Category: 23462-75-1

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.

Step 1: The mixture of 38_1 (1.20 g, 11.99 mmol, 1.40 eq) and benzyl N- aminocarbamate (1.42 g, 8.56 mmol, 1.00 eq) in MeOH (15 mL) was stirred at 30C for 2 h. NaBCN (2.69 g, 42.82 mmol, 5.00 eq) was added. The resulting mixture was stirred at 30 C for 16 h. The mixture was concentrated and diluted with water (50 mL) and EA (50 mL). The organic layer was concentrated and purified by column chromatography (PE:EA=10:1~2:1) to give 38_2 (1.50 g, 5.99 mmol, 70% yield) as a colorless oil. LCMS: RT = 0.568 min, m/z 273.2 [M+H]+ NMR (CDCb, 400 MHz) S 7.40-7.35 (m, 5H), 6.25 (s, 1H), 5.26-5.14 (m, 2H), 3.86-3.73 (m, 3H), 3.48-3.30 (m, 2H), 1.91-1.85 (m, 2H), 1.59-1.46(m, 2H).

23462-75-1, 23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BEN NERIAH, Yinon; BRACHYA, Guy; BURSTAIN, Ido; MINZEL, Waleed; SNIR-ALKALAY, Irit; VACCA, Joseph; LI, Dansu; (129 pag.)WO2017/21969; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1-Synthesis of 3-((trimethylsilyl)ethynyl)tetrahydro-2H-pyran-3-ol A solution of dihydro-2H-pyran-3(4H)-one (200 mg, 2 mmol) in THF was treated with n-BuLi (2 mL) at -78 C. for about 30 min. Ethynyltrimethylsilane (300 mg, 3 mmol) was then added and the reaction mixture was stirred for 3 hr. Purification by gel chromatography afforded the title compound (200 mg, 50%); 1H NMR (400 MHz, DMSO) delta 0.15 (s, 9H), 1.52-1.55 (m, 1H), 1.62-1.67 (m, 1H), 1.80-1.88 (m, 1H), 3.23-3.26 (m, 1H), 3.37-3.44 (m, 1H), 3.49-3.56 (m, 2H), 5.52 (s, 1H)., 23462-75-1

23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Genentech, Inc.; US2012/214762; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,23462-75-1

A 50 mL 3-neck flask with inert gas valve and septum was charged 1.318 g (9.684 mmol) benzohydrazide and 15 mL EtOH. (1.04 g, 10.20 mmol) dihydro-2H-pyran-3(4H)-one was syringed into the flask. Suspension became clear solution after the temperature reaches 60 oC. The mixture tempearture keeps at 60 oC for 7h until benzohydrazide was completely consumed as monitored by GC-MS. White precipitate developed after the temperature was cooled down to RT. The solid was filtered and washed with 1:1 mixture of EtOAc/hexanes. Extra product was obtained by purifying the filtrate on silica column using EtOAc. Total product of 1.76 g was obtained as white solid in 82 % yield. 1H NMR (400 MHz, CDCl3 : 7.56 (br s, 1H), 7.80-7.82 (m, 2H), 7.52-7.56 (m, 1H), 7.44-7.48 (m, 2H), 4.31 (br s, 2H), 3.79-3.85 (t, J = 5.2 Hz, 2H), 2.54-2.57 (t, J = 6.6 Hz, 2H), 1.89-1.95 (quint, J = 6.4 Hz, 2H); 13C NMR (100 MHz, CDCl3): 164.24, 156.49, 133.33, 131.92, 128.68, 127.26, 71.40, 67.14, 24.96, 24.22; HRMS for [C12H14N2O2+H+]: observed 219.1142, calculated 219.1128.

As the paragraph descriping shows that 23462-75-1 is playing an increasingly important role.

Reference£º
Article; Haddad, Nizar; Qu, Bo; Rodriguez, Sonia; Van Der Veen, Lars; Reeves, Diana C.; Gonnella, Nina C.; Lee, Heewon; Grinberg, Nelu; Ma, Shengli; Krishnamurthy, Dhileepkumar; Wunberg, Tobias; Senanayake, Chris H.; Tetrahedron Letters; vol. 52; 29; (2011); p. 3718 – 3722;,
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.

[01 77j Synthesis of ethyl 6,7-dihydro-5H-thieno [3 ,2-b]pyran-2-carboxylatewas similar to that of ethyl 6,7-dihydro-4H-thieno[3,2-c]pyran-2-carboxylate in Example 3, except dihydro-2H- pyran-3(4H)-one was substituted for dihydro-2H-pyran-4(3H)-one. The residue was purified by column chromatography (silica, petroleum ether/EtOAc = 8:1) to give product ethyl 6,7-dihydro- 5H-thieno[3,2-b]pyran-2-carboxylate (319 mg, yield: 30%) as a white liquid. ESI-MS (M+H):213.1. ?H NMR (400 MHz, CDC13) (5: 7.26 (s, 1H), 4.31 (q, J = 7.2 Hz, 2H), 4.17 (t, J = 5.2 Hz, 2H), 2.79 (t, J = 6.8 Hz, 2H), 2.08-2.02 (m, 2 H), 1.35 (t, J = 6.8 Hz, 3H).

23462-75-1, 23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1. Synthesis of Intermediate 11-2. To a mixture of trimethylsulfoxonium iodide (12.2 g, 59.8 mmol) in DMSO (40 mL) was added NaH (2.38 g, 60% in mineral oil, 59.8 mmol) portionwise at 5 C under N2 and the mixture was stirred at 5 C for 30 mins. Intermediate 11- 1 (5 g, 49.9 mmol) in DMSO (40 mL) was added dropwise maintaining the temperature below 15 C and stirring was continued at 15 C for 20 hrs. The reaction was quenched at 10 C with water (200 mL) and extracted with DCM (2 x 200 mL). The combined organic phases were washed with brine (200 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (0%~50% EtOAc in PE) to afford Intermediate 11-2 (2 g, 35%) as a colorless oil. (0356) 1H NMR (400 MHz, CDCl3) delta 3.81-3.60 (m, 3H), 3.49 (d, J = 12.0 Hz, 1H), 2.73-2.65 (m, 2H), 2.03-1.82 (m, 2H), 1.81-1.62 (m, 2H)., 23462-75-1

As the paragraph descriping shows that 23462-75-1 is playing an increasingly important role.

Reference£º
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, G.; MARTINEZBOTELLA, Gabriel; HARRISON, Boyd, L.; REID, John, Gregory; (113 pag.)WO2017/173358; (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.23462-75-1,Dihydro-2H-pyran-3(4H)-one,as a common compound, the synthetic route is as follows.

To a stirred solution of dihydro-2H-pyran-3(4H)-one (10 g, 100 mmol) in tetrahydrofuran (100 mL), methanol (100 mL) under nitrogen atmosphere was added ethanamine (2M in THF) (49.9 mL, 100 mmol), followed by 4A molecular sieves (4 g). The reaction mixture was stirred for 12 h at room temperature. To this was added NaBH4 (11.34 g, 300 mmol) portionwise at 0 C. and the reaction mixture was stirred at room temperature for 3 h. Reaction mixture was quenched with water (10 mL) and concentrated under reduced pressure to get semi-solid which was quenched with 10% sodium bicarbonate (500 mL). It was extracted with ethyl acetate (2*200 mL), washed with brine (100 mL). Organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to get 59A (yellow liquid, 11 g, 85 mmol, 85% yield). 1H NMR (400 MHz, DMSO-d6) delta 3.74-3.65 (m, 4H), 2.70 (m, 1H), 2.67 (m, 2H), 1.98-1.57 (m, 4H), 1.02 (t, J=7.2 Hz 3H)., 23462-75-1

As the paragraph descriping shows that 23462-75-1 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; Balog, James Aaron; Cherney, Emily Charlotte; Guo, Weiwei; Huang, Audris; Markwalder, Jay A.; Seitz, Steven P.; Shan, Weifang; Williams, David K.; Murugesan, Natesan; Nara, Susheel Jethanand; Roy, Saumya; Thangavel, Soodamani; Sistla, Ramesh Kumar; Cheruku, Srinivas; Thangathirupathy, Srinivasan; Kanyaboina, Yadagiri; Pulicharla, Nagalakshmi; (495 pag.)US2016/289171; (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.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

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.

[00520] To a solution of 142-1 (200.0 mg, 2.0 mmol, 1.0 eq) in DME (4.0 mL) was added t-BuOK (224.4 mg, 2.0 mmol, 1.0 eq) and 142-2 (484.2 mg, 2.2 mmol, 1.1 eq). The mixture was stirred at 80 C for 16 hour under an N2 atmosphere. TLC (Petroleum ether : ethyl acetate=3/l) showed a new spot appeared. The reaction was filtered and concentrated under reduced pressure to give a crude product. The crude product was diluted with water (5 mL) and washed with EtOAc (lOmL x 2). The combined organic layers were concentrated to give crude 142-3 (60. 0 mg, 0.53 mmol, 26.3% yield) as a yellow oil., 23462-75-1

23462-75-1 Dihydro-2H-pyran-3(4H)-one 90109, 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

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 8A 6,7-dihydro-4H-pyrano[3,4-d][1,3]thiazol-2-amine To a solution of dihydro-2H-pyran-3(4H)-one (purchased from JW-Pharmlab) (5.0 g, 50 mmol) in cyclohexane (100 mL) were added pyrrolidine (4.3 mL, 52 mmol) and p-toluenesulfonic acid monohydrate (0.05 g). The reaction mixture was refluxed for 3 h with a Dean-Stark trap, cooled and concentrated. The residue was dissolved in methanol (80 mL) and then sulfur (1.66 g, 52 mmol) was added. To the mixture was added a solution of cyanamide (2.52 g, 52 mmol) in methanol (20 mL) at 0 C. The reaction mixture was stirred at room temperature overnight, filtered, concentrated and purified by column chromatography using an Analogix IT280 (SiO2, 0-5% methanol in dichloromethane) to afford 0.4 g (5%) of the title compound. MS (ESI+) m/z 157 (M+H)+., 23462-75-1

As the paragraph descriping shows that 23462-75-1 is playing an increasingly important role.

Reference£º
Patent; Abbott Laboratories; US2008/287510; (2008); 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.23462-75-1,Dihydro-2H-pyran-3(4H)-one,as a common compound, the synthetic route is as follows.

Example 26A 6,7-dihydro-5H-pyrano[3,2-d]thiazol-2-amine A mixture of dihydro-2H-pyran-3(4H)-one (0.5 g, 5.0 mmol, Small Molecules Inc), piperidine (0.5 mL, 5.0 mmol, Aldrich) and p-toluenesulfonic acid monohydrate (10 mg, 0.05 mmol) in cyclohexane (20 mL) was refluxed for 6 h with a Dean-Stark trap. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol (10 mL). To the above solution were added sulfur (0.16 g, 5.0 mmol) and a solution of cyanamide (0.21 g, 5.0 mmol) in methanol (3 mL) at 0 C. The reaction mixture was stirred at room temperature for 16 h and then concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix Intelliflash280 (SiO2, 0-5% methanol in methylene chloride) to obtain 60 mg of a product containing two regioisomers (6,7-dihydro-4H-pyrano[3,4-d]thiazol-2-amine (Example 8A) and the title compound 6,7-dihydro-5H-pyrano[3,2-d]thiazol-2-amine (3:1)). MS (ESI+) m/z 157 (M+H)+., 23462-75-1

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

Reference£º
Patent; Abbott Laboratories; US2008/287510; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics