Heterocyclic Building Blocks-Tetrahydropyrans

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.

Example 1 Preparation of 1-(4-tetrahydropyranyl)but-1-en-3-one 5.0 g of magnesium were introduced into 100 ml of anhydrous tetrahydrofuran. 25 g of 4-chlorotetrahydropyran were added dropwise under reflux under a nitrogen atmosphere, and the mixture was refluxed for 2 hours. A solution of 23.5 g of 1-(dimethylamino)but-1-en-3-one in 20 ml of anhydrous tetrahydrofuran was subsequently added dropwise to the reaction mixture, cooled to from 0 to 5 C., at a rate such that the internal temperature did not exceed 50 C., and the mixture was stirred at room temperature for a further 2 hours. For work-up, the reaction mixture was poured into a mixture of ice and dilute HCl, and extracted 3 times with 200 ml of chloroform, and the extracts were washed with saturated sodium chloride solution and dried over MgSO4. Removal of the solvent gave 24.0 g (75%) of 1-(4-tetrahydropyranyl)but-1-en-3-one having a boiling point of 117 C./10 mmHg.

1768-64-5, The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BASF Aktiengesellschaft; US5221753; (1993); 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.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 of2-((1 H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((6-(4-chlorophenyl)spiro[3.5]non-6-en-7-yl)methyl)piperazin-1 -yl)benzoic acid (1.75 g, 3 mmol), 3-nitro-4- (((tetrahydro-2H-pyran-4-yl)methyl)am ino)benzenesulfonam ide (1.43 g, 4.5) reacted in EDCI (1.15 g, 6 mmol) and 4-(N,N-dimethylamino)pyridine (550 mg, 4.5 mmol) and dichloromethane (40 ml) at room temperature overnight, and then water was added. The aqueous[2,3-b]pyridin-5-yl)oxy)-4- (4-((6-(4-chlorophenyl)spiro[3.5]non-6-en-7-yl)methyl)piperazin-1 -yl)-N-((3-nitr o-4-((tetrahydro-2H-pyran-4-yl)methyl)am ino)phenyl)sulfonyl)benzam ide (1.7 g, 64.4%) was obtained as a yellow solid.1H NMR (400 MHz, methanol-d4) O 8.70 (d, J = 2.3 Hz,1 H), 8.01 (d, J =2.7 Hz, 1 H), 7.87 (d, J = 9.2, 2.3 Hz, 1 H), 7.66 (d, J = 8.9 Hz, 1 H),7.55 (d, J =2.7 Hz, 1H), 7.47 (d, J = 3.4 Hz, 1H), 7.38 (d, J = 8.4 Hz, 2H), 7.10 (d, J =8.4Hz, 2H), 6.97 (d, J = 9.2 Hz, 1 H), 6.77 (dd, J = 8.9, 2.4 Hz, 1 H), 6.44 (d, J =3.4Hz, 1 H), 6.34 (d, J = 2.4 Hz, 1 H), 4.02 – 3.94 (m, 3H), 3.66 (5, 3H), 3.49 -3.38 (m,2H), 3.41 – 3.25 (m, 7H), 2.42 (5, 3H), 2.26 (5, 3H), 2.00 – 1.67 (m, 4H),1.45- 1.38(m, 2H)., 1228779-96-1

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ASCENTAGE PHARMA (SUZHOU) CO., LTD.; YANG, Dajun; ZHAI, Yifan; WANG, Guangfeng; (88 pag.)WO2020/24826; (2020); A1;,
Tetrahydropyran – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1240390-36-6,tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Step 2 2-{(3R,4R)-4-[7-(1-Methyl-1H-benzoimidazol-4-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester To a solution of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (1-methyl-1H-benzoimidazol-4-yl)-amide (0.037 g, 0.108 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.035 g, 0.161 mmol) in dioxane (3 mL) was added triethylamine (0.075 mL, 0.538 mmol). The reaction mixture was heated at 100 C. overnight. The reaction mixture was cooled and then diluted with dichloromethane, washed with aqueous sodium carbonate, then brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was then purified by chromatography (silica, 40 g, 0 to 5% 0.7N ammonia in MeOH in dichloromethane) to give {(3R,4R)-4-[7-(1-methyl-1H-benzoimidazol-4-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (0.050 g, 0.095 mmol, 88.8%) as a light orange solid. LCMS m/z [M+H]=524.

1240390-36-6, As the paragraph descriping shows that 1240390-36-6 is playing an increasingly important role.

Reference£º
Patent; Hoffmann-La Roche Inc.; Chen, Shaoqing; Hermann, Johannes Cornelius; Le, Nam T.; Lucas, Matthew C.; Padilla, Fernando; US2013/178460; (2013); A1;,
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713-95-1, 6-Heptyltetrahydro-2H-pyran-2-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

713-95-1, EXAMPLE 4 Preparation of N-[2,6-bis(1-methylethyl)phenyl]-6-heptyltetrahydro-2-oxo-2H-pyran-3-carboxamide The title compound was prepared from (+-)-delta-dodecanolactone (5.0 g, 0.025 mol), 2,6-diisopropylphenyl isocyanate (5.12 g, 0.025 mol), and lithium diisopropylamide (0.025 mol) using the procedure described in Example 1. MS: 401 (M+).

As the paragraph descriping shows that 713-95-1 is playing an increasingly important role.

Reference£º
Patent; Warner-Lambert Company; US5185349; (1993); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 1.07 g (1.90 mmol) of the compound from Example 8A in 20 ml of DMF under argon were added 256 mg (2.28 mmol) of potassium tert-butoxide. After stirring at RT for 5 min, 408 mg (2.28 mmol) of 4-(bromomethyl)tetrahydropyran were added, and the mixture was stirred at bath temperature 100C. for 2 h. Subsequently, a further 136 mg (0.76 mmol) of 4-(bromomethyl)-tetrahydropyran were added and the mixture was stirred at bath temperature 100C. for another 2 h. After cooling to RT, the mixture was combined with the reaction mixtures from two similarly conducted prior experiments (batch size in each case 47 mg (0.08 mmol) of the compound from Example 8A). After removing the DMF, 60 ml of water and 60 ml of ethyl acetate were added to this combined mixture. After the phases had been separated, the aqueous phase was extracted once with 30 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. The residue was taken up in a mixture of cyclohexane and ethyl acetate (9:1) and purified by means of column chromatography (120 g of silica gel, eluent: cyclohexane/ethyl acetate 9:1). 590 mg (47% of theory, purity 100%) of the title compound were obtained. [0384] 1H NMR (400 MHz, CDCl3): delta [ppm]=8.66 (s, 1H), 8.28 (d, 1H), 8.14 (dd, 1H), 7.95 (d, 2H), 6.92 (d, 2H), 4.78-4.62 (m, 2H), 4.21-4.13 (m, 1H), 4.03 (dd, 2H), 3.89-3.81 (m, 4H), 3.50-3.40 (m, 3H), 3.07-2.93 (m, 1H), 2.19-2.03 (m, 2H), 2.03-1.87 (m, 2H), 1.76 (dd, 2H), 1.72-1.61 (m, 1H), 1.47 (qd, 2H), 0.63-0.53 (m, 2H), -0.09 (s, 9H). [0385] LC/MS (Methode 1, ESIpos): Rt=1.51 min, m/z=560 [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; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMANN, Andreas; BROHM, Dirk; JOeRISSEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (44 pag.)US2017/114049; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

83-87-4, (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

83-87-4, (1) Weigh the hydroxyacetylated glucose intermediate (35 g, 89.7 mmol) obtained in step (1)Triethylamine (4.75 g, 46.9 mmol),3,4-dimethoxyphenol (20G, 129.7 mmol),Sequentially added to dichloromethane (250mL) at 0 C conditions,Boron trifluoride ethyl ether silica gel (50 g)Then naturally warmed to room temperature for 9 hours; then the organic phaseWashed successively with saturated sodium bicarbonate, saturated brine, filtered,Concentrated, recrystallized from anhydrous methanol,A yield of 94.3% was obtained for 40.95 g of glycoside intermediate substituted at the position of glucose anomeric carbon.

As the paragraph descriping shows that 83-87-4 is playing an increasingly important role.

Reference£º
Patent; Dongying Daoyi Bio-pharmaceutical Technology Co., Ltd.; Weifang Hongnuo He Tai New Materials Technology Co., Ltd.; Li Fahui; (5 pag.)CN107151260; (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.720706-20-7,(4-Amino-4-tetrahydropyranyl)methanol,as a common compound, the synthetic route is as follows.

720706-20-7, To a stirred solution of 2, 4-dichloro-5-((4-methoxybenzyl) oxy) pyrimidine (2 g, 7.04 mmol) in isopropyl alcohol (30 mL) under an argon atmosphere were added diisopropylethylamine (2.4 mL, 14.08 mmol) and (4-aminotetrahydro-2H-pyran-4-yl) methanol (900 mg, 7.04 mmol) at room temperature. The reaction mixture was stirred at 120 oC for 48 h. After consumption of starting material (monitored by TLC), the volatile components were evaporated in vacuo. The crude material was purified by column chromatography using 20-30% EtOAc:hexanes to afford (4-((2-chloro-5-((4-methoxybenzyl) oxy) pyrimidin-4-yl) amino) tetrahydro-2H-pyran-4-yl) methanol (1 g, 38%) as a white solid. 1H NMR (CDCl3, 400 MHz): delta 7.66 (s, 1H), 7.30 (d, 2H), 6.94 (d, 2H), 5.47 (s, 1H), 5.03 (s, 2H), 4.60 (t, 1H), 3.87-3.83 (m, 5H), 3.80-3.73 (m, 2H), 3.68-3.60 (m, 2H), 1.97-1.87 (m, 4H); LCMS: 379.9 (M+1); (column; X-select CSH C-18 (50 ¡Á 3.0 mm, 3.5 mum); RT 3.07 min. 0.05% Aq TFA: CH3CN; 0.8 mL/min); TLC: 50% EtOAc:hexane (Rf: 0.3).

As the paragraph descriping shows that 720706-20-7 is playing an increasingly important role.

Reference£º
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/109109; (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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

Cesium carbonate (450 mg, 1.4 mmol) was added to a solution of N-(4-((7-hydroxy-6-methoxyquinazolin-4-yl)oxy)phenyl)-2-( 4-isopropyl-1H-1 ,2,3-triazol-1-yl)acetamide (20010 mg, 0.5 mmol) and 4-bromotetrahydro-2H-pyran (456 mg, 2.8 mmol) in DMF (3 mL) undernitrogen. The resulting mixture was stirred at 100C for 3 hours. The crude product waspurified by preparative HPLC. Fractions containing the desired product were combined andconcentrated under vacuum to afford the title compound as a white solid (124 mg, 52%). 1HNMR (400 MHz, DMSO-d6) 8 1.26 (6H, d), 1.61 – 1.75 (2H, m), 2.09 (2H, d), 2.95 – 3.0715 (lH, m), 3.57- 3.59 (2H, m), 3.86- 3.95 (2H, m), 3.98 (3H, s), 4.94- 4.96 (lH, m), 5.30 (2H,s), 7.25-7.33 (2H, m), 7.55 (2H, d), 7.64- 7.73 (2H, m), 7.90 (lH, d), 8.54 (lH, s), 10.59 (lH,s); m/z: ES+ [M+H]+ 519.

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

Reference£º
Patent; ASTRAZENECA AB; GRECU, Tudor; KETTLE, Jason, Grant; PACKER, Martin, John; PEARSON, Stuart, Eric; SMITH, James, Michael; (58 pag.)WO2018/197643; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4677-18-3, 2-(Tetrahydro-2H-pyran-4-yl)ethanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4677-18-3

Example 165: l-(2-Fluorobenzyl)-N-(l-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-pyrazol-4- yl)- 1 H-pyrazo lo [3 ,4-d]pyrimidin-6-amineThe following compound was made according to the procedure in Example 1, using l-(2- (tetrahydro-2H-pyran-4-yl)ethyl)-1H-pyrazol-4-amine and l-(bromomethyl)-2-fluorobenzeneTo prepare l-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-pyrazol-4-amine, diethyl azodicarboxylate (500mg, 451mu1, 2.86mmol) was added dropwise to a solution of 2- (tetrahydro-2H-pyran-4-yl) ethanol (287mg, 2.2mmol), 4-nitropyrazole (250mg, 2.2mmol), and triphenylphosphine (696mg, 2.64mmol) in anhydrous THF (lOmL). The reaction mixture was stirred at rt for 2h, diluted with DCM (lOOmL) and washed with water (50mL). The organics were collected, dried over MgS04, filtered and reduced in vacuo. The crude product was purified by flash chromatography (Petroleum ether 100% to petroleum ether/ethyl acetate, 70:30) to give the desired intermediate. The residue was dissolved in methanol (lOmL), palladium on carbon (50mg) was added and the reaction was stirred under a balloon of hydrogen for 18h. The resulting mixture was filtered through Celite and the filtrate concentrated in vacuo to afford l-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-pyrazol-4-amine which was used without further purification. 1H NMR (d6-DMSO) delta 9.88 (s, 1H), 8.92 (s, 1H), 8.19 – 7.99 (m, 2H), 7.57 (s, 1H), 7.40 – 7.32 (m, 1H), 7.30 – 7.19 (m, 2H), 7.19 – 7.12 (m, 1H), 5.60 (s, 2H), 4.13 (t, J = 7.0 Hz, 2H), 3.80 (dd, J = 11.5, 2.6 Hz, 2H), 3.21 (td, J = 11.5, 1.8 Hz, 2H), 1.72 (q, J = 7.0 Hz, 2H), 1.58 (dd, J = 12.8, 1.8 Hz, 2H), 1.50 – 1.33 (m, 1H), 1.26 – 1.10 (m, 2H); LC-MS method B, (ES+) 422.1, RT = 8.81min.

The synthetic route of 4677-18-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CELLZOME LIMITED; RAMSDEN, Nigel; HARRISON, Richard John; OXENFORD, Sally; BELL, Kathryn; PITON, Nelly; DAGOSTIN, Claudio; BOUSSARD, Cyrille; RATCLIFFE, Andrew; WO2011/48082; (2011); 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.83-87-4,(3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate,as a common compound, the synthetic route is as follows.

83-87-4, To a solution of 30.0 g (76.8 mmol, 1 eq.) penta-O-acetyl-alpha/beta-D-glucopyranose (1) cooled to 0 C in 150 mL abs. dichloromethane 15.2 g (122 mmol, 1.6 eq.) thiocresol and 14.0 mL BF3Et2O (100 mmol, 1.3 eq.) were added slowly. After the addition, the solution was allowed to warm to room temperature and was stirred 24h. The organic phase was neutralized with sat.aq. NaHCO3 (3 ¡Á 70 mL), water (2 ¡Á 70 mL) and brine (50 mL). The organic layer was dried with MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography on silica (cHex/EtOAc, 2:1).

83-87-4 (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 10293747, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Johannes, Manuel; Reindl, Maximilian; Gerlitzki, Bastian; Schmitt, Edgar; Hoffmann-Roeder, Anja; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 155 – 161;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics