Heterocyclic Building Blocks-Tetrahydropyrans

344329-76-6, Tetrahydro-2H-pyran-4-carboxamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 129 A suspension of Example B5 (0.032 g, 0.249 mmol) in DCE (2.1 mL) was treated drop-wise with oxalyl chloride (0.022 mL, 0.249 mmol), stirred at RT for 0.5 h, then heated at 80¡ã C. for 1 h. The mixture was cooled to RT, treated with a solution of pyridine (0.101 mL, 1.247 mmol) and Example A20 (0.062 g, 0.208 mmol) in THF (2.1 mL) and stirred at RT overnight. The mixture was treated with satd. NaHCO3, extracted with DCM (5*) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM). The material was treated with MeCN and the resulting solid was collected via filtration and dried to afford N-((6-methyl-5-((2-(2-methylthiazol-5-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)tetrahydro-2H-pyran-4-carboxamide (17 mg, 16percent) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.01 (s, 1H); 10.87 (s, 1H), 8.39 (d, J=5.8 Hz, 1H), 8.32 (s, 1H), 7.91 (d, J=8.8 Hz, 1H), 7.64 (d, J=8.8 Hz, 1H), 7.55 (d, J=2.4 Hz, 1H), 6.71 (dd, J=5.8, 2.4 Hz, 1H), 3.88 (m, 2H), 3.36-3.28 (m, 2H), 2.73-2.67 (m, 1H), 2.65 (s, 3H), 2.26 (s, 3H), 1.68-1.66 (m, 4H); MS (ESI) m/z: 454.2 (M+H+).

344329-76-6, The synthetic route of 344329-76-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); 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.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

In a 100mL three-necked flask, under nitrogen, was added thereto 3-isobutylglutaric anhydride (1.70g, 0.01mol), (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,N,4-trimethyl-N-(4-nitrobenzyl) pentan-1-ylammonium chloride (590mg, 1.0mmol), and 50mL methyl tert-butyl ether to dissolve solids. At -10C, was added with stirring benzyl mercaptan (1.50g, 0.012mol). It was stirred for 16h. The solvent was removed under reduced pressure to give the thiol ester 2.84g, yield 96%, ee value of 95%.

185815-59-2, 185815-59-2 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Shenzhen Huaxian Pharmaceutical Tech Co., Ltd.; Lan, Wenlong; (9 pag.)CN105753726; (2016); A;,
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.

4-(Bromomethyl)tetrahydropyran (97.6 mul; 0.74 mmol) is added to a mixture of methyl 5-[(4-ethylphenyl)isobutylsulfamoyl]-1H-indazole-7-carboxylate (280.0 mg; 0.67 mmol) and cesium carbonate (329 mg; 1 mmol) in 1-methyl-2-pyrrolidone (2.8 ml). The reaction medium is stirred at a temperature of 80 C. overnight. The crude product is filtered and then purified by preparative HPLC (C18 column, eluent: acetonitrile in water/0.1% of formic acid). The methyl 5-[(4-ethylphenyl)isobutylsulfamoyl]-1-(tetrahydropyran-4-ylmethyl)-1H-indazole-7-carboxylate (223.4 mg; 63%) is obtained in the form of a white solid. 1H NMR (DMSO-d6) delta: 0.85 (d, J=6.6 Hz, 6H), 1.18 (t, J=7.6 Hz, 3H), 1.25 (dt, J=11.1, 5.3 Hz, 4H), 1.33-1.55 (m, 1H), 1.86-2.12 (m, 1H), 2.60 (q, J=7.6 Hz, 2H), 3.18 (td, J=11.1, 3.6 Hz, 2H), 3.35 (s, 2H), 3.79 (dt, J=11.4, 3.3 Hz, 2H), 3.93 (s, 3H), 4.57 (d, J=7.2 Hz, 2H), 6.93-7.06 (m, 2H), 7.12-7.23 (m, 2H), 7.80 (d, J=1.7 Hz, 1H), 8.37 (d, J=1.9 Hz, 1H), 8.48 (s, 1H). MS: [M+H]=514

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; OUVRY, Gilles; THOREAU, Etienne; BOUIX-PETER, Claire; (85 pag.)US2017/342062; (2017); A1;,
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585-88-6, Maltitol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,585-88-6

20.0 g of maltitol was placed in a heat-dried 200 ml four-necked flask and purged with nitrogen, and 100 ml of dehydrated DMF was added and the temperature was raised to 90 C. To this solution, 3.0 g of methyl salicylate and 0.3 g of potassium carbonate (dried by being covered with a heat gun under reduced pressure) were added and reacted for 4 hours at 96 to 110 C under reduced pressure (125 to 155 mm Hg). After completion of the reaction, the reaction solution was concentrated under reduced pressure, ethyl acetate was added to the residue, and the mixture was refluxed for 1 hour. After cooling to room temperature, the precipitate was removed by filtration and concentrated under reduced pressure to obtain 3.5 g of a brown liquid. Unreacted raw materials were removed using a chromatographic separation apparatus (apparatus: Kprep (manufactured by YMC), developing solvent: methanol / ultrapure water = 50/50, flow rate: 10 ml / min) and the structural isomers were collectively collected & 1.4 g of light pink oil was obtained.

As the paragraph descriping shows that 585-88-6 is playing an increasingly important role.

Reference£º
Patent; UENO FINE CHEMICALS INDUSTRY LIMITED; MAEDA, KAZUHISA; MOTOMURA, YOSUKE; YAMAZAKI, KAE; SHONO, YUKO; OTSUKA, RYOICHI; (9 pag.)JP6151542; (2017); B2;,
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.

A mixture of (tert-butoxycarbonyl)-L-valine (3.64 g, 16.75 mmol), 4-(bromomethyl)tetrahydro-2H- pyran (3.00 g, 16.75 mmol) and NaHCO3 (2.81 g, 33.50 mmol) in DMF (30 mL) was stirred at 70 C for 12 hours under N2 atmosphere. The reaction mixture was diluted with H20 (100 mL) and extracted with MTBE (50 mL x 2). The combined organic layers were washed with brine (20 mL x 2), dried overNa2SO4, filtered and concentrated under reduced pressure to give (tetrahydro-2H-pyran-4-yl)methyl(tert-butoxycarbonyl)-L-valinate (5 g, yield 94.63%, pale yellow oil) which was used into the next stepwithout further purification. 1H NMR (400 MHz, CDCI3) O 5.01 (d, J = 8.4 Hz, 1H), 4.22 (dd, J = 8.8 Hz,4.8 Hz, 1H), 4.00-3.97 (m, 4H), 3.40 (t, J= 11.2 Hz, 2H), 2.16-2.11 (m, 1H), 1.96-1.90 (m, 1H), 1.63 (d, J= 13.2 Hz, 2H), 1.45 (s, 9H), 0.97 (d, J 6.4 Hz, 3H), 0.90 (d, J 7.2 Hz, 3H)., 125552-89-8

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

Reference£º
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; CARTER, David Scott; HALLADAY, Jason S.; JACOBS, Robert T.; LIU, Yang; PLATTNER, Jacob J.; ZHANG, Yong-Kang; WITTY, Michael John; (149 pag.)WO2017/195069; (2017); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

83-87-4, (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

83-87-4, This compound was prepared following a procedure adopted in similar cases.20 beta-d-Glucose pentaacetate (3.83 g, 9.82 mmol) and BF3¡¤Et2O (1.24 mL, 9.82 mmol), previously dissolved in 15 mL of dry dichloromethane, were added under a nitrogen atmosphere to a solution of (4-iodo-phenoxy)-trimethylsilane 17 (2.39 g, 8.18 mmol) in 15 mL of CH2Cl2 kept at room temperature. After 12 h the reaction mixture was washed with saturated aqueous bicarbonate 50 mL¡Á3 and brine 50 mL¡Á2 and dried over anhydrous Na2SO4. Evaporation of the solvent at reduced pressure gave the crude product that was purified by column chromatography over silica gel, using a mixture of petroleum ether/ethyl acetate 6:4 as eluent obtaining 10a as a white solid (3.65 g, 81% yield). (Found: C, 43.61, H, 4.20. C20H23IO10 requires C, 43.65, H, 4.21); Rf (petroleum ether/ethyl acetate 6:4) 0.49; mp 144-145 C (methanol). deltaH (CDCl3, 400 MHz): 1.99 (3H, s, CH3), 2.00 (3H, s, CH3), 2.01 (3H, s, CH3), 2.03 (3H, s, CH3), 3.78-3.86 (1H, m, CH), 4.12 (1H, dd, J 12.3, 2.4 Hz, CH2), 4.24 (1H, dd, J 12.3, 5.4 Hz, CH2), 5.00 (1H, d, J 7.6 Hz, anomeric CH), 5.11 (1H, t, J 9.6 Hz, CH), 5.18-5.29 (2H, m, 2CH), 6.70-6.75 (2H, app d, J 9.0 Hz, Ph), 7.52-7.57 (2H, app d, J 9.0 Hz, Ph). deltaC (CDCl3, 100 MHz) 20.5 (CH3), 20.6 (2CH3), 20.8 (CH3), 61.8 (CH2), 68.1 (CH, glucose ring), 71.0 (CH, glucose ring), 72.0 (CH, glucose ring), 72.5 (CH, glucose ring), 86.2 (C-I, Ph), 98.9 (anomeric CH), 119.2 (C, Ph), 138.4 (C, Ph), 156.6 (C, Ph), 169.2 (CO), 169.3 (CO), 170.2 (CO), 170.5 (CO). numax/cm-1 (KBr): 818, 1041, 1224 (s, C-O-C), 1432, 1485, 1587, 1750 (s, CO), 2961.

83-87-4 (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 10293747, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Hassan Omar, Omar; Babudri, Francesco; Farinola, Gianluca M.; Naso, Francesco; Operamolla, Alessandra; Pedone, Adriana; Tetrahedron; vol. 67; 2; (2011); p. 486 – 494;,
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

Intermediate 10: 2-Chloromethyl-3, 5, 7, 8-tetrahydro-pyrano[4, 3-d]pyrimidin-4-one A mixture of crude 4-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester (1780 g, 1 1 mol) and NEt3 (830 g, 8.2 mol) in MeOH (3560 mL) was cooled to 0C under N2. A solution of 2-chloro-acetamidine (567 g, 4.4 mol) in 890 mL of MeOH was added dropwise over 50 minutes. The reaction mixture was stirred at 0C for 30 minutes and then at about 20C for 16 hours. LCMS at 215nm and TLC (DCM:MeOH=10:1 ) analysis showed that most of 4-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester was consumed. The mixture was then filtered and concentrated to give black oil, which was subsequently purified by flash column chromatography on silica gel and eluted with DCM to give yellow solid/oil mixture, which was further triturated with MTBE (-1200 mL) and H20: CHsCN: EA=1 :1 :2 (-600 mL) to give the title compound as a white solid (318 g). MS m/z 201.2 (M+H). CHN analysis: calculated (results). C 47.89 (47.95), H 4.52 (4.401 ), N 13.96 (13.76).

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; NOVARTIS AG; CHEN, Zhuoliang; CHEUNG, Atwood, Kim; CHIN, Donovan, Noel; FAN, Jianmei; MILLER-MOSLIN, Karen, Marie; SHULTZ, Michael, David; SMITH, Troy, D.; TOMLINSON, Ronald, Charles; TOURE, Bakary-Barry; VISSER, Michael, Scott; WO2013/12723; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

65412-03-5,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.

A mixture of Example 512A (50MG, 0.15 mmol) and 2- (TETRAHYDRO-PYRAN-4-YL)- ethylamine (38.3 mg, 0.30 mmol) in dioxane (2.0 mL) was heated 11 hours at 50 C, cooled to room temperature, and concentrated under vacuum. The residue was purified by preparative HPLC to give 30.3 mg (53%) of the desired PRODUCT. 1H NMR (300 MHz, DMSO-d6) 8 10.05 (s, 1H), 8.56 (br s, 1H), 8.16 (s, 1H), 7.70 (d, J=8.5 Hz, 1H), 7.11 (d, J=2.0 Hz, 1H), 7.00-7. 08 (m, 3H), 6.97 (dd, J=2.0, 8.5 Hz, 1H), 4.00-4. 04 (m, 2H), 3.78-3. 86 (m, 2H), 3.20-3. 30 (m, 3H), 2.88-3. 00 (m, 2H), 1.49-1. 58 (m, 4H), 1.11-1. 19 (m, 2H).

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

Reference£º
Patent; ABBOTT LABORATORIES; WO2004/76424; (2004); A1;,
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

At room temperature,2a (0.350 g, 1.14 mmol) was dissolved in N, N-dimethylacetamide (4 mL), intermediate 1 (0.338 g, 1.04 mmol) was added and stirred at 0 C for 1 hour. Sodium tris (acetoxy) borohydride (0.285 g, 1.34 mmol) was added to the reaction solution and allowed to warm to room temperature for 16 hours. The reaction solution was cooled to C, water was added in that order, and the pH was adjusted to 8 with ammonia to precipitate a white solid. The reaction solution was filtered and the filter cake was washed successively with water (5 mL x 3), petroleum ether (10 mL x 1). The filter cake was dried to give a white solid 2b (0.230 g, yield 48.4%)., 951127-25-6

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; FENG, JIAN-CHUAN; PENG, FEI; CHEN, QING-PING; (89 pag.)TW2017/8224; (2017); A;,
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.83-87-4,(3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate,as a common compound, the synthetic route is as follows.,83-87-4

To a solution of D-glucose (3.00 g, 16.6 mmol) in dry pyridine (33 mL) at 0 C under a nitrogen atmosphere was slowly added acetic anhydride (31.5 mL, 333 mmol). The reaction mixture was stirred at 0C for 1 h before a catalytic amount of DMAP (200 mg,1.67 mmol) was added. As the reaction mixture was allowed to reach rt, it becomes slightly exothermic. After 6 h, the clear yellow mixture was slowly poured into rapidly stirred ice-water (125 mL),giving a sticky solid. After EtOAc extraction (345 mL), evaporation of the solvent and co-evaporation with dry toluene (320 mL), peracetylated glucose was obtained as a yellow solid (5.84 g, 90%). A solution of pentaacetyl-D-glucopyranose (2.00 g, 5.1 mmol) in DCM(20 mL) was stirred in an ice bath while HBr/HOAc (6 mL, 45 wt %) was added drop-wise. After an hour, the solution was washed with ice-water and cold saturated NaHCO3 solution, dried over MgSO4, and concentrated to leave the glucosyl bromide as a pale yellow oil (1.83 g).

As the paragraph descriping shows that 83-87-4 is playing an increasingly important role.

Reference£º
Article; Vo, Quan V.; Trenerry, Craige; Rochfort, Simone; Hughes, Andrew B.; Tetrahedron; vol. 69; 41; (2013); p. 8731 – 8737;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics