Day: September 7, 2020

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.

A mixture of 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(4-oxocyclohexyl) benzoic acid (2.0g, 5.71mmol), 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzene sulfonamide (1.8 g, 5.71 mmol), EDCI (1.64 g, 8.57 mmol), DMAP (1.05 g, 8.57 mmol) and TEA (1.15 g, 16.42 mmol) in DCM (20 mL) was stirred at ambient temperature for 20 hours. The reaction mixture was concentrated in vacuum, then purified by chromatography column on silica (eluent: DCM/MeOH = 100/1 to 50/1) to afford 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy) -N- ((3- nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) phenyl) sulfonyl)-4-(4-oxocyclohexyl) benzamide (1.5 g). MS (ESI) m/e [M+1] + 648.1.

1228779-96-1, The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

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.127956-11-0,Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate,as a common compound, the synthetic route is as follows.

The pyranone-2-carboxylic acid methyl ester was first poured into the autoclave and the temperature was lowered to -78C.The temperature was added with hydrogen fluoride and sulfur tetrafluoride, the molar ratio of beta-keto acid ester and SF4 and HF was 1:3:18, and the temperature was raised to 100C. The reaction was carried out for 24 hours to obtain the intermediate 1,1-difluoro-2-pyrancarboxylic acid. Methyl esters.The reaction solution was diluted with water and then extracted with ethyl acetate.The aqueous phase was washed twice with saturated sodium bicarbonate solution and the organic phase was dried and spin-dried to give the intermediate 1,1-difluoro-2-pyrancarboxylic acid methyl ester., 127956-11-0

127956-11-0 Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate 14666555, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Wuhan Yao Ming Kant, Immanuel New Drug Development Co., Ltd.; He Xin; Wu Rongfu; Liu Zhouya; Ma Jianyi; Zhang Zhiliu; Jiang Luyong; Ma Rujian; (6 pag.)CN107903205; (2018); 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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

(r) 2-alpha, 3-alpha-dihydroxy-4beta-[2-(tetrahydropyran-4-yl)-ethylamino-9-adenyl]-cyclopentane-1beta-N-ethylcarboxamide; the starting 2-(tetrahydro-pyran-4-yl)-ethylamine can be prepared from tetrahydropyran-4-one e.g. by Wittig condensation with diethyl cyanomethyl phosphonate followed by hydrogenation and reduction with lithium aluminum hydride;

29943-42-8, 29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Ciba-Geigy Corporation; US4954504; (1990); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4295-99-2, 4-Cyanotetrahydro-4H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4295-99-2

In a 50 ml glass flask provided with stirrer, thermometer and reflux condenser, 1.05 g (9.5 mmol) of 4-cyanotetrahydropyran having a purity of 99% synthesized in Example 5, and 10 ml (60 mmol) of 6 mol / l hydrochloric acid was added, the mixture was reacted at 80 to 90C for 7 hours. After completion of the reaction, the reaction solution was analyzed by gas chromatography (internal standard method) and 1.06 g of tetrahydropyran-4-carboxylic acid was obtained (reaction yield: 86%).

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; UBE INDUSTRIES LIMITED; NISHINO, SHIGEYOSHI; HIROTSU, KENJI; SHIMA, HIDEYOSHI; IWAMOTO, KEIJI; HARADA, TAKASHI; (13 pag.)JP5673729; (2015); B2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

b) (Z)-Phenyl N’-cyano-N-(3,4-difluorophenyl)-N-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)carbamimidate; To a solution of (Z)-phenyl N’-cyano-N-(3,4-difluorophenyl)carbamimidate (286 mg, 1.05 mmol) and 2-(3-bromopropoxy)tetrahydro-2H-pyran (369 mg, 277 muL, 1.57 mmol) in DMF (10.5 mL) was added at room temperature under an athmosphere of nitrogen potassium carbonate (289 mg, 2.09 mmol). The suspension was heated to 85 C. over night. Additional 2-(3-bromopropoxy)tetrahydro-2H-pyran (140 muL, 0.8 mmol) and potassium carbonate (145 mg, 1.05 mmol) was added and the reaction was heated for 5 hours to 85 C. Water was added and the reaction was extracted twice with diethyl ether. The combined organic layers were washed with water and with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a light yellow viscous oil (202 mg, 46%) after column chromatography on silica gel using a gradient of heptane/ethyl acetate 4:1 to 1:1 (v/v) as eluent.MS ISP (m/e): 332.1 (100) [(M-THP+H)+], 416.3 (5) [(M+H)+].1H NMR (DMSO-D6, 300 MHz): delta (ppm)=7.38 (t, 2H), 7.26-7.16 (m, 3H), 7.05 (m, 3H), 4.52 (t, 1H), 3.97 (t, 2H), 3.85 (m, 2H), 3.48 (m, 2H), 2.00 (pent, 2H), 1.79 (m, 1H), 1.68 (m, 1H), 1.55 (m, 4H)).

33821-94-2, The synthetic route of 33821-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Baumann, Karlheinz; Goetschi, Erwin; Green, Luke; Jolidon, Synese; Knust, Henner; Limberg, Anja; Luebbers, Thomas; Thomas, Andrew; US2011/190269; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydropyran-4-methanol (5.0 g, 43 mmol) in dichlormethane (30 mL) was added triethylamine (7.2 mL, 51.6 mmol). The mixture was cooled to 0 C., and methane sulfonyl chloride (4.0 mL, 51.6 mmol) was added. The mixture was stirred in an ice bath for several hours and was slowly warmed to RT. The reaction then was stirred at RT for 18 h. The reaction was concentrated in vacuo. The residue was taken up in EtOAc and was washed with saturated NaHCO3. The organic layer was dried [MgSO4], filtered, and concentrated in vacuo to give the mesylate Part A(v)(a) compound (8.3 g, quantitative yield) as a white, needle-like solid.

14774-37-9, 14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Bristol-Myers Squibb Company; US2008/21052; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 2: Preparation of (3R)-5-methyl-3 -(2-oxo-2 (F(I RVl -phenylethyll amino lethvD hexanoic acid compound (24); [0076] A three-necked flask equipped with an addition funnel, thermometer pocket , drying tube and mechanical stirrer, was charged with ethyl acetate (100 ml), (R)-(+)- phenylethylamine (26.69 g, 0.0.22mole) and 4-dimethylaminopyridine (2.69 g, 0.15. mole). The mixture was cooled to a temperature of -50 to -60 C, followed by addition of a solution of 3-isobutyl glutaric anhydride (25 g, 0.147 mole) in ethyl acetate (50 ml), over a period of 25-30 minutes, and stirring for additional 1.5-2 hours, at a temperature of -50 to -60C. The mixture was then extracted with 5-4 percent aqueous solution of NaOH (500 ml), and the aqueous phase was separated. The pH of the aqueous phase was adjusted to 2-2.5 by adding a solution hydrochloric acid (1-12N). The aqueous phase was further extracted with ethyl acetate (1 x 150 ml and 1 x 100 ml), followed by drying the combined ethyl acetates extracts over anhydrous sodium sulfate, and stripping off the solvent to obtain a residue. The residue was crystallized from ethyl acetate and toluene mixture to get 35.43 g (82.87 percent yield) of a white solid of (3R)-5-methyl-3-(2-oxo-2-{[(lR)-l-phenylethyl]amino}ethyl) hexanoic acid with an optical purity of 99.4 percent, as measured by chiral HPLC., 185815-59-2

185815-59-2 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2007/35789; (2007); 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.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Preliminary experiments related to the acylative KR of the racemic sec-thiol 1 with glutaric anhydride (2a) in the presence of bifunctional (thio)urea-derived organocatalysts 10-12 and sulphonamide 13 (Table 1 ). Initial results were far from encouraging – acylation proceeded smoothly at low catalyst loading (5 mol%), but resulted in products of low enantiomeric excess (entries 1 -4). Of the four catalysts tested sulphonamide 13 proved superior to the (thio)urea- derivatives and could promote the KR with a very modest selectivity (kfast/kS|0W) of 1.5 (13% ee at 50% conv., entry 4). Further experimentation identified methyl ie f-butylether (MTBE) as the optimal solvent overall, although the KR of 1 was slower but more selective in THF (entries 4-7).[0061] These results represented the first examples of direct catalytic asymmetric KR of a thiol. Subsequently, KR reactions using 3-substituted achiral anhydride electrophiles 3a-5 were tried. This complicated matters considerably, as now control over the formation of 4 possible thioester diastereomers is required. In addition, it allowed for the possibility of a conceptually novel type of catalytic process where both kinetic resolution and anhydride desymmetrisation occur simultaneously. Gratifyingly, this proved to be the case – use of anhydrides 3a-5 resulted in more enantioselective acylations (entries 8-1 1 ), with methyl glutaric anhydride (3a) proving optimal. Using this electrophile the resolved thiol could be isolated in 33% ee at 50% conversion (using either 1 or 5 mol% of catalyst 13), corresponding to S = 2.7.[0062] Product esters 7a and 7b were both formed with excellent enantioselectivity (>90% ee) and with encouraging diastereocontrol (67:33 dr, entry 8). With respect to the anhydride, the desymmetrisation aspect of the reaction was highly selective – the parameter eedesymm (Table 1 ) represents the percentage excess of products derived from attack of the thiol 1 at one prochiral anhydride carbonyl moiety over the other (i.e. the enantiomeric excess of the desymmetrised product if the combined thioester diastereomers were substituted by an achiral (non-hydroxide) nucleophile without racemisation). It is also noteworthy that in the presence of triethylamine as an achiral catalyst the diastereoselectivity is reversed, with 19 as the major diastereomer.[0063] Next the steric and electronic characteristics of the catalyst were systematically varied through the synthesis and evaluation of sulfonamides 14-17. While the electron deficient pentafluorophenyl-substituted catalyst fared a little better than 13, less acidic analogues 15-17 respectively possessed enhanced selectivity profiles (entries 12-15). Given the superiority of the hindered promoter 16, it was decided to accentuate the steric bulk of the sulfonamide further via the synthesis of the novel catalyst 18, which proved almost as active as 13 yet promoted the acylation with a synthetically useful KR selectivity of 8.5 (entry 16). Further optimisation of the reaction conditions (entries 17-19) resulted in the KR of thiol 1 with outstanding selectivity (S = 25.5) – allowing the isolation of resolved (f?)-1 in 90% ee at 54% conversion, along with ester 7a (formed as the major diastereomer, 89:11 dr) in 98% ee, with an excellent attendant eedesymm of 96% (entry 19).; [0064] Thus, under optimum conditions 18 is capable of mediating the highly efficient and selective KR of a substrate class previously outside the orbit of direct enantioselective catalytic acylation, with the simultaneous desymmetrisation of a synthetically useful class of inexpensive achiral anhydride acylating agent – also with excellent enantioselectivity. To demonstrate that the desymmetrisation and kinetic resolution processes are synergistic, we next carried out the process under optimum conditions using the non-prochiral anhydrides 2a, 2b and 3b (entries 20-22). Kinetic resolution was either too slow or proceeded with lower enantioselectivity using these electrophiles.[0065] Attention now turned to the question of substrate scope (Table 2). It was found that variation of the steric bulk of both the aromatic and aliphatic substituent is well tolerated by the catalyst – for example, a-Me, -Et, -‘Pr and -fBu derivatives of benzyl mercaptan (i.e. 1 and 20- 22, entries 1 -4) could be resolved with excellent selectivity (up to S > 50), resulting in the isolation of the unreacted thiol with >90% ee at ca. 50% conversion. A strong correlation between increasing aliphatic substituent bulk and selectivity was observed; however it is noteworthy that even the challenging substrate 20 (where the steric discrepancy between the two carbon-based substituents is smallest) could be resolved with synthetically useful selectivity. Variation of the characteristics of the aromatic substituent produced interesting results – substitution in the para-position either slightly reduces or has no impact onenantioselectivity (23-25, entries 5-7), while steri…

185815-59-2, 185815-59-2 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; THE PROVOST, FELLOWS AND SCHOLARS OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH, NEAR DUBLIN; CONNON, Stephen Joseph; PESCHIULLI, Aldo; PROCURANTI, Barbara; WO2011/70028; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

EXAMPLE 3 ll- (4- [2- (2-hydroxyethoxy) ethyl]-l- piperazinyl) dibenzo [b, f] [1, 43thiazepine (base Quetiapine) To 10.43 g (63.4 MMOLS) OF 2- (2-CHLOROETHOXY)-TETRAHYDRO- 2H-pyrane are added successively 5 g (14. 7 mmols) of 2- (4- dibenzo [b, f] [1.4] THIAZEPINE-11-IL-PIPERAZINE-1-IL) ethanol, 5 g of powdered potassium hydroxide and 0.49 g of Aliquat 336 catalyst. The mixture is heated at 40C for 20 hours with thorough stirring. The synthesis proceeds as in Example 1, yielding 4.23 g (75%) of the product of the title as a light yellow oil, having IR AND 1H-RMN spectra identical to those of the product obtained in Example 1., 5631-96-9

The synthetic route of 5631-96-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LABORATORIOS VITA, S.A.; WO2005/14590; (2005); 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.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.

To a solution of 2,2,6,6-tetramethyl-tetrahydro-pyran-4-one (3.00 g, 19.20rnmol), p-toluenesulfonylrnethyl isocyanide (4.90 g, 24.96 rnmol), and t-butanol (3.06ml, 32.64 mmol) in 75 ml dimethoxyethane at 0 C was added potassium tbutoxide(5.38 g, 48.01 mrnol) at such a rate that the temperature did not increase15 above 10 C. After addition was cmnplete the mixture was allow to attain RT andthen heated at 35 C overnight. The mixture was then cooled to RT and 50 ml ofdiethyl ether was added and the mixture was filtered. The filtrate was concentratedand redissolved in 50 ml of diethyl ether and filtered to remove the ppt. The filtratewas again concentrated and then dissolved in 50 rnl of 2.25 M KOH and refluxed20 overnight. The mixture was cooled and washed with 2 X 50 ml of DCM. The pH ofthe aqueous layer was then adjusted to 2 with cone HCI and the product extractedwith EtOAc (2 X 50 ml). The organic phase was dried over Na2S04, filtered andconcentrated to give 2.85 g (80%) of the title compound as an off-white solid whichwas used without further purification.1H NMR (CHLOROFORM-d) o: 2.78 (tt, J = 12.9, 3.3 Hz, 1 H), 1.77 (dd, J = 12.9, 3.3 Hz, 2H), 1.39 (t, J = 12.9 Hz, 2H), 1.20 (s, 6H), 1.17 (s, 6H).

1197-66-6, The synthetic route of 1197-66-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; WALL, Mark; SUBASINGHE, Nalin; SUI, Zhihua; FLORES, Christopher; WO2014/28803; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics