiv; MAHAJAN, Vishal, Ashok; SAWARGAVE, Sangameshwar, Prabhakar; WO2013/128378; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics