Day: November 4, 2020

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.

70 mg (1.76 mmol, 1.1 eq.) of NaH was added into the solution of 455 mg (1.4 mmol, 1 eq.) 2 in DMF, and stirred for 1 hr at rt. 211 mg (1.76 mmol, 1.1 eq.) of 4-chloro-2H-tetrahydropyran was then added and stirred overnight. After the reaction was complete, water was added, and then all the solvent was removed by filtration and the product was purified by column chromatography to obtain 942 mg of 3, with a yield of 60%.

1768-64-5, As the paragraph descriping shows that 1768-64-5 is playing an increasingly important role.

Reference£º
Patent; Zhejiang Beta Pharma Incorporation; Fujian Haixi Pharmaceuticals, Inc.; Kang, Xinshan; Long, Wei; Ma, Cunbo; Wang, Yanping; Shen, Xiaoyan; Hu, Yunyan; Tan, Fenlai; Wang, Yinxiang; US2013/225587; (2013); 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.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

Step a Intermediate 203 -Bromo-N-methyl-N-(tetrahydro-2H-pyran-4-yl)benzenesulfonaniide To a solution of N-methyltetrahydro-2H-pyran-4-amine (0.710 g, 6.16 mmol) and Et3N (1.227 ml, 8.81 mmol) in DCM (10 ml) cooled to 0 C was added dropwise a solution of 4-bromobenzene-l-sulfonyl chloride (1.5 g, 5.87 mmol) in DCM (10 ml). The reaction was allowed to warm to r.t. and stirred for 20 h. The reaction was concentrated under reduced pressure and the resultant white solid dissolved in EtOAc and filtered. The filtrate was concentrated under reduced pressure and the resulting solid dried under high vacuum to yield 4-bromo-N-methyl-N-(tetrahydro-2H-pyran-4- yl)benzenesulfonamide as an off-white solid (1.94 g, 99 %). ? NMR (400 MHz, DMSO- 57.79 (m, 4H), 3.87 – 4.01 (m, 1 H), 3.73 – 3.86 (m, 2H), 3.33 – 3.37 (m, 1H), 3.29 (m, 1H), 2.70 (s, 3H), 1.54 – 1 .70 (m, 2H), 1.11 – 1.27 (m, 2H)

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; RUPRAH, Parminder, Kaur; MERCHANT, Kevin, John; WALSH, Louise, Marie; KERR, Catrina, Morven; FIELDHOUSE, Charlotte; HARRISSON, David; MAINE, Stephanie; HAZEL, Katherine; WO2013/27001; (2013); 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.223734-62-1,2-((S)-Dec-1-yn-5-yloxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Example 1. Preparation of chiral benzyl alcohol (A-l); A 50-mL, two-necked, round-bottom flask equipped with a mechanical stirrer was charged with zinc triflate (2.16g, 0.0059 mol) and (+)-N-methylephiderine (0.814 g, 0.0045 mol) in toluene (10 mL). To this mixture triethyl amine was added (0.459 g, 0.0045 mol) and this gelatinous mixture was stirred at ambient temperature for 30-60 minutes. To this mixture was then treated with a solution of alkyne (1.08 g, 0.0045 mol) in toluene (1 mL), stirred at ambient temperature for 15 minutes followed by solution of aldehyde (0.250 g, 0.0014 mol). Progress of the reaction was monitored by TLC (completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent: 20% ethyl acetate in hexanes). After stirring the mixture for 3 h TLC indicated completion of reaction. At this stage reaction mixture was quenched by slow addition of saturated ammonium chloride (10 mL). This was stirred for 5-10 minutes and organic layer containing desired compound was separated. Aqueous layer was washed with ethyl acetate (10 mL). The combined organic layers were washed with brine (15 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain a crude product (2.0 g). The crude product was purified by column chromatography using 250- 400 mesh silica gel. A solvent gradient of ethyl acetate in hexanes (5-20%) was used to elute the product from the column. All fractions containing the desired product were combined and concentrated in vacuo to give pure chiral benzyl alcohol A-l (0.360g, -87%) compound was characterized by .H, 13C NMR, IR, LCMS and chiral HPLC data. 1H NMR (CDC13, 300 MHz): delta 0.87 (t, 3H), 1.18-1.86 (m, 17H), 2.28 (dt, 1H), 2.34-2.45 (m, 2H), 3.40- 3.53 (m, 1H), 3.54- 3.62 (m, 1H), 3.63-3.75 (m, 1H), 3.81 (s, 3H, OCH3), 3.83-3.92 (m, 1H), 4.62-4.66 (m, 1H), 4.89-5.05 (m, 2H), 5.59-5.61 (merged two s, 1H), 5.91-6.04 (m, 1H), 6.85-6.82 (d, 1H), 7.20- 7.26 (m, 1H), and 7.31-7.36 (m, 1H); 13C NMR (CDC13, 75 MHz): delta 14.13, 14.18, 14.98, 15.56, 19.96, 21.14, 22.71, 24.77, 25.34, 25.57, 29.51, 31.17, 31.23, 32.07, 32.19, 32.69, 33.51, 33.94, 35.13, 55.86, 60.49, 62.12, 62.18, 62.82, 75.36, 75.89, 80.20, 80.53, 86.97, 87.42, 97.31, 98.06, 1 10.63, 1 14.80, 1 19.18, 1 19.27, 125.86, 127.44, 127.50, 137.15, 140.78, 157.68; IR: 341 1 , 2230, 1638, 1259, 1 133, 1023, 755 cm”1; MS( /z): [M+Na]+ 437.35.

223734-62-1, 223734-62-1 2-((S)-Dec-1-yn-5-yloxy)tetrahydro-2H-pyran 11149121, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UNITED THERAPEUTICS CORPORATION; BATRA, Hitesh; PENMASTA, Raju; SHARMA, Vijay; TULADHAR, Sudersan M.; WALSH, David A.; WO2011/153363; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

287193-07-1, Ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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 x 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 evaporatedin 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

287193-07-1 Ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate 54067561, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; NOVO NORDISK A/S; Ontogen Corporation; EP1214325; (2005); B1;,
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

j00195J Into a 25-mL vial, was placed a solution of methyl 2-oxospiro[pyrrolidine-3,2?- thiochromane]-6?-carboxylate 1,1-dioxide (150 mg, 0.48 mmol, 1 equiv) in DMF (4 mL). This was followed by the addition of NaH (60% dispersion in oil, 39 mg, 1.62 mmol, 2 equiv) at 0 C over 10 mi 4-(Bromomethyl)oxane (261 mg, 1.46 mmol, 3 equiv) was then added. The resulting solution was stirred for 4 h at room temperature. The reaction was quenched with a solution of aq. NH4C1. The resulting solution was extracted with 3×20 mL of EtOAc. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give 144.8 mg (73% yield) of the title compound as a light yellow oil. MS: (ES, m/z):408 [M+H]., 125552-89-8

As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Patent; FORMA THERAPEUTICS, INC.; NG, Pui Yee; DAVIS, Heather; BAIR, Kenneth W.; MILLAN, David S.; RUDNITSKAYA, Aleksandra; ZHENG, Xiaozhang; HAN, Bingsong; BARCZAK, Nicholas; LANCIA JR., David; (212 pag.)WO2016/168660; (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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

Example 78: Preparation of 5-[5-FIuoro-2-oxo-l,2-dihydro-indol-(3Z)- ylidenemethyll-2,4-dimethyl-lH-pyrrole-3-carboxylic acid [(S)-2,5-dioxo- 1- (tctrahydro-pyran-4-ylmethyl)-pyrrolidin-3-yl]-amide75C 60a yeaStepl : Compound 75c (200mg, 0.93mmol), 60a (201mg, 1.12mmol), KI (163mg, 0.98mmol), K2CO3 (644mg, 4.67mmol) and acetonitrile (2OmL) were mixed in a microwave vial. The resulting mixture was reacted under microwave condition at 14O0C for Ih. After being cooled, the mixture was filtered. The filtrate was evaporated and the residue was purified by column chromatography (EA::PE=1 :3) to provide 78a (224mg, 77%)., 125552-89-8

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

Reference£º
Patent; XCOVERY, INC.; WO2008/33562; (2008); A2;,
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.23462-75-1,Dihydro-2H-pyran-3(4H)-one,as a common compound, the synthetic route is as follows.

23462-75-1, Cap- 177a and Cap- 177b, step a1, 1,3,3-Tetramethylguanidine (0.985 niL, 7.85 mmol) was added to a stirred solution of methyl 2-(benzyloxycarbonylamino)-2-(dimethoxyphosphoryl)acetate (2.0 g, 6.0 mmol) in EtOAc (40 mL) and the mixture was stirred at rt under 2 for 10 min. Then dihydro-2H-pyran-3(4H)-one (0.604 g, 6.04 mmol) was added and the mixture was stirred at rt for 16 h. The reaction mixture was then cooled in freezer for 10 min and neutralized with aq. citric acid (1.5 g in 20 mL water). The two phases were partitioned and the organic layer was washed with 0.25 N aq.HCl and brine, and then dried (MgS04) and concentrated to a colorless oil. The crude material was purified by flash silica chromatography (loading solvent: DCM, eluted withEtOAc/Hexanes, gradient from 20% to 30% EtOAc) to yield two isomeric products: The first eluted product was (Z)-methyl 2-(benzyloxycarbonylamino)-2-(2H-pyran- 3(4H,5H,6H)-ylidene)acetate (490 mg) (white solid), and the second was (E)-methyl 2-(benzyloxycarbonylamino)-2-(2H-pyran-3(4H,5H,6H)-ylidene)acetate (433 mg) (white solid). LC-MS retention time 1.398 min (for Z-isomer) and 1.378min (for E- isomer); m/z 304.08 (for Z-isomer) and 304.16 (for E-isomer) (MH-). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with aPHENOMENEX Luna lOu C18 3.0x50mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% Solvent A / 0% Solvent B to 0% Solvent A / 100% Solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where Solvent A was 5% MeOH / 95% H2O / 10 mM ammonium acetate and Solvent B was 5%> H20 / 95%> MeOH / 10 mM ammonium acetate. MS data was determined using a MICROMASS Platform for LC in electrospray mode. ? NMR (400 MHz, chloroform-d) (for Z-isomer) delta ppm 7.30 – 7.44 (m, 5 H), 6.18 (br. s., 1 H), 5.10 – 5.17 (m, 2 H), 4.22 (s, 2 H), 3.78 (br. s., 3 H), 2.93 – 3.02 (m, 2 H), 1.80 (dt, J=l 1.7, 5.8 Hz, 2 H), 1.62 (s, 2 H). XH NMR (400 MHz, chloroform-d) (for E-isomer) delta ppm 7.31 – 7.44 (m, 5 H), 6.12 (br. s., 1 H), 5.13 – 5.17 (m, 2 H), 4.64 (br. s., 2 H), 3.70 – 3.82 (m, 5 H), 2.49 (t, J=6.5 Hz, 2 H), 1.80 (br. s., 2 H). (Note: the absolute regiochemistry was determined by XH NMR shifts and coupling constants).

The synthetic route of 23462-75-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BELEMA, Makonen; SRINIVASU, Pothukanuri; BENDER, John A.; LOPEZ, Omar D.; CHEN, Qi; RAMPULLA, Richard A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; MEANWELL, Nicholas A.; WO2012/21591; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 15-1 and Compound 1-2 (1 eq) were dissolved in acetonitrile.(3 eq) DIPEA was added and the reaction was heated at 60 C overnight.After the reaction was completed, it was washed with water and extracted with ethyl acetate three times.The combined organic phases were washed with saturated brine.After drying anhydrous sodium sulfate, mix the sample on the column.CH2Cl2: MeOH = 100:1 – 30:1 gave compound 15-2.

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; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Tan Wenfu; Liu Xiaohua; Huang Wenjing; Zhang Yu; Yang Jun; (37 pag.)CN110143974; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

951127-25-6, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,951127-25-6

60b (1.03 g, 1.83 mmol) was dissolved in dimethylacetamide (15 mL)Intermediate 1 (0.61 g, 1.83 mmol) was added at room temperature for 30 min.The reaction system was cooled to 0 C, sodium borohydride triacetate (0.98 g, 4.46 mmol) was added, reacted for 30 minutes, The reaction was continued at room temperature for 2 hours.The reaction solution was cooled to 0 C, water (40 mL) was added in that order, and the water was adjusted to 9 with aqueous ammonia (5 mL). The solid was precipitated and washed with water (50 mL x 3). The solid was dissolved in dichloromethane and treated with dichloromethane ), The organic phase was combined, washed with saturated brine solution (50 mL x 1), dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated and the column chromatography was separated and purified (dichloromethane / methanol (v / v) = 20: 1 ),A yellow solid 60c (0.57 g, yield 58%) was obtained.

As the paragraph descriping shows that 951127-25-6 is playing an increasingly important role.

Reference£º
Patent; Sichuan Haisco Pharmaceutical Co.,Ltd.; FAN, JIANG; ZHANG, CHEN; PENG, FEI; WU, YE; FENG, JIANCHUAN; WANG, JIANMIN; ZHENG, SUXIN; WEI, YONGGANG; YE, FEI; (350 pag.)TW2017/8220; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2,2-Dimethyltetrahydropyran-4-one 1 (5.0 g, 32.0 mmol) was dissolved in methanol (4.7 ml) and carbon disulfide (4.7 ml, 48.8 mmol) was added in one portion. Malononitrile (2.6 g, 39.0 mmol) was added portionwise and, finally, triethylamine (1.95 ml) was added dropwise. The reaction mixture was stirred at room temperature for 48 h. An orange precipitate was formed, which was filtered (3.90 g), its 1H NMR being consistent with the desired compound 2. From the filtrates, 0.89 g more of 6-amino-3,3-dimethyl-8-thioxo-4,8-dihydro-1H,3H-thiopyrano[3,4-c]pyran-5-carbonitrile were isolated by flash chromatography, eluting first with CH2Cl2 and next with the mixture of solvents CH2Cl2:MeOH 98:2. Yield = 48%. 1H NMR (200 MHz, CDCl3) delta ppm 1.30 (s, 6 H), 2.62 (s, 2 H), 4.66 (s, 2 H), 7.91 (s, 2 H)., 1194-16-7

The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Taltavull, Joan; Serrat, Jordi; Grcia, Jordi; Gavald, Amadeu; Cordoba, Mnica; Calama, Elena; Montero, Jose Luis; Andres, Miriam; Miralpeix, Montserrat; Vilella, Dolors; Hernandez, Begona; Beleta, Jorge; Ryder, Hamish; Pags, Lluis; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 4946 – 4956;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics