Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.873397-34-3,Tetrahydro-2H-pyran-3-carboxylic acid,as a common compound, the synthetic route is as follows.,873397-34-3

A mixture of methyl 2,3,4,5-tetrahydro-1,4-benzoxazepine-8-carboxylate (250 mg, 1.21 mmol, 1 equiv), tetrahydro-2H-pyran-3-carboxylic acid (157 mg, 1.21 mmol, 1 equiv), DIEA (469 mg, 3.63 mmol, 3 equiv), and HATU (552 mg, 1.45 mmol, 1.2 equiv) and in DMF (4 mL) was stirred overnight at room temperature. The reaction was then quenched by the addition of water (2 mL). The resulting solution was extracted with CH2Cl2 (3¡Á10 mL) and washed with brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under vacuum. The crude racemic mixture was purified by chiral Prep-HPLC (Column: Chiralpak IA 2¡Á25 cm, 5 m; Mobile Phase A: hexanes; Mobile Phase B: EtOH; Flow rate: 20 mL/min; Gradient: 30percent B for 26 min; Detector, UV 254, 220 nm) to afford single isomers of the title compound. The first eluting isomer was isolated as a white solid (55 mg, 14percent yield). MS: (ES, m/z): 320 [M+H]+. The second eluting isomer was isolated as a white solid (55 mg, 14percent yield). MS: (ES, m/z): 320 [M+H]+.

The synthetic route of 873397-34-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Forma Therapeutics, Inc.; Zheng, Xiaozhang; Ng, Pui Yee; Han, Bingsong; Thomason, Jennifer R.; Zablocki, Mary-Margaret; Liu, Cuixian; Davis, Heather; Rudnitskaya, Aleksandra; Lancia, JR., David; Bair, Kenneth W.; Millan, David S.; Martin, Matthew W.; (190 pag.)US2016/222028; (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.14774-36-8,(Tetrahydropyran-3-yl)methanol,as a common compound, the synthetic route is as follows.

14774-36-8, To a solution of Compound 29 (100 mg, 0.34 mmol) in THF (4 mL) was added (0759) tetrahydropyran-3-ylmethanol (117.65 mg, 1.01 mmol), PPli3 (177.1 mg, 0.68 mmol) and then DIAD (136.54 mg, 0.68 mmol). The resulting mixture was stirred at 20 C under N2 for 16 hours . The reaction solution was concentrated to give the crude product, which was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 10% to 20%) and Prep- TLC (silica gel, PE: EtOAc = 4: 1) to afford A-58 (50 mg) as a solid. A-58 was purified by SFC (Chiralcel AD (250 mm x 30 mm, 5 muiotaeta); A = C02 and B = EtOH (0.1% NH3H20); 38C; 50 mL/min; 30% B over 11 minutes; multiple injections) to afford Enantiomer 1, randomly assigned as Compound 66 (Rt = 6.8 min) and Enantiomer 2, randomly assigned as Compound 67 (Rt = 9.2 min). Compound 66 (14.37 mg, 0.04 mmol) 1H NMR (CDCI3 400MHz) deltaEta = 8.00 (d, 2H), 7.48 (s, 2H), 7.33 (d, 2H), 4.01 – 3.80 (m, 4H), 3.56 – 3.35 (m, 2H), 2.43 – 2.30 (m, 1H), 1.96 – 1.85 (m, 1H), 1.82 – 1.72 (m, 1H), 1.69 – 1.59 (m, 1H), 1.49 – 1.37 (m, 1H). LCMS Rt = 1.32 min using Method A, MS ESI calcd. for Ci9Hi8F3N204 (0760) [M+H]+ 395.1, found 395.0. Compound 67 (15.66 mg, 0.04 mmol) 1H NMR (CDC13, 400MHz) deltaEta = 8.00 (d, 2H), 7.48 (s, 2H), 7.33 (d, 2H), 4.00 – 3.81 (m, 4H), 3.55 – 3.46 (m, 1H), 3.41 (dd, 1H), 2.43 – 2.31 (m, 1H), 1.96 – 1.86 (m, 1H), 1.82 – 1.72 (m, 1H), 1.69 – 1.59 (m, 1H), 1.49 – 1.37 (m, 1H). LCMS Rt = 1.33 min using Method A, MS ESI calcd. for Ci9Hi8F3N204 [M+H]+ 395.1, found 395.1.

14774-36-8 (Tetrahydropyran-3-yl)methanol 85769, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4677-18-3,2-(Tetrahydro-2H-pyran-4-yl)ethanol,as a common compound, the synthetic route is as follows.

To a solution of 2-(tetrahydro-2H-pyran-4-yl)ethan-l-ol (300 mg, 2.304 mmol) and TEA (0.964 mL, 6.91 mmol) in THF (10 mL) was added dropwise Ms-Cl (0.269 mL, 3.46 mmol) at 0 C. The reaction mixture was stirred for 20 hours at 25 C. The reaction mixture was poured into water (20 mL), extracted by EtOAc (30 mL), washed with 1M HC1 (5 ml), sat NaHCCh, (10 ml) and brine (10 ml). The organic layer was dried over Na2S04, filtered and concentrated to give 2-(tetrahydro-2H-pyran-4-yl)ethyl methanesulfonate (300 mg, 1.329 mmol, 57.7 % yield) as a brown oil which was used in the next step without purification.

4677-18-3, As the paragraph descriping shows that 4677-18-3 is playing an increasingly important role.

Reference£º
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; EASTMAN, Kyle J.; KADOW, John F.; GILLIS, Eric P.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; (0 pag.)WO2020/3093; (2020); A1;,
Tetrahydropyran – Wikipedia
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14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 25: (Tetrahydro-2H-pyran-4-y0methyl methanesulfonate (Tetrahydro-2H-pyran-4-yl)methanol (29.9 mg, 0.257 mmol) was dissolved in dichloromethane (DCM) (4 mL). To this solution was added triethylamine (0.108 mL, 0.772 mmol). The reaction was cooled to 0 C, methanesulfonyl chloride (0.03 mL, 0.386 mmol) added and the reaction left to stir overnight, allowing the reaction to warm to 20 C. The reaction was concentrated in vacuo. The product was partitioned between ethyl acetate (20 mL) and aqueous saturated sodium bicarbonate (20 mL). The organic phase was dried and concentrated in vacuo, before being used in the next reaction with no further purification or characterisation, 49 mg., 14774-37-9

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

Reference£º
Patent; GLAXO GROUP LIMITED; BIRAULT, Veronique; CAMPBELL, Amanda Jennifer; HARRISON, Stephen; LE, Joelle; SHUKLA, Lena; WO2013/160418; (2013); A1;,
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4295-99-2,4295-99-2, 4-Cyanotetrahydro-4H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Lithium bis(trimethylsilyl)amide (1M in THF, 27 mL, 27 mmol) was added dropwise to a solution ofoxane-4-carbonitrile (2.0 g, 18 mmol) in THF (10 mL) at 0 C. The reaction mixture was warmed to rt,stirred for 10 min and cooled back to 0 C. Allyl bromide (3.30 g, 27 mmol) was added dropwise, thesolution warmed to room temperature and stirred overnight. The reaction mixture wasconcentrated in vacuo and saturated aqueous NH4Cl (20 mL) was added. The phases were separatedand the aqueous phase was extracted with EtOAc (3 ¡Á 50 mL). The combined organic extracts weredried and concentrated in vacuo to give the amine (2.37 g, [87%]) as a colourless oil that was usedstraight in the next step.

As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

Reference£º
Article; Craven, Philip; Aimon, Anthony; Dow, Mark; Fleury-Bregeot, Nicolas; Guilleux, Rachel; Morgentin, Remy; Roche, Didier; Kalliokoski, Tuomo; Foster, Richard; Marsden, Stephen P.; Nelson, Adam; Bioorganic and Medicinal Chemistry; vol. 23; 11; (2015); p. 2629 – 2635;,
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.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.

5-bromo-2-(2,2,6,6-tetramethyl-tetrahydro-2H-pyran-4-ylamino)benzonitrile To a solution of 2,2,6,6-tetramethyloxan-4-one (350 mg, 2.24 mmol) in dichloromethane (60 mL) was added 2-amino-5-bromobenzonitrile (500 mg, 2.54 mmol), tetramethylammonium triacetoxyborohydride (700 mg, 2.66 mmol) and trifluoroacetic acid (0.375 mL) at room temperature. The resulting solution was stirred for 4 h at room temperature and then water (50 mL) was added. The mixture was extracted with ethyl acetate (50 mL*3). The organic phases were combined, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with ethyl acetate in hexane (0% to 70% gradient) to yield 5-bromo-2-[(2,2,6,6-tetramethyloxan-4-yl)amino]benzonitrile as yellow solid (180 mg, 24%).

1197-66-6, 1197-66-6 2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one 11829691, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (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.110238-91-0,Methyl tetrahydro-2H-pyran-4-carboxylate,as a common compound, the synthetic route is as follows.

Synthesis of 2-Methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid Step 1: Synthesis of (Tetrahydro-pyran-4-yl)-methanol To a solution of 250 mL of LiAlH4 (2.3M solution in THF, 0.575 mol) in THF (200 mL) is added dropwise a solution of 130 mL (0.974 mol) of tetrahydro-pyran-4-carboxylic acid methyl ester in THF (900 mL) under nitrogen atmosphere (CAUTION: highly exothermic reaction.). The temperature is kept at 40-45 C with an ice-bath. Upon complete addition, the reaction is stirred at room temperature for 1.5 h. The reaction is cooled in an ice-bath and quenched with addition of water (22 mL), 15% aqueous NaOH solution (21 mL) and water (66 mL). The resulting precipitate is removed by filtration through Celite and is rinsed with THF (300 mL). The filtrate is concentrated under reduced pressure to afford 102.5 g of (tetrahydro-pyran-4-yl)-methanol as a colorless oil. Yield: 91%; 1H NMR (400 MHz, CHLOROFORM- d) delta ppm 1.20 – 1.39 (2 H, m), 1.56 – 1.83 (3 H, m), 2.03 (1 H, br. s.), 3.29 – 3.52 (4 H, m), 3.89 – 4.05 (2 H, m)

110238-91-0, The synthetic route of 110238-91-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BERRY, Angela; RIETHER, Doris; ERMANN, Monika; JENKINS, James Edward; MUSHI, Innocent; WO2011/88015; (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.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

A solution of tetrahydro-2H-pyran-4-ol (25.0 g, 245 mmol), TEA (51 mL, 367 mmol) and trimethylamine hydrochloride (2.34 g, 24.5 mmol) were stirred in DCM (750 mL) at RT for 10 minutes and cooled to 0C. 4-Methylbenzenesulfonyl chloride (51.3 g, 269 mmol) was added and the mixture stirred at RT for 17h. The mixturewas treated with N,N-dimethylethane-1,2-diamine (31.6 mL, 294 mmol) and water. The aqueous layer was extracted three times with DCM. The combined organic portions were concentrated under reduced pressure and purified via column chromatography (silica gel, hexane/ EE gradient) to give 58.5 g (93% yield) of the title compound.1H NMR (400 MHz, DMSO-d6) 6 [ppm] 1.51 – 1.61 (m, 2 H) 1.74 (dq, J=13.04, 3.65 Hz, 2 H) 2.42 (5, 3 H) 3.39 (ddd, J=11.75, 8.97, 3.03 Hz, 2 H) 3.71 (dt, J=11.81,4.71 Hz, 2 H) 4.69 (tt, J=8.65, 4.23 Hz, 1 H) 7.47 (d, J=8.08 Hz, 2 H) 7.81 (d, J=8.34 Hz, 2 H)., 2081-44-9

The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

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;,
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.65412-03-5,4-(2-Aminoethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

General procedure: Step A: A mixture of 19 TFA salt (9 mg, 0.06 mmol), 11 (32 mg,0.07 mmol) and Cs2CO3 (45 mg, 0.14 mmol) in DMF (0.63 mL)was stirred at 65 C for 12 h. The reaction mixture was filtered,and the crude product was purified by preparative TLC on silicagel eluting with 80% EtOAc/hexanes to give 5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-(((hexahydrofuro[2,3-b]furan-3a-yl)methyl)amino)-N-(thiazol-2-yl)benzenesulfonamide (20 mg, 54%)as a white foam. 1H NMR (500 MHz, CDCl3) d 7.77 (d, J = 6.9 Hz,1H), 7.40 (d, J = 3.5 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 6.98 (d,J = 3.5 Hz, 1H), 6.43-6.30 (m, 3H), 5.47 (s, 1H), 5.21 (s, 2H), 5.05-4.95 (m, 1H), 4.09 (dd, J = 8.8, 5.0 Hz, 4H), 3.82-3.70 (m, 7H),3.35 (d, J = 5.2 Hz, 2H), 2.14-1.98 (m, 4H). 584.2 (M+H)+. Step B:A solution of 5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-(((hexahydrofuro[2,3-b]furan-3a-yl)methyl)amino)-N-(thiazol-2-yl)benzenesulfonamide (20 mg, 0.034 mmol) and TFA (0.05 mL) inDCM (0.34 mL) was stirred at rt for 1 h. The solvents wereremoved, and residue was purified via preparative HPLC (MethodC) to give 4 (6 mg)., 65412-03-5

As the paragraph descriping shows that 65412-03-5 is playing an increasingly important role.

Reference£º
Article; Wu, Yong-Jin; Guernon, Jason; McClure, Andrea; Luo, Guanglin; Rajamani, Ramkumar; Ng, Alicia; Easton, Amy; Newton, Amy; Bourin, Clotilde; Parker, Dawn; Mosure, Kathleen; Barnaby, Omar; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick; Herrington, James; Chen, Ping; Sivarao; Bristow, Linda J.; Meanwell, Nicholas A.; Bronson, Joanne; Olson, Richard; Thompson, Lorin A.; Dzierba, Carolyn; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5490 – 5505;,
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.624734-17-4,3-Methoxydihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

General procedure: Toa solution of ((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone (119 mg, 0.33 mmol, 1 eq) in DCM at rtwas added acetic acid (0.01 mL, 0.17 mmol, 0.5 eq),3-methoxytetrahydro-4H-pyran-4-one (131 mg, 1.0 mmol, 3 eq) and sodiumtriacetoxyborohydride (355 mg, 1.67 mmol, 5 eq). After stirring overnight, saturated NaHCO3was added, the solution extracted with DCM, the organics combined, dried overMgSO4, and concentrated.Purification by chromatography (12 g) eluting with 4 to 8% methanol/DCMwith ammonia afforded compound 2a ((3aS,5S,6aR)-5-((3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone(83 mg, 50%). 1H NMR (CHLOROFORM-d)d: 8.72 (br. s., 1H), 7.70 (br. s., 1H), 4.98 -5.14 (m, 1H), 4.70 – 4.89 (m, 2H),3.80 – 4.18 (m, 5H), 3.25 – 3.75 (m, 8H), 3.07 – 3.24 (m, 2H), 2.53 – 2.89 (m,1H), 2.01 – 2.48 (m, 4H), 1.39 – 1.88 (m, 5H).ESI-MS (m/z): Calculated for C23H30F3N3O4:470.2 (M+1); found: 470.2., 624734-17-4

The synthetic route of 624734-17-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Winters, Michael P.; Teleha, Christopher A.; Kang, Fu-An; McComsey, David; O’Neill, John C.; Hou, Cuifen; Kirchner, Thomas; Wang, Ping; Johnson, Dana; Sui, Zhihua; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2137 – 2140;,
Tetrahydropyran – Wikipedia
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