Category: Tetrahydropyrans

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.

Compound L, the free base of venetoclax (4-(4-{[2-(4-chlorophenyl)-4,4- dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-({3-nitro-4-[(tetrahydro-2H-pyran-4- ylmethyl)amino]phenyl}sulfonyl)-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide), may be prepared as follows. Compound K (3.39 g), Compound A (1.87 g), 1-ethyl-3-[3- (dimethylamino)propyl]-carbodiimide hydrochloride (2.39 g), and 4-dimethylaminopyridine (1.09 g) were stirred in CH2Cl2 (40 mL) for 24 hours. The reaction was cooled and chromatographed on silica gel with 25-100% ethyl acetate/hexanes, then 10% methanol/ethyl acetate with 1% acetic acid, to give the product (1.62 g, 32%) as a solid.1H NMR (300 MHz, dimethylsulfoxide-d6) 11.65 (br s, 1H), 8.55 (br s, 1H), 8.04 (d, 1H), 7.89 (dd, 1H), 7.51 (m, 3H), 7.33 (d, 2H), 7.08 (m, 1H), 7.04 (d, 2H), 6.68 (dd, 1H), 6.39 (d, 1H), 6.19 (d, 1H), 3.84 (m, 1H), 3.30 (m, 4H), 3.07 (m, 4H), 2.73 (m, 2H), 2.18 (m, 6H), 1.95 (m, 2H), 1.61 (dd, 2H), 1.38 (m, 2H), 1.24 (m, 4H), 0.92 (s, 6H).

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.

Reference£º
Patent; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (732 pag.)WO2016/24230; (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.951127-25-6,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

To a solution of 5-bromoisoindoline hydrochloride (3.00 g, 12.5 mmol) and tert- butyl N-[(2R,3S)-2-(2,5-difluorophenyl)-5-oxo-tetrahydropyran-3-yl]carbamate (4.14 g, 12.7 mmol) in DMAc (120 mL) is added triethylamine (3.5 mL, 25.1 mmol). The resulting mixture is stirred at 10 C for 15 minutes. Then HO Ac (2.26 g, 37.6 mmol) is added and the mixture is stirred for 1 hour. Sodium triacetoxyborohydride (10.6 g, 50.1 mmol) is added to the solution at 0 C. The resulting mixture is stirred at 10 C for 16 hours. The pH of the reaction mixture is adjusted to 5-6 with 1 M HCl aqueous solution. The resulting solution is diluted with water (800 mL) and extracted with EtOAc (3 x300 mL). The combined organic extracts are washed with brine (3 x500 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product is purified by silica gel flash chromatography eluting with DCM : MeOH (50: 1) to give the title compound (5.50 g, 84.4%) as a brown solid. ES/MS (m/z) (79Br/81Br) 511.4/513.4 [M +H].

951127-25-6 tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate 44193925, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD; HO, Koc Kan; QUAN, Weiguo; ZHOU, Jingye; (51 pag.)WO2018/102256; (2018); 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.23462-75-1,Dihydro-2H-pyran-3(4H)-one,as a common compound, the synthetic route is as follows.

Step 1: tert-butylN-(tetrahydropyran-3-ylamino)carbamatej1453] To a solution of dihydro-2H-pyran-3(4H)-one (CAS: 23462-75-1, 0.6 g, 5.99 mmol, 1.0 equiv) and tertbutyl carbazate (CAS: 870-46-2, 0.792 g, 5.99 mmol, 1.0 equiv) in anhydrous dichloromethane (20 mE) at 0 C. was added acetic acid (0.685 mE, 11.98 mmol, 2.0 equiv) and sodium triacetoxyborohydride (CAS: 56553-60-7, 3.81 g, 17.97 mmol, 3.0 equiv). The reaction mixture was warmed up to RT and stirred for 24 h. The reaction mixture was then basified with a solution of 2 M sodium hydroxide (45 mE) and a saturated solution of sodium hydrogencarbonate (30 mE). The two phases were separated, and the aqueous phase was extracted with dichloromethane. The combined organic phases were washed with a saturated solution of sodium hydrogencarbonate and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel (eluent system:heptane/ethyl acetate 70/30) to afford tert-butyl 2-(oxan-3- yl)hydrazine- 1 -carboxylate.

The synthetic route of 23462-75-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AbbVie S.a.r.l.; Galapagos NV; Akkari, Rhalid; Alvey, Luke Jonathan; Bock, Xavier Marie; Claes, Pieter Isabelle Roger; Cowart, Marlon D.; De Lemos, Elsa; Desroy, Nicolas; Duthion, Beranger; Gfesser, Gregory A.; Gosmini, Romain Luc Marie; Housseman, Christopher Gaetan; Jansen, Koen Karel; Ji, Jianguo; Kym, Philip R.; Lefrancois, Jean-Michel; Mammoliti, Oscar; Menet, Christel Jeanne Marie; Newsome, Gregory John Robert; Palisse, Adeline Marie Elise; Patel, Sachin V; Pizzonero, Mathieu Rafael; Shrestha, Anurupa; Swift, Elizabeth C.; Van der Plas, Steven Emiel; Wang, Xueqing; (454 pag.)US2017/101406; (2017); 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

4-oxo-5- (p-tolyl) -1,4-dihydropyridazine-3-carboxylic acid ethyl ester hydrochloride (4.2 g, 14.3 mmol, 1.0 eq) was dissolved in DMF (30 mL), Potassium carbonate (7.88 g, 57.2 mmol, 4.0 eq) and 4- (bromomethyl) tetrahydro-2H-pyran (3.06 g, 17.1 mmol, 1.2 eq) were added, and the reaction was heated to 50 C with stirring for 5 hours. The reaction was detected by LC-MS. The insoluble matter was removed by suction filtration. The filtrate was concentrated.The crude product was purified by silica gel column chromatography (100-200 mesh silica gel, EA / PE = 10-50%), and then recrystallized with a mixed solvent of DCM and MTBE (1:10) to obtain the product (1.6 g, yield: 32% ).

125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; Wan Zhonghui; (107 pag.)CN110041316; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

62071-40-3, 4-(Tetrahydropyran-4-yl)phenylamine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

29 mg of 6-chloro-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 20) and 35 mg of 4-(tetrahydro-2H-pyran-4-yl)aniline were dissolved in 0.35 mL of 1,4-dioxane, to which 8.0 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane, 17 mg of 1,1′-bis (diphenylphosphino)ferrocene and 12 mg of sodium tert-butoxide were added, and stirred using a microwave reaction apparatus under an argon atmosphere at 100 C. for 1 hour. After cooling, the solvent was evaporated and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=20:1) to obtain 7 mg (16%) of the title compound as a white crystalline powder.m.p. 228-237 C.1H-NMR (400 MHz, CDCl3) delta: 1.55-1.70 (4H, m), 3.35-3.46 (3H, m), 3.90-3.97 (2H, m), 4.42 (2H, d, J=5.8 Hz), 5.74 (1H, s), 7.00 (2H, d, J=6.4 Hz), 7.06 (2H, d, J=8.5 Hz), 7.15 (1H, t, J=9.5 Hz), 7.30 (2H, d, J=8.5 Hz), 8.37 (1H, s), 8.79 (1H, s), 9.05 (1H, t, J=5.6 Hz).

62071-40-3 4-(Tetrahydropyran-4-yl)phenylamine 20365472, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Kitamura, Takahiro; Yamada, Hajime; Takemura, Shunji; Ashikawa, Masanori; Ishikawa, Tetsuya; Miyake, Yoshiharu; Kouketsu, Akiyasu; Sato, Seiichi; Ishiwata, Hiroyuki; Tabunoki, Yuichiro; Shibasaki, Manabu; Ozawa, Takatoshi; Shigemi, Ryota; Doi, Takeshi; Tamura, Masahiro; US2011/237590; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a suspension of 48.6 mmol of the proper phenyl derivative and 71.3 mmol of AlCl3 in 60 mL of dry DCM, cooled at 0C, a solution of 32.4 mmol of the proper anhydride in 30 mL of dry DCM was added. The reaction was stirred at rt for 12 h except for the synthesis of 10, which needed only 1 h to proceed to completion. The mixture was then quenched with water and concentrated sulfuric acid; the organic phase was separated from the aqueous one and the solvent evaporated under vacuum. The residue was dissolved in EtOAc, extracted with a 10% NaOH aqueous solution, then acidified with a 1N HCl aqueous solution and re-extracted with EtOAc. Finally the organic phase was dried over MgSO4, filtered and concentrated in vacuo to afford pure compounds 11-13. 5-(3,4-dimethoxyphenyl)-5-oxopentanoic acid (11) 92% yield. 1H NMR (300 MHz, CDCl3): delta = 7.51-7.54 (m, 1H), 7.47 (s, 1H), 6.82 (d, 1H, J = 9.1 Hz), 3.88 (s, 3H), 3.87 (s, 3H), 2.97 (t, 2H, J = 7.8 Hz), 2.44 (t, 2H, J = 7.8 Hz), 2.02 (m, 2H) ppm.

As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

Reference£º
Article; Guariento, Sara; Karawajczyk, Anna; Bull, James A.; Marchini, Gessica; Bielska, Martyna; Iwanowa, Xenia; Bruno, Olga; Fossa, Paola; Giordanetto, Fabrizio; Bioorganic and Medicinal Chemistry Letters; vol. 27; 1; (2017); p. 24 – 29;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

951127-25-6, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

70 f (1.78 g, 3.2 mmol) was dissolved in N,N-dimethylacetamide (10 mL)Intermediate 1 (1.15 g, 3.52 mmol) was added and reacted at room temperature for 30 min.The reaction system was cooled to 0 C, Sodium borohydrophosphate (1.37 g, 6.24 mmol) was added, reacted for 30 minutes, The reaction was continued at room temperature for 2 hours. The reaction solution was cooled to 0 C, water (40 mL) was added in that order, aqueous ammonia (5 mL) was added to adjust the pH to 9, and the solid was washed with water (50 mL x 3). The solid was dissolved in dichloromethane, dichloromethane ), The organic phase was combined, washed with saturated brine solution (50 mL), dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated, and purified by silica gel column chromatography (dichloromethane / methanol (v / v) = 20: 1) ,A 70 g (1.15 g, yield 85%) of a white solid was obtained.

The synthetic route of 951127-25-6 has been constantly updated, and we look forward to future research findings.

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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

To a solution of diisopropylamine (2.19 ml. 15.36 mmol) in TetaF (20 mL) at-78 C, was added ?-butyl lithium ( 6.46 ml, 2.5M in hexane, 16.15 mmol) dropwise. The resulting mixture was stirred at -78 C for 30 min and was then added to a mixture of 1 ,1 -dimethylethyl {2-[[(l/?,2/?)-2-hydroxy-l-methyl-2- phenylethyl](methyl)amino]-2-oxoethyl}methylcarbamate (2.65 g ,7.88 mmol) and lithium chloride (2.Og, 47.3 mmol) via cannula at -23 C. The resulting mixture was stirred for 24 h and allowed to warm to room temperature before it was recooled in an ice bath and quenched with HCl (IM, 15.8 ml ). The mixture was then extracted with EtOAc (3 x 20 ml) and the combined extracts washed with saturated NH Cl, brine, dried, filtered, and concentrated. This crude product was purified by column chromatography (16O g silica gel 60, 230-400 mesh, 25,30,40, then 50% EtOAc/hexanes) to provide 1,1 -dimethylethyl [(15)-2-[[(l/?,2/?)-2-hydroxy-l- methyl-2-phenylethyl](methyl)amino]-2-oxo-l-(tetrahydro-2H-pyran-4- ylmethyl)ethyl]methylcarbamate (510 mg, 95% pure and 1.2 g, 80% pure, 42% combined yield). MS (m/z) 435.2 (M+eta+).

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

Reference£º
Patent; VITAE PHARMACEUTICALS, INC.; WO2008/156817; (2008); 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.344329-76-6,Tetrahydro-2H-pyran-4-carboxamide,as a common compound, the synthetic route is as follows.

(2) cooling the 4-formamide tetrahydropyran mixed solution prepared in the step 1 to a temperature of 5 ¡ã C, adding a NaOH solution,After stirring uniformly, NaBrO solution was added dropwise thereto. After the completion of the dropwise addition, the reaction was continued at this temperature for 2 hours, and then the temperature was raised to 50 ¡ã C for 1 hour, then cooled to room temperature, extracted with dichloromethane, and the organic phase was combined. After dichloromethane was removed by pressure distillation, recrystallization was carried out to obtain 4-aminotetrahydropyran.Preferably, the molar volume ratio of tetrahydropyran-4-carboxylic acid to water in the step (1) is 5 mol/L.The concentration of ammonia water in the step (1) is 13 mol/L; the amount of tetrahydropyran-4-carboxylic acid and ammonia in the step (1)The molar volume ratio is 10:1 mol/L.The mass concentration of the NaOH solution in the step (2) is 40percent, the 4-formamide tetrahydropyran mixed solution and the NaOH solutionThe volume-to-volume ratio was 7:1; the mass concentration of the NaBrO solution in the step (2) was 15percent.The molar ratio of tetrahydropyran-4-carboxylic acid to NaBrO was 1:1.5.The obtained 4-aminotetrahydropyran had a purity of 99.2percent and a product yield of 91.8percent.

The synthetic route of 344329-76-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Suzhou Aitike Pharmaceutical Chemical Co., Ltd.; Hu Haiwei; (6 pag.)CN108003122; (2018); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 3L three-necked RB flask were charged [500ML] of methylene chloride, 250gr of aluminum chloride and 45gr of fluorobenzene (benzene content 300ppm) under nitrogen atmosphere. ‘The reaction mixture was cooled to [10C] and a solution of [LOOGR] of glutaric anhydride, 45gr of fluorobenzene (benzene content 300ppm) and [500ML] of methylene chloride was added slowly over a period of 3hrs between [10-15C.] The reaction mixture was maintained for another one hour at the same temperature. The reaction mixture was slowly poured onto a mixture of crushed ice (700gr) and conc. HCI [(300ML)] below [10C.] The reaction mass temperature was allowed to reach [25C] and methylene chloride distilled off from the reaction mixture below [50C.] After cooling the reaction mixture to [20C,] solids were filtered off and washed with [500ML] of water. The wet cake thus obtained was suspended in [250-300ML] of methylene chloride and filtered. The solid compound was dissolved in [600ML] of 4% sodium hydroxide, treated with [LOGR] of activated charcoal and filtered. The filtrate was acidified with conc. HCI and the precipitated acid was filtered. After washing the wet cake with [500ML] of water, it was dissolved in [500ML] of acetone. The acetone solution was slowly cooled to [15-20C] and the solid filtered, washed with chilled acetone (50ml) and dried at [50-70C] to get 122gr of white crystalline solid, m. p. [143C.] Purity by [HPLC] is 99.65%. Desfluoro impurity is less than 0.05%. Example 2 Preparation of [4- (4-FLUOROBENZOY) LBUTYRIC ACID] of formula-I using fluorobenzene (benzene content [500PPM)] with methylene chloride as solvent: Into a 3L three-necked RB flask were charged [500MI] of methylene chloride, 250gr of aluminum chloride and 45gr of fluorobenzene (benzene content 500ppm) under nitrogen atmosphere. The reaction mixture was cooled to [10C] and a solution of [LOOGR] of glutaric anhydride, 45gr of fluorobenzene (benzene content [500PPM)] and [500ML] of methylene chloride was added slowly over a period of 3hrs between [10-15C.] The reaction mixture was maintained for another one hour at the same temperature. The reaction mixture was slowly poured onto a mixture of crushed ice (700gr) and conc. [HCL] [(300ML)] below [10C.] The reaction mass temperature was allowed to reach [25C] and methylene chloride distilled off from the reaction mixture below [50C.] After cooling the reaction-mixture to [20OC-1 SOLIDS :] were filtered off and washed with [500ML] of water. The wet cake thus obtained was suspended in [250-300ML OF] methylene chloride and filtered. The solid compound was dissolved in [600ML] of [4%] sodium hydroxide, treated with [10GR] of activated charcoal and filtered. The filtrate pH was adjusted’to 1.0-2. 0 with conc. [HCL] and the precipitated acid of formula-I was filtered. After washing the wet cake with [500ML] of water, it was dissolved in [500ML] of acetone. The acetone solution was slowly cooled to [15-20C,] maintained for 2h, and the solid filtered, washed with chilled acetone [(50ML)] and dried at [50-70C] to get 120gr of white crystalline solid of [FORMULA-1,] m. p. 143-143. [5C.] Purity by [HPLC] is 99. [7%.] Desfluoro impurity is less than 0.05%. Example 3 Preparation of [4- (4-FLUOROBENZOY)] lbutyric acid of formula-I using fluorobenzene (benzene content 700ppm) with methylene chloride as solvent: Tnto a 3L three-necked RB flask were charged 500ml of methylene chloride, 250gr of aluminum chloride and 45gr of fluorobenzene (benzene content [700PPM)] under nitrogen atmosphere. The reaction mixture was cooled to [10C] and a solution of [LOOGR] of glutaric anhydride, 45gr of fluorobenzene (benzene content 700ppm) and [500ML] of methylene chloride was added slowly over a period of 3hrs between [10-15C.] The reaction mixture was maintained for another one hour at the same temperature. The reaction mixture was slowly poured onto a mixture of crushed ice (700gr) [AND CONC. HCI (300ML)] below [10C.] The reaction mass temperature was allowed to reach [25C] and methylene chloride distilled off from the reaction mixture below [50C.] After cooling the reaction mixture to [20C,] solids were filtered off and washed with [500ML] of water. The wet cake thus obtained was suspended in [250-300ML] of methylene chloride and filtered. The solid compound was dissolved in [600ML] of 4% sodium hydroxide, treated with [LOGR] of activated charcoal and filtered. The filtrate pH was adjusted to 1.0-2. 0 with conc. [HCL] and the precipitated acid of formula-I was filtered. After washing the wet cake with [500ML] of water, it was dissolved in 500ml of acetone. The acetone solution was slowly cooled to [15-20C,] maintained for 2h, and the solid filtered, washed with chilled acetone [(50ML)] and dried at [50-70C] to get 123gr of white crystalline solid [OF FORMULA-1,] m. p. [143C.] Purity by [HPLC] is 99.6%. Desfluoro impurity is less than 0.05%.

108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Natco Pharma Limited; Venkaian Chowdary Nannapaneni; WO2003/104180; (2003); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics