Tag: M.W:100-200

220641-87-2, N-Methyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 32 7V-Methyl-iV-(tetrahvdro-2H-pyran-4-v?-[2,l,31-benzothiadiazole-5-carboxamideN-Methyltetrahydro-2H-pyran-4-amine (0.4 g, 3.4 mmol), [2,l,3]-benzothiadiazole-5- carboxylic acid (0.23g, 1.4mmol ), DMAP (0.2 g: l.mmol), HOBT (0.2 g, 1.5 mmol), triethylamine (1.0 ml) and EDCI (Ig, 6.4mmol) were dissolved in DMF (30 ml). The mixture was stirred at room temperature for 18h and then concentrated under vacuum. Chloroform (100 ml) was added and the mixture washed with water (100 ml) and H2SO4 (^ pH 2) and NaHCO3 solution (100 ml). The aqueous was extracted with chloroform (100 ml) and the combined organics were dried (MgSO4), concentrated under vacuum, and the crude product was purified on a silica gel column eluting with chloroform/THF (90:10), to give the product as an oil which crystallized on standing. Mp = 106-108C, 1H NMR (300 MHz, CDCl3, rotamers) delta 8.06 (d, J = 9.0 Hz, IH); 8.01 (s, IH); 7.60 (d, J = 9.0 Hz, IH); 4.92-4.75 and 4.15-3.10 (m, 5H); 3.10-2.80 (m, 3H) and 2.05-1.50 ppm (s, 4H).

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

Reference£º
Patent; CORTEX PHARMACEUTICALS, INC.; WO2008/143963; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1197-66-6, 2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Zinc powder (520mg, 8mmol) was added 20mL of tetrahydrofuran, was added titanium tetrachloride (0.44mL, 4mmol), the reaction was refluxed for 2 hours, cooled to 0 deg.] C, was added lithium tetrahydroaluminate (76mg, 2mmol), with stirring under ice 10 minutes, triethylamine (0.28 mL, 2 mmol) was added and the reaction was refluxed for 1 hour. Prefabricated 5 mL(4-bromophenyl) (1- (tetrahydro-2H-pyran-2-yl) -1H-indazol-5-yl) methanone1c (193mg, 0.5mmol) and 2,2,6,6-tetramethyl-dihydro -2H- pyran -4 (3H) – tetrahydrofuran-one (200mg, 1.28mmol), the reaction was refluxed for 1 hour. After completion of the reaction, the reaction was quenched with 10mL water and extracted with ethyl acetate (10mL ¡Á 3), the organic phase was concentrated under reduced pressure, purified by silica gel column chromatography with eluent systems resulting residue was purified B to give the title product5 – ((4-bromophenyl) (2,2,6,6-tetramethyldihydro-2H-pyran-4 (3H) -ylidene) methyl) -1- (tetrahydro-2H-pyran-2-yl) -1H-indazole10a (190 mg, white solid) in 74.5% yield.

1197-66-6, The synthetic route of 1197-66-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Yang, Fanglong; Wang, Chunfei; Wang, Yang; He, Mingxun; Hu, Qiyue; He, Feng; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; (53 pag.)CN106518768; (2017); A;,
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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 23: 3-methyl-8-(tetrahydro-2H-pyran-3-vn-4-((4-r3-(trifluoromethyl)phenvnpiperazin-1-yl)carbonyl)-1-oxa-8-azaspiror4.51dec-3-en-2-one Triethylamine (0.08 mL, 0.65 mmol) and dihydro-pyran-3-one (108 mg 1.08 mmol) were added into a solution of 3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1-oxa-8- azaspiro[4.5]dec-3-en-2-one dihydrochloride (Example 1 , 100 mg, 0.20 mmol) in anhydrous dichloroethane (5 mL) cooled at 0C. Sodium triacetoxyborohydride (137 mg, 0.65 mmol) and trimethylorthoformate (120 mg, 1.08 mmol) were added and the resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with dichloromethane (20 mL) and washed with water (20 mL) and brine (20 mL). The organic layer was dried (MgS04) and concentrated under vacuum. After purification by flash chromatography (silica), the title compound was obtained as a white solid. 1H NMR (CDCI3, 400 MHz): delta 7.45-7.42 (m, 1 H), 7.24 (d, J = 9.0 Hz, 1 H), 7.20 (s, 1 H), 7.11 (d, J = 7.6 Hz, 1 H), 3.81-3.80 (m, 2H), 3.71-3.69 (m, 2H), 3.55 (s, 2H), 3.15 (s, 4H), 2.81-2.80 (m, 2H), 2.32-2.31 (m, 4H), 2.17 (s, 2H), 1.89-1.88 (m, 2H), 1 .75 (s, 3H), 1.69-1.61 (m, 2H), 1.48-1.38 (m, 3H). LCMS (Method D): Mass found (M+ 508.3), Rt (min): 3.88, Area (%): 93.6 (Max. Chrom.), 94.5 (254 nm). HPLC (Method A): Rt (min): 3.89, Area (%): 93.6 (Max. Chrom.), 94.4 (254 nm).

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; ARES TRADING S.A.; JORAND-LEBRUN, Catherine; SWINNEN, Dominique; GERBER, Patrick; KULKARNI, Santosh; WO2012/130915; (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.

To a suspension of 3-((1R,5S,9r)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)benzamide hydrochloride (300 mg, 0.97 mmol), dihydro-2H-pyran-3(4)-one (194 mg, 1.93 mmol) in tetrahydrofuran (16 ml) was added triethylamine (0.34 ml, 2.50 mmol) and the reaction mixture was stirred at room temperature for 20 minutes. Sodium triacetoxyborohydride (614 mg, 2.89 mmol) was added and the mixture stirred at room temperature overnight. The reaction was quenched with aqueous solution of sodium hydrogen carbonate and extracted with dichloromethane (*3). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica chromatography eluting with 1-5% methanol in dichloromethane. The enantiomers were separated by chiral supercritical fluid chromatography to give 3-((1R,5S,9s)-9-methoxy-3-((S)-tetrahydro-2H-pyran-3-yl)-3-azabicyclo[3.3.1]nonan-9-yl)benzamide (81 mg, 25% yield) and 3-((1R,5S,9R)-9-methoxy-3-((R)-tetrahydro-2H-pyran-3-yl)-3-azabicyclo[3.3.1]nonan-9-yl)benzamide (71 mg, 19% yield). The stereochemistry was arbitrarily assigned.

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; Alkermes, Inc.; Wynn, Thomas Andrew; Alvarez, Juan C.; Moustakas, Demetri Theodore; Haeberlein, Markus; Pennington, Lewis D.; US2019/241524; (2019); 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.108-55-4,Dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Paclitaxel-2-O-hemiglutarate was prepared according to the method described bySundaram et al. [38]. In brief, paclitaxel (100 mg, 0.117 mM) and glutaric anhydride (13.70 mg,0.12 mM) were dissolved in 15 mL of DCM, and 10 L of dry pyridine was added to the reactionmixture as a base catalyst. The reaction was stirred under nitrogen for 48 h at room temperature.The progress of the reaction was monitored by TLC using hexane:ethyl acetate (7:3, v/v). The crudemixture was purified by silica gel chromatography. The compound was obtained as a white solid(76 mg, 95% yield). HR-MS (ESI) (m/z) [C52H57NO17]: calcd 967.3626; found 968.3479 [M + H]+

108-55-4, 108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; El-Sayed, Naglaa Salem; Shirazi, Amir Nasrolahi; Sajid, Muhammad Imran; Park, Shang Eun; Parang, Keykavous; Tiwari, Rakesh Kumar; Molecules; vol. 24; 7; (2019);,
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

To a mixture of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate(20 g, 116 mmol) in anhydrous THF (300 mE) was addedlithium aluminum hydride (8.8 g, 232 mmol) portionwise at0 C. The mixture was stirred at 11-13 C. for 18 h. TEC(petroleum ether: ethyl acetate=3: 1) showed no startingmaterial remaining. The mixture was quenched with water(9 mE), 10% aq. NaOH solution (9 mE) and water (18 mE)successively at 0 C., filtered and concentrated underreduced pressure to give crude 2-(tetrahydro-2H-pyran-4-yl)ethanol (11.7 g, 77%) as an oil, which was used for thenext step directly without further purification. ?H NMR(CDC13, 400 MHz): oe 3.86-3.90 (m, 2H), 3.58-3.61 (t, J=6.4Hz, 2H), 3.32-3.35 (t, J=11.6 Hz, 2H), 2.69-2.70 (m, 1H),1.61-1.63 (m, 3H), 1.54-1.60 (m, 2H), 1.43-1.45 (m, 2H).

103260-44-2, As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

Reference£º
Patent; Vitae Pharmaceuticals, Inc.; Claremon, David A.; Yuan, Jing; Zhao, Wei; Zheng, Yajun; (54 pag.)US9481674; (2016); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

110238-91-0, Methyl tetrahydro-2H-pyran-4-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,110238-91-0

Intermediate 108: Tetrahvdro-2H-pyran-4-ylmethanolMethyl tetrahydro-2H-pyran carboxylate (SC/143233, Aldrich) (5.0 g) in dry THF (10 ml.) was added drop wise to a cooled solution of 1 M lithium aluminium hydride in THF (32 ml_), keeping the temperature below 10 0C. On completion of the addition, the exotherm was allowed to subside before allowing the reaction mixture to warm to room temperature. The reaction was then stirred for 2 hours. The reaction was quenched with water (2 ml.) added very carefully and with cooling, followed by 2N sodium hydroxide (2 ml_). To resultant suspension was then added water (100 ml.) and then extracted with dichloromethane (100 ml_, 3 times). The organic layer was separated, combined and dried by passing through a hydrophobic frit. The organic was evaporated under reduced pressure to give colourless mobile oil that was then placed under high vacuo for 30 minutes at room temperature. This gave the title compound as colourless mobile oil (2.4367 g).1 H NMR (CDCI3): 4.04-3.96 (2H, m), 3.54-3.47 (2H, m), 3.46-3.36 (2H, m), 1.82 – 1.61 (3H, m), 1.57-1.50 (1 H, m), 1.40-1.27 (2H, m)

As the paragraph descriping shows that 110238-91-0 is playing an increasingly important role.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/101867; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 4; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; A three-neck-flask (0.25 L) is charged with quinidine (11 mmol), 3-isobutyl glutaric anhydride (10 mmol) and toluene (50 ml). The mixture is cooled at -55 C. Methanol (30 mmol) is added dropwise over a period of 10 min to the cooled suspension. The reaction is stirred at for 96 h. The solution is concentrated to dryness, and the resulting residue is dissolved in diethyl ether (65 ml). The solution is washed with HCl-2N, and the aqueous layer is back-extracted with ether. The combined organic layers are dried with MgSO4, and filtered. The filtrate is evaporated to dryness. Example 5; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a flame-dried 250 ml single, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30.5 vol) at -75 C. The reaction was stirred for 21 hours. The solution was concentrated to dryness, and the resulting residue was dissolved in diethyl ether (125 ml). The solution was washed with HCl-2N (40 ml¡Á3), and the aqueous layer was back-extracted with ether. The combined organic layers were evaporated until dryness, to give 3.56 g of a yellow oil of S-hemiester ((S)-3-((methoxycarbonyl)methyl)-5-methylhexanoic acid) (Optical purity 90%, Yield -91%). Example 6; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three-necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30.5 vol) at -50 C. The reaction was stirred for 2 hours. The slurry was washed with H2SO4-2N (40 ml¡Á3). The organic layer was evaporated until dryness, to have 3.7 g yellow oil of S-Hemiester (Optical purity 90% Yield -95%). Example 7; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three-necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (12.5 g, 38.6 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30.5 vol) at -78 C. The reaction was stirred for 22.5 hours. The slurry was washed with HCl-2N (40 ml¡Á3). The organic layer was evaporated until dryness, to have 3.63 g yellow oil of S-Hemiester (Optical purity 90%, Yield -93%). Example 8; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (33 ml, 10 vol) at -78 C. The reaction was stirred for 19 hours. The solution was washed with HCl-2N (25 ml¡Á3). The organic layer was evaporated until dryness, to give 3.38 g yellow oil of S-Hemiester (Optical purity 90%, Yield -87%). Example 9; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three-necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30 vol) at -78 C. The reaction was stirred for 2 hours. The slurry was washed with H2SO4-2N (40 ml¡Á3). The organic layer was evaporated until dryness, to give 3.4 g yellow oil of S-Hemiester (Optical purity 95%, Yield -93%). Example 10; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (88 mmol) and Quinidine (100 mmol) in Toluene (30 vol) at -50 C., Methanol (273 mmol) was added drop-wise. The reaction was stirred at -50 C. for 17 h. The solution was washed with H2SO4-2N. The organic layer was evaporated to dryness to obtain S-Hemiester. (Optical purity -94%, Yield -94%). Example 11; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (19.3 mmol) and Quinidine (22 mmol) in Toluene (20 vol) at -50 C., Methanol (59.8 mmol) was added drop-wise. The reaction was stirred at -50 C. for 17 hours. The solution was washed with H2SO4-2N. The organic layer was evaporated to dryness to obtain S-Hemiester. (Optical purity -95%, Yield -89%). Example 12; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (19.3 mmol) and Quinidine (22 mmol) in Toluene (10 vol) at -50 C., Methanol (59.8 mmol) was added drop-wise. The reaction was stirred at -50 C. for 4 hours. The solution was washed with H2SO4-2N. The organic layer was evaporated to dryness to obtain S-Hemiester. (Optical purity -94%, Yield -92%). Example 13; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (19.3 m…

185815-59-2, The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hedvati, Lilach; Gilboa, Eyal; Avhar-Maydan, Sharon; US2007/293694; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

40191-32-0, Tetrahydro-2H-pyran-4-carbonyl chloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,40191-32-0

Into a 8-mL vial, were placed methyl (R)-3-(trifluoromethyl)-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine-8-carboxylate (25 mg, 0.09 mmol, 1 equiv), CH2Cl2 (1.5 mL), Et3N (28 mg, 0.28 mmol, 3 equiv) and tetrahydro-2H-pyran-4-carbonyl chloride (16 mg, 0.11 mmol, 1.2 equiv). The resulting solution was stirred for 16 h at room temperature. The crude product was purified by Prep-TLC (EtOAc/pet. ether, 1:1) to afford the title compound as yellow oil (35 mg, 99% yield). MS: (ES, m/z): 388 [M+H]+.

40191-32-0 Tetrahydro-2H-pyran-4-carbonyl chloride 2795505, aTetrahydropyrans compound, is more and more widely used in various fields.

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.5631-96-9,2-(2-Chloroethoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

5631-96-9, N-tert-Butyloxycarbonyl-N-[(tetrahydropyranyl)oxy] ethyl-O-benzylhydroxylamine (30) To a stirred solution of N-tert-butyloxycarbonyl-O-benzylhydroxylamine 28 (5.79 g, 25.96 mmol) in dry DMF (50 ml) was added NaH (60%, 1.2 g, 30 mmol) slowly during 15 min period under argon atmosphere at 0 C. The reaction was allowed to stir at 0 C. for 30 min and at room temperature for 1 h. 1-Chloro-2-(tetrahydropyranyl)oxy-ethane 29 (4.95 g, 30 mmol) was added and the reaction mixture was heated at 80 C. for 12 h. The reaction was cooled and evaporated to dryness. The residue was suspended in water (50 ml), pH of the solution adjusted to 7 and extracted in EtOAc (150 ml). The EtOAc extract was washed with water and brine, dried and evaporated to dryness. The residue was purified by flash chromatography over silica gel using hexane?CH2 Cl2 as the eluent. The required fractions were collected and evaporated to give 6.0 g (66%) of an oily product. 1 H-NMR (CDCl3): delta1.48 (s, 9H, Boc), 1.49-1.84 (m, 6H, 3.CH2), 3.48-3.70 (m, 4H, 2.CH2), 3.86 (m, 2H, CH2), 4.60 (t, 1H, CH), 4.84 (s, 2H, CH2 Ph) and 7.32-7.42 (m, 5H, Ph).

The synthetic route of 5631-96-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ICN Pharmaceuticals, Inc.; US5969135; (1999); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics