Day: August 24, 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A solution of (Z)-phenyl N’-cyano-N-(3,4-difluorophenyl)carbamimidate (17.69 g, 64.70 mmol), 2-(3-bromopropoxy)tetrahydro-2H-pyran (22.80 g, 17.10 mL, 97.10 mmol) and K2CO3 (17.90 g, 129.00 mmol) in DMF (200 mL) was heated overnight at 85C. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (Hept:EtOAc 90: 10 to 50:50) to give 3-cyano-l-(3,4-difluorophenyl)-2-phenyl-l-(3- tetrahydropyran-2-yloxypropyl)isourea as a white solid (26.90 g, 49%). MS (ES+) m/z: 416.2 [M+H]+.

As the paragraph descriping shows that 33821-94-2 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; JAKOB-ROETNE, Roland; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; SARIE, Jerome Charles; VASTAKAITE, Greta; (70 pag.)WO2018/60300; (2018); 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

Tetrahydro-2H-pyran-3-ol (0.051 g, 0.499 mmol was taken into THF (1 mL) followed by the addition of 1M potassium butoxide in THF (0.5 mL, 0.5 mmol). The mixture was stirred for about 10 min, then (i?)- 2-(2-fluoropyridin-4-yl)-8-phenyl-7,8-dihydro-6H-pyrrolo[2′,r:2,3]imidazo[4,5-6]pyridine (0.055 g, 0.166 mmol, Preparation 84) in THF (1 mL) was added and the mixture was heated at about 120 C for about 20 min in a microwave. The reaction was cooled to rt, quenched with water and extracted with 100 mL EtOAc. The organics were collected, passed through a phase separator, concentrated under reduced pressure and the residue purified via silica gel chromatography eluting with 75-100% EtOAc/heptanes to afford the title compound (0.03 g, 45 %); LC/MS (Table 1, Method ab) Rt = 0.89 min; MS m/z: 413 (M+ H)+. (TNF IC50 = B).

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Reference£º
Patent; ABBVIE INC.; BREINLINGER, Eric, C.; COX, Phil, B.; DAANEN, Jerome; DIETRICH, Justin; DJURIC, Stevan; DOMBROWSKI, Amanda, W.; FRANK, Kristine, E.; FRIEDMAN, Michael, M.; GOMTSYAN, Arthur; LI, Huan-Qui; LONGENECKER, Kenton; OSUMA, Augustine; ROWLEY, Ann, Marie; SCHMIDT, Robert; VASUDEVAN, Anil; WILSON, Noel; (378 pag.)WO2016/168641; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydro-pyran-4-one (1.3 kg, 12.98 mol) and carbonic acid dimethyl ester (11.69 kg, 129.8 mol) was added solid potassium ferf-butoxide (1.89 kg, 16.08 mol) in portions at -10C over 2 h under nitrogen protection. The suspension was stirred at room temperature 10 h after the addition. LCMS (215nm) indicated that tetrahydro-pyran-4-one had been completely consumed. The reaction was acidified by HCl (2 N) to pH 6~7 and then the phases were separated. The organic phase was washed with water (3 Lx2) and the combined aqueous phases were extracted with MTBE (2.5 Lx2). The combined organic phase was concentrated under reduced pressure at 25C to remove most of MTBE. The residue was distilled out by oil pump (~200 Pa) at 74 C to give the title compound as colorless oil (545 g, 26.3%). CHN analysis: calculated (results). C 53.16 (53.10), H 6.37 (6.245), N 0.00 (0.00).

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

Reference£º
Patent; NOVARTIS AG; CHEUNG, Atwood, Kim; CHIN, Donoval, Noel; FAN, Jianmei; SHULTZ, Michael, David; TOMLINSON, Ronald, Charles; WO2013/10092; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 75 g (0.75 mol) of Compound 22 in THF (150 mL) is added a suspension of 28.4 g (0.75 mol) LiAlH4 in THF (600 mL) under nitrogen atmosphere maintaining the temperature below 30 C. with the aid of an ice-bath. Then the reaction is allowed to warm to room temperature and stirred for 5 h. The reaction is quenched by addition of saturated aqueous NH4Cl solution until effervescence ceased. The resulting precipitate is removed by filtration through Celite and washed with THF (150 mL). The filtrate is concentrated under reduced pressure to afford 71.1 g of Compound 23 as a pale yellow oil. Yield: 92%, 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 1.54 (2H, m), 1.81-1.92 (2H, m), 2.11 (1H, br. s.), 3.38-3.47 (2H, m), 3.83 (1H, tt, J=9.10, 4.38 Hz), 3.94 (2H, dt, J=11.88, 4.15 Hz).

As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/71196; (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

I: Toluene-4-sulfonic acid tetrahydropyran-4-ylmethyl ester intermediate p-Toluenesulfonyl chloride (29.8 g, 157 mmol) was added portionwise to a mixture of tetrahydro-2/-/-pyran-4-yl-methanol (20.0 g, 172 mmol) and pyridine (25.2 ml, 313 mmol) in dichloromethane (200 ml). The mixture was stirred at room temperature for 17 h, then quenched with aqueous hydrochloric acid (2 M; 100 ml). The layers were separated and the aqueous layer extracted with dichloromethane (2 x 100 ml). The organic layers were combined and concentrated in vacuo. Recrystallisation from dichloromethane: n-heptane (5:1 ) afforded toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester. The mother liquors were further purified by silica gel column chromatography eluting with 50% dichloromethane in n-heptane to yield a further quantity of toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester (total yield 41.6 g, 154 mmol).

As the paragraph descriping shows that 14774-37-9 is playing an increasingly important role.

Reference£º
Patent; AKZO NOBEL N.V.; WO2007/23143; (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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

General procedure: To a solution of Compound 141C (300 mg, 0.71 mmol) in dry THF (10 mL) was dropped a solution of phenylmagnesium bromide in THF (1 M, 1 mL, 1.0 mmol) at -78 over 5 minutes. The mixture was stirred at -78 for 1 hour. The reaction mixture was poured into saturated aqueous ammonium chloride solution (50 mL) and extracted with ethyl acetate (50 mL x 3). The combined organic layers was washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified with flash column chromatography on silica gel (ethyl acetate in petroleum, 20% v/v) to furnish Compound 141. LC-MS (ESI) m/z: 501 [M+H]+;1H-NMR (CDCl3, 400 MHz): delta (ppm) , 4.45 (s, 1H), 7.33-7.40 (m, 9 H), 7.45 (m, 2H), 7.59-7.61 (m, 2H).To a mixture of magnesium (159 mg, 6.6 mmol) and a small amount of iodine in anhydrous THF (10 mL) were added 1,2-dibromomethane (0.1 mL) and heated at 50 C for 10 minutes. To the mixture was dropped a solution of Compound 174A (1 g, 4.4 mmol) in THF (2 mL) and stirred at 80 C for 2 hours. The resulting Grignard reagent 174B was cooled down to room temperature and used directly in the next step.Compound 174 was synthesized by employing the procedure described for Compound 141 using Grignard reagent 174B in lieu of phenylmagnesium bromide. LC-MS (ESI) m/z: 1163 [2M+Na]+;1H-NMR (CDCl3, 400 MHz): delta (ppm) 1.64-1.71 (m, 1H), 1.82- 1.90 (m, 1H), 2.10-2.19 (m, 2H), 2.39-2.46 (m, 2H), 4.58-4.64 (m, 1H), 6.77 (d, J = 8.4 Hz, 2H), 7.27-7.29 (m, 2H), 7.30-7.34 (m, 4H), 7.37-7.38 (m, 2H), 7.56 (d, J = 8.0 Hz, 2H).Compounds 207B and 207 were synthesized by employing the procedures described for Compounds 174B and 141 using Compounds 207A, 207B, and at -60 C in lieu of Compounds 174A, phenylmagnesium bromide, and -78 C.Compound 207B as a Grignard reagent solution, which was directly used in the next step. Compound 207. LC-MS (ESI) m/z: 509 [M+H]+;1H-NMR (DMSO-d6, 400 MHz): delta (ppm) 1.02-1.12 (m, 1H), 1.54-1.65 (m, 2H), 1.75-1.86 (m, 1H), 1.94-2.01 (m, 1H), 304-3.18 (m, 2H), 3.77-3.86 (m, 2H), 3.39 (d, J = 8.4 Hz, 2H), 7.53 (d, J = 8.8 Hz, 2H), 7.68- 7.79 (m, 5H).

25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; (552 pag.)WO2017/214505; (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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

Step 1: (5-Methyl-i ,2-oxazol-3-yl)(oxan-4-yl)methanol4-Bromooxane (270 jiL, 2.42 mmol) was added drop wise to a stirred suspension of magnesium (58.9 mg, 2.42 mmol) and one crystal of iodine in THF (1700 jiL) at ambient temperature. The reaction mixture was stirred for 1 h before 5-methyl-i ,2 – oxazole-3-carbaldehyde (119 jiL, i.28 mmol) was added in a single portion. The reaction mixture was then stirred for 16 h. The reaction mixture was quenched with a minimumamount of saturated aqueous ammonium chloride (5 mL), and the volatiles were removed under reduced pressure. The crude reaction material was purified using reverse phase preparatory HPLC (TFA/acetonitrile/water). (5-Methyl-i ,2 -oxazol-3 -yl)(oxan-4- yl)methanol (90.9 mg, 0.461 mmol, 36 %) was isolated as a colorless oil. LC/MS (M+H) = 198.2; LC/MS RT = 0.84 mm (Column: Phenomenex Luna 30 x 2.0 mm 3u; MobilePhase A: 10:90 acetonitrile:water with 0.1% TFA; Mobile Phase B: 90:10 acetonitrile:water with 0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 2 mm; Flow: 1 mL/min).

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To 15 mL methanol were added 2-(7-fluoro-1-(2-fluorobenzyl)-1H-indazol-3 -yl)pyrimidine-4 ,5, 6-triamine (0.20 g, 0.54 mmol) and1-(tetrahydro-2H-pyran-4-yl)ethanone (0.10 g, 0.78 mmol). Then acetic acid (0.16 mL, 2.8 mmol)was added at 0 C. The mixture was heated to room temperature and stirred for 1 hour, thencooled to 0 C, and to the mixture was added sodium cyanoborohydride (0.17 g, 2.7 mmol).Then the resulting mixture was stirred at room temperature overnight. The reaction mixture wasconcentrated in vacuo to remove the solvent, and to the residue was added saturated aqueoussodium bicarbonate ( 40 mL ). The resulting mixture was extracted with ethyl acetate (30 mL x 2).The combined organic layers were washed with water (50 mL) and saturated brine (50 mL),dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated on a rotaryevaporator and the residue was purified by silica gel chromatograph ( dichloromethane /methanol(v/v) = 200/1, 0.5% triethylamine) to give a light yellow solid (0.11 g, 42.0%) MS (ESI, pos.ion) m/z: 480.7 (M+ 1);1H NMR (400 MHz, DMSO-d6) 8 (ppm) 8.56 (d, J = 8.0 Hz, 1H), 7.38-7.30 (m, 1H), 7.27- 7.19 (m, 2H), 7.19-7.09 (m, 2H), 6.97 (t, J = 7.0 Hz, 1H), 5.90 (s, 4H), 5.81 (s, 2H), 3.96-3.85 (m, 2H), 3.31-3.21 (m, 3H), 2.89-2.76 (m, 1H), 1.82- 1.74 (m, 1H), 1.72- 1.64 (m, 1H),1.64-1.51 (m, 1H), 1.40-1.26 (m, 2H), 0.95 (d, J= 6.4 Hz, 3H);19F NMR (376 MHz, DMSO-d6) 8 (ppm) -118.77 (d, J = 7.1 Hz), -134.46 (d, J = 7.1 Hz).

As the paragraph descriping shows that 137052-08-5 is playing an increasingly important role.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZUO, Yinglin; WANG, Xiaojun; YANG, Chuanwen; WANG, Jiancheng; CAO, Shengtian; WU, Fangyuan; ZHANG, Yingjun; GOLDMANN, Siegfried; (193 pag.)WO2018/188590; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of tetrahydropyran-4-ol (2.0 g, 20 mmol) and diisopropylethylamine (3.00 g, 23.5 mmol) in DCM (20 mL) was cooled to 0 C and methanesulfonyl chloride (2.50 g, 21.5 mmol) was added drop wise and stirred at rt for 2 h. The mixture was concentrated to dryness to give the title Compound (3.72 mg, 100% yield), which was used in the next step directly

2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; XIAO, Kun; ZHANG, Feihuang; ZHU, Yaoping; (528 pag.)WO2017/100662; (2017); 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

General procedure: Protocol A. To a suspension of the corresponding carboxylic acid 7-9 (0.25 mmol) in DMF (1 mL) were added DIEA (0.75 mmol, 3.0 eq), TBTU (0.325 mmol, 1.3 eq), HOBt (0.075 mmol, 0.3 eq) and the reaction mixture was stirred at rt for 5 min, followed by addition of the corresponding alcohol (1.1-5.0 eq). The reaction mixture was stirred at rt for 1-16h, then diluted with EtOAc (100 mL), washed with aqueous saturated sodium carbonate solution (50 mL), 0.1M HCl (50 mL), water (50 mL) and brine (50 mL). The organic phase was then dried over MgSO4 and concentrated under reduced pressure to afford the desired ester. Protocol B. To a solution of the corresponding carboxylic acid 7-9 (1.0 eq) in DCM were successively added DCC (1.0 eq), HOBt (1.0 eq) and DIEA (3.0 eq). The solution was stirred at rt for 30 minutes before the addition of the corresponding alcohol (1.1-5.0 eq). The reaction mixture was stirred at rt for 1-16h and then the solvent was removed in vacuo. The residue was partitioned between DCM and water and extracted with DCM. The organic layer was separated, washed consecutively with 2M sodium carbonate (or 1N NaOH), 1N HCl, brine, dried over MgSO4, and evaporated. Protocol C. To a solution of the corresponding carboxylic acid 7-9 (0.25 mmol) in THF or DCM (1 mL) cooled to 0 C was added 1-chloro-N,N,2-trimethyl-1-propenylamine, (0.5 mmol, 2.0 eq). The reaction mixture was stirred for 1-3h while warming up to rt, followed by addition of the corresponding alcohol (1.2 eq). The reaction mixture was stirred at rt for 1-16h and then the solvent was evaporated under reduced pressure. The residue was diluted with EtOAc and washed with saturated NaHCO3. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure.

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Reference£º
Article; Boland, Sandro; Defert, Olivier; Alen, Jo; Bourin, Arnaud; Castermans, Karolien; Kindt, Nele; Boumans, Nicki; Panitti, Laura; Van De Velde, Sarah; Stalmans, Ingeborg; Leysen, Dirk; Bioorganic and Medicinal Chemistry Letters; vol. 23; 23; (2013); p. 6442 – 6446;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics