Heterocyclic Building Blocks-Tetrahydropyrans

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

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

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

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

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,185815-59-2

A 100 ml three-necked round-bottom flask, under nitrogen atmosphere, is added with 98% hydrazine hydrate (19.5 g, 0.382 mols), sodium hydroxide (12.4 g, 0.309 mol) in water (150 ml) and the solution is cooled to a temperature of -5C. A solution of 3-isobutyl-glutaric anhydride (50.0 g, 0.294 mol) in toluene (200 ml) is dropped therein in about 1-2 h, keeping the temperature below 0-5C. The mixture is reacted for about 1 h, then the phases are separated, the aqueous phase is concentrated to small volume, thereby obtaining a white solid which is taken up into isopropanol (100 ml) and filtered. The solid is dried under vacuum at a temperature of 30-35C for 16-18 hours. 56.7 g of product are obtained, in an 86% yield. 1H-NMR (300 MHz, D2O, 28C): delta 2.20-1.90 (m, 5H); 1.50 (m, 1H); 1.05 (m, 2H); 0.75 (d, 6H).

As the paragraph descriping shows that 185815-59-2 is playing an increasingly important role.

Reference£º
Patent; Dipharma Francis S.r.l.; EP2067768; (2009); A1;,
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- Methyltetrahydro-2H-pyran-4-amine (12.4 mg, 0.11 mmol) was added to a solution of (S)-isopropyl 2-(6-(bromomethyl)-5-(4-(4-fluorophenethoxy)phenyl)-2-methyl-4-(7- azaspiro[3.5]nonan-7-yl)pyridin-3-yl)-2-(tert-butoxy)acetate (25 mg, 0.036 mmol) and Hunig’s base (0.02 mL, 0.11 mmol) in abs. EtOH (0.5 mL) and the solution was stirred for 4 h at rt. UPLC (M+H) = 730.5. KOH (20.16 mg, 0.36 mmol) was added to the solution above and the temperature was raised to 80 C for 16 h. TFA (0.028 mL, 0.359 mmol) was added and the reaction mixture was concentrated. The crude product was purified by prep HPLC to obtain (S)-2-(tert-butoxy)-2-(5-(4-(4- fluorophenethoxy)phenyl)-2-methyl-6-((methyl(tetrahydro-2H-pyran-4- yl)amino)methyl)-4-(7-azaspiro[3.5]nonan-7-yl)pyridin-3-yl)acetic acid 8.3 mg (33%). 1H NMR (500 MHz, DMSO) delta 7.39-7.36 (m, 2H), 7.31 (d, J=8.4 Hz, 1H), 7.13 (t, J=9.1 Hz, 2H), 7.06-7.04 (m, 3H), 5.86 (s, 1H), 4.27-4.19 (m, 2H), 3.92-3.87 (m, 2H), 3.80 (d, J=14.8 Hz, 1H), 3.41 (br. s, 3H), 3.24 (t, J=9.9 Hz, 2H), 3.21-3.16 (m, 2H), 3.06 (t, J=6.2 Hz, 2H), 2.72/2.58 (s, 3H), 2.55 (s, 3H), 2.26 (br. s, 1H), 1.84-1.47 (series of m, 14H), 1.13 (s, 9H). UPLC (M+H) = 688.5.

220641-87-2, The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; KADOW, John F.; NAIDU, B. Narasimhulu; ROMINE, Jeffrey Lee; SIVAPRAKASAM, Prasanna; ST. LAURENT, Denis R.; (204 pag.)WO2017/25864; (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.61363-56-2,2H-Pyran-3,5(4H,6H)-dione,as a common compound, the synthetic route is as follows.

61363-56-2, 1L four-necked bottle, under nitrogen atmosphere,Compound II (32.00 g, 0.28 mol, 1.0 e.q.) was dissolved in THF (300 mL).Add ammonium carbonate (80.71 g, 0.84 mol, 3.0 e.q.),Warmed to reflux and stirred for 8 h.TLC test showed that the raw materials were reacted.The reaction liquid was purified by sand column chromatography to obtain Compound III as a yellow solid 20.0 g.The yield was 63.3%.

The synthetic route of 61363-56-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nanjing Yaoshi Technology Co., Ltd.; Nanjing Furunkaide Bio-pharmaceutical Co., Ltd.; Li Jilong; Qi Lei; Fei Qinlong; Li Hui; (15 pag.)CN108395421; (2018); 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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

Intermediate 4Tetrahydro~2H-pyran-4-carbonitrile. A solution of tetrahydro-4Hr-pyran-4- one (25 g, 250 mmol) and toluenesulfonylmethyl cyanide (53.7 g, 275 mmol) dissolved in ethylene glycol dimethylether (1 L) was cooled to 0 C. Added dropwise over 30 min was a solution of potassium t-butoxide (56 g, 500 mmol) dissolved in t-butanol (350 mL) and ethylene glycol dimethylether (150 mL). After stirring the resulting mixture for 3 h at room temp, diethyl ether (1 L) was added and the organic phase was washed with saturated aqueous NaHCO3. The organic phase was dried (Na2SO4) and concentrated. The residue was distilled at 39 C 1.7 mm Hg to give the title compound as a colorless oil (10.87 g, 39% yield). 1H NMR (300 MHz, CDCl3) delta: 3.91-3.83 (2H, m), 3.61-3.54 (2H, m), 2.89-2.80 (IH, m), 1.97-1.78 (4H, m)., 29943-42-8

As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/58646; (2007); 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

Prepared as described by adaptation of the following literature reference: Watson, R.J. et al. Tetrahedron Lett. 2002, 43, 683-685. To 224 g (0.83 mol) of toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester in methyl isobutylketone (1.6 L) are added 189 g (1 .66 mol) of potassium thioacetate. The suspension is stirred at 70 C for 4.5 h. The reaction mixture is cooled to RT and water (1 .8 L) is added. The organic layer is washed with 10% aq. K2C03 solution (1.8 L) and water (1 L). The organic layer is filtered through Celite (20 g), activated charcoal (20 g) and Na2S04 (20 g) and the filtrate is concentrated under reduced pressure. The residual oil is azeotroped with methylcyclohexane (200 mL) and n-heptanes (250 mL) to afford 138 g of thioacetic acid S-(tetrahydro-pyran-4- ylmethyl) ester. Yield: 96%; ESI-MS: 175 [M+H]+

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; BINDER, Florian; DOODS, Henri; MUELLER, Stephan, Georg; NICHOLSON, Janet, Rachel; SAUER, Achim; WO2014/184327; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 4(5)-3-(2-(Cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid (III) – (opposite enantiomer to Example 3)Quinidine (17.2g, 52.8mmol) was suspended in toluene (23OmL). Cinnamyl alcohol (9.3 g, 69mmol) was added and the reaction mixture was cooled to -35 0C. The solution of 3- isobutylglutaric anhydride (9.Og, 52.8mmol) in toluene (6mL) was added during 15 min and the reaction mixture was stirred at -38 C for 24 hours. Working up is carried out analogously to the preparation of the compound from Example 3. Combined extracts were warmed to 35 0C and (S)- alpha-phenylethylamine (5.8 g, 48mmol) was added, followed by seed crystals (10 mg). The mixture was stirred for 4 hours at 25C and filtered to obtain 14.6 g of (5)-alpha-phenylethylamine salt of (S)- 3-(2-(cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid. Salt was suspended in toluene (90 mL) and stirred with 3% HCl (600 mL) until clear solution was obtained. Aqueous acidic solution was separated and organic layer was washed once again with 3% HCl (2OmL). Evaporation of toluene afforded 10.2 g (65%) of monoester as viscous yellowish oil. HPLC analysis on Chiralpak AS column, hexane/EtOH/TFA=95/5/0.1 revealed 91.4 % ee.1H NMR (CDCl3), delta/ppm: 0.87 (d, 6H, J=6.5 Hz), 1.21-1.27 (m, 2H), 1.56-1.70 (m, IH), 2.38-2.48 (m, 5H), 4.73 (dd, 2H, Jy=6.5 Hz, J2=1.2 Hz), 6.27 (dt, IH J/=15.8 Hz, J2=6.5 Hz), 6.65 (d, IH, J=15.8 HZ), 7.22-7.40 (m, 2H).13C NMR (CDCl3), delta/ppm: 22.34, 25.07, 29.64, 38.30, 38.48, 43.26, 64.92, 122.95, 126.50, 127.96, 128.49, 134.18, 136.07, 172.26, 178.64., 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 fields.

Reference£º
Patent; PLIVA ISTRAZIVANJE I RAZVOJ D.O.O.; MCLEISH, Nicholas, Alistair, Maxwell; WO2008/9897; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics