Heterocyclic Building Blocks-Tetrahydropyrans

101691-94-5, 4-(Iodomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of crude 9-hydroxy-6-isobutyi- 1 0-methoxy-2-oxo-7H-pyrido [2,1 -a]phthalazine-3-carboxylic acid (60 mg) in DMF (3 mL) was added potassium carbonate (74.2mg, 537 jimol) and 4-(iodomethyl)tetrahydro-2H-pyran (91 mg, 402 iimol), The mixture washeated at 100 C with stirring for 3 hrs, and then cooled to rt, To the above mixture was addedwater (3 mL) and sodium hydroxide (10.7 mg, 268 imol). The resulting mixture was stirred at rtfor 2 hrs, and then acidified with 6 M hydrochloric acid. The mixture was partitioned betweenbrine and DCM, The organic layer was separated and concentrated under reduced pressure. Theresidue was purified by prep-HPLC to give 6-isobutyl- 1 0-rnethoxy-2-oxo-9-(tetrahydropyran-4-ylmethoxy)-7H-pyrido [2,1 -a]phthalazine-3 -carboxylic acid (5 mg), ?H NMR (400MHz, CDC13)oe ppm 8.60 (s, 1H), 7.20 (s, 1H), 7.04 (s, 1H), 6.72 (s, 1H), 4.36 – 4.16 (m, 2H), 4.08 – 4.01 (m,2H), 3.94 (s, 3H), 3.92 (d, 2H), 3.52 – 3.43 (m, 2H), 2.53 (d, 2H), 2.24 – 2.19 (m, 1H), 2.05 – 1.99(m, 1H), 1.69-1.60 (m, 2H), 1.54 – 1.42 (m, 2H), 0.96 (d, 6H). MS obsd. (ESIj [(M+H)]: 443., 101691-94-5

101691-94-5 4-(Iodomethyl)tetrahydro-2H-pyran 2795507, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; WANG, Yongguang; YANG, Song; (47 pag.)WO2017/17043; (2017); 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)., 14774-37-9

The synthetic route of 14774-37-9 has been constantly updated, and we look forward to future research findings.

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.

Step 2: 2-Methoxy-1-(tetrahydro-2H-pyran-4-yl)ethanoneA dry 50 mL flask under nitrogen was charged with magnesium (197 mg, 8.11 mmol) and a crystal of iodine. The solids were stirred vigorously while being warmedwith the heat gun to aerosolize the iodine. Upon cooling to room temperature, it was treated with THF (4 mL). The mixture was warmed with a heat gun and treated with a solution of 4-bromotetrahydro-2H-pyran (0.678 mL, 6.08 mmol) in THF (4 mL) dropwise via a dry addition funnel. When addition was complete, the mixture was placed in a preheated oil bath, and the mixture held at reflux for 30 mm. After cooling to room temperature, the solution was transferred to a stirred solution of N,2-dimethoxy-N- methylacetamide (270 mg, 2.03 mmol) in THF (12 mL) at -78 C. After stirring for 5 mm, the ice bath was removed and the reaction allowed to warm to room temperature. The reaction was placed in a 0 C bath, quenched by addition of sat. aq. ammoniumchloride, concentrated, diluted with EtOAc, washed with water, then brine, dried over magnesium sulfate, filtered, and concentrated to give 260 mg (81%) as clear oil. Material was used without purification. ?H NMR (400 MHz, CDC13) oe 4.1 1(s, 2H), 4.05-4.0(m, 2H), 3.5-3.44(m, 2H), 3.45(s, 3H), 2.8(m, 1H), 1.64(m, 2H), 1.32(m, 2H).

25637-16-5, The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31608-22-7,2-(4-Bromobutoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

2-[4-(2,3-Difluorophenoxy)-butoxy]-tetrahydropyran (20) To a solution of 2-(4-bromobutoxy)-tetrahydropyran (18) (1 equi.) and commercially available 2,3-difluorophenol (19) (1 equi.) in DMF (3 mL/mmole), cesium carbonate (1.25 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile gave 2-[4-(2,3-difluorophenoxy)-butoxy]-tetrahydropyran(20), as a white solid (84%)., 31608-22-7

As the paragraph descriping shows that 31608-22-7 is playing an increasingly important role.

Reference£º
Patent; Wand, Michael; Gough, Neil; Chen, Xin Hua; US2003/17278; (2003); 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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

(u) 2-(m,p-dimethoxyphenyl)-ethyl, m.p. 188-191; The amine starting material for compound (e), 2-(tetrahydropyran-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

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

Reference£º
Patent; Ciba-Geigy Corporation; US4977144; (1990); 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.14774-37-9,Tetrahydropyran-4-methanol,as a common compound, the synthetic route is as follows.

Preparation 1; Methanesulfonic acid tetrahydropyran-4-ylmethyl ester; A solution of 90 g (774.8 mmol) of tetrahydropyran-4 -methanol and 129.6 mL (929.76 mmol, 1.2 eq.) of triethylamine in 775 mL of anhydrous DCM was cooled to 00C with in an ice bath. Methanesulfonyl chloride (66.2 mL, 852.28 mmol, 1.1 eq.) of was then added dropwise over 60 minutes while maintaining the temperature around O0C. The reaction mixture was stirred for 30 minutes at O0C and quenched with a saturated solution of sodium bicarbonate (800 mL) . The aqueous layer was extracted with DCM (800 mL) . The combined organic layers were washed with water (2 x 800 mL) , brine (800 mL) and dried over sodium sulfate. After filtration and concentration in vacuo, a yellowish solid (146.1 g, 97%) was obtained corresponding to the methanesulfonic acid tetrahydropyran-4-ylmethyl ester.IH NMR (400 MHz, DMSOd6): delta [ppm] 4.02 (d, 2H), 3.82 (m, 2H), 3.27 (t x d, 2H), 3.14 (s, 3H), 1.89 (m, IH), 1.55 (m, 2H), 1.21(q x d, 2H) .; Preparation 13; Methanesulfonic acid tetrahydropyran-4-ylmethyl ester; A solution of 90 g (774.8 mmol) of tetrahydropyran-4 -methanol and 129.6 mL (929.76 mmol, 1.2 eq.) of t?ethylamine m 775 mL of anhydrous DCM was cooled to 00C m an ice bath. Methanesulfonyl chloride (66.2 mL, 852.28 mmol, 1.1 eq.) was then added dropwise over 60 minutes while maintaining the temperature around 00C. The reaction mixture was stirred for 30 minutes at 00C and quenched with a saturated solution of sodium bicarbonate (800 mL) . The aqueous layer was extracted with DCM (800 mL) . The combined organic layers were washed with water (2 x 800 mL) , brine (800 mL) and dried over sodium sulfate. After filtration and concentration m vacuo, a yellowish solid (146.1 g, 97%) was obtained corresponding to the methanesulfonic acid tetrahydropyran-4-ylmethyl ester .IH NMR (400 MHz, DMSO-O6): delta [ppm] 4.02 (d, 2H), 3.82 (m, 2H), 3.27 (t x d, 2H), 3.14 (s, 3H), 1.89 (m, IH), 1.55 (m, 2H), 1.21 (q x d, 2H) ., 14774-37-9

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

Reference£º
Patent; VIROCHEM PHARMA INC.; WO2007/143847; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

127956-11-0, Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2c (5.5g, 34.97mmol) and ammonium acetate (8.1g, 104.9mmol) in methanol (100mL) were stirred at room temperature overnight. The mixture was concentrated in vacuo, and diluted with water (50mL) and extracted with DCM (50mL¡Á3). The separated organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting crude methyl 4-amino-5,6-dihydro-2H-pyran-3-carboxylate 3c was then dissolved in acetonitrile (50mL), and 2,2,2-trichloroacetyl isocyanate (7.2g, 38.46mmol) was added. The resulting mixture was stirred for 30min, and the precipitated solids were collected and dissolved in a solution of ammonia in methanol (10mL, 7N). Then the resulting mixture was heated at 70C for 1h. The reaction was cooled down and the precipitated solids were collected and dried to afford the diol (4c) (3.8g, yield 65%, purity 97%) as a white solid. MS (ESI) m/z 169.2 [M+H]+., 127956-11-0

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

Reference£º
Article; Wang, Xueyuan; Bai, Enhe; Zhou, Hui; Sha, Sijia; Miao, Hang; Qin, Yanru; Liu, Zhaogang; Wang, Jia; Zhang, Haoyang; Lei, Meng; Liu, Jia; Hai, Ou; Zhu, Yongqiang; Bioorganic and Medicinal Chemistry; vol. 27; 3; (2019); p. 533 – 544;,
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Tetrahydropyran – an overview | ScienceDirect Topics

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of appropriate crude acid (1 eq) in CH2Cl2 wereadded EDCI (3 eq), DMAP (0.3 eq) and DIPEA (3 eq). The solutionwas stirred at room temperature for 0.5 h and compound 23 [7] (0.8eq) was added. The resulting mixture was stirred for another 8 hand water was added. The layers were separated, and the aqueouslayer was extracted with CH2Cl2. The combined organic layer waswashed with brine, dried over anhydrous Na2SO4, filtered, andconcentrated under vacuo. The residue was prified by chromatography(CH2Cl2/CH3OH 40:1) to provide target compounds 27a-i,28a-d and 34a-c., 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
Article; Liu, Xiaohua; Zhang, Yu; Huang, Wenjing; Luo, Jia; Li, Yang; Tan, Wenfu; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 149 – 165;,
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.25850-22-0,2,2-Dimethyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

Production Example 321 (0641) 5-Benzyloxymethylisoxazole-3-carboxylic acid (0.24 g, 1.0 mmol), 4-amino-2,2-dimethyltetrahydropyran (0.18 ml, 1.2 mmol) and 1-hydroxybenzotriazole (0.01 g, 0.1 mmol) were added to chloroform (amylene addition product) (2.5 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.24 g, 1.2 mmol) was added to the mixture at room temperature, and the mixture was stirred overnight. Then, dilute hydrochloric acid was added thereto, and the mixture was extracted twice with chloroform. The organic layer was passed through a short column to remove impurities, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.29 g of N-(2,2-dimethyltetrahydropyran-4-yl)-5-benzyloxymethylisoxa zole-3-carboxamidc: (hereinafter, referred to as Compound of Present Invention (335)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.26(3H, s), 1.29(3H, s), 1.33-1.40(1H, m), 1.41-1.52(1H, m), 1.89-2.00(2H, m), 3.72-3.84(2H, m), 4.27-4.38(1H, m), 4.61(2H, s), 4.65(2H, s), 6.62(1H, br s), 6.72(1H, s), 7.30-7.40(5H, m)

25850-22-0, As the paragraph descriping shows that 25850-22-0 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

388109-26-0, Ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

388109-26-0, Step 1:To a solution of ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g).

The synthetic route of 388109-26-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; Metcalf, Brian W.; (29 pag.)US9248199; (2016); B2;,
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Tetrahydropyran – an overview | ScienceDirect Topics