Tag: M.W:100-200

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A flask was charged with AlCl3 (78.8 mmol, 10.5 g, 2.3 equiv) and dry CH2Cl2 (25 ml) under calcium chloride guard tube and the formed suspension was stirred on ice bath. Subsequently, a solution of glutaric anhydride 10 (34.3 mmol, 3.91 g) in dry CH2Cl2 (15 ml) was added dropwise (t < 7 C). The resulting mixture was stirred on ice bath for 30 minutes and bromobenzene 11b (34.3 mmol, 5.39 g, 1.0 equiv) was carefully added afterwards. The cooling bath was removed and the mixture was stirred at room temperature for 19 hours, then it was poured into ice water (15 ml), acidified with conc. H2SO4 (10 ml), the aqueous layer was extracted with ethyl acetate (1 x 100 ml, 2 x 50 ml), the combined organics were dried over Na2SO4, filtered and concentrated. The crude product was dissolved in ethyl acetate and the resulting solution was added dropwise to a vigorously stirred cold hexanes (1 L). The precipitate was filtered off and dried to provide 5-(4-bromophenyl)-5-oxopentanoic acid (7.93 g, 85%) as a yellow powder;2 mp 125-127 C; 1H NMR (300 MHz, CDCl3): delta = 2.07 (m, 2H), 2.50 (t, J = 7.2 Hz, 2H), 3.04 (t, J = 7.2 Hz, 2H), 7.60 (m, 2H), 7.82 (m, 2H). 5-(4-Bromophenyl)-5-oxopentanoic acid (25.0 mmol, 6.78 g), paraformaldehyde (86.3 mmol, 2.59 g, 3.4 equiv) and piperidine (0.57 ml, 0.24 equiv) were dissolved/suspended in pyridine (42 ml) and stirred at 70 C for 21 hours. Afterwards, the mixture was poured into 1M H2SO4 (200 ml)/conc. H2SO4 (15 ml), the aqueous layer was extracted with ethyl acetate (1 x 150 ml, 2 x 100 ml), the combined organics were washed with half-saturated brine (300 ml), dried over Na2SO4, filtered and concentrated. The crude product was crystallized from ethyl acetate to yield 4-(4-bromobenzoyl)pent-4-enoic acid 9b (3.93 g, 56%) as an orange-yellow solid; mp 127-128 C; 1H NMR (300 MHz, CDCl3): delta = 2.63 (t, J = 6.9 Hz, 2H), 2.80 (t, J = 6.9 Hz, 2H), 5.67 (s, 1H), 5.95 (s, 1H), 7.60 (m, 4H); 13C NMR (75 MHz, CDCl3): delta = 27.2, 32.6, 127.3, 127.4, 131.0, 131.6, 136.3, 145.8, 178.9, 196.6. 108-55-4, 108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Sivak, Ivan; Berke?, Du?an; Ko?i?ek, Jozef; Kolarovi?, Andrej; Tetrahedron Letters; vol. 57; 10; (2016); p. 1079 – 1082;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

127956-11-0, Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 2 (1.58 g, 10 mmol) and ammonium acetate (2.3 g, 30 mmol) in of MeOH (20 mL) was stirred overnight at room temperature. The mixture was concentrated under vacuum, dichloromethane (100 mL) and water (20 mL) were added, and the separated organic layer was dried over sodium sulfate and concentrated in vacuo. The crude product 3 was dissolved in 20 mL of CH3CN and treated with 2,2,2-trichloro-acetyl isocyanate (3.76 g, 20 mmol) and the mixture was stirred for 30 minutes. The resulting solid was collected by filtration and dissolved in NH3 in MeOH (8 mL, 7 N), the mixture was heated at 70C. After cooling to room temperature, a solid formed and was collected by filtration to give compound 4 (1.2 g, 71%). 1H NMR (300 MHz, DMSO-d6): delta 10.98 (br, 2H), 4.19 (s, 2H), 3.76 (t, J = 5.4 Hz, 2H), 2.38 (t, J = 5.4 Hz, 2H).

127956-11-0, 127956-11-0 Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate 14666555, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ZHOU, Han-Jie; PARLATI, Francesco; WUSTROW, David; WO2014/15291; (2014); A1;,
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,125552-89-8

To a stirred solution of Intermediate 3 (250 mg, 1 mmol) and 4-(bromomethyl)tetrahydro-2H-pyran (449 mg, 2.51 mmol) in anhydrous MeCN (7 mL)was added dipotassium carbonate (347 mg, 2.51 mmol). The reaction mixture wasstirred overnight at 100C, cooled to RT, filtered through Celite and concentrated under reduced pressure. The resulting material was purified by chromatography using si[ica ge[ (gradient: hexane/EE) to give 1.0 g (76 % yie[d) of the tit[e compound as a co[our[ess oi[.1H NMR (500MHz, CDC[3): 6 [ppm] 8.08 (t, J = 1.4 Hz, 1H), 7.69-7.67 (m, 1H), 7.57 (dd, J = 2.5, 1.4 Hz, 1H), 7.53 – 7.51 (m, 1H), 4.05 – 4.00 (m, 2H), 3.94 (s, 3H),3.92 (d, J = 6.5 Hz, 2H), 3.49 – 3.42 (m, 2H), 2.53 – 2.52 (m, 3H), 2.14 – 2.03 (m,1H), 1.80- 1.75 (m, 2H), 1.53- 1.43 (m, 2H).LCMS (Ana[ytica[ Method A) Rt = 1 .45 min, MS (ESipos): m/z = 348 (M+H).

125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; EVOTEC AG; DAVENPORT, Adam James; BRAEUER, Nico; FISCHER, Oliver Martin; ROTGERI, Andrea; ROTTMANN, Antje; NEAGOE, Ioana; NAGEL, Jens; GODINHO-COELHO, Anne-Marie; (703 pag.)WO2016/91776; (2016); A1;,
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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

A solution of 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-(1-methoxypropan-2-yl)quinoline-3,4-diamine (for a preparation see Intermediate 2) (9.1 g) in DCM (300 ml) was treated with pyridine (30 ml) and tetrahydro-2H-pyran-4-carbonyl chloride (5.0 ml) and the solution stirred under nitrogen at ambient temperature for 3.5 h and then left standing overnight (ambient temperature, under nitrogen). The volatiles were evaporated in vacuo and the residue partitioned between DCM and water. The organic phase was washed with water ¡Á2 and the combined aqueous extracted with DCM. The combined organic phases were washed with brine, dried (hydrophobic frit) and reduced to dryness in vacuo. The combined aqueous including the brine wash (pH4) was basified with solid sodium hydrogen carbonate and the aqueous extracted with DCM x2. The organic fractions were dried (hydrophobic frit), combined with the previous material and reduced to dryness in vacuo to give a brown foam. This foam was further dried in vacuo, triturated with diethyl ether, the suspension chilled (ice/water bath) and the solid isolated by filtration. The solid was washed with a little diethyl ether and air-dried to give N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-4-((1-methoxypropan-2-yl)amino)quinolin-3-yl)tetrahydro-2H-pyran-4-carboxamide as a beige solid (11.95 g, 100%). [0159] NMR (D6-DMSO): deltaH 9.49 (s, 1H), 8.38 (s, 1H), 7.70 (s, 1H), 7.63 (s, 1H), 5.33 (d, 1H), 3.96-3.90 (m, 6H), 3.43-3.28 (m partially obscured by water, 7H), 2.69 (m, 1H), 2.32 (s, 3H), 2.12 (s, 3H), 1.81-1.67 (m, 4H), 1.19 (d, 3H). LCMS (formate): Rt 0.69 mins, MH+469

40191-32-0, 40191-32-0 Tetrahydro-2H-pyran-4-carbonyl chloride 2795505, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; GlaxcoSmithKline LLC; Demont, Emmanuel Hubert; Jones, Katherine Louise; Watson, Robert J.; US2014/171462; (2014); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

To a solution of 133 g (1.31 mol) of Compound 23 in pyridine (1.5 L) are added 373 g (1.95 mol) of p-toluenesulfonylchloride portionwise at 10 C. After complete addition the reaction is allowed to warm to room temperature and stirred for 18 h. The reaction is poured onto a stirred mixture of aqueous HCl/ice. The resulting precipitate is isolated by filtration and dissolved in DCM (1 L). The organic layer is washed with 1M aqueous HCl solution (1 L), followed by saturated aqueous NaHCO3 solution (1 L) and is then dried over Na2SO4. Filtration and concentration of the filtrate under reduced pressure gives 300 g of Compound 24 as an orange oil. Yield: 90%, ES-MS: m/z: 257 [M+H], 279 [M+Na]., 2081-44-9

2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/71196; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of (2.01 g, 5.46 mmol) of curcumin, and (112 mg, 0.92 mmol) of DMAP in 100 mL THF was added (1.33 mL, 9.55 mmol) of Et3N. (0.685 g, 6 mmol)glutaric anhydride (95%) in 5 mL THF was added slowly dropwise to the curcumin solution. The mixture was stirred and refluxed under argon overnight. THF was removed under vacuum, 55 mL EtOAc was added, followed by the addition of 15 mL1M HC1, the mixture was stirred for 10 minutes. The organic phase was separated and extracted with EtOAc three times; the solvent was removed and dried. The product was purified via column chromatography, eluting with CH2C12: MeOH, 95: 5. Yield:69 %. 1HNMR (CDC13, 400 MHz): oe 7.65 (d, J= 16Hz, 2H), 7.20-6.95 (m, 5H), 6.96 (d, 1H), 6.48-6.57 (m, 2H), 5.85 (s, 2H), 3.98 (s, 3H), 3.90 (s, 3H), 2.75-2.7 1 (t, J= 8 Hz, 2H), 2.61-2.57 (t, J= 8 Hz, 2H), 2.15-2.12 (t, J= 8 Hz, 2H). 13C NMR (CDC13, 100 MHz): oe 184.56, 181.80, 178.26, 170.84, 151.28, 148.03, 146.84, 141.09, 139.40,134.12, 127.53, 124.25, 123.07, 121.73, 120.99, 114.89, 111.37, 109.69, 101.58,55.96, 32.82, 19.92. LC-MS: 483 [M+Hj (figure 1).

108-55-4, As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

Reference£º
Patent; DONG SUNG PHARM. CO., LTD.; JALDE, Shivakumar S; KIM, Yong Wan; SON, Kwang Hee; LEE, Hwan Suk; (53 pag.)WO2018/236193; (2018); A1;,
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

General procedure: A mixture of 7a (0.2 mmol), an appropriate bromide or methanesulfonate (0.4 mmol), K2CO3 (0.6 mmol), DIEA (0.4 mmol) and KI (0.04 mmol) in 4 mL DMF was heated at 55 o C-80 o C for 2 days until the completion of the reaction. The mixture was treated with EtOAc (100 mL), washed with brine and then dried over with Na2SO4, filtered, and evaporated. The crude product was purified by chromatograph (CHCl3/MeOH) to give the corresponding products., 125552-89-8

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

Reference£º
Article; Jiang, Xiaolong; Zhou, Ji; Ai, Jing; Song, Zilan; Peng, Xia; Xing, Li; Xi, Yong; Guo, Junfeng; Yao, Qizheng; Ding, Jian; Geng, Meiyu; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 105; (2015); p. 39 – 56;,
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

A mixture of -1- (4- (4-chloro-lH-pyrazol-l-yl) pyridin-3- yl) piperidine-4-carboxylic acid (0.50 g) , N-methyltetrahydro- 2H-pyran-4-amine (0.16 g) , HATU (0.81 g) , triethylamine (0.91 mL) and DMF (8.2 mL) was stirred at room temperature for 3 hr. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) , and the obtained solid was crystallized from ethyl acetate/hexane to give the title compound (0.43 g). XH NMR (300 MHz, CDC13) 51.45-1.65 (2H, m) , 1.65-2.11 (6H, m) , 2.61 (1H, brs), 2.71-2.97 (5H, m) , 3.13 (2H, d, J = 11.7 Hz), 3.37-3.59 (2H, m), 3.94-4.16 (2H, m) , 4.66-4.84 (1H, m) , 7.59 (1H, s), 7.66 (1H, s) , 8.40 (lH, s) , 8.46 (1H, s) , 8.59 (1H, s).

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOIKE, Tatsuki; IKEDA, Shuhei; WO2015/190613; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

127956-11-0, Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To the mixture of 2-ethylisothiourea (9.07 g, 49.00 mmol, HBr salt) in H20 (50.00 mL) under dark was added Na2c03 (5.19 g, 49.00 mmol). Then to the mixture was added methyl 4-oxotetrahydro-2H-pyran-3-carboxylate (7.75 g, 49.00 mmol). The mixture was stirred under dark at 25 c for 16 h TLC (petroleum ether/EtOAc=1:1, Rf=0.3) showed one new main spot. The mixture was filtered, the solid was washed with water (30 mL), petroleum ether/EtOAc=20: 1 (20 mL). Then the solid was dried under reduced pressure to afford the title compound (8.01 g, crude) as an off-white solid. ?H NIVIR (400 MHz, DMSO-d6) oe 10.69 (s, 1H), 5.87 (s, 1H), 3.83 (s, 1H), 3.63-3.49 (m, 3H), 3.00-2.89 (m, 2H), 2.40 (s, 1H), 1.24 (t, J= 7.2 Hz, 3H).

127956-11-0, As the paragraph descriping shows that 127956-11-0 is playing an increasingly important role.

Reference£º
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; POYUROVSKY, Masha; BARSOTTI, Anthony; KIM, Ji-In; LIU, Kevin; MORRIS, Koi; (143 pag.)WO2016/210331; (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.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

To a solution of 1-tetrahydro-2H-pyran-4-ylethanone (166mg, 1.30 mmol) in MeOH (7.5 mL) hydrazine hydrate (55-60% in water, 0.90 mL, 17.61 mmol) was added. Thereaction mixture was heated to refluxforl6 h, cooled andconcentrated under reduced pressure to give crude 1-tetrahydropyran-4-ylethanone hydrazone (171 mg, 1.20 mmol, 93% yield) as a colourless oil. 1H NMR (400 MHz, CDCI3, ): 4.92 (5, 2H), 4.03-3.98 (m, 2H), 3.45-3.40 (m, 2H), 2.38-2.30 (m, 1H), 1.73 (5, 3H), 1.65-1.63 (m, 4H)., 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; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics