Tag: M.W:100-200

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

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

103260-44-2, a) 2-Methyl-2-(tetrahydro-pyran-4-yl)-propionic acid ethyl ester; A solution of 1 g (tetrahydro-pyran-4-yl)-acetic acid ethyl ester [103260-44-2] in 3 ml of dry tetrahydrofuran is added dropwise to a solution of lithium dissopropyl amide (freshly prepared from 1 ml diisopropyl amine and 4. 3 ml 1. 6 M butyllithium solution in hexanes) in 5 ml of dry tetrahydrofuran at-78C. The reaction mixture is stirred for 15 minutes at-78C and then 0. 46 mi of methyl iodide are added and the mixture is allowed to warm to 0C over a period of 15 minutes. The reaction mixture is re-cooled to-78C and then a solution of lithium diisopropyl amide (freshly prepared from 1 ml diisopropyl amine and 4. 3 ml 1. 6 M butyllithium solution in hexanes) in 5 ml of dry tetrahydrofuran is added dropwise. The solution is stirred for 15 minutes at-78C and then 0. 46 ml of methyl iodide are added and the mixture is allowed to warm to room temperature. After 2 hours, the reaction mixture is quenched with 20 mi of 1M HO and then extracted with tert-butyl methyl ether (2x). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf = 0. 27 (1 : 5 EtOAc-heptane)

103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90304; (2005); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

5631-96-9, 2-(2-Chloroethoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5631-96-9, 2,3-Dicyanohydroquinone (10.0 g, 0.062 mol), K2CO3 (19.0 g, 0.137 mol), chloride 1 (22.6 g , 0.137 mol), and KI (100 mg) in 200 mL DMF were stirred at 60 C for 48 h, when additional chloride 1 (11.3 g, 0.068 mol, 1.1 equiv) was added. After 48 h, the mixture was poured onto ice (500 g) and filtered to yield a beige solid, which was recrystallized from MeOH to yield dinitrile 2 (14.8 g, 57 %) as a white crystalline solid: IR (neat) numax 2940, 2231 cm-1; 1H NMR (500 MHz, CDCl3) delta 1.54 – 1.80 (m, 12H), 3.53 – 4.28 (m, 12H), 4.71 (br s, 2H), 7.28 (s, 2H); 13C NMR (125 MHz, CDCl3) delta 155.5, 119.1, 113.1, 105.7, 99.4, 70.0, 65.6, 62.5, 30.6, 25.4, 19.5; MALDI-MS calcd. for C22H28N2NaO6: [M + Na]+ 439.5, found: 439.6; ESI-MS calcd. for C44H56N4NaO12: [2M + Na]+ 855.4, found: 854.9. ESI-HRMS calcd. for C22H28N2NaO6: [M + Na]+ 439.184, found: 439.1844; calcd. for C44H56N4NaO12: [2M + Na]+ 855.3787, found: 855.3786.

As the paragraph descriping shows that 5631-96-9 is playing an increasingly important role.

Reference£º
Article; Trivedi, Evan R.; Blumenfeld, Carl M.; Wielgos, Todd; Pokropinski, Sharon; Dande, Prasad; Hai, Ton T.; Barrett, Anthony G.M.; Hoffman, Brian M.; Tetrahedron Letters; vol. 53; 41; (2012); p. 5475 – 5478;,
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

A mixture of 4-(bromomethyl)tetrahydropyran (1.0 g; 5.58 mmol) and sodium hydrogen sulfide (0.44 g; 7.82 mmol) in dimethylformamide (4 ml) is stirred at room temperature for 2 hours. The reaction medium is diluted with ether and acidified by addition of concentrated HCl and then extracted. The organic phases are combined, washed with water, dried over magnesium sulfate, filtered and concentrated to dryness. The bis[(tetrahydropyran-4-yl)methane bisulfide (565.00 mg; 77%) obtained in the form of a clear oil is used directly in the next reaction. (0559) MS: [M+H]=263, 125552-89-8

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

Reference£º
Patent; GALDERMA RESEARCH & DEVELOPMENT; MUSICKI, Branislav; BOUIX-PETER, Claire; OUVRY, Gilles; THOREAU, Etienne; (132 pag.)US2018/170869; (2018); 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.85064-61-5,Tetrahydropyranyl-4-acetic acid,as a common compound, the synthetic route is as follows.

85064-61-5, General procedure: N,N-Diisopropylethylamine (132 mL), 4-hydroxycyclohexane-1-carboxylic acid (33 mg) and propylphosphonicanhydride (1.6 mol/L N,N-dimethylformamide solution, 238 mL) were added to a solution of the compound (50 mg)obtained in Reference Example 14-1 in N,N-dimethylformamide (2 mL), and the mixture was stirred at room temperatureovernight. The mixture was purified by preparative LC-MS to give the title compound (Example 3-2) (25 mg) which wasa trans isomer as a highly polar compound, as a colorless amorphous substance.1H NMR (500 MHz, DMSO-d6) delta ppm 1.09 – 2.03 (m, 14.5 H) 2.85 – 2.98 (m, 0.5 H) 3.00 – 3.20 (m, 1.5 H) 3.21 – 3.40(m, 1 H) 3.78 – 4.08 (m, 3.5 H) 4.35 – 4.45 (m, 0.5 H) 4.48 – 4.58 (m, 1 H) 6.73 (s, 1 H) 7.36 – 7.96 (m, 3 H) 8.23 – 8.33 (m, 1 H).MS ESI/APCI Multi posi: 385 [M+H]+. The title compound (Example 3-3) (23.7 mg) which was a cis isomer as a less polar compound was obtainedas a colorless amorphous substance.1H NMR (600 MHz, DMSO-d6) delta ppm 1.13 – 2.02 (m, 12 H) 2.45 – 2.63 (m, 1.5 H) 2.84 – 2.95 (m, 0.5 H) 2.99 – 3.17 (m,1 H) 3.26 – 3.37 (m, 1 H) 3.71 – 4.09 (m, 4.5 H) 4.19 – 4.30 (m, 1 H) 4.38 – 4.46 (m, 0.5 H) 6.73 (br s, 1 H) 7.38 – 7.93(m, 3 H) 8.24 – 8.35 (m, 1 H). MS ESI/APCI Multi posi: 385 [M+H]+.

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; Taisho Pharmaceutical Co., Ltd.; TANAKA, Hiroaki; BOHNO, Ayako; HAMADA, Makoto; ITO, Yuji; KOBASHI, Yohei; KAWAMURA, Madoka; (235 pag.)EP3418276; (2018); 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.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.,1197-66-6

(b) Ethyl 2-cyano-2-(2,2,6,6-tetramethyloxan-4-ylidene)acetate (C6) A mixture of 2,2,6,6-tetramethyloxan-4-one (C4)(4.683 g, 0.030 mol), ammonium acetate (0.231 g, 0.003 mol) and ethyl cyanoacetate (C5)(Aldrich, CAS: 105-56-6, CAT: E18425), (5.0865 g, 0.045 mmol) was heated under reflux in toluene (150 mL) for 3 days using a Dean-Stark trap. Analytical TLC indicated a new UV active compound and some starting material plus other impurities (visualised by UV and PMA stain). The reaction was allowed to cool to room temperature, the solvent evaporated, and the pale yellow oil subjected to purification (silica, 80 g, ethyl acetate/hexane; 10/90, 13 x 100 mm tubes). Fractions 15-17 were the most pure by analytical TLC (UV active and stains with PMA; starting material runs slightly lower is not UV active and stains very strongly with PMA) and collected to give the required product as a light yellow crystalline solid (1.9300 g). Fractions 9-14 (1.5249 g) and fractions 18-45 (2.6121 g) were collected separately and re-purified. Fractions 9-14 were purified using chromatography (silica, 25 g, 5/95 ethyl acetate/hexane, 13 x 100 mm tubes) to give the product as colourless crystals (1.2737 g). Fractions 18-45 were purified using chromatography (silica, 40 g, 5/95 ethyl acetate/hexane, 13 x 100 mm tubes) to give the product as a colourless, sweet smelling oil that crystallized on standing (2.6008 g). Total yield of the alkylidene: (5.8045 g, 77%). H NMR (500 MHz, CDCIs) delta 4.27 (q, 2H, J = 7.2 Hz, CH2CH3), 3.04 (s, 2H, 2 x CH), 2.66 (s, 2H, 2 x CH), 1.33 (t, 3H, J = 7.2 Hz, CH3CH2), 1.24 (s, 6H, 2 x CH3), 1.19 (s, 6H, 2 x CH3). 3C NMR (125 MHz, CDCI3) delta 173.68, 161.54, 115.18, 104.97, 75.61 , 75.58, 61.85, 47.22, 42.51 , 30.69, 30.51 , 14.07.

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; CANCER THERAPEUTICS CRC PTY LTD; STEVENSON, Graeme Irvine; GARAVELAS, Agatha; COSGROVE, Kelly Leanne; REYNOLDS, Kristie Anne; FRANKEN, Nicole Cecilia; WHITTELL, Louise Renee; WIJESEKERA, Hasanthi Punyama; WO2014/41349; (2014); 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.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.,220641-87-2

[01465] Step 1 : Synthesis of methyl 3,6-dichloro-4-[methyl(oxan-4-yl)amino]pyridine-2- carboxylate – – – -[01466] To a stirred solution of methyl 3,4,6-trichloropyridine-2-carboxylate (600 mg, 2.50 mmol) in DMF (12ml) was added TEA (696 mu, 4.99 mmol) followed by N-methyloxan-4- amine (287 mg, 2.50 mmol)and the reaction mixture was heated at 100C for 20h. The reaction mixture was then cooled to room temperature and poured onto water ( 100ml), followed by extraction of the product into EtOAc (3x 100ml), washing of the combined organics with brine (50ml), drying with Na2S04 and evaporation. The crude product was then purified over a l Og silica Isolute column eluting with a gradient of 0% to 60% EtOAc in heptane to afford the title compound as a white solid (1 14 mg, 14%). LC-MS 100%, 1 .91 min (3.5 minute LC-MS method), m/z= 319.3/320.9, ‘H NMR (500 MHz, Chloroform-d) 5 6.87 (s, 1 H), 4.15 – 4.00 (m, 2H), 3.98 (s, 3H), 3.93 – 3.71 (m, 1 H), 3.54 – 3.24 (m, 2H), 2.82 (s, 3H), 1.94 (dd, J = 12.1 , 4.7 Hz, 2H), 1 .70 (d, J = 10.2 Hz, 2H). (br. s., 4 H) 1 .48 (s, 9 H)

As the paragraph descriping shows that 220641-87-2 is playing an increasingly important role.

Reference£º
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); 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

Example 70(IS, 2R) and (IR, 2S)-2-(4-chlorophenyl)-l’-((tetrahydro-2H-pyran-4-yl)spiro[cyclopropane-l,3′-indolin]-2′-oneRacemic (I S, 2R)-2-(4-chlorophenyl)spiro[cyclopropane-l,3′-indolin]-2′-one and (1R, 2S)- 2-(4-chlorophenyl)spiro[cyclopropane-l,3′-indolin]-2′-one (270 mg, 1.0 mmol, 1.0 equiv.) were added to a stirred solution of sodium hydride (60 %, 60 mg, 1.5 mmol) in 5 mL of DMF under argon atmosphere at 0C. After stirring for 1 hour, 4-bromomethyl- tetrahydropyran (215 mg, 1.2 mmol) was added. The reaction mixture was stirred for 14 hours at room temperature. The crude product was purified by HPLC to give the title compound as a white solid (258 mg, 70 %). LC/MS m/e calcd. for C22H22CINO2: 367, observed (M+H)+: 368.2 1H MR (400 MHz, MeOD-d4) 5ppm 1.39 – 1.55 (m, 2 H) 1.65 (dd, J=13.14, 1.77 Hz, 2 H) 2.11 – 2.25 (m, 3 H) 3.22 (t, J=8.46 Hz, 1 H) 3.37 – 3.47 (m, 2 H) 3.79 (d, J=7.33 Hz, 2 H) 3.94 – 4.04 (m, 2 H) 6.09 (d, J=7.58 Hz, l H) 6.76 (t, J=7.58 Hz, 1 H) 7.11 (d, J=7.83 Hz, 1 H) 7.17 – 7.25 (m, 3 H) 7.33 (d, J=8.34 Hz, 2 H). MS calcd. For C22H22CINO2 367, obsd. (ESf) [(M+H)+] 368.

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; HUANG, Mengwei; FENG, Lichun; HE, Yun; YUN, Hongying; WO2011/69298; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics