Heterocyclic Building Blocks-Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.110238-91-0,Methyl tetrahydro-2H-pyran-4-carboxylate,as a common compound, the synthetic route is as follows.

[0511] Concentrated aqueous ammonia (50 mL) was added to methyl tetrahydro-2H-pyran-4-carboxylate (50 g, 347 mmol) and the reaction mixture was stirred for 43.5 hours at room temperature. The reaction mixture was then cooled in an ice water bath, after which the precipitate was filtered out and dried under reduced pressure at 40¡ã C. to afford 33.4 g of the title compound (74.6percent yield). [0512] 1H NMR (400 MHz, DMSO-d6) delta 1.45-1.62 (m, 4H), 2.28 (tt, J=11.1, 4.4 Hz, 1H), 3.26 (ddd, J=11.4, 11.4, 2.7 Hz, 2H), 3.82 (br d, J=11.4 Hz, 2H), 6.74 (br s, 1H), 7.21 (br s, 1H)., 110238-91-0

110238-91-0 Methyl tetrahydro-2H-pyran-4-carboxylate 2773520, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Hibi, Shigeki; Hoshino, Yorihisa; Kikuchi, Koichi; Shin, Kogyoku; Takahashi, Yoshinori; Fujisawa, Masae; Shibata, Hisashi; Ino, Mitsuhiro; US2004/224974; (2004); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-65-0, (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of Example 203A (1.9 g, 7.0 mmol), 2-amino-5-methylthiazole (0.80 g, 7.0 mmol) and tetrabutylammonium iodide (1.3 g, 3.5 mmol) in 3 mL of N,N- dimethylformamide was warmed to 85 0C and was allowed to stir for 24 hours. The mixture was diluted with 10 mL OfCH2Cl2, washed with 10% aqueous NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 10% methanol in ethyl acetate then 9:1 :0.1 CH2Cl2 : methanol : NH4OH) afforded the title compound. MS (DCI/NH3) m/z 213 (M+H)+, 101691-65-0

Big data shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; ABBOTT LABORATORIES; WO2009/67613; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1240390-36-6, tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

10554] A mixture of compound 30-A (553 mg, 2.556 mmol), the pyrone 6-B (619 mg, 2.556 mmol), and NaHCO3 (435 mg, 5.178 mmol) in water (5 mE) and ethanol (5 mE) was stirred at room temperature. After 30 mm, the reaction mixture was concentrated to remove most of the solvent and the residue was mixed with dichioromethane (about 40 mE) and stirred vigorously before drying (Mg504). The dried solution was concentrated. The residue was dissolved in Dichloromethane (2 mE) and treated with 4 N HC1 in dioxane (6 mE). Afier 40 mm, the mixture was concentrated and dried in vacuum overnight. A mixture of the residue and DI3U (1.9 mE, 12.71 mmol) in toluene (19 mE) was stirred at 1000 C. After 30 mm, the reaction mixture was cooled down to room temperature, dissolved in dichloromethane, and concentrated. The residue was purified by column chromatography on silica gel (40 g column) using ethyl acetate-20% methanol in ethyl acetate as eluents to obtain impure compound 30-C. The impure compound 30-C was dissolved in DMF and purified by preparative HPEC to get compound 30-C as 1:1 mixture with trifluoroacetic acid. ?H NMR (400 MHz, Chloroform-d) oe 9.92 (s, 1H), 8.33 (s, 1H), 7.67 (s, 1H), 4.51 (dt, J=12.2, 4.1 Hz, 1H), 4.21-4.04 (m, 3H), 3.95 (s, 3H), 3.84 (s, 3H), 3.73 (d, J=12.8 Hz, 1H), 3.54 (td, J=12.3, 2.2 Hz, 1H),2.24 (qd, J=12.6, 4.8 Hz, 1H), 1.94 (dd, J=13.1, 4.9 Hz, 1H). ECMS-ESI (mlz): [M+H] calculated for C,4H,7N205: 309. 11. found: 309.17.

1240390-36-6, The synthetic route of 1240390-36-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Gilead Sciences, Inc.; Bacon, Elizabeth M.; Cai, Zhenhong R.; Cottell, Jeromy J.; Ji, Mingzhe; Jin, Haolun; Lazerwith, Scott E.; Morganelli, Philip Anthony; Pyun, Hyung-jung; (101 pag.)US2016/176870; (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.4677-18-3,2-(Tetrahydro-2H-pyran-4-yl)ethanol,as a common compound, the synthetic route is as follows.,4677-18-3

General procedure: To the solution of 2-tetrahydropyran-4-ylethanol (13.26 1iL, 1 equiv.) in THF (500 1iL) at 0C, DIPEA (24.4 1iL, 1.4 equiv.) and triphosgene (11.9 mg, 0.4 equiv.) were added. Reaction mixture was stirred at 0 C for 15 mm, and at RT for 15 mm. Then DIPEA was added (48.8 1iL, 2.8 equiv.), followed by the solution of 3-[1-(azetidin-3-ylsulfonyl)-4-piperidyl]-1H-pyrrolo[2,3-b]pyridine (32 mg, 1 equiv.) in THF (1 mL). The reaction mixture was left to stir at room temperature overnight. Solvent was removed in vacuo, and the obtained residue was purified by flash chromatography on silica gel (eluting with DCM / MeOH gradient; 0-10 % of MeOH). After collecting the appropriate fractions, solvent was removed in vacuo and the obtained white solid was triturated with diethyl ether toafford the expected product (19.24 mg). LCMS: IVIW (calcd): 476.59; MS (ES, m/z):477.71 [M+H].

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

Reference£º
Patent; E-THERAPEUTICS PLC; RO?CIC, Maja; KOLUND?IC, Filip; ?IHER, Dinko; POLJAK, Tanja; VADLAMUDI, Srinivasamurthy; STUBBERFIELD, Colin; (503 pag.)WO2018/78360; (2018); A1;,
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

A mixture of 5-[(4-chlorophenyl)methyl]-4-[3-(trifluoromethoxy)phenoxy]-1,3,5,8-tetraazatricyclo[8.3.0.0^[2,6]]trideca-2(6),3-diene-7,9-dione(150 mg, 300 mmol, 1 equiv.), 2-(3-bromopropoxy)oxane (198.1 mg, 890 mmol, 3.000 equiv.) and K2CO3 (122.7 mg, 0.89 mmol, 3.0 equiv.) in DMF (15.0 mL) was stirred at 50 C for 16 hours. The reaction was cooled to room temperature and added EtOAc (100 mL) and H2O (100 mL). The organic layer was washed with brine (2×30 mL) and concentrated under reduced pressure which was purified by reverse phase flash with the following conditions (Column: Spherical C18 Column, 20-40um, 120 g; Mobile Phase A: Water (0.1% HOAc), Mobile Phase B: ACN; Flow rate: 60 mL/min; Gradient: 90% B to 98% B in 10 min, 254 nm) to afford 5-[(4-chlorophenyl)methyl]-8-[3-(oxan-2-yloxy)propyl]-4-[3-(trifluoromethoxy)phenoxy]-1,3,5,8-tetraazatricyclo[8.3.0.0^[2,6]]trideca-2(6),3-diene-7,9-dione (185 mg, 96.31%) as a light yellow oil.1H NMR (400 MHz, Chloroform-d) delta 7.43 (t, J = 8.3 Hz, 1H), 7.30 (s, 4H), 7.27 – 7.19 (m, 2H), 7.13 (d, J = 8.3 Hz, 1H), 5.73 (d, J = 14.9 Hz, 1H), 5.43 (d, J = 15.1 Hz, 1H), 4.65 – 4.49 (m, 1H), 4.15 (ddt, J = 19.0, 13.7, 7.1 Hz, 1H), 3.98 -3.61 (m, 4H), 3.46 (tt, J = 16.5, 7.6 Hz, 4H), 2.85 (dt, J = 12.2, 6.3 Hz, 1H), 2.18 – 2.02 (m, 2H), 1.99 – 1.77 (m, 3H), 1.76 – 1.48 (m, 6H)., 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; GOLDFINCH BIO, INC.; DANIELS, Matthew, H.; YU, Maolin; HARMANGE, Jean-Christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; CASTLE, Neil, A.; MALOJCIC, Goran; (0 pag.)WO2019/173327; (2019); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1172623-99-2,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

1H (11.53 g, 35.03 mmol) was dissolved in dichloromethane (130 mL) Cooling to 0C ,Dess-Martin oxidant (29.72 g, 70.06 mmol) was added portionwise to the reaction solution, Naturally rose to room temperature for 4 hours. Cooling to 0C ,Saturated sodium bicarbonate solution (60 mL) was added dropwise to the reaction solution, stirred for 20 minutes,The organic phase was washed with saturated sodium bicarbonate solution (30 mL x 2), and the organic phase was dried over anhydrous sodium sulfate and dried over anhydrous sodium sulfate (60 mL x 3). The organic phase was washed with saturated sodium bicarbonate solution (30 mL x 2) , Filtered and concentrated by column chromatography (petroleum ether / ethyl acetate (v / v) = 10: 1-4: 1) to give white crystalline powder intermediate 1 (10.85 g, yield 94.7%). (30 mL x 2), and the solvent was concentrated to give a white solid, 1H (7.9 g, 84% yield).

1172623-99-2, As the paragraph descriping shows that 1172623-99-2 is playing an increasingly important role.

Reference£º
Patent; Sichuan Haisco Pharmaceutical Co.,Ltd.; FAN, JIANG; ZHANG, CHEN; PENG, FEI; WU, YE; FENG, JIANCHUAN; WANG, JIANMIN; ZHENG, SUXIN; WEI, YONGGANG; YE, FEI; (350 pag.)TW2017/8220; (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.127956-11-0,Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate,as a common compound, the synthetic route is as follows.

[0523] To the mixture of 2-ethylisothiourea (9.07 g, 49.00 mmol, HBr salt) in H20 (50.00 mL) under dark was added Na2C03 (5.19 g, 49.00 mmol). Then to the mixture was added methyl 4-oxotetrahydro-2H-pyran-3-carboxylate (7.75 g, 49.00 mmol). The mixture was stirred under dark at 25 C for 16 h TLC (petroleum ether/EtOAc=l : 1, Rf=0.3) showed one new main spot. The mixture was filtered, the solid was washed with water (30 mL), petroleum ether/EtOAc=20: l (20 mL). Then the solid was dried under reduced pressure to afford the title compound (8.01 g, crude) as an off-white solid. 1H NMR (400 MHz, DMSO-i/6) delta 10.69 (s, 1H), 5.87 (s, 1H), 3.83 (s, 1H), 3.63-3.49 (m, 3H), 3.00-2.89 (m, 2H), 2.40 (s, 1H), 1.24 (t, J= 7.2 Hz, 3H)., 127956-11-0

The synthetic route of 127956-11-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; KIM, Ji-In; POYUROVSKY, Masha; LIU, Kevin; BARSOTTI, Anthony; MORRIS, Koi; (344 pag.)WO2016/210330; (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.14774-37-9,Tetrahydropyran-4-methanol,as a common compound, the synthetic route is as follows.

Prepared as described by adaptation of the following literature reference: Radziszewski, J. G. et al. J. Am. Chem. Soc. 1993, 115, 8401. To 97 g (810 mmol) of (tetrahydro-pyran-4-yl)-methanol in 2-methyltetrahydrofuran (190 mL) are added 165 mL of 50% aq. NaOH solution. To this stirred suspension is added dropwise with cooling a solution of p-toluene-sulfonylchloride (283 g, 1.46 mol) in 2-methyltetrahydrofuran (280 mL). The reaction is stirred at 30-35 C. for 18 h. The suspension is poured into a mixture of ice-water (280 mL) and aq. HCl solution (37%, 203 mL). After addition of methylcyclohexane (1.4 L) and further ice-water (0.2 L), the reaction mixture is stirred for 2 h in an ice-bath. The resulting crystalline precipitate is isolated by filtration and washed with methylcyclohexane (0.5 L) and water (0.5 L). Drying under reduced pressure at 40 C. gave 216 g of toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester. Yield: 99%; ESI-MS: 271 [M+H]+, 14774-37-9

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

Reference£º
Patent; Boehringer Ingelheim International GmbH; Riether, Doris; Binder, Florian Paul Christian; Doods, Henri; Mueller, Stephan Georg; Nicholson, Janet Rachel; Sauer, Achim; US8865744; (2014); B1;,
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

Step 2: Synthesis of Toluene-4-sulfonic acid tetrahydro-pyran-4-yl ester To a solution of 133 g (1.31 mol) of tetrahydro-pyran-4-ol in pyridine (1.5 L) are added 373 g (1.95 mol) of p-toluenesulfonylchloride portionwise at 10 C. After complete addition the reaction is allowed to warm to room temperature and stirred for 18 h. The reaction is poured onto a stirred mixture of aqueous HCl/ice. The resulting precipitate is isolated by filtration and dissolved in DCM (1 L). The organic layer is washed with 1M aqueous HC1 solution (1 L), followed by saturated aqueous NaHC03 solution (1 L) and is then dried over Na2S04.Filtration and concentration of the filtrate under reduced pressure gives 300 g of toluene-4- sulfonic acid tetrahydro-pyran-4-yl ester as an orange oil. Yield: 90%, ES-MS: m/z: 257[M+H], 279 [M+Na]. 1H-NMR (250 MHz, CHLOROFORM-d) delta ppm 1.66 – 1.96 (4 H, m), 2.45 (3 H, s), 3.47 (2 H, ddd, 7=11.76, 8.19, 3.50 Hz), 3.79 – 3.95 (2 H, m), 4.69 (1 H, tt, 7=8.13, 4.13 Hz), 7.35 (2 H, d, 7=8.07 Hz), 7.76 – 7.87 (2 H, m)

2081-44-9, As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BERRY, Angela; RIETHER, Doris; ERMANN, Monika; JENKINS, James Edward; MUSHI, Innocent; WO2011/88015; (2011); 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.53911-68-5,4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Prepared by refluxing an equimolar mixture of 3-(4-chlorophenyl)glutaric anhydride and commercial 4-chloro-2-hydroxyaniline in dichloromethane for 0.5 h. After cooling to rt the precipitated product is isolated by suction filtration, washed, and dried to provide 90% of N-(2-hydroxy-4-chlorophenyl)-3-(4-chlorophenyl)glutaramic acid as light red crystals. 2, 53911-68-5

53911-68-5 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione 104639, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics