Category: 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.

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

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

Step 1 : Preparation of (S)-benzyl 1 -(fluoromethyl)-4- ((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en- 2-yl)-3a-((2-(tetrahydro-2H-pyran-4-yl)ethyl)amino)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)cyclohex-3-enecarboxylate A suspension of (S)-benzyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a-amino- 5a,5b,8,8, 11 a-pentamethyl- 1 -(prop- 1 -en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)-l-(fluoromethyl)cyclohex-3-enecarboxylate (50 mg, 0.076 mmol), 4-(2-bromoethyl)tetrahydro-2H-pyran (15 mg, 0.076 mmol), K3PO4 (49 mg, 0.229 mmol) and Nal (19 mg, 0.114 mmol) in MeCN (1 mL) was flushed with nitrogen, sealed, and stirred at 90 C for 18 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel column (0-40% EtOAc/Hexane) using ELS detector to give the desired product as a solid (30 mg, 51%). LCMS m/e 768.55 (M+H)+, 3.033 minutes (Method 8). ‘H NMR (400MHZ, CHLOROFORM-d) delta 7.39 – 7.29 (m, 5H), 5.32 (s, 1H), 5.22 – 5.14 (m, 2H), 5.14 – 5.10 (m, 1H), 4.71 (d, J=2.0 Hz, 1H), 4.62 – 4.55 (m, 1H), 4.58 (s, 1H), 4.51 – 4.43 (m, 1H), 4.01 – 3.93 (m, 4H), 2.65 – 2.52 (m, 2H), 2.50 – 2.36 (m, 2H), 2.18 – 0.87 (m, 34H), 1.69 (s, 3H), 1.05 (s, 3H), 0.95 (s, 3H), 0.90 (s, 3H), 0.89 (s, 3H), 0.85 (s, 3H). 19F NMR (376MHz, CHLOROFORM-d) delta -225.06 (s, IF).

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; SIT, Sing-Yuen; CHEN, Yan; CHEN, Jie; SWIDORSKI, Jacob; VENABLES, Brian Lee; SIN, Ny; MEANWELL, Nicholas A.; REGUEIRO-REN, Alicia; HARTZ, Richard A.; XU, Li; LIU, Zheng; WO2015/157483; (2015); 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.

Example 44A Di-tert-butyl [2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl](2-oxo-2-{6-[2-(tetrahydro-2H-pyran-4-yl)ethoxy]-1-benzofur-2-yl}ethyl)malonate To a mixture of 200 mg (0.36 mmol) of the compound from Example 43A in 0.75 ml of DMF under argon were added, at RT, 45 mg (0.40 mmol) of potassium tert-butoxide and, after stirring for 5 min at RT, 86 mg (0.44 mmol) of 4-(2-bromoethyl)tetrahydro-2H-pyran, dissolved in 0.25 ml of DMF. The mixture was stirred at a bath temperature of 70 C. for 1.5 h. After cooling to RT, in each case 50 ml of water and ethyl acetate were added, and after phase separation, the aqueous phase was extracted once with 50 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. The residue was taken up in dichloromethane and purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 7:3). 82 mg (32% of theory, purity 94%) of the title compound were obtained. 1H-NMR (400 MHz, CDCl3): delta [ppm]=8.30 (dd, 1H), 8.08 (d, 1H), 7.89 (td, 1H), 7.77-7.72 (m, 1H), 7.57-7.51 (m, 2H), 7.01 (d, 1H), 6.93 (dd, 1H), 4.60-4.53 (m, 2H), 4.07 (t, 2H), 3.98 (dd, 2H), 3.71 (s, 2H), 3.42 (td, 2H), 2.69-2.63 (m, 2H), 1.84-1.76 (m, 3H), 1.73-1.65 (m, 2H), 1.54-1.30 (m, 2H, hidden), 1.49 (s, 18H). LC/MS (Method 1, ESIpos): Rt=1.48 min, m/z=676 [M+H]+.

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

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMAN, Andreas; BROHM, Dirk; JOeRIssEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (120 pag.)US2017/121315; (2017); 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.

A stirred mixture b-ketoester 7 (550 mg, 1.65 mmol), bromide 8 (335 mg, 1.73 mmol), KI (302 mg, 1.8 mmol), K2CO3 (251 mg, 1.8 mmol) and dry DMF (5 mL) was heated at 70 C for 3 h. The mixture was diluted with EtOAc (90 mL), washed with 1% aq HC1 (15 mL) and brine (15 mL), and dried over Na2S04. Removal of the solvent left a yellow oil (1.34 g) which was chromatographed on a 12 g silica cartridge, eluted with a 0 – 70% EtOAc in hexanes gradient, to give P3-001 (495 mg, 67% yield). LC-MS tR 5.41 min, m/z 446.

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; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; FOX CHASE CHEMICAL DEVELOPMENT CENTER, INC.; SMITHGALL, Thomas; REITZ, Allen; WROBEL, Jay; TICE, Colin; HAIMOWITZ, Thomas; CARLSEN, Marianne; LOUGHRAN, Marie; YE, Hong; (183 pag.)WO2020/81856; (2020); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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 13A Di-tert-butyl [2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl](2-oxo-2-{5-[2-(tetrahydro-2H-pyran-4-yl)ethoxy]-1-benzofur-2-yl}ethyl)malonate To a mixture of 200 mg (0.36 mmol) of the compound from Example 7A in 0.75 ml of DMF under argon were added, at RT, 45 mg (0.40 mmol) of potassium tert-butoxide and, after stirring for 5 min at RT, 86 mg (0.44 mmol) of 4-(2-bromoethyl)tetrahydro-2H-pyran, dissolved in 0.25 ml of DMF. The mixture was stirred at a bath temperature of 70 C. for 1.5 h. After cooling to RT, in each case 50 ml of water and ethyl acetate were added, and after phase separation, the aqueous phase was extracted once with 50 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. The residue was taken up in dichloromethane and purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 7:3). 111 mg (43% of theory, purity 94%) of the title compound were obtained. LC/MS (Method 1, ESIpos): Rt=1.59 min, m/z=676 [M+H]+.

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

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMAN, Andreas; BROHM, Dirk; JOeRIssEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (120 pag.)US2017/121315; (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,4677-20-7

4-(2-Bromoethyl)tetrahydro-2H-pyran (200 mg, 1.00 mmol), 3,7-dimethyl-1H-purin-2,6(3H,7H)-dione (186 mg, 1.00 mmol), potassium iodide (17.0 mg, 0.100 mmol) and potassium carbonate (414 mg, 3.00 mmol) were dissolved in N,N-dimethylformamide (4 mL). The reaction solution was heated to 130 C. and allowed for reaction for 3 hours, and then the reaction solution was than cooled to 25 C. The reaction was quenched by adding saturated brine, followed by extraction with ethyl acetate (50 mL*3). The organic phases were dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and then purified by high performance preparative plate (ethyl acetate, Rf-0.5) to give a product 3,7-dimethyl-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-purin-2,6(3H,7H)-dione (224 mg) with a yield of 77%. 1H NMR: (400 MHz, Methonal-d4) delta7.86 (s, 1H), 4.06-4.01 (m, 2H), 3.97 (s, 3H), 3.92 (dd, J=12, 3.2 Hz, 2H), 3.53 (s, 3H), 3.44-3.38 (m, 2H), 1.73 (d, J=12.8 Hz, 2H), 1.61-1.55 (m, 3H), 1.38-1.24 (m, 2H). MS-ESI calculated value: [M+H]+ 293; measured value: 293.

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

Reference£º
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Linyun; CHEN, Xiaoxin; ZHANG, Peng; LIU, Xing; ZHANG, Li; LIU, Zhuowei; CHEN, Shuhui; LONG, Chaofeng; (75 pag.)US2018/148451; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics