Category: 220641-87-2

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

EXAMPLE 36 iV-Methyl-iV-tetrahvdro-lH-pyran^-ylquinoxaline–carboxamide To a suspension of quinoxaline-6-carboxylic acid (0.7g, 4 mmol) and N-methyltetrahydro- 2H-pyran-4-amine (0.7 g, mmol), in DMF (6 ml) and dichloromethane (6 ml), were added DMAP (0.49 g, 4 mmol), etaOBT (0.54 g, 4 mmol), NEt3 (1.6 ml) and EDCI (1.26g). The reaction mixture was stirred at room temperature for 4h and then concentrated under vacuum. The crude product was purified on a silica gel column eluting with chloroform/methanol/ triethylamine (95:5:0.5) to give an oil (1.5g) which formed a beige solid upon trituration with dichloromethane/diethyl ether. Mp = 130-131C, LC-MS, MH+ = 272; 1H NMR (300 MHz, CDCl3) delta 8.91 (s, 2H); 8.18 (d, J = 8.4 Hz, IH); 8.11 (s, IH); 7.79 (d, J = 8.4 Hz, IH); 4.95- 3.50 (m, 5H); 3.07 and 2.91 (s + s, 3H); 2.02-1.65 ppm (m, 4H)., 220641-87-2

220641-87-2 N-Methyltetrahydro-2H-pyran-4-amine 6991950, aTetrahydropyrans compound, is more and more widely used in various fields.

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

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

Step C:; A 25 mL round bottom flask were charged with 86-3 (0.022 g, 0.038 mmol), methylene chloride (2 mL), N-methyl-N-tetrahydro-2H-pyran-4-ylamine (0.009 g, 0.56 mmol), sodium triacetoxyborohydride (0.032 g, 0.15 mmol), molecular sieves (20 mg) and triethyl amine (0.019 g, 0.188 mmol). The mixture was stirred at room temperature for 12 hours. The reaction mixture was quenched with MeOH and stirred for 20 minutes, then filtered and concentrated. The resulting residue was purified by RP HPLC (YMC column, 20% to 80% acetonitrile in water) to afford product 86-4 as a TFA salt (m/z (ES) (M+H)+= 683)., 220641-87-2

The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; WO2007/41052; (2007); 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.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

To a mixture of 2-chloropyrimidine-5-boronic acid (32 mg, 0.2 mmol) and N-methyl-N-tetrahydro-2H-pyran-4-ylamine (26 mu, 0.21 mmol) in EtOH (2 mL) was added triethylamine (0.070 mL, 0.5 mmol). The resulting mixture was stirred at 75 C for 5 h. Solvents were removed to give crude (2-(methyl(tetrahydro-2H-pyran-4- yl)amino)pyrimidin-5-yl)boronic acid as a light yellow solid. LCMS [M + H] 238.2. The title compound (white solid, 5.4 mg, 9%) was prepared similar to Example 29 using crude (2-(methyl(tetrahydro-2H-pyran-4-yl)amino)pyrimidin-5-yl)boronic acid (0.2 mmol) and (S)-N-(5-bromo-2-(3,4-dimethylpiperazin-l-yl)-4-fluorophenyl)-6-oxo- 4-(trifluoromethyl)-l,6-dihydropyridine-3-carboxamide (49.1 mg, 0.1 mmol). ‘H NMR (500MHz, CHLOROFORM-d) delta = 8.73 (br s, 1H), 8.57 (s, 2H), 8.52 – 8.40 (m, 1H), 7.87 (br s, 1H), 7.11 – 6.91 (m, 2H), 4.98 (br t, J=11.9 Hz, 1H), 4.11 (br dd, J=4.0, 11.4 Hz, 2H), 3.61 (br t, J=11.6 Hz, 2H), 3.11 (s, 3H), 3.05 – 2.82 (m, 4H), 2.70 – 2.55 (m, 1H), 2.38 (br s, 3H), 2.30 – 2.16 (m, 1H), 1.94 (dq, J=4.4, 12.2 Hz, 2H), 1.70 (br d, J=11.5 Hz, 2H), 1.13 (br s, 3H); LCMS [M + H]+ 604.5., 220641-87-2

The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (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.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

To a solution of A2 (100 mg, 0.3 12 mmol) in DCM (4 mL) was added TEA (156 mg, 1.55 mmol) and HATU (112 mg, 0.468 mmol) at 25 C. After stirring at 25 C for 30 minutes, N-methyltetrahydro-2H- pyran-4-amine (57.4 mg, 0.499 mmol) was added. The mixture was stirred at 25 C for 16 hrs, quenchedwith water (4 mL) and extracted with DCM (2 x 4 mL). The organic layers were washed with brine (2 x5 mL), dried over Na2SO4 , filtered, concentrated in vacuo to give a crude product, which was purifiedby silica gel chromatography eluted with PE/EtOAc = 3/1 to afford the desired compound. Thecompound was lyophilized to give a solid (80 mg) that was further re-crystallized (85 C) from MeCN(2 mL) and water (20 mL) to give Compound 10 (66 mg, 51%) as a solid.1H NMR (400 MHz, CDCl3) delta 4.85-4.70 (m, 0.5H), 4.15-3.95 (m, 2H), 3.55-3.40 (m, 1.5H), 2.90-2.70 (m, 3H), 2.69-2.60 (m, 1H), 2.35-2.20 (m, 1H), 1.90-1.60 (m, 1OH), 1.59-1.16 (m, 18H),1.15-1.00 (m, 3H), 0.72 (s, 3H).LCMS Rt = 1.005 min in 2.0 mm chromatography, 30-90 AB, purity 100%, MS ESI calcd. for C26H44N03 [M+Hf?418, found 418.

220641-87-2, 220641-87-2 N-Methyltetrahydro-2H-pyran-4-amine 6991950, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, J.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; SALITURO, Francesco, G.; GRIFFIN, Andrew; BLANCO-PILLADO, Maria, Jesus; (296 pag.)WO2018/13613; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

N- Methyltetrahydro-2H-pyran-4-amine (12.4 mg, 0.11 mmol) was added to a solution of (S)-isopropyl 2-(6-(bromomethyl)-5-(4-(4-fluorophenethoxy)phenyl)-2-methyl-4-(7- azaspiro[3.5]nonan-7-yl)pyridin-3-yl)-2-(tert-butoxy)acetate (25 mg, 0.036 mmol) and Hunig’s base (0.02 mL, 0.11 mmol) in abs. EtOH (0.5 mL) and the solution was stirred for 4 h at rt. UPLC (M+H) = 730.5. KOH (20.16 mg, 0.36 mmol) was added to the solution above and the temperature was raised to 80 C for 16 h. TFA (0.028 mL, 0.359 mmol) was added and the reaction mixture was concentrated. The crude product was purified by prep HPLC to obtain (S)-2-(tert-butoxy)-2-(5-(4-(4- fluorophenethoxy)phenyl)-2-methyl-6-((methyl(tetrahydro-2H-pyran-4- yl)amino)methyl)-4-(7-azaspiro[3.5]nonan-7-yl)pyridin-3-yl)acetic acid 8.3 mg (33%). 1H NMR (500 MHz, DMSO) delta 7.39-7.36 (m, 2H), 7.31 (d, J=8.4 Hz, 1H), 7.13 (t, J=9.1 Hz, 2H), 7.06-7.04 (m, 3H), 5.86 (s, 1H), 4.27-4.19 (m, 2H), 3.92-3.87 (m, 2H), 3.80 (d, J=14.8 Hz, 1H), 3.41 (br. s, 3H), 3.24 (t, J=9.9 Hz, 2H), 3.21-3.16 (m, 2H), 3.06 (t, J=6.2 Hz, 2H), 2.72/2.58 (s, 3H), 2.55 (s, 3H), 2.26 (br. s, 1H), 1.84-1.47 (series of m, 14H), 1.13 (s, 9H). UPLC (M+H) = 688.5.

220641-87-2, The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; KADOW, John F.; NAIDU, B. Narasimhulu; ROMINE, Jeffrey Lee; SIVAPRAKASAM, Prasanna; ST. LAURENT, Denis R.; (204 pag.)WO2017/25864; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

d) Synthesis of 4-isopropyl-2-(methyl-tetrahydro-pyran-4-yl-amino)-thiazole-5-carboxylic acid ethyl ester To a solution of 2-bromo-4-isopropyl-thiazole-5-carboxylic acid ethyl ester (0.50 g, 1.80 mmol) in 1-methyl-2-pyrrolidone (10 ml) are added potassium carbonate (0.37 g, 2.70 mmol) and N-methyltetrahydro-2H-pyran-4-amine (0.62 g, 5.40 mmol) at RT and the reaction mixture is heated at 150 C. for 16 h. After completion of the reaction, the mixture is diluted with methyl tert-butyl ether (20 ml) and washed with water (3*20 ml) and brine (3*20 ml). The organic layer is dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 10% EtOAc/hexane) to yield 4-isopropyl-2-(methyl-tetrahydro-pyran-4-yl-amino)-thiazole-5-carboxylic acid ethyl ester (0.56 g, 1.92 mmol, 99%).

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

Reference£º
Patent; GRUeNENTHAL GMBH; LUCAS, Simon; Kuehnert, Sven; Bahrenberg, Gregor; Schroeder, Wolfgang; US2014/148454; (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.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

A solution of N-methyl-(tetrahydro-pyran-4-yl)-amine (0.25 g, 2.17 mmol), Cs2CO3 (1.41 g, 4.34 mmol) and compound 4 (0.85 g, 2.17 mmol) in THF (20 mL) is stirred at room temperature for 72 h. The reaction mixture is filtered through Celite , the solids are washed with ethyl acetate and DCM and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography (silica, eluent: heptanes, 50-100% ethyl acetate) to yield 374 mg of compound 5. Yield 41%;. LC-MS (LC Method b): retention time: 1.51 min, m/z 424 [M+H], 220641-87-2

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; HICKEY, Eugene, Richard; RIETHER, Doris; WU, Lifen; ZINDELL, Renee; BLUMIRE, Nigel; ERMANN, Monika; GLENN, Edward, Thomas; KHOR, Someina; ZAWADZKI, Przemyslaw; WO2010/147792; (2010); 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.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

N-Methyltetrahydro-2H-pyran-4-amine (19 mg,(bromomethyl)phenyl)boronic acid (23.60 mg, 0.111 mmol) were suspended in15 acetonitrile (2 mL). K2C03 (37.9 mg, 0.275 mmol) was added, then the reaction mixture was stirred at room temperature for lOh. The reaction mixture was concentrated, dioxane (1 mL) and water (0.5 mL), phosphoric acid, potassium salt (46.6 mg, 0.22 mmol) and 7- bromo-5 -(1 -(tetrahydro-2H-pyran-4-yl)- 1 H- 1,2,3 -triazol-5 -yl)pyrrolo[2, 1 -f] [1 ,2,4]triazin- 4-amine (20 mg, 0.055 mmol) (Intermediate Ri) were added to the residue. The reaction20 vessel was evacuated, backfilled with N2 and then degassed by bubbling N2 while being sonicated. Tetrakis triphenylphosphine (7 mg, 5.49 .imol) was added and the degassing process was repeated. The reaction mixture was heated at 140 C in a microwave for 45 mm. The reaction complex was filtered, washed with water and extracted with ethyl acetate (10 mL x 3). The organic layers were combined, dried and concentrated. The25 crude mixture was purified by preparative LC method C to provide 7-(3-((methyl (tetrahydro-2H-pyran-4-yl)amino)methyl)phenyl)-5 -(1 -(tetrahydro-2H-pyran-4-yl)- 1 H- 1 ,2,3-triazol-5-yl)pyrrolo[2, 1 -f] [1 ,2,4]triazin-4-amine (8.2 mg, 41% yield). LC/MS(M+H) = 489.30. ?HNMR(500 MHz, MeOD) 5 1.72 (m, 2H), 1.85 (m, 2H), 2.01 (m,2H), 2.29 (s, 3H), 2.42 (m, 2H), 2.75 (m, 1H), 3.42 (m, 2H), 3.47 (m, 2H), 3.73 (s, 2H),4.06 (m, 4H), 4.56 (m, 1H), 6.97 (s, 1H), 7.37 (d, 2H), 7.47 (t, 1H), 7.84 (s, 1H), 7.95 (m,2H), 8.01 (s, 1H).

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

[01477] To a stirred solution of methyl 3-bromo-4,6-dichloropyridine-2-carboxylate (600 mg, 2. ] mmol) in DMF (5ml) was added TEA (587 mu, 4.21 mmol) followed by N-methyloxan-4- amine (240 mg, 2.1 mmol) and the reaction mixture was heated at 80C for 20h. The reaction mixture was then cooled to room temperature and poured onto water ( 100ml), followed by extraction of the product into EtOAc (3x 100ml), washing of the combined organics with brine (50ml), drying with Na2S04 and evaporation. The crude product was then purified over a l Og silica Isolute column eluting with a gradient of 0% to 100% EtOAc in heptane to afford the title compound as a white solid (1 10 mg, 14%). LC-MS 100%, 1 .94 min (3.5 minute LC-MS method), m/z= 362.8/365.2/346.8, NMR (250 MHz, Chloroform-d) delta 6.87 (s, 1 H), 4.17 – 3.99 (m, 2H), 3.98 (s, 3H), 3.93 – 3.70 (m, 1 H), 3.41 (t, J = 1 0.9 Hz, 2H), 2.81 (s, 3H), 1 .93 (dd, J = 1 1 .9, 4.6 Hz, 2H), 1 .71 (d, J = 10.3Hz, 2H).

220641-87-2, The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

A mixture of 63 mg (0.15 mmol) E-4, 17 mg (0.15 mmol) methyl-(tetrahydro-pyran-4-yl)-amine, 500 muL NMP and 1 mL dioxane is stirred at 90C for 1 h. The reaction mixture is purified with RP chromatography (C18, 10-80% acetonitrile in water containing 0.1% formic acid). Yield: 12 mg (16%). HPLC-MS: M+H = 514; tR = 0 min.

220641-87-2, 220641-87-2 N-Methyltetrahydro-2H-pyran-4-amine 6991950, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; The designation of the inventor has not yet been filed; EP2546249; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics