Category: Tetrahydropyrans

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.

[00497] To a solution of 122-1 (50.0 mg, 0.16 mmol, 1. 0 eq) in DMF (5.0 mL) was added K2C03 (45.23 mg, 0.33 mmol, 2.0 eq) and 122-2 (32.4 mg, 0.120 mmol, 1.2 eq). The mixture was stirred at 100 C for 24 hours under an N2 atmosphere. LCMS showed the desired compound was formed. The reaction was filtered to give a crude product. The crude product was purified by prep-HPLC to give the title compound (27.33 mg, 70.19 umol, 42.85% yield). LCMS (ESI): RT = 0.932 min, mass calc. for Ci9Hi8F3N50 389.15, m/z found 390.0[M+H]+; 1HNMR (400 MHz, CDCl3-i 9.08 (s, 1H), 8.21 (dd, J= 1.4, 7.9 Hz, 1H), 7.54 (d, J= 8.5 Hz, 3H), 7.41- 7.35 (m, 1H), 7.29 (d, J= 8.5 Hz, 2H), 7.05 (t, J= 7.3Hz, 1H), 5.07 – 4.95 (m, 1H), 4.16 (td, J= 3.3, 12.0 Hz, 2H), 3.64 (dt, J = 2.3, 11.5 Hz, 2H), 2.46 – 2.24 (m, 4H).

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

Reference£º
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-65-0, (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2 [0340] (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate obtained in Step 1 (1.20 g, 4.44 mmol) was dissolved in acetone (15 mL), sodium iodide (2.00 g, 13.3 mmol) was added thereto, and under reflux with heating, the mixture was stirred for 4 hours. After cooling the reaction mixture to room temperature, the precipitated solid was removed by filtration, and the filtrate was evaporated under reduced pressure. Chloroform was added to the residue, and the precipitated solid was removed by filtration. The filtrate was concentrated under reduced pressure, whereby 4-(iodomethyl)tetrahydro-2H-pyran (0.946 g, 94%) was obtained. 1H NMR (300 MHz, CDCl3, delta): 3.99-3.96 (m, 2H), 3.37 (td, J = 11.7, 2.1 Hz, 2H), 3.10 (d, J = 6.6 Hz, 2H), 1.81-1.65 (m, 3H), 1.37-1.24 (m, 2H)., 101691-65-0

As the paragraph descriping shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; Kyowa Hakko Kirin Co., Ltd.; FURUTA, Takayuki; SAWADA, Takashi; DANJO, Tomohiro; NAKAJIMA, Takahiro; UESAKA, Noriaki; EP2881394; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

344329-76-6, Tetrahydro-2H-pyran-4-carboxamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 17 A solution of Example B5 (0.103 g, 0.800 mmol) in DCE (3 mL) was treated with oxalyl chloride (0.070 mL, 0.800 mmol) and heated at 80¡ã C. for 4 h. The mixture was cooled to RT, added to a solution of Example A6 (0.09 g, 0.320 mmol) and TEA (0.129 g, 1.280 mmol) in DCM (2 mL) and stirred at RT overnight. The mixture was concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford N-((6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)tetrahydro-2H-pyran-4-carboxamide (88 mg, 63percent) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.00 (s, 1H), 10.87 (s, 1H), 8.35 (d, J=5.7 Hz, 1H), 8.25 (s, 1H), 7.95 (s, 1H), 7.90 (d, J=8.8 Hz, 1H), 7.62 (d, J=8.8 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 3.89-3.87 (m, 2H), 3.84 (s, 3H), 3.32-3.28 (m, 2H), 2.70-2.67 (m, 1H), 2.25 (s, 3H), 1.72 (d, J=12.9 Hz, 2H), 1.61-1.58 (m, 2H); MS (ESI) m/z: 437.2 (M+H+).

344329-76-6, As the paragraph descriping shows that 344329-76-6 is playing an increasingly important role.

Reference£º
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

First add 1- (tetrahydro-2H-pyran-4-yl) ethanone (10g, 78.02mmol) to 50mL of methanol,After cooling to -10 C, liquid bromine (4.0 mL, 78.02 mmol) was added to the reaction under an argon atmosphere.It was then reacted at 0 C for 45 min, followed by 10 C for 45 min.Sulfuric acid (27.5mL, 11M) was added to the above system, returned to room temperature and stirred overnight.After the reaction was completed, saturated brine and ethyl acetate were added for extraction, and the organic phases were combined, washed sequentially with saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title product.

137052-08-5, The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Wang Yazhou; Zhang Yan; Wang Xiaowei; Wang Hai; Guo Zhuang; Lv Kunzhi; Chang Yujie; Chen Hongyan; Xu Guofeng; (37 pag.)CN111072645; (2020); 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.110238-91-0,Methyl tetrahydro-2H-pyran-4-carboxylate,as a common compound, the synthetic route is as follows.

A solution of methyl tetrahydro-2H-pyran-4-carboxylate (5 g, 34.6 mmol) in anhydrous diethyl ether was chilled in an ice bath and 1 M LiAlH4 in diethyl ether (52 mL, 51.9 mmol) was added dropwise under an N2 atmosphere. The reaction was allowed to warm to room temperature with stirring overnight. The reaction was quenched by slowly adding 1 N aqueous NaOH (3 mL). The slurry was filtered through a pad of Celite. The Celite pad was rinsed with diethyl ether followed by methanol and the solution was dried in vacuo to yield (tetrahydro-2H- pyran-4-yl)methanol (4 g, 34.6 mmol) as a clear oil. [M+eta] calc’d for C6H]2O2, 117; found, 117., 110238-91-0

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

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/97578; (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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

The mixture of (cis-or trans-) 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(4- (2- (2-chlorophenyl) pyrrolidin-1-yl) cyclohexyl) benzoic acid (142 mg, 0.28 mmol; product of step 6), triethylamine (85 mg, 0.84 mmol), 2- (7-azabenzotriazol-1-yl) -N, N, N’, N’-tetramethyluronium hexafluorophosphate (125 mg, 0.33 mmol) in DCM (20 mL) was stirred for 2 hours. To the resulting reaction were added 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (104 mg, 0.33 mmol) and DMAP (3 mg, 0.03 mmol) and stirred overnight. The reaction mixture was concentrated in vacuum and purified by chromatography column on silica (eluent: PE/EA = 1/1 to DCM/MeOH = 10/1) to afford a crude product, which was purified with Pre-TLC (DCM/MeOH, 25/1) to give the product Example D1a (17.5 mg, 7.71%). 1H NMR (400 MHz, DMSO-d 6) delta ppm: 12.16 (br, 1H), 11.78 (br, 1H), 8.61 (m, 2H), 8.05 (s, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 (s, 1H), 7.55 (m, 1H), 7.51 (d, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.27 (d, J = 8.0 Hz, 1H), 7.16 (d, J = 8.0 Hz, 1H), 7.00 (t, J = 8.0 Hz, 1H), 6.94 (d, J = 8.0 Hz, 1H), 6.86 (t, J = 8.0 Hz, 1H), 6.51 (s, 1H), 6.44 (s, 1H), 4.10 (d, J = 8.0 Hz, 1H), 3.85 (d, J = 8.0 Hz, 2H), 3.30-3.23 (m, 5H), 3.16-3.10-3.04 (m, 2H), 2.67-2.55 (m, 1H), 2.42-2.33 (m, 3H), 2.13-1.99 (m, 2H), 1.87-1.82 (m, 2H), 1.67-1.58 (m, 4H), 1.41-1.26 (m, 6H). MS (ESI, m/e) [M+1] + 813.2.

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; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (2019); 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

Example 7: 6-Amino-2-butylamino-9-r2-(tetrahvdro-2H-pyran-4-yl)ethyll-7,9-dihvdro- 8H-purin-8-one To a solution of /V2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (100 mg) in dry N,N-dimethylformamide (1 ml) at room temperature and under nitrogen was added potassium carbonate (158 mg) in one go. The reaction was stirred at 6O C for 1.5 hours and then cooled to 5O C. A solution of 4-(2- bromoethyl)tetrahydro-2H-pyran (60 mg) in dry N,N-dimethylformamide (0.5 ml) was added in one go and the reaction heated at 5O C overnight. The reaction was diluted with ethyl acetate (15 ml) and washed with water (5 ml). The organic layer was separated and concentrated in vacuo. The product was purified by C18 reverse phase chromatography using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluant (20-60%) to afford a yellow viscous oil (47mg) that was dissolved in dry methanol (4 ml) at room temperature and under nitrogen was added 4.0M hydrogen chloride in 1 ,4-dioxane (0.8 ml) in one go. The reaction was left to stir at room temperature overnight. The reaction was neutralised by the addition of 2.0M sodium hydroxide solution and concentrated in vacuo. The residue was taken up in water (5 ml) and the solid filtered and dried in vacuo (60C) for 30 minutes. This afforded the title compound as a beige solid (23mg). MS calcd for (C16H26N6O2)+ = 334 MS found (electrospray): (M+H)+ =3351H NMR ((CDa)2SO): delta 9.78 (1 H, s), 6.08-6.21 (3H, br. s), 3.80 (2H, m), 3.65 (2H, t), 3.21 (2H, m), 3.16 (2H, m), 1.66 (2H, m), 1.57 (2H, m), 1.36-1.49 (3H, m), 1.29 (2H, m), 1.13 (2H, m), 0.88 (3H, t)., 4677-20-7

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

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/101867; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-65-0, (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 5-bromo-2-chloropyridin-3-amine (1 .3 g, 6.27 mmol) in DMF (20 mL) was added slowly sodium hydride (60 wt.% in mineral oil, 0.301 g) was stirred for 20 min, followed by addition of (tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (1.694 g, 6.27 mmol). The resulting reaction mixture was stirred at room temperature for 58 hrs, diluted with EtOAc, washed with water, brine, dried over sodium sulphate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, EtOAc/hexane = 22/78) providing 5-bromo-2-chloro-N-((tetrahydro-2H-pyran-4- yl)methyl)pyridin-3-amine (1 .27 g). LCMS (m/z): 305.0 [M+H]+; Rt = 0.89 min., 101691-65-0

The synthetic route of 101691-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; BARSANTI, Paul, A.; HU, Cheng; JIN, Xianming; NG, Simon, C.; PFISTER, Keith, B.; SENDZIK, Martin; SUTTON, James; WO2012/101064; (2012); 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.287193-07-1,Ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of 4-oxo-tetrahydro-2H-pyran-2-carboxylic acid ethyl (0.6 g, 3.5 mmol) in absolute ethanol (6 ml) was added sulfur (0.12 g, 3.85 mmol) and tert-butyl cyanoacetate (0.64 g, 4.55 mmol). The solution was stirred under nitrogen in a 50 C. oil bath and morpholin (0.61 ml, 7.0 mmol) was added. The reaction was stirred for 18 hours and then cooled to ambient temperature and excess sulfur removed by filtration. The filtrate was concentrated in vacuo and reconstituted in ethyl acetate (50 ml). The organic phase was washed with brine (2*10 ml), dried (Na2SO4), filtered, and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using a gradient of ethyl acetate/hexane (20 to 25% gradient) as eluent. Pure fraction of the two isomers were collected and the solvent evaporated in vacuo which afforded 0.47 g of 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3,5-dicarboxylic acid 3-tert-butyl ester 5-ethyl ester (A) and 0.3 g of 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3,7-dicarboxylic acid 3-tert-butyl ester 7-ethyl ester (B) in 62% combined yield. (A)1H-NMR (300 MHz, CDCl3) delta 5.96 (bs, 2H), 4.77-4.61 (m, 2H), 4.32-4.18 (m, 3H), 3.19-3.12 (m, 1H), 2.90-2.80 (m, 1H), 1.52 (s, 9H), 1.29 (t, 3H, J=7 Hz).(B)1H-NMR (300 MHz, CDCl3) delta 5.10 (s, 1H), 4.28-4.13 (m, 3H), 3.98-3.91 (m, 1H), 2.82-2.76 (m, 2H), 1.51 (s, 9H), 1.31 (t, 3H, J=7 Hz)., 287193-07-1

As the paragraph descriping shows that 287193-07-1 is playing an increasingly important role.

Reference£º
Patent; Novo Nordisk A/S; US7019026; (2006); 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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

EXAMPLE 1F (128 mg), EXAMPLE 1G (73 mg), 1-ethyl-3-(3-(dimethylamino)propyl)-carbodiimide hydrochloride (88 mg), and 4-dimethylaminopyridine (28 mg) were stirred in CH2Cl2 (3 mL) for 24 hours. The mixture was cooled and chromatographed on silica gel with 0-10% methanol/ethyl acetate. 1H NMR (300 MHz, DMSO-d6) delta 11.15 (br s, 1H), 8.63 (dd, 1H), 8.49 (d, 1H), 7.80 (dd, 1H), 7.44-7.53 (m, 5H), 7.36 (m, 3H), 7.22 (m, 3H), 7.01 (s, 1H), 6.92 (d, 1H), 6.78 (d, 1H), 6.44 (s, 1H), 4.17 (m, 2H), 3.86 (dd, 2H), 3.33 (m, 6H), 3.16 (m, 4H), 2.66 (s, 6H), 2.37 (br s, 4H), 1.91 (m, 1H), 1.63 (d, 2H), 1.29 (m, 2H)., 1228779-96-1

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

Reference£º
Patent; ABBOTT LABORATORIES; US2010/160322; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics