Month: November 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1240390-36-6,tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Step 1 6-Chloro-4-(6-methyl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid amide (150 mg, 0.57 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (185 mg, 0.85 mmol) were dissolved in 1,4-dioxane (2.8 mL) and N,N-diisopropylethylamine (0.25 mL, 1.4 mmol). The reaction mixture was stirred at 150 C. for 4 d. Further tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (50 mg, 0.23 mmol) and N,N-diisopropylethylamine (0.04 mL, 0.23 mmol) was added in four portions (every 36 h for 144 h). The mixture was cooled, and then water and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with sodium chloride solution and dried over sodium sulfate. After concentration, the residue was purified by chromatography (silica, 0 to 7% methanol in dichloromethane) to give {(3R,4R)-4-[6-carbamoyl-5-(6-methyl-pyridin-2-ylamino)-pyridazin-3-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (60 mg, 18%) as a clear amorphous residue. This was 83% pure and was used directly without further purification. MS (EI/CI) m/z: 444 [M+H]., 1240390-36-6

As the paragraph descriping shows that 1240390-36-6 is playing an increasingly important role.

Reference£º
Patent; Hoffman-La Roche Inc.; Hermann, Johannes Cornelius; Kennedy-Smith, Joshua; Lucas, Matthew C.; Padilla, Fernando; Soth, Michael; US2013/178478; (2013); 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.4677-18-3,2-(Tetrahydro-2H-pyran-4-yl)ethanol,as a common compound, the synthetic route is as follows.,4677-18-3

Step 2: Synthesis of Compound D3To a solution of 1.63 g (12.5 mmol) of compound D2 in pyridine (15 mL) are added 3.58 g (18.8 mmol) of p-toluenesulfonylchloride. The reaction is stirred at room temperature for 5 h. The reaction mixture is concentrated under reduced pressure. The residue is dissolved 2M aqueous HC1 solution (20 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts are dried over Na2S04, filtered and the solvent is removed to give 1.9 g of compound D3 as off-white crystalline solid. Yield: 53%; ES-MS: m/z 285 [M+H]; 1H-NMR (500 MHz, CHLOROFORM-d) delta ppm 1.17 – 1.29 (2 H, m), 1.45 – 1.52 (2 H, m), 1.57 – 1.67 (3 H, m), 2.46 (3 H, s), 3.32 (2 H, td, 7=11.78, 1.93 Hz), 3.91 (2 H, dd, 7=11.28, 4.13 Hz), 4.08 (2 H, t, 7=6.14 Hz), 7.36 (2 H, d, 7=8.07 Hz), 7.80 (2 H, d, 7=8.44 Hz)

The synthetic route of 4677-18-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; ZINDELL, Renee, M.; ERMANN, Monika; WO2011/109324; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

TETRAHYDROPYRAN-3-OL (J. Org. Chem. , 1985,50, 1582) (4.66mL, 49MMOL) was dissolved in dichloromethane (137mL) and the solution treated with tetrabromomethane (19. 48g, 58MMOL). The reaction mixture was cooled to 0C and treated dropwise with a solution of TRIPHENYLPHOSPHINE (17. 98g, 69MMOL) in dichloromethane. The reaction mixture was allowed to return to room temperature and stirred for 4 hours. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography on silica gel eluting with DICHLOROMETHANE : methanol 98: 2 to yield the title product as a yellow oil, 6. 3G. 1H NMR (CDC13, 400MHZ) 8 : 2.02 (m, 2H), 2. 18 (m, 2H), 3.54 (t, 2H), 3.96 (m, 2H), 4.31 (m, 1 H)., 19752-84-2

As the paragraph descriping shows that 19752-84-2 is playing an increasingly important role.

Reference£º
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/96810; (2004); 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.141095-78-5,2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

Synthesis of 2-((2-chloro-4-(methylamino)pyrimidin-5-yl)oxy)-1-(tetrahydro-2H-pyran-4-yl) ethan-1-one To a stirred solution of the 2-chloro-4-(methylamino)pyrimidin-5-ol (3 g, 18.8 mmol) in CH3CN (60 mL) was added cesium carbonate (12.2 g, 37.70 mmol) followed by 2-bromo-1-(tetrahydro-2H-pyran-4-yl) ethan-1-one (3.9 g 18.8 mmol) at 0 C. and stirred for 1 h. After consumption of the starting material (monitored by TLC), the reaction was quenched with a sodium carbonate solution (20 mL) and extracted with EtOAc (2*20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford 2-((2-chloro-4-(methylamino)pyrimidin-5-yl)oxy)-1-(tetrahydro-2H-pyran-4-yl) ethan-1-one (2.5 g) as a yellow solid and used without further purification. LC-MS: 286.1 (M+); (column; X-Select CSH C-18 (50*3.0 mm, 3.5 mum); RT 2.86 min. 0.05% Aq TFA:ACN; 0.8 mL/min); TLC: 30% EtOAc:hexanes (Rf: 0.5)., 141095-78-5

The synthetic route of 141095-78-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FORUM Pharmaceuticals Inc.; Burnett, Duane A.; Bursavich, Matthew Gregory; McRiner, Andrew J.; (484 pag.)US2017/44182; (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.

0382] The crude N-methyltetrahydro-2H-pyran-4-amine (104 mg, 0.9 mmol) was dissolved in NMP (0.8 mL). To the solution, Cs2CO3 (366 mg, 1.13 mmol) and 4-(4,6- dichloropyrimidin-2-yl)morpholine (prepared as in Method 22) (80 mg, 0.34 mmol) were added at room temperature. The reaction mixture was heated to 950C. After 90 minutes, the reaction mixture was cooled to room temperature, filtered and purified by reverse phase preparative etaPLC yielding 24 mg (23%) of pure 6-chloro-N-methyl-2-morpholino- N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine. LC/MS (m/z): 313.2 (MH+), Rt 2.61 minutes., 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; NOVARTIS AG; WO2007/84786; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The title compound was prepared following the procedure for Intermediate 28, starting from 4- (bromomethyl)tetrahydro-2f/-pyran (0.16 g, 0.89 mmol) and /V-tert-butyl-2-({[2-(4-chloro-2- hydroxyphenyl)ethyl]sulfonyl}amino)benzenesulfonamide (0.20 g, 0.45 mmol) with cesium carbonate (0.22 g, 0.67 mmol) in DMF (3 mL). Purification by chromatography on silica using gradient elution 16-50 % EtOAc in heptane gave 126.4 mg (52 % yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) delta ppm 1.03 – 1.13 (m, 9 H) 1.17 – 1.32 (m, 2 H) 1.48 – 1.64 (m, 2 H) 1.79 – 1.94 (m, 1 H) 2.89 – 3.04 (m, 2 H) 3.25 (td, 2 H) 3.44 – 3.55 (m, 2 H) 3.75 – 3.87 (m, 4 H) 6.91 (dd, 1 H) 7.00 (d, 1 H) 7.17 (d, 1 H) 7.27 – 7.37 (m, 1 H) 7.58 – 7.70 (m, 2 H) 7.89 (dd, 1 H) 8.01 (s, 1 H) 8.77 (s, 1 H); MS (ES ) m/z 543, 545, 547 [M-H]

125552-89-8, The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ACTURUM LIFE SCIENCE AB; SOeDERMAN, Peter; SVENSSON, Mats A; KERS, Annika; OeHBERG, Liselott; HOeGDIN, Katharina; HETTMAN, Andreas; HALLBERG, Jesper; EK, Maria; BYLUND, Johan; NORD, Johan; (0 pag.)WO2016/85392; (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.344329-76-6,Tetrahydro-2H-pyran-4-carboxamide,as a common compound, the synthetic route is as follows.

2-ethyl-3-iodopyrazolo[1,5-a]pyridine 2.0 g (7.36mmol), tetrahydro-2H-pyrane-4-carboxamide 1.43 g (11.1mmol, 1.5eq), cuprous iodide (1.47mmol, 0.2eq) 0.28 g, 2,2-dimethyl-1,3-propanediamine (0.6eq) 0.452 g, potassium triphosphate (K3 PO4 ¡¤NH2 O) and 20 ml of xylene(10vol) under a nitrogen atmosphere (14.7mmol, 2.0eq) 3.39 g, 125 degrees temperature in heated, stirred for 18 hours. In the slowly cooled to a temperature of 95, 95 degrees 30 minutes after stirring, the temperature is slowly cooled within the 55 degree. 20 ml water (10vol) is added, the heating is stopped and gradual cooling to room temperature. In addition to the water temperature is sufficiently lowered from 6 ml of concentrated ammonia (3vol) ([35 degrees), for about 1 hour with stirring. The resulting suspension was filtered, washed with 12 ml of water (6vol), the resulting solid was returned to the reaction vessel, 12 ml of water, concentrated ammonia water added was stirred 0.5 hour to about 2 ml (1vol). The resulting suspension was filtered again, the resulting solid was 10 ml water (5vol), followed by 6 ml of ethyl acetate was washed (3vol). The filtration product was dried under reduced pressure, 1.56 g of the subject compound is a white solid, 78percent yield was obtained.

344329-76-6, 344329-76-6 Tetrahydro-2H-pyran-4-carboxamide 13197203, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Eisai R & D Management Co., Ltd.; Hoshino, Takehisa; Sato, Keizo; Shimomura, Naoyuki; (7 pag.)JP2017/100995; (2017); A;,
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.40191-32-0,Tetrahydro-2H-pyran-4-carbonyl chloride,as a common compound, the synthetic route is as follows.

Intermediate 4 [(S)-1-(Tetrahydro-pyran-4-carbonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester To a vigorously stirring solution of tetrahydro-2H-pyran-4-carbonyl chloride (0.455 g, 3.06 mmol) in CH2Cl2 (10 mL) was added simultaneously portionwise sat. NaHCO3(aq) (10 mL) and a solution of the (S)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (570 mg, 3.06 mmol) at rt. The resulting biphasic mixture was stirred vigorously at rt for 3 h. The organic layer was separated by filtration through a phase separation tube, concentrated in vacuo and purified by flash chromatography on silica gel with CH2Cl2/MeOH to give [(S)-1-(tetrahydro-pyran-4-carbonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester as a colourless gum (0.623 g, 68% yield) LCMS: [M+H]+=299.6, Rt(7)=0.73 min.

40191-32-0, The synthetic route of 40191-32-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; US2015/342951; (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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

To a solution of 3- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy) -4′- ((4′-chloro-5,5-dimethyl-3, 4, 5, 6-tetrahydro- [1, 1′-biphenyl] -2-yl) methyl) – [1, 1′-biphenyl] -4-carboxylic acid (30 mg, 0.0533 mmol) in DCM (50 mL) was added HATU (30.4 mg, 0.08 mmol) and triethylamine (27 mg, 0.267 mmol). The mixture was stirred at room temperature for 1 hour. Then to the mixture were added 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (33.6 mg, 0.107 mmol). The mixture was stirred at room temperature for overnight. The mixture was washed with brine, dried over Na 2SO 4, concentrated and purified by chromatography column on silica (eluent: EA/PE = 1/1 then MeOH/DCM = 1/10) to give the crude product. The crude product was further purified by prep-TLC (MeOH/DCM = 1/20) to give the product (1.79 mg, 3.9%). 1H NMR (400 MHz, DMSO-d 6) delta ppm: 12.35 (s, 1H), 11.73 (s, 1H), 8.68-8.50 (m, 2H), 8.10-8.02 (m, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.67-7.56 (m, 2H), 7.56-7.48 (m, 1H), 7.43 (d, J = 8.0 Hz, 3H), 7.37 (d, J = 8.2 Hz, 2H), 7.17 (d, J = 8.2 Hz, 2H), 7.10 (d, J = 8.0 Hz, 2H), 6.99 (s, 1H), 6.40 (s, 1H), 5.41-5.21 (m, 1H), 3.85 (d, J = 8.5 Hz, 2H), 3.28-3.15 (m, 6H), 2.07-1.94 (m, 4H), 1.94-1.79 (m, 3H), 1.67-1.54 (m, 2H), 1.38-1.31 (m, 2H), 0.91 (s, 6H). MS (ESI, m/e) [M+1] + 860.1.

1228779-96-1, 1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (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.4295-99-2,4-Cyanotetrahydro-4H-pyran,as a common compound, the synthetic route is as follows.

a 4-[[4-(2-Hydroxyethyl)phenyl]methyl]tetrahydropyran-4-carbonitrile Obtained by operating as in example 87a, from 6.3 g (62.2 mmoles) of diisopropylamine in 104 ml of tetrahydrofuran, 38.7 ml (62.0 mmoles) of a 1.6M solution of n-butyllithium in hexane, 9.3 g of 1,3-dimethylimidazolidin-2-one, 8.8 g (56.7 mmoles) of 2,3,5,6-tetrahydro-4H-pyran-4-carbonitrile (prepared according to Gibson C. S. and Johnson J. D. A., J. Chem. Soc. (1930), 2525-30) in 93 ml tetrahydrofuran and 17.7 g (62 mmoles) of the compound prepared in example 26a. After purification by chromatography on a column of silica in a hexane-ethyl acetate (1:1) mixture, there is obtained 10.5 g (yield=75.5%) oil. I.R. (film): nu (OH)=3400 cm-1; (C N)=2220 cm-1. N.M.R. (CDCl3): delta=1.55 (1H,s, exchangeable with D2 O); 1.6-1.9 (4H,m); 2.8 (2H,s); 2.8 (2H,t, J=6.75 Hz); 3.4-4.2 (6H,m); 7.1 (4H,s).

4295-99-2, The synthetic route of 4295-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Lipha Lyonnaise Industrielle Pharmaceutique; US5387709; (1995); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics