Day: September 8, 2020

33024-60-1, Tetrahydro-2H-pyran-4-amine hydrochloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-Aminotetrahydropyran hydrochloride (Intermediate 8A, 0. [413G,] 3. 0mmol) was added to a mixture of Intermediate 51 (0.268g, [L.] Ommol) and N, N-diisopropylethylamine (0. [87ML,] [5.] [0MMOL)] in acetonitrile (3ml). The resulting mixture was heated at [85 ¡ãC FOR] 24 hours. Volatiles were removed in vacuo and the residue was dissolved in chloroform (1. [5ML)] and applied to a SPE cartridge (silica, 5g). The cartridge was eluted successively with [ET20,] EtOAc and EtOAc-MeOH (9/1). Fractions containing the desired product were combined and concentrated in vacuo to give the desired product contaminated with starting material (Intermediate [51).] Further purification using a SPE cartridge (silica, 5g) eluting with ethyl acetate-cyclohexane (1/3) afforded Example 189 (0.248g). LCMS showed [MH+ =] 333; [TRET] = 2.75min., 33024-60-1

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

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/24728; (2004); 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.110238-91-0,Methyl tetrahydro-2H-pyran-4-carboxylate,as a common compound, the synthetic route is as follows.

Preparation 3: (Tetrahydropyran-4-yl)methanol To a suspension Of LiAlH4 (56g, 1.47mol) in diethyl ether (2L) under argon was added methyl tetrahydro-2H-pyran-4-carboxylate (27Og, 1.88mol) in diethyl ether (ca.20OmL) under reflux over a period of 1.75h. After addition was complete reflux was continued for a further Ih. TLC (diethyl ether) indicated a small amount of ester remained, so further LiAlH4 (1Og, 0.26mol) was added and reflux continued for Ih. Water (66mL) was added, then 15% NaOH solution (66mL), followed by further water (198mL). The solid was filtered and dried to give the crude product, which was redissolved in DCM (800 ml), dried(MgSO4), filtered and the solvent removed to afford the title compound (207g, 94% yield). NMR was consistent with the above structure.

110238-91-0, As the paragraph descriping shows that 110238-91-0 is playing an increasingly important role.

Reference£º
Patent; Prosidion Ltd; WO2007/51845; (2007); 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.

Prepared as described by adaptation of the following literature reference: Radziszewski, J. G. et al. J. Am. Chem. Soc. 1993, 115, 8401. To 97 g (810 mmol) of (tetrahydro-pyran-4-yl)-methanol in 2-methyltetrahydrofuran (190 mL) are added 165 mL of 50% aq. NaOH solution. To this stirred suspension is added dropwise with cooling a solution of p-toluene-sulfonylchloride (283 g, 1.46 mol) in 2-methyltetrahydrofuran (280 mL). The reaction is stirred at 30-35 C. for 18 h. The suspension is poured into a mixture of ice-water (280 mL) and aq. HCl solution (37%, 203 mL). After addition of methylcyclohexane (1.4 L) and further ice-water (0.2 L), the reaction mixture is stirred for 2 h in an ice-bath. The resulting crystalline precipitate is isolated by filtration and washed with methylcyclohexane (0.5 L) and water (0.5 L). Drying under reduced pressure at 40 C. gave 216 g of toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester. Yield: 99%; ESI-MS: 271 [M+H]+

14774-37-9, As the paragraph descriping shows that 14774-37-9 is playing an increasingly important role.

Reference£º
Patent; Boehringer Ingelheim International GmbH; Riether, Doris; Binder, Florian Paul Christian; Doods, Henri; Mueller, Stephan Georg; Nicholson, Janet Rachel; Sauer, Achim; US8865744; (2014); B1;,
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.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

70 g of 3-isobutylglutaric acid dry product and 70 g of acetic anhydride at 120 temperature reaction 2h,To give 3-isobutylglutaric anhydride.The solution of 3-isobutylglutaric anhydride (75 g) was then slowly added dropwise to 180 g of aqueous ammonia,The control temperature is 10 C.3-isobutyl glutaric anhydride added, continue to react 2h.Finally, the pH of the solution was adjusted to 2 to 3 with hydrochloric acid and filtered to obtain a white powder solid,That is, the final product 3-isobutyl glutaric acid monoamide, liquid content of 99.8%The yield was 95%, the overall yield was 77.5%Figure 4 is a liquid phase detection of 3-isobutylglutaric acid monoamide.

185815-59-2, 185815-59-2 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Suzhou Yingnuoxin Pharmaceutical Technology Co., Ltd.; Chen, Jiaqi; Xia, Chenyi; Han, Xi; Xu, Liang; Tang, Huozhen; (12 pag.)CN106278931; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

220641-87-2, N-Methyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N-Methyl-4-(3-nitrophenyl)-N-(tetrahydro-2H-pyran-4-yl)-1H-imidazole-1- carboxamide A solution of N-methyltetrahydro-2H-pyran-4-amine (2.15 g, 18.7 mrnol) in tetrahydrofuran (THF) (6 mL) was added to a stirred solution of phenyl 4-(3- nitrophenyl)-IH-imidazole-1-carboxylate (2.89 g, 9.3 mmol) in THF (40 mL) at room temperature. The yellow solution was allowed to stir at reflux overnight. The solvent was evaporated in vacuum and the product was recrystallised from propan-2-ol. N-methyl-4-(3 -nitrophenyl)-N-(tetrahydro-2H-pyran-4-yl)- 1 H-imida.zole- 1 -carboxamide (0.938 g, 30 % yield)., 220641-87-2

As the paragraph descriping shows that 220641-87-2 is playing an increasingly important role.

Reference£º
Patent; BIAL – PORTELA & C?, S.A.; ROSA, Carla Patricia da Costa Pereira; NORONHA, Rita Gusmao de; KISS, Laszlo Erno; WO2015/12708; (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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

IO a solution ot mercury sultate (LA g) and SULTUNC acid (5″/0, 6UU ML), was gradually added dimethylvinylethynylcarbinole (230 g) with vigerous stirring FOR-1 h and the temperature was raised slowly to 85 C. Mercury sulfate (18 g) was added in portions over 4 h at 85 C. The upper layer was separated, and the lower layer was neutralized with potassium carbonate and extracted with ether twice. The separated upper layer was added to the ethereal extracts, washed with potassium carbonate, water and dried over magnesium sulfate. The ether was evaporated, and the residue distilled under vacuum, then distilled at 1 atm (168-175 C) to provide the product pyrone (140 g, 53%). A suspension of sodium (11 g) in dry toluene (150 mL) was heated to reflux, stirred vigerously, cooled to room temperature, and a first part of solution (5-6 mL) of chloroacetic acid ethyl ester (63 g, 0.5 mol) and the above 2, 2-DIMETHYLTETRAHYDROPYRANE-4-ONE (64 g, 0.5 mol) was added. The remaining part of the solution was added dropwise at 23 C. After 3-4 h and full consumption of sodium, dry methanol (8 mL) was added. The mixture was carefully quenched into ice water (100 mL), ether was added, the upper layer separated, the aqueous extracted with ether, the ethereal extracts combined, washed with water, and dried over magnesium sulfate. The solvent was evaporated, and the residue was distilled in vacuo (101 C, 2 mmHg) to provide the product (74 g, 70%). This product 5, 5-dimethyl-1, 6-dioxaspyro-2,5-octane-2-carbonic acid ethyl ester (214 g, 1 mol) was added to a solution of sodium hydroxide (40 g, 1 mol) in water (100 mL) with stirring over 30 min at 30 C. The reaction mixture was stirred for 2 h, water (200 ML) was added to dissolve precipitates, and the aqueous solution of the sodium salt of 5, 5-dimethyl-1, 6- dioxaspyro-2,5-octane-2-carbonic acid was heated to 90 C. Hydrochloric acid (1 mol, 15-20%) was added dropwise for 4 h, the forming aldehyde was simultaneously distilled, saturated with NACI, extracted with ether (3X200 mL), the organic extracts dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was distilled in vacuo (61 C at 7 MMHG) to provide the aldehyde intermediate (80 g, 55%). To a cold 2,2-dimethyl-4-formyltetrahydropyran (17 g, 0.5 mol) was added a solution of potassium permanganate (79 g, 0.5 mol) in water (1 L), keeping the temperature at 25 C. The mixture was maintained for 6 h, filtered from MNO2, washed with water, the combined filtrate evaporated to the volume of 175 ML, acidified with HC1, extracted with diethyl ether, and the organic extracts dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was distilled under vacuum at 123 C (5 MMHG) to yield 71 g (90%) of the desired acid. This carboxylic acid was incorporated into Example 82 by following the procedures of Examples 78 and 71, US Patent 6,489, 354 and Example 11 from tent-butyl 3-BENZYL-1-OXA-8- azaspiro [4.5] decane-8-carboxylate. Mass Spectrum m/e = 585 (M+1)., 1194-16-7

As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Patent; MERCK & CO., INC.; WO2004/58763; (2004); 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.

25850-22-0, (4) (2E)-3-{3-cyano-1-[(4-fluorophenyl)(phenyl)methyl]-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-(2,2-dimethyltetrahydro-2H-pyran-4-yl)prop-2-enamide To a solution of (2E)-3-{3-cyano-1-[(4-fluorophenyl)(phenyl)methyl]-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (1.00 g, 2.35 mmol) in THF (10 ml) were added DMF (0.10 ml) and oxalylchloride (0.246 ml, 2.82 mmol), which was stirred at room temperature for 1 hour and the solvent was distilled off under reduced pressure. The residue was added under ice-cooling to a solution of 2,2-dimethyltetrahydro-2H-pyran-4-ylamine (455 mg, 3.53 mmol), triethylamine (1.09 ml, 7.81 mmol) and THF (10 ml), 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 recrystallized from ethyl acetate and hexane to yield the objective product as a solid material. Yield (amount) 1.04 g, yield (rate) 82.5% 1H-NMR (CDCl3) delta: 1.17-1.42 (8H, m), 1.81-1.91 (2H, m), 2.56 (3H, s), 2.75 (3H, s), 3.62-3.74 (2H, m), 4.14-4.22 (1H, m), 5.48 (1H, d, J = 7.6 Hz), 6.73-7.46 (12H, m), 7.99 (1H, s). IR (KBr) cm-1; 3285, 2215, 1661, 1622, 1591, 1547, 1510, 1333, 1231, 1195, 735.

25850-22-0 2,2-Dimethyltetrahydro-2H-pyran-4-amine 3809203, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1535922; (2005); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4677-20-7, 4-(2-Bromoethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4677-20-7

4-(2-Bromoethyl)tetrahydro-2H-pyran (200 mg, 1.00 mmol), 3,7-dimethyl-1H-purin-2,6(3H,7H)-dione (186 mg, 1.00 mmol), potassium iodide (17.0 mg, 0.100 mmol) and potassium carbonate (414 mg, 3.00 mmol) were dissolved in N,N-dimethylformamide (4 mL). The reaction solution was heated to 130 C. and allowed for reaction for 3 hours, and then the reaction solution was than cooled to 25 C. The reaction was quenched by adding saturated brine, followed by extraction with ethyl acetate (50 mL*3). The organic phases were dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and then purified by high performance preparative plate (ethyl acetate, Rf-0.5) to give a product 3,7-dimethyl-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-purin-2,6(3H,7H)-dione (224 mg) with a yield of 77%. 1H NMR: (400 MHz, Methonal-d4) delta7.86 (s, 1H), 4.06-4.01 (m, 2H), 3.97 (s, 3H), 3.92 (dd, J=12, 3.2 Hz, 2H), 3.53 (s, 3H), 3.44-3.38 (m, 2H), 1.73 (d, J=12.8 Hz, 2H), 1.61-1.55 (m, 3H), 1.38-1.24 (m, 2H). MS-ESI calculated value: [M+H]+ 293; measured value: 293.

As the paragraph descriping shows that 4677-20-7 is playing an increasingly important role.

Reference£º
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Linyun; CHEN, Xiaoxin; ZHANG, Peng; LIU, Xing; ZHANG, Li; LIU, Zhuowei; CHEN, Shuhui; LONG, Chaofeng; (75 pag.)US2018/148451; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Synthesis of tetrahydro-pyran-4-carbaldehydePyridinium chlorochromate (37.8 g, 175.0 mmol) is added to a solution of (tetrahydro-pyran- 4-yl)-methanol (13.6 g, 117.0 mmol) in DCM (50.0 mL) at 00C. The reaction mixture is stirred at room temperature for 12 hours. The reaction mixture is filtered through a pad of celite that is washed with diethyl ether. The filtrate is concentrated under reduced pressure to afford the title compound.

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BERRY, Angela; CIRILLO, Pier Francesco; HICKEY, Eugene Richard; RIETHER, Doris; WU, Lifen; ZINDELL, Renee M.; WO2010/96371; (2010); 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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

To a solution of [4-(7-Hydroxymethoxyquinazolin-4-yl)piperidin-l-yl][4- (trifluoromethoxy)phenyl]methanone (100 mg, 0.24 mmol) in 1 mL of N,N-dimethyl formamide were added potassium iodide, (41 mg, 0.3 mmol) and 4-(bromomethyl)-tetrahydro-2H-pyran, 119 mg (0.72 mmol). The resulting solution was stirred 12 h at 80C. After chromatography, the title compound was obtained as a brown solid (24 mg, 26%). After filtration, removal of the solvent and susequent chromatography, the product was obtained as a white solid in 10% yields (12 mg). MS (ESIpos): m/z = 502 (M+H)+; LC-MS[Method 2] : R, = 1.52 min; 1H-NMR (400 MHz, DMSO -d6) d 1.63-1.72 (m, 2H), 1.86-1.90 (m, 4H), 2.06-2.09 (m, 2H), 3.07-3.08 (m, 1H), 3.56 (t, 2H), 3.68-3.69 (m, 1H), 3.88 (t, 2H), 3.96-3.99 (m, 1H), 4.61-4.62 (m, 2H), 4.90-4.94 (m, 1H), 7.36 (d, 1H), 7.44-7.46 (m, 3H), 7.59 (d, 2H), 8.38 (d, 1H), 9.09 (s, 1H).

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

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; NGUYEN, Duy; WORTMANN, Lars; FARIA ALVARES DE LEMOS, Adelaide, Clara; BOeMER, Ulf; SUeLZLE, Detlev; HOLTON, Simon; LECHNER, Christian; (147 pag.)WO2019/170543; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics