Heterocyclic Building Blocks-Tetrahydropyrans

40191-32-0, Tetrahydro-2H-pyran-4-carbonyl chloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,40191-32-0

Example 21Synthesis of N-(3-{3-[4-(1-aminocyclobutyl)phenyl]-2-(2-aminopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-5-yl}phenyl)tetrahydro-2H-pyran-4-carboxamide hydrochlorideStep 1Synthesis of N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydro-2H-pyran-4-carboxamideTo a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (220 mg) and triethylamine (0.182 mL) in N,N-dimethylacetamide (1.5 mL) chilled to 0 C. was added tetrahydro-2H-pyran-4-carbonyl chloride (prepared from tetrahydro-2H-pyran-4-carboxylic acid (156 mg) and oxalyl chloride (0.15 mL) in dichloromethane (2.5 mL)) dropwise. After being stirred at room temperature for 1 h, the reaction mixture was diluted with ethyl acetate and washed with 1 M citric acid aqueous solution (3 times) then brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (10-100% ethyl acetate in hexanes) gave the product (267 mg, 81%). 1H-NMR (400 MHz, CDCl3) delta: 7.92-7.87 (m, 1H), 7.68-7.66 (m, 1H), 7.57-7.53 (m, 1H), 7.35 (t, 1H, J=7.6 Hz), 7.14 (br s, 1H), 4.10-4.03 (m, 2H), 3.46 (ddd, 2H, J=11.5, 11.5, 2.8 Hz), 2.51-2.42 (m, 1H), 1.97-1.80 (m, 4H), 1.34 (s, 12H); LCMS: 332 [M+H].

As the paragraph descriping shows that 40191-32-0 is playing an increasingly important role.

Reference£º
Patent; ArQuele, Inc.; US2012/329791; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Methylmaganesium bromide (1.831 mL, 5.49 mmol) was added dropwise via syringe to a solution of dihydro-2H-pyran-3(4H)-one (500 mg, 4.99 mmol) in Diethyl ether (50 mL) at -20 C. and stirred at this temp for 1 hr before warming up to RT. The reaction was quenched with sat. ammonium chloride and extracted with ether. The organic layer was washed with brine, collected, dried over MgSO4, filtered and partially evaporated to give the crude product 3-methyltetrahydro-2H-pyran-3-ol (480 mg, 83% yield) as an oil. 1H NMR (400 MHz, CHLOROFORM-d) delta 3.90-3.81 (m, 1H), 3.55-3.50 (m, 1H), 3.40 (td, J=11.3, 2.8 Hz, 1H), 3.31 (d, J=11.3 Hz, 1H), 2.16 (br. s., 1H), 1.94-1.81 (m, 1H), 1.78-1.69 (m, 1H), 1.59-1.47 (m, 2H), 1.18-1.11 (m, 3H)., 23462-75-1

23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); 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.23462-75-1,Dihydro-2H-pyran-3(4H)-one,as a common compound, the synthetic route is as follows.

Dihydro-2//-pyran-3(4H)-one (100 mg, 1.00 mmol), /er/-butyl carbazate (145 mg, 1.10 mmol, Ll equiv) and acetic acid (0.280 niL, 4.99 mmol, 5 equiv) were combined in 1 ,2-dichloroethane(3 raL), stirred at ambient temperature for 10 minutes and treated with sodium triacetoxyborohydride (296 mg, 1,34 mmol, 1.4 equiv). After stirring for 1 hour, the mixture was poured into water and extracted with ethyl acetate (3 x 50 niL), The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo to provide the titled compound., 23462-75-1

23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP &; DOHME CORP.; BESHORE, Douglas, C.; KUDUK, Scott, D.; WO2010/123716; (2010); A1;,
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

A solution of 2 – ((1 H-pyrrolo [2,3 -b] pyridin-5- yl) oxy) -4- 5,Tetrahydro- [1,1′-biphenyl] -2-yl) methoxy) azetidin- 1 -yl) benzoic acid (50 mg, 0.089 mmol, 1.0 eq) and3-nitro-4-(((Tetrahydro-2H-pyran-4- yl) methyl) amino) benzenesulfonamide (31 mg, 0.098 mmol, 1.1 eq)8 mL of DCM, EDCI (34 mg, 0.18 mmol, 2.0 eq) and DMAP (13 mg, 0.107 mmol, 1.2 eq)at rt 7h. The reaction was stopped, poured into water and the organic phase was separated. The organic phase was dried over anhydrous sodium sulfate, spun dry and passed through a plug of PE / EA (v / v) =1/1 do eluent to obtain 35mg yellow powder product., 1228779-96-1

As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.

Reference£º
Patent; Sun Yat-sen University; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Kou Yuhui; Hu Bolin; Jiang Haigang; Ye Jiuyong; Liu Zhiqiang; Xie Hongming; Zhang Yingjun; Yan Ming; (39 pag.)CN106749233; (2017); 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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

A suspension solution of152F (30 mg, 0.089 mmol), 4-(bromomethyl)tetrahydropyran (16.73 mg, 0.093 mmol)and C52CO3 (43.5 mg, 0.133 mmol) in DMF (1 mL) was heated to 120 C for 20 mm and 140 C for 1 h under microwave conditions. The reaction mixture was concentrated invacuo. Water (2 mL) was added and stirred for 5 minutes. The solid was collected as the crude product which was purified by column chromatography on the Isco system to yield152G (25 mg, 65% yield). MS(ESI) m/z 435.2 (M+H)., 125552-89-8

The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; HART, Amy C.; PITTS, William J.; MASTALERZ, Harold; GUO, Junqing; BROWN, Gregory D.; (148 pag.)WO2016/100166; (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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

Example 4 N-(4-Ethoxy-6-{4-oxo-2-[(tetrahydro-pyran-4-ylmethyl-amino)-4H-thiazol-5-ylidenemethyl}-quinolin-2-yl]-acetamide a) Preparation of c-(tetrahydro-pyran-4-yl)-methylammonium acetate A cold (ice water bath) solution of tetrahydro-4H-pyran-4-one (7.5 g, 75 mmol) and tosylmethylisocyanide (16.05 g, 82.4 mmol) in DME (125 ml) was treated with a suspension of potassium t-butoxide (16.8 g, 150 mmoles) in t-butyl alcohol (250 ml). The reaction mixture was stirred at room temperature for 31/2 hours, and then diluted with ether (250 ml). The mixture was successively washed with water and brine, then dried over sodium sulfate, filtered, and concentrated. The crude product was purified by short path distillation under high vacuum to give the nitrile as colorless oil (2.98 g). This material was dissolved in 1M borane/tetrahydrofuran (THF) (134 ml, 134 mmol) and stirred at rt overnight. Excess borane was quenched by adding methanol (rt, 1 h), and the mixture was concentrated to dryness. The residue was dissolved in 4N HCl/dioxane, stirred at rt for 1 h and then concentrated under reduced pressure. The solid residue was triturated with ether and collected by suction filtration. A suspension of this material (1.81 g, 11.9 mmol) in THF (30 ml) was treated with 1N NaOH (11.9 ml, 11.9 mmol) at rt for ? h. The THF was removed by distillation and the aqueous solution was saturated with NaCl then extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was treated with acetic acid (0.68 ml, 11.9 mmol) to provide, after drying in a vacuum oven, c-(tetrahydro-pyran-4-yl)-methylammonium acetate (1.71 g).

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

Reference£º
Patent; Chen, Li; Chen, Shaoqing; Michoud, Christophe; US2006/63804; (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.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

Under nitrogen atmosphere, magnesium (6.05 g, 249 mmol) was suspended in THF (30 ml). A catalytic amount of iodine and dibromoethane (0.4 ml) were added. The mixture was heated to 60C and 4-chlorotetrahydro-2H-pyran (5 g, 41.5 mmol) in THF (5 ml) was added dropwise. The mixture was stirred at 60C for 2.5 h. The mixture was cooled to 0C and N-[[5-benzyloxy-l-[2- [tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-2-pyridyl]methylene]-2-methyl-propane-2- sulfinamide (Intermediate 5, 6.78 g, 13.82 mmol) in THF (20 ml) was added. The resulting mixture was stirred at rt for 45 min. The reaction was quenched with ammonium chloride solution and extracted with EtOAc (2x). The combined organic layers were washed with brine, dried with sodium sulfate and concentrated to afford the title intermediate as an orange gum (8.7 g). Purification by chromatography (Si02, 10% MeOH in DCM) gave the title intermediate as an orange oil (7.3 g, 56 %). MS, ES+ m/z, 577 (M+H)+.

1768-64-5, 1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LIEBER INSTITUTE FOR BRAIN DEVELOPMENT; BARROW, James; ERNST, Glen; SWINNEN, Dominique; MONTEL, Florian; DEFAYS, Sabine; (224 pag.)WO2017/91818; (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.33024-60-1,Tetrahydro-2H-pyran-4-amine hydrochloride,as a common compound, the synthetic route is as follows.

Example 79 (2E)-3-{1-[bis(4-fluorophenyl)methyl]-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-(tetrahydro-2H-pyran-4-yl)prop-2-enamide To a solution of (2E)-3-{1-[bis(4-fluorophenyl)methyl]-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (250 mg, 0.570 mmol) in THF (2.5 ml) were added DMF (0.025ml) and oxalylchloride (0.060 ml, 0.680 mmol), the mixture was stirred at room temperature for 1 hour and the solvent distilled off under reduced pressure. The residue was added under ice-cooling to a solution of tetrahydro-2H-pyran-4-ylamine hydrochloride (136 mg, 1.13 mmol), triethylamine (0.472 ml, 3.39 mmol) and THF (3 ml), and the mixture was stirred under ice-cooling for 2 hours and at room temperature for 12 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to give the objective product as a solid material. The resultant material was recrystallized from hexane and ethyl acetate. Yield (amount) 200 mg, yield (rate) 66.7percent 1H-NMR (CDCl3) delta: 1.43-1.58 (2H, m), 1.87-1.92 (2H, m), 2.56 (3H, s), 2.75 (3H, s), 3.42-3.50 (2H, m), 3.94-4.05 (3H, m), 5.56 (1H, d, J = 7.8 Hz), 6.78 (1H, d, J = 15.3 Hz), 6.91-7.21 (9H, m), 7.43 (1H, d, J = 15.3 Hz), 7.92 (1H, s). IR (KBr) cm-1; 3277, 2924, 2216, 1661, 1607, 1549, 1510, 1231, 1161, 1013, 837, 801, 733.

33024-60-1, As the paragraph descriping shows that 33024-60-1 is playing an increasingly important role.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1535922; (2005); 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.23462-75-1,Dihydro-2H-pyran-3(4H)-one,as a common compound, the synthetic route is as follows.

To a stirred solution of the dihydro-2H-pyran-3(4H)-one (commercially available from Pharm lab Product list, 21.6 g, 0.216 mol) in 160 ml of dry THF , trimethyl silyl chloride(58.7g, 68.5 ml, 0.54 mol) was added under argon at room temperature, then the mixture was allowed to stir 10 minutes .At this mixture triethylamine (59.7g, 82.2 ml, 0.59 mol) was added dropwise and under vigorous stirring (strong precipitation). The resulting suspension was heated to reflux for 48 hours, then the mix was cooled to r.t and concentrated to 1/3 of the volume at the rotavapor (T=40C, p=200 mbar). At this crude 300 ml of pentane were added to allow the complete precipitation of TEA.HCI and the suspension was filtered.The solid was washed with 100 ml of pentane and the resulting filtrate was separated.The desired product was isolated by fract. Distillation; pentane and THF residue were removed at athmospheric pressure and the sililenolether was isolated at Tdist=58-60C p=5mbar. Obtained 28.7 g of the title compound as colourless oilMS (ES) (mlz): 172 [M+H]+1H NMR (CDCI3 ) :delta 0.20 (s,9H), 1.92-2.32 (m, 2H), 3.67 (t, J=5.5 Hz, 2H), 3.78-3.95 (m,2H), 4.78-5.05 (m,1 H), 23462-75-1

23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Glaxo Group Limited; WO2009/43883; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 3,4,5-tribromo-1 /-/-pyrazole (21 g, 69 mmol) in THF (200 mL) were added tetrahydro-2H-pyran-3-ol (8.5 g, 83 mmol), PPh3(36 g, 138 mmol), DIAD (27 g, 138 mmol) at 0 C. The resulting mixture was stirred at 0 C for 3 hrs. The mixture was poured into water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous Na2S04and concentrated. The crude was purified by column chromatography on silica gel (PE: EtOAc= 10: 1 ) to give the title compound as oilsolid (10 g, yield 50%)., 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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DING, Xiao; HO, Ming-Hsun; REN, Feng; YU, Haihua; ZHAN, Yang; (290 pag.)WO2019/12093; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics