Heterocyclic Building Blocks-Tetrahydropyrans

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

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Tetrahydro-pyran-4-ol (1 eq, 4.9 mmol, 0.5 g) is dissolved in dry DCM (10 ml) under an inert atmosphere of argon. NEt3 (3 eq, 14.69 mmol, 2.047 ml) is then added at 00C, followed by methanesulfonyl chloride (1.1 eq, 5.39 mmol, 0.417 ml) and the reaction mixture is stirred at room temperature overnight. The reaction mixture is quenched with NaHCCh (IM, 3ml) and extracted with DCM. This organic portion is washed with water and brine, dried over MgSCM, filtered and concentrated in vacuo to afford the title compound .

2081-44-9, The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; WO2009/87212; (2009); 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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

A mixture of 2-((lH-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(l-((6-(4- chlorophenyl)spiro[3.5]non-6-en-7-yl)methyl)piperidin-4-yl)benzoic acid (200 mg, 0.34 mmol), 3-nitro-4-(((tetrahycko-2H-pyran-4-yl)memyl)amino)benzenesulfonamide (162 mg, 0.52 mmol), EDCI (130 mg, 0.68 mmol), 4-(N,N-dimethylamino)pyridine (63.4 mg, 0.52 mmol) in dichloromethane (15 ml) was stirred at room temperature for overnight, followed by purification by silica gel column chromatography to afford 2-((lH-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(l-((6-(4-chlorophenyl)spiro[3.5]non-6-en- 7-yl)methyl)piperidin-4-yl)-N-((3-nitro-4-(((tetrahydro-2H-pyran-4- yl)methyl)amino)phenyl)sulfonyl)benzamide (170 mg, 57.3 %) as yellow solid. 1H NMR (400 MHz, DMSO-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; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Chia, Wei; CHEN, Jianyong; (131 pag.)WO2018/27097; (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.25850-22-0,2,2-Dimethyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

Step 3 : 6-(3- {[4-(2,2-Dimethyltetrahvdro-2h-pwan-4-yl)-3-oxopiperazm- 1 -yllcarbonvU -4-fluoro benzyl)-4,5-dimethylpyridazin-3(2H)-one trifluoroacetate (JJ3).To a 0.4 M solution containing the intermediate JJ2 (leq) and 2,2-dimethyltetrahydro-2H-pyran- 4-amine (1.5 eq) in MeOH, were added NaBH3(CN) (1.5 eq) and catalytic AcOH. The reaction was heated in a MW apparatus (100 0C , 7 min). After evaporation of the solvent the crude intermediate was dissolved in DMF, then HATU (2 eq) and DIPEA (2 eq) were added and the mixture heated in MW apparatus (120 0C, 10 min). The crude product was purified by preparative RP-HPLC using H2O (0.1% TFA) and MeCN (0.1% TFA) as eluents and the combined fractions were evaporated under reduced pressure to afford the title compound (JJ3). 1H-NMR (300 MHz, DMSO-d6, 300K) delta: 12.65 (IH, bs), 7.36-7.14 (3H, m), 4.79-4.54 (IH, m), 4.20-4.10 (lH,m), 3.95 (2H, s), 3.86-3.50 (4H, m), 3.46-3.14 (3H, m), 1.99 (6H, s), 1.69-1.35 (4H, m) 1.22-1.10 (6H, m). MS (ES). C25H3iFN4O4 required: 470, found 471 (M+H) +.

25850-22-0, The synthetic route of 25850-22-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2009/63244; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2,2-Dimethyltetrahydropyran-4-one (5.Og, 32.0 mmol, see Preparation 3) is solved in methanol (4.7 ml) and carbon disulfide (4.7 ml, 48.8 mmol) is added in one portion. Malononitrile (2.6g, 39.0 mmol) is added portionwise and, finally, triethylamine (1.95 ml). The reaction mixture is stirred at room temperature for 48h. An orange precipitate is formed, which is filtered (3.9Og) and is consistent with the desired compound. From the liquid phase, 0.89g more of 6-amino-3,3-dimethyl-8-thioxo-4,8- dihydro-1H,3H-thiopyrano[3,4-c]pyran-5-carbonitrile were isolated by flash chromatography, eluting first with CH2CI2 and next with the mixture of solvents CH2CI2: MeOH 98:2. Yield= 48%. 1H NMR (200 MHz, CDCI3) delta ppm 1.30 (s, 6 H), 2.62 (s, 2 H), 4.66 (s, 2 H), 7.91 (s, 2 H)

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

Reference£º
Patent; ALMIRALL PRODESFARMA, S.A.; WO2006/58723; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

80 mg (0.38 mmol) of Example 11 B were dissolved in 1 ml_ of absolute ethanol, 262 mg (1.52 mmol) of ethyl tetrahydropyran-4-yl-acetate, and 45.1 mg (1.10 mmol) of sodium hydride (60 % suspension in mineral oil) were added. The reaction mixture was heated to 1500C for 40 min in a microwave oven. Cooling to 200C was followed by evaporation of the solvent under reduced pressure. The residue was treated with water (10 ml_), acidified with HCI (10 % in water) and extracted two times with dichloromethane (2 ml_). The organic layer was dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure. The residue was triturated with ether to give 65 mg (53.7 %) of the product as a white solid.HPLC-MS (Method Grad_C8_NH4COOH): Rt: 1.89 minMS (ESI pos): m/z = 319 (M+H)+.

103260-44-2, The synthetic route of 103260-44-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/121919; (2009); 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.25637-18-7,4-Iodotetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

NEt3 (1. 3mL, 9. 0MMOL) and 4-iodotetrahydropyran (1.93g, 9. 0MMOL) were added to a stirred solution of ethyl (4-MERCAPTOPHENYL) acetate (1. 21g, 6. 0mmol) in anhydrous DMF (LOML) at 0 C. The mixture was allowed to warm to room temperature over 3d, then the solvents were removed under reduced pressure. The residue was partitioned between Et20 (LOOML) and saturated aqueous NH4CL (50ML), the aqueous phase being extracted further with ET20 (45mL). The combined ethereal extracts were washed with H20 (50ML), H20-SATURATED aqueous NA2C03 (1: 1, 50ML), and brine (50ML), before being dried (MGS04). Filtration, solvent evaporation, and flash chromatography (IH-ET20, 10: 1 to 2: 1) afforded the title compound: RF (IH-ET20, 2: 1) =0. 31.

25637-18-7, The synthetic route of 25637-18-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; OSI PHARMACEUTICALS, INC.; WO2004/72031; (2004); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

A dry 50 mL flask under nitrogen was charged with magnesium (197 mg, 8.11 mmol) and a crystal of iodine. The solids were stirred vigorously while being warmed with the heat gun to aerosolize the iodine. Upon cooling to room temperature, it was treated with THF (4 mL). The mixture was warmed with a heat gun and treated with a solution of 4-bromotetrahydro-2H-pyran (0.678 mL, 6.08 mmol) in THF (4 mL) dropwise via a dry addition funnel. When addition was complete, the mixture was placed in a preheated oil bath, and the mixture held at reflux for 30 min. After cooling to room temperature, the solution was transferred to a stirred solution of N,2-dimethoxy-N-methylacetamide (270 mg, 2.03 mmol) in THF (12 mL) at -78 C. After stirring for 5 min, the ice bath was removed and the reaction allowed to warm to room temperature. The reaction was placed in a 0 C. bath, quenched by addition of sat. aq. ammonium chloride, concentrated, diluted with EtOAc, washed with water, then brine, dried over magnesium sulfate, filtered, and concentrated to give 260 mg (81%) as clear oil. Material was used without purification. 1H NMR (400 MHz, CDCl3) delta 4.11 (s, 2H), 4.05-4.0 (m, 2H), 3.5-3.44 (m, 2H), 3.45 (s, 3H), 2.8 (m, 1H), 1.64 (m, 2H), 1.32 (m, 2H)., 25637-16-5

25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; Norris, Derek J.; Delucca, George V.; Gavai, Ashvinikumar V.; Quesnelle, Claude A.; Gill, Patrice; O’Malley, Daniel; Vaccaro, Wayne; Lee, Francis Y.; DeBenedetto, Mikkel V.; Degnan, Andrew P.; Fang, Haiquan; Hill, Matthew D.; Huang, Hong; Schmitz, William D.; Starrett, JR., John E.; Han, Wen-Ching; Tokarski, John S.; Mandal, Sunil Kumar; (220 pag.)US2016/176864; (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.125995-03-1,Atorvastatin lactone,as a common compound, the synthetic route is as follows.

To lactone intermediate (V) ( 100 g, 0.185 mol) dissolved in methanol ( 500 ml ) was slowly added sodium hydroxide ( 8.0 g dissolved in 80 ml water ) at 25 to 30 0C and the reaction mass was stirred at 45 to 5O0C for 2 hrs when the HPLC indicated the reaction to be complete. Methanol was distilled off under vacuum, water (100.0 ml) and methanol (100.0 ml) were added and the solution was extracted twice with methyl tertiary butyl ether ( 500 ml and 125 ml each), the combined MTBE layer was washed with a mixture of water ( 90 ml) and methanol (10 ml). The pH of the combined aqueous layer was adjusted to 7.8 to “6.2 with 6N hydrochloric acid and the mixture was diluted with methanol (1.0 It ) and then suspension of calcium acetate (16.0 g in 1.0 It water) was added to the reaction mixture at 25 to 3O0C. The mixture was then poured into water ( 2.0 It ), extracted with dichloromethane ( 2 x 1.5 It) and the combined dichloromethane layer was concentrated at 40 to 42 0C to approx 700 ml. The concentrated solution was fine filtered through Whatman filter, cooled to 10 to 150C and diisopropyl ether (3.0 It) was slowly added keeping the temperature below 150C. The mixture was stirred for 15 min at 10 to 150C, centrifuged, washed with cold diisopropyl ether (100 ml) and dried under vacuum at 55 to 6O0C for 24 hrs to obtain amorphous Atorvastatin calcium as a white to off white powder. Yield: 98.72 g (92.21 %); Purity (HPLC): 99.45 %, Assay (HPLC): 99.1%. Calcium content: 3.30 %; Moisture content (by K.F):1.12 %; Residual solvents: Methanol < 0.05 %, THF < 0.05 %, Dichloromethane < 0.02 %, Diisopropyl ether < 0.02 %., 125995-03-1

The synthetic route of 125995-03-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MOREPEN LABORATORIES LIMITED; WO2006/48893; (2006); 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.5631-96-9,2-(2-Chloroethoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

5631-96-9, EXAMPLE 2 ll- (4- [2- (2-hydroxyethoxy) ethyl]-l- piperazinyl) dibenzo [b, f] [1, 4] thiazepine (base Quetiapine) To 10.43 g (63.4 mmols) of 2- (2-CHLOROETHOXY)-TETRAHYDRO- 2H-pyrane are added successively 5 g (14. 7 mmols) of 2- (4- dibenzo [B, F] [1. 4] THIAZEPINE-11-IL-PIPERAZINE-1-IL) ethanol, 5 g of powdered potassium hydroxide and 0.49 g 18-corona-6 catalyst. The mixture is heated at 40C for 6 hours with thorough stirring. The synthesis proceeds as in Example 1, yielding 4.65 g (82%) of the product of the title as a light yellow oil, having IR AND 1H-RMN SPECTRA identical to those of the product obtained in Example 1.

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

Reference£º
Patent; LABORATORIOS VITA, S.A.; WO2005/14590; (2005); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics