Downstream synthetic route of 4677-18-3

As the paragraph descriping shows that 4677-18-3 is playing an increasingly important role.

4677-18-3, 2-(Tetrahydro-2H-pyran-4-yl)ethanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4677-18-3

2-(4-Oxanyl)ethyl methanesulfonate To a stirring solution of 2-(4-oxanyl)ethanol (9.63 g, 74.0 mmol) in dry dichloromethane (350 mL) was added distilled triethylamine (20.62 mL, 96.2 mmol) at 0 C., followed by drop-wise addition of methanesulfonyl chloride (7.44 mL, 96.2 mmol) over 15 min. The reaction was stirred for 16 h under N2 and slowly allowed to come to ambient temperature. The reaction was washed with saturated NaHCO3 (100 mL) and the aqueous phase was extracted with dichloromethane (1*50 mL). The combined organic extracts were dried (K2CO3), filtered and concentrated by rotary evaporation to yield 11.9 g of a colorless oil (77.0% yield).

As the paragraph descriping shows that 4677-18-3 is playing an increasingly important role.

Reference£º
Patent; Targacept, Inc.; US2004/220214; (2004); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 1768-64-5

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

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of 4 (0.054g, 0.20mmol), K2CO3 (0.11g, 0.8mmol), DMF (2.0mL), and 4-chlorotetrahydro-2H-pyran (0.072g, 0.60mmol) in a 10mL microwave tube was heated under microwave irradiation at 200C for 30min. After cooling to room temperature, (4-(N-methylsulfamoyl)phenyl)boronic acid (0.065g, 0.30mmol), Pd(PPh3)4 (0.023g, 0.020mmol), and H2O (1.0mL) were added sequentially. The resulting mixture was stirred at room temperature for 1.0min and then heated under microwave irradiation at 150C for 15min. After cooling to room temperature, the mixture was quenched with H2O and extracted with EtOAc (3¡Á). The combined organic layers were dried (Na2SO4) and concentrated. The combined organic layer was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by an ISCO silica gel column to provide the title compound 14 as a white solid (0.052g, 61% over 2 steps)., 1768-64-5

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

Reference£º
Article; Liu, Jing; Zhang, Weihe; Stashko, Michael A.; DeRyckere, Deborah; Cummings, Christopher T.; Hunter, Debra; Yang, Chao; Jayakody, Chatura N.; Cheng, Nancy; Simpson, Catherine; Norris-Drouin, Jacqueline; Sather, Susan; Kireev, Dmitri; Janzen, William P.; Earp, H. Shelton; Graham, Douglas K.; Frye, Stephen V.; Wang, Xiaodong; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 83 – 93;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 25850-22-0

The synthetic route of 25850-22-0 has been constantly updated, and we look forward to future research findings.

25850-22-0, 2,2-Dimethyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(4) (2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4R)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide(2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4S)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide To a solution of (2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (861 mg, 2.32 mmol) in THF (8 ml) were added DMF (0.10 ml) and oxalylchloride (0.243 ml, 2.79 mmol), the mixture was stirred at room temperature for 1 hour and the solvent was distilled off under reduced pressure. The residue was added under ice-cooling to a solution of 2,2-dimethyltetrahydro-2H-pyran-4-ylamine (600 mg, 4.64 mmol), triethylamine (1.08 ml, 7.71 mmol) and THF (6 ml), the mixture was stirred under ice-cooling for 2 hours, the reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane : ethyl acetate = 2 : 1 to 1 : 1) to separate two kinds of diastereomers. Firstly eluted diastereomer: (2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4R)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide Yield (amount) 195 mg, yield (rate) 17.4%1H-NMR (CDCl3) delta: 1.24-1.40 (8H, m), 1.80-2.30 (6H, m), 2.59 (3H, s), 2.76 (3H, s), 2.90-3.23 (2H, m), 3.65-3.80 (2H, m), 4.19-4.24 (1H, m), 5.51 (1H, d, J = 8.0 Hz), 6.49 (1H, d, J = 7.5 Hz), 6.68-7.26 (7H, m). IR (KBr) cm-1; 3268, 2215, 1661, 1622, 1588, 1553, 1507, 1427, 1331, 1262, 1198, 735, 748. Later eluted diastereomer: (2E)-3-{3-cyano-4,6-dimethyl-1-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4S)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide Yield (amount) 145 mg, yield (rate) 12.9%1H-NMR (CDCl3) delta: 1.20-1.36 (8H, m), 1.76-2.29 (6H, m), 2.59 (3H, s), 2.76 (3H, s), 2.90-3.16 (2H, m), 3.65-3.80 (2H, m), 4.19-4.23 (1H, m), 5.48 (1H, d, J = 7.8 Hz), 6.50 (1H, d, J = 8.1 Hz), 6.71-7.26 (7H, m). IR (KBr) cm-1; 3268, 2215, 1661, 1620, 1588, 1549, 1507, 1449, 1427, 1368, 1331, 1262, 1198, 750, 733., 25850-22-0

The synthetic route of 25850-22-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1535922; (2005); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 7525-64-6

The synthetic route of 7525-64-6 has been constantly updated, and we look forward to future research findings.

7525-64-6, 4-Methyltetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7525-64-6

Example’7-2 2-Chloro-N- (4-methyltetrahydro-2H-pyran-4-yl) acetamide To a solution of 4-methyltetrahydro-2H-pyran-4-ol obtained in Example 7-1 in chloroacetonitrile (0. 65mL), was added a mixture of acetic acid and conc. sulfuric acid (1/1, 1. 6mL) dropwise with cooling on an ice bath. The reaction mixture was warmed to room temperature and stirred for 3hrs. The reaction mixture was quenched by adding 3N NaOH. The resulting solution was extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous NaCl, dried over MgS04, and concentrated in vacuo. The residue was purified with silica gel chromatography (hexane/ethyl acetate = 1/2) to give the target compound as a white powder (630 mg). 1H-NMR (300MHz, CDC13) : 6 1.46 (3H, s), 1.83-1. 67 (2H, m), 2.14-2. 00 (2H, m), 3.67-3. 55 (2H, m), 3.81-3. 67 (2H, m), 4.00 (2H, s), 4.03 (1H, br-s). Mass (ES+) m/z : 192.16 (M+1).

The synthetic route of 7525-64-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; WO2005/42533; (2005); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 85064-61-5

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

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, Oxalyl chloride (5 ml) and DMF (1 drop) were added to a solution of (TETRAHYDROPYRAN-4-YL) acetic acid (10 g) in DCM. The mixture was stirred for 3 h, then EVAPORATED IN VACUO and thoroughly azeotroped with toluene. The residue was dissolved in THF and added dropwise to a solution of (R)- BENZYLOXAZOLIDINONE (12.1 g) and nBuLi (2.5M in hexanes, 30 ml) in THF (200 ml) AT-78¡ãC. The solution was stirred for 2 h, then quenched with saturated aqueous ammonium chloride and evaporated in vacuo. The mixture was extracted with ethyl acetate, solvent washed with water and brine, dried and evaporated to give the title compound as a colourless solid (14 g). MS 304 (M + H).

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

Reference£º
Patent; CELLTECH R & D LIMITED; WO2004/113312; (2004); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 4677-20-7

4677-20-7, 4677-20-7 4-(2-Bromoethyl)tetrahydropyran 22637012, aTetrahydropyrans compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4677-20-7,4-(2-Bromoethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

Example 51 can be prepared according to method 14 with modifications known to one of ordinary skill in the art. The last step of the preparation is provided: A mixture of 4-(2- bromoethyl)tetrahyd ro-2H-pyran (12.54 mg, 0.065 mmol), (E)-1-(4-(5-carbamoyl-2-(1-ethyl-3-methyl-i H-pyrazole-5-carboxamido)-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl)-2-(1-ethyl-3- methyl-i H-pyrazole-5-carboxamido)-7-hydroxy-i H-benzo[d]imidazole-5-arboxamide (45 mg, 0.065 mmol) and potassium carbonate (22.44 mg, 0.162 mmol) was heated for 3hr at 85 C in DMSO (650 p1) and NMP (650 p1), then cooled. The residue was purified via acidic reverse phase chromatography (5% to 50% in 0.1% TEA in MeCN to 0.1% TEA in water; 50x30mmPhenomenex Eclipse, 5M C18 column, 20 mm gradient). The pure fractions were partitioned between EtOAc and aqueous saturated sodium bicarbonate, the organic layer was separated, dried over sodium sulfate and evaporated in vacuoto provide the title compound (8mg, l5.3% yield) as a white solid. 1H NMR (DMSO-d6, 600MHz): (ppm) 12.83 (br s, 2 H), 7.97-8.00 (m, 1 H), 7.93 (br s, 2 H), 7.69 (dd, 3=8.4, 1.5 Hz, 1 H), 7.63 (s, 1 H), 7.41 (d, J=8.3 Hz, 1 H),7.33 (br d, 3=11.4 Hz, 2 H), 7.29 (s, 1 H), 6.55 (s, 1 H), 6.52 (s, 1 H), 5.96-6.02 (m, 1 H),5.70-5.79 (m, 1 H), 4.93 (br d, J=5.0 Hz, 2 H), 4.82 (br d, J=5.3 Hz, 2 H), 4.49-4.58 (m, 4 H),3.96 (br t, J=6.7 Hz, 2 H), 3.75 (br dd, 3=11.2, 2.9 Hz, 2 H), 3.16-3.23 (m, 2 H), 2.12 (d,3=12.7 Hz, 6 H), 1.50-1.53 (m, 1 H), 1.45-1.49 (m, 2 H), 1.43 (br d, J=ii.9 Hz, 2 H), 1.28 (m,6 H), 1.08 (br dd, J=12.0, 3.6 Hz, 2 H); LCMS (LCMS Method K): Rt = 0.90 mi [M+H] =805.5.

4677-20-7, 4677-20-7 4-(2-Bromoethyl)tetrahydropyran 22637012, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHARNLEY, Adam Kenneth; DARCY, Michael Gerard; DODSON, Jason W.; DONG, Xiaoyang; FAVRE, David; HUGHES, Terry Vincent; KANG, Jianxing; LEISTER, Lara Kathryn; LI, Yuehu; LIAN, Yiqian; MEHLMANN, John F.; NEVINS, Neysa; RAMANJULU, Joshi M.; ROMANO, Joseph J.; WANG, Gren Z.; YE, Guosen; ZHANG, Daohua; (489 pag.)WO2019/69269; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 7525-64-6

As the paragraph descriping shows that 7525-64-6 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7525-64-6,4-Methyltetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.,7525-64-6

A solution of 4- methyltetrahydro-2H-pyran-4-ol (2.87 g, 24,7 mmol) in benzene (30 mL) was treated with Burgess’ Reagent (6.18 g, 25.9 mmol, 1.05 equiv) and placed into an oil bath preheated to 30 0C for 4 hours. The mixture was purified by silica gel gradient chromatography (100:0 to 90:10; hexanes : ethyl acetate), providing the titled compound.

As the paragraph descriping shows that 7525-64-6 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP &; DOHME CORP.; BESHORE, Douglas, C.; KUDUK, Scott, D.; WO2010/96338; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 29943-42-8

29943-42-8, The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 12: tetrahydro-2H-pyran-4-ylhydrazine, trifluoroacetate; Tetrahydro-4H-pyran-4-one (Apollo; 924 muL; 10.0 mmol) and te/f-butyl carbazate (1 .39 g; 10.50 mmol) were dissolved in ethanol (10 mL) and stirred at room temperature overnight. The solvent was removed in vacuo and the residue was redissolved in 1 :1 wate?acetic acid (10 mL) and sodium cyanoborohydride (660 mg; 10.50 mmol) added. The mixture was stirred at room temperature for 3 hours and then 2:1 ethyl acetate: 10% aqueous potassium carbonate (50 mL) added. The organic layer was separated, washed with brine, passed through a hydrophobic frit and the solvent removed in vacuo. The residue was redissolved in DCM (10 mL) and trifluoroacetic acid (1 mL) added and the mixture stirred overnight. The solvent was removed in vacuo to yield Intermediate 12 as a semi-solid slurry which was used directly without any purification. 1H NMR: (DMSOd6, 400MHz) delta 4.08-3.76 (2 H, m), 3.41 -3.27 (2 H, m), 3.23-3.14 (1 H, m), 1 .99-1.83 (2 H, m), 1 .59-1.43 (2 H, m). LC/MS: 1 17 (M+H)+.

29943-42-8, The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; BAKER-GLENN, Charles; BLACKABY, Wesley; KNIGHT, Chris; WO2010/142628; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 5631-96-9

5631-96-9 2-(2-Chloroethoxy)tetrahydro-2H-pyran 254951, aTetrahydropyrans compound, is more and more widely used in various fields.

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

General procedure: A mixture of 3 (2.64 g, 4.02 mmol), commercially available 2-(2-chloroethoxy) tetrahydro-2H-pyran (4) (0.79 g, 4.82 mmol), K2CO3 (1.11 g, 8.04 mmol) and KI (0.13 g, 0.80 mmol) in N,N-dimethylformamide (DMF) (40 mL) under argon was stirred overnight at 90C. After cooling to room temperature, themixture was diluted with CHCl3 (200 mL) and H2O (200 mL). The aqueous phase was extracted with CHCl3 (100 mL, twice), and the combined organic phases were washed with brine (50 mL), dried over MgSO4 and evaporated to give crude 5. Purification of the crude sample by column chromatography over silica gel (hexane/EtOAc) gave pure 5 (1.22 g, 39% yield)., 5631-96-9

5631-96-9 2-(2-Chloroethoxy)tetrahydro-2H-pyran 254951, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Hattori, Yoshiyuki; Hara, Eriko; Shingu, Yumiko; Minamiguchi, Daiki; Nakamura, Ayako; Arai, Shohei; Ohno, Hiroaki; Kawano, Kumi; Fujii, Nobutaka; Yonemochi, Etsuo; Biological and Pharmaceutical Bulletin; vol. 38; 1; (2015); p. 30 – 38;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Analyzing the synthesis route of 130290-79-8

As the paragraph descriping shows that 130290-79-8 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.130290-79-8,(Tetrahydro-2H-pyran-4-yl)methanamine,as a common compound, the synthetic route is as follows.,130290-79-8

A mixture of 4-fluoro-3-nitrobenzenesulfonamide (2.18 g), l-(tetrahydropyran-4- yl)methylamine (1.14 g), and triethylamine (1 g) in tetrahydrofuran (30 mL) were stirred overnight, neutralized with concentrated HC1 and concentrated. The residue was suspended in ethyl acetate and the precipitates were collected, washed with water and dried to provide the title compound.

As the paragraph descriping shows that 130290-79-8 is playing an increasingly important role.

Reference£º
Patent; ABBOTT LABORATORIES; CATRON, Nathaniel D.; CHEN, Shuang; GONG, Yuchuan; ZHANG, Geoff G.; WO2012/71336; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics