Category: 4677-20-7

4677-20-7, 4-(2-Bromoethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 7: 6-Amino-2-butylamino-9-r2-(tetrahvdro-2H-pyran-4-yl)ethyll-7,9-dihvdro- 8H-purin-8-one To a solution of /V2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (100 mg) in dry N,N-dimethylformamide (1 ml) at room temperature and under nitrogen was added potassium carbonate (158 mg) in one go. The reaction was stirred at 6O C for 1.5 hours and then cooled to 5O C. A solution of 4-(2- bromoethyl)tetrahydro-2H-pyran (60 mg) in dry N,N-dimethylformamide (0.5 ml) was added in one go and the reaction heated at 5O C overnight. The reaction was diluted with ethyl acetate (15 ml) and washed with water (5 ml). The organic layer was separated and concentrated in vacuo. The product was purified by C18 reverse phase chromatography using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluant (20-60%) to afford a yellow viscous oil (47mg) that was dissolved in dry methanol (4 ml) at room temperature and under nitrogen was added 4.0M hydrogen chloride in 1 ,4-dioxane (0.8 ml) in one go. The reaction was left to stir at room temperature overnight. The reaction was neutralised by the addition of 2.0M sodium hydroxide solution and concentrated in vacuo. The residue was taken up in water (5 ml) and the solid filtered and dried in vacuo (60C) for 30 minutes. This afforded the title compound as a beige solid (23mg). MS calcd for (C16H26N6O2)+ = 334 MS found (electrospray): (M+H)+ =3351H NMR ((CDa)2SO): delta 9.78 (1 H, s), 6.08-6.21 (3H, br. s), 3.80 (2H, m), 3.65 (2H, t), 3.21 (2H, m), 3.16 (2H, m), 1.66 (2H, m), 1.57 (2H, m), 1.36-1.49 (3H, m), 1.29 (2H, m), 1.13 (2H, m), 0.88 (3H, t)., 4677-20-7

As the paragraph descriping shows that 4677-20-7 is playing an increasingly important role.

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

4677-20-7, 4-(2-Bromoethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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)tetrahydro-2H-pyran (12.54 mg, 0.065 mmol), (E)-l-(4-(5-carbamoyl-2-(l-ethyl-3- methyl-lH-pyrazole-5-carboxamido)-lH-benzo[d]imidazol-l-yl)but-2-en-l-yl)-2-(l-ethyl-3- methyl-lH-pyrazole-5-carboxamido)-7-hydroxy-lH-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 muIota) and NMP (650 muIota), then cooled. The residue was purified via acidic reverse phase chromatography (5% to 50% in 0.1% TFA in MeCN to 0.1% TFA in water; 50x30mm Phenomenex Eclipse, 5muMu C18 column, 20 min 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 vacuoXa provide the title compound (8mg, 15.3% yield) as a white solid. *H NMR (DMSO-cfe, 600MHz): delta (ppm) 12.83 (br s, 2 H), 7.97-8.00 (m, 1 H), 7.93 (br s, 2 H), 7.69 (dd, 7=8.4, 1.5 Hz, 1 H), 7.63 (s, 1 H), 7.41 (d, 7=8.3 Hz, 1 H), 7.33 (br d, 7=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), (2225) 5.70-5.79 (m, 1 H), 4.93 (br d, 7=5.0 Hz, 2 H), 4.82 (br d, 7=5.3 Hz, 2 H), 4.49-4.58 (m, 4 H), 3.96 (br t, 7=6.7 Hz, 2 H), 3.75 (br dd, 7=11.2, 2.9 Hz, 2 H), 3.16-3.23 (m, 2 H), 2.12 (d, 7=12.7 Hz, 6 H), 1.50-1.53 (m, 1 H), 1.45-1.49 (m, 2 H), 1.43 (br d, 7=11.9 Hz, 2 H), 1.28 (m, 6 H), 1.08 (br dd, 7=12.0, 3.6 Hz, 2 H); LCMS (LCMS Method K): Rt = 0.90 min, [M+H]+ = 805.5.

4677-20-7, The synthetic route of 4677-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHARNLEY, Adam Kenneth; DARCY, Michael G.; DODSON, Jason W.; DONG, Xiaoyang; HUGHES, Terry V.; KANG, Jianxing; LEISTER, Lara Kathryn; LIAN, Yiqian; LI, Yue; MEHLMANN, John F.; NEVINS, Neysa; RAMANJULU, Joshi M.; ROMANO, Joseph J.; WANG, Gren Z.; YE, Guosen; ZHANG, Daohua; (451 pag.)WO2017/175147; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4677-20-7, 4-(2-Bromoethyl)tetrahydropyran 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 2-bromoethanol (0.038g, 0.30mmol) in a 10mL microwave tube was heated under microwave irradiation at 150C for 10min. 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 residue was purified by an ISCO silica gel column to provide the title compound 12 (0.044g, 57%) as a white solid.

4677-20-7, The synthetic route of 4677-20-7 has been constantly updated, and we look forward to future research findings.

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

4677-20-7, 4-(2-Bromoethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4677-20-7

f) To a solution of 5-chloro-2-hydroxybenzaldehyde 162 mg (1 .0 mmol) in DMF (2 ml_), 172 mg of K2C03 (1 .2 mmol) and 4-(2-bromoethyl)tetrahydro-2H-pyran (200 mg, 1 .0 mmol) were added. Reaction was stirred at 405C overnight. Then, it was allowed to cool to room temperature. Water was added and a white precipitated appeared. The mixture was extracted with EtAcO (x3), and the organic phases combined and washed with a 10% solution of NaCI in water. It was dried with anhydrous Na2S04, filtered and the solvent evaporated to obtain 5-chloro-2-(2- (tetrahydro-2H-pyran-4-yl)ethoxy)benzaldehyde (220 mg, 80%).

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

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; DRACONIS PHARMA, S.L.; ALMIRALL, S.A.; TORRENS JOVER, Andoni; MERCE VIDAL, Ramon; CALDENTEY FRONTERA, Francesc Xavier; RODRIGUEZ GARRIDO, Antonio, David; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/37960; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4677-20-7, 4-(2-Bromoethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4677-20-7

5-Ethyl-1 -methyl-1H-pyrazol-3-amine hydrogen chloride (1/1) (purchased from Enamine, 1.00 g, 6.19 mmol), 4-(2-bromoethyl)oxane (CAS 4677-20-7, 310, 2.1 mmol), potassium carbonate (1.14 g, 8.25 mmol) and potassium iodide (34.2 mg, 206 pmol) were dissolved in 1 1 ml_ acetonitrile and the mixture was stirred for 10 min at 1 10’O in the microwave. The reaction mixture was cooled down to rt and concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate twice. The combined organic layers were filtered through a waterresistant filter and the filtrate was concentrated under reduced pressure. The crude product was purified by HPLC under basic conditions to give 220 mg of the title compound (88% purity). LC-MS (Method2): Rt = 0.92 min; MS (ESIpos): m/z = 237 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) d [ppm] = 1.04 – 1.26 (m, 5H), 1.40 (q, 2H), 1.50 – 1.62 (m, 3H), 2.40 – 2.48 (m, 2H), 2.96 (br t, 2H), 3.25 (td, 2H), 3.46 (s, 3H), 3.81 (dd, 2H), 4.79 (br s, 1H), 5.22 (s, 1H).

The synthetic route of 4677-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; THEDE, Kai; MENGEL, Anne; CHRIST, Clara; KUHNKE, Joachim; JOHANNES, Sarah, Anna, Liesa; BUCHGRABER, Philipp; KLAR, Ulrich; SACK, Ulrike; KAULFUSS, Stefan; FERNANDEZ-MONTALVAN, Amaury, Ernesto; WERBECK, Nicolas; MOeNNING, Ursula; NOWAK-REPPEL, Katrin; MORTIER, Jeremie, Xavier; MCCARREN, Patrick, Ryan; SERRANO-WU, Michael, H.; LEMKE, Chris; MCKINNEY, David; FITZGERALD, Mark; NASVESCHUK, Christopher; LAZARSKI, Kiel; FERRARA, Steven, James; FURST, Laura; WEI, Guo; HARVEY, Rebecca, Ann; PAYNE, Daniel; PESNOT, Thomas; WILSON, Craig; (464 pag.)WO2019/96914; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4677-20-7,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.

Into a 50-mL 3-necked round-bottom flask, was placed tert-butyl N-[2-[([3-[4-(3- hydroxycyclobutoxy)phenyl] -1 -(oxan-2-yl)- 1 H-pyrazol-4-yl]methyl)(methyl)amino] ethyl] – N-methylcarbamate (500 mg, 0.97 mmol, 1.00 equiv),N,N-dimethylformamide (10 mL). The temperature was cooled to 0C. To this was added sodium hydride (120 mg, 5.00 mmol, 5.15 equiv, 60% in mineral oil) in batches. The mixture was stirred for 1 h at R.T. Then to the mixture was added 4-(2-bromoethyl)oxane (470 mg, 2.43 mmol, 2.51 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 30 mL of water. The resulting solution was extracted with 3×3 0 mL of ethyl acetate. The resulting mixture was washed with 3×30 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0%-60%). The collected fractions were combined and concentrated under vacuum. This resulted in 450 mg (74%) of tert-butyl N-methyl-N-[2- [methyl([ [1 -(oxan-2-yl)-3 -(4- [3 -[2-(oxan-4-yl)ethoxy] cyclobutoxy]phenyl)1H-pyrazol-4-yl]methyl])amino]ethyl]carbamate as yellow oil. LCMS (Method A, ESI): RT = 1.37mm, m/z =627.4 [M+H].

The synthetic route of 4677-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EPIZYME, INC.; MITCHELL, Lorna, Helen; SWINGER, Kerren, Kalai; SHAPIRO, Gideon; BORIACK-SJODIN, Paula, Ann; (104 pag.)WO2016/44556; (2016); A2;,
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.4677-20-7,4-(2-Bromoethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

(rac)-Ethyl 4-chloro-3-ethyl-7-{3-[(6-fluoronaphthalen-1 -yl)oxy]propyl}-2-methyl- 10,11 ,12,13,14,15-hexahydro-2H-pyrazolo[3′,4′:8,9][1 ,6]diazacycloundecino[10,11 ,1 -hi]indole- 8-carboxylate (see Intermediate 115, 50.0 mg, 81.0 pmol), 4-(2-bromoethyl)oxane (17.2 mg, 89.1 pmol) and cesiumcarbonate (132 mg, 405 pmol) were dissolved in 410 mI_ DMF and the reaction mixture was stirred at 600 in a sealed ve ssel under nitrogen atmosphere. The reaction mixture was diluted with water and dichloromethane, stirred for a few minutes, filtered through a silicone coated filter and concentrated under reduced pressure. The crude product was purified by HPLC chromatography under basic conditions to provide the target compound in 99% purity: 23 mg. LC-MS (Methode 2): Rt = 1.85 min; MS (ESIpos): m/z = 730 [M+H]+ 1 H-NMR (400MHz, DMSO-d6): d [ppm]= 0.55 – 0.74 (m, 1 H), 0.75 – 0.96 (m, 7H), 1.00 – 1.13 (m, 3H), 1.13 – 1.32 (m, 7H), 1.83 – 1.93 (m, 2H), 2.03 – 2.27 (m, 4H), 2.35 – 2.47 (m, 2H), 2.88 (td, 1 H), 2.97 (d, 1 H), 3.19 – 3.31 (m, 2H), 3.50 (br d, 1 H), 3.59 (br dd, 1 H), 3.72 – 3.93 (m, 5H), 4.04 – 4.16 (m, 1 H), 4.17 – 4.39 (m, 4H), 6.90 (dd, 1 H), 7.24 (d, 1 H), 7.37 – 7.50 (m, 3H), 7.67 (dd, 1 H), 7.75 (d, 1 H), 8.30 (dd, 1 H). As side product of the reaction to Intermediate 202the target compound was isolated in 98% purity: 12 mg. LC-MS (Methode 2): Rt = 1.77 min; MS (ESIpos): m/z = 774 [M+H]+ 1 H-NMR (400MHz, DMSO-d6): d [ppm]= 0.83 (t, 3H), 0.91 (br d, 2H), 0.98 – 1.17 (m, 4H), 1.18 – 1.31 (m, 5H), 1.32 – 1.56 (m, 5H), 2.13 – 2.31 (m, 4H), 3.08 – 3.31 (m, 4H), 3.75 (br dd, 2H), 3.80 – 3.98 (m, 6H), 3.99 – 4.35 (m, 5H), 4.36 – 4.53 (m, 2H), 6.86 (dd, 1 H), 7.25 (br d, 1 H), 7.34 – 7.49 (m, 3H), 7.66 (dd, 1 H), 7.80 (d, 1 H), 8.24 (dd, 1 H).

4677-20-7, As the paragraph descriping shows that 4677-20-7 is playing an increasingly important role.

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; THEDE, Kai; MENGEL, Anne; CHRIST, Clara; KUHNKE, Joachim; JOHANNES, Sarah, Anna, Liesa; BUCHGRABER, Philipp; KLAR, Ulrich; SACK, Ulrike; KAULFUSS, Stefan; FERNANDEZ-MONTALVAN, Amaury, Ernesto; WERBECK, Nicolas; MOeNNING, Ursula; NOWAK-REPPEL, Katrin; LEMKE, Chris; SERRANO-WU, Michael, H.; MCKINNEY, David; FITZGERALD, Mark; NASVESCHUK, Christopher; LAZARSKI, Kiel; FERRARA, Steven, James; FURST, Laura; WEI, Guo; MCCARREN, Patrick, Ryan; HARVEY, Rebecca, Ann; PAYNE, Daniel; PESNOT, Thomas; WILSON, Craig; (683 pag.)WO2019/96905; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4677-20-7,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.

Intermediate 28: 2-(ButyloxyV8-(methyloxyV9-(2-{r2-(tetrahvdro-2H-pyran-4- yl)ethylloxy)ethyl)-9H-purin-6-amineTo 2-[6-amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]ethanol (0.03 g, 0.107 mmol) in dry THF (3ml) was added potassium f-butoxide solution in THF (0.160 ml, 0.160 mmol) followed by 4-(2-bromoethyl)tetrahydro-2H-pyran (0.031 g, 0.160 mmol) in THF 2ml) and the resulting white suspension was heated at 500C for 18 hours then at 7O0C for 7 hours. Additional 4-(2-bromoethyl)tetrahydro-2H-pyran, (0.031 g, 0.160 mmol) and potassium f-butoxide solution in THF (0.160 ml, 0.160 mmol) were added and the mixture heated at 7O0C for 72 hours. The mixture was cooled and quenched with water (5ml), extracted with DCM (2x5ml), the organic phase was isolated by separation through a hydrophobic frit and evaporated. The sample was dissolved in 1 :1 MeOH:DMSO (1 ml) and purified by Mass Directed AutoPrep. The solvent was dried under a stream of nitrogen to give the title compound as a colourless gum (3.1 mg). LCMS: tRET = 2.17 min; MH+ 394

The synthetic route of 4677-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; CAMPOS, Sebastien, Andre; COE, Diane, Mary; SMITH, Stephen, Allan; TRIVEDI, Naimisha; WO2010/18132; (2010); 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.4677-20-7,4-(2-Bromoethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

Intermediate 17: 2-Butoxy-8-methoxy-9-r2-(tetrahvdro-2/-/-pyran-4-yl)ethyll-9/-/-purin- 6-amine2-Butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (0.2 g) in anhydrous N, N- dimethylformamide (5 ml.) was treated with anhydrous potassium carbonate (0.315 g) and then heated to 600C for 1 hour. On cooling to room temperature, to the above was added 4-(2-bromoethyl)tetrahydro-2H-pyran (0.110 g) and the reaction was warmed to 500C, overnight. The reaction mixture was quenched with water (5 ml.) and extracted into ethyl acetate (3 times, 100 ml. combined total volume). The separated organic layers were combined and passed through a hydrophobic frit to dry. The organic phase was stripped to give a gum which was purified by C-ibeta reverse phase chromatography using water (containing 0.1 % formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (20-60%) to afford the title compound as a white solid (11 1 mg). MS calcd for (Ci7H27N5Os)+ = 349 MS found (electrospray): (M+H)+ = 3501 H NMR (CDCI3): 5.20 (2H, s), 4.24 (2H, t), 4.10 (3H, s), 3.94 (4H, overlapping m), 3.31 (2H, m), 1.78-1.65 (6H, overlapping m), 1.52-1.39 (3H, overlapping m), 1.30 (2H, m), 0.95 (3H, t).

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