Heterocyclic Building Blocks-Tetrahydropyrans

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

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

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.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.108-55-4,Dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

EXAMPLE 2; Synthesis of Mono-carbonyl butanoic acid 3; To a solution of 2.01 g (5.46 mmol) of curcumin, 1 12 mg (0.92 mmol) of DMAP, and 0.685 g (6 mmol) glutaric anhydride (95%) in 100 ml THF was added 1.33 ml (9.55 mmol) Et3N. The reaction was stirred at reflux under argon overnight. Purified on column chromatography, eluting with CH2Cl2-CH2Cl2)MeOH, 95:5. Yield 84%. NMR 1H (CDCl3), delta (ppm): compound (3),1.97-2.14 (m, 2H); 2.43-2.79 (m, 4H); 3.87-3.95 (d, 6H); 5.83 (s, 2H); 6.45-6.59 (t, 2H); 6.91-7.18 (m, 6H); 7.57-7.65 (d, 2H). 13C NMR (CDCl3), delta (ppm): 19.98; 32.76; 55.82; 101.61 ; 109.86; 1 1 1.36; 1 15.04; 120.95; 121.54; 123.05; 124.16; 127.35; 133.89; 139.38; 139.99; 141.06; 147.03; 148.22; 151.23; 170.98; 177.374; 181.73; 184.65. MS (ESI) calcd. for C26H26O9: 482.48; found: 483.2 [M+H]+. See Robert E. Gawley; Mykhaylo Dukh; Claudia M. Cardona; Stephan H. Jannach; Denise Greathouse. Org. Lett.., Vol. 7, No. 14, 2005.2953-2956.

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

Reference£º
Patent; RESEARCH FOUNDATION OF THE CITY UNIVERSITY OF NEW YORK; WO2008/45534; (2008); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1245724-46-2, (S)-Tetrahydro-2H-pyran-3-amine hydrochloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(3S)-Tetrahydro-2H-pyran-3-amine hydrochloride (1.99 g, 14.5 mmol) in MeCN (10 ml) was added dropwise to a mixture of DIPEA (6.30 ml, 36.2 mmol) and ethyl 2,4- dichloropyrimidine-5-carboxylate (3.2 g, 14.5 mmol) in MeCN (60 ml) at 0C over a period of 5 minutes under air. The reaction mixture was stirred for 4 h, slowly allowing to warm to rt as the ice bath melted. The reaction mixture was stirred at rt for 18 h. The reaction mixture was evaporated to dryness to remove MeCN, diluted with EtOAc (100 mL), and washed with water then sat. brine. The organic layer was dried over MgS04, filtered and evaporated to afford crude product. The crude product was purified by fee, eluting with 0 – 40% EtOAc in heptane to afford the title compound (3.24 g, 78%) as a yellow oil;lH NMR (400 MHz, DMSO) 1.32 (3H, t), 1.49 – 1.6 (1H, m), 1.63 – 1.79 (2H, m), 1.83 – 1.94 (1H, m), 3.48 (1H, dd), 3.54 – 3.65 (2H, m), 3.74 (1H, dd), 4.08 – 4.19 (1H, m), 4.33 (2H, q), 8.57 (1H, d), 8.64 (1H, s); m/z [M-H]-284.

As the paragraph descriping shows that 1245724-46-2 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; TING, Attilla, Kuan, Tsuei; (103 pag.)WO2018/114999; (2018); 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

Preparation 4: Methanesulfonicacid (tetrahydropyran-4-yl)methyI ester; To a mixture of Preparation 3 (216.5g, 1.87mol) and triethylamine (299mL) in DCM (1.3L) at <10C was added under argon a solution of methanesulfonyl chloride (236g, 160mL)in DCM (200mL) over 2h 50min, maintaining the temperature at 5-10C throughout. Subsequent washing with water (1L), 1M HC1 (500mL), 5% NaHC03 (300mL), water (300mL), drying (MgS04) and then removal of the solvent afforded the title compound (328g, 90% yield). NMR was consistent with the above structure. 14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various. Reference£º
Patent; PROSIDION LIMITED; WO2006/16174; (2006); A1;,
Tetrahydropyran – Wikipedia
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

Example 1G 4-{4-[(4′-chloro-1,1′-biphenyl-2-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 EXAMPLE 1E (115 mg), EXAMPLE 1F (67 mg), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (82 mg), and 4-dimethylaminopyridine (26 mg) were stirred in CH2Cl2 (3 mL) for 24 hours. The reaction was cooled and chromatographed on silica gel with 0-5% methanol/ethyl acetate. 1H NMR (300 MHz, dimethylsulfoxide-d6) delta 11.48 (brs, 1H), 8.34 (br s, 1H), 8.31 (m, 1H), 7.90 (d, 1H), 7.68 (m, 1H), 7.58 (m, 2H), 7.46 (m, 4H), 7.35 (m, 2H), 7.21 (dd, 1H), 6.76 (m, 4H), 6.28 (m, 2H), 3.02 (m, 2H), 2.89 (m, 4H), 2.80 (m, 4H), 2.40 (m, 3H), 1.59 (m, 2H), 1.25 (m, 4H), 0.87 (m, 2H).

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

Reference£º
Patent; ABBOTT LABORATORIES; US2010/305122; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

85064-61-5, Tetrahydropyranyl-4-acetic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Triethylamine (14.84 mmol) was added to a solution of the carboxylic acid (7.42 mmol) in THF (31.0 mL, 0.2 M) at room temperature, stirred for 10 min, and then cooled to 0 C before addition of pivaloyl chloride (8.90 mmol). After 30 min at 0 C, lithium chloride (0.5 M in THF, 8.90 mmol) was added, followed by (R)-(+)- or (S)-(-)-4-benzyloxazolidin-2-one (8.90 mmol) and the mixture was stirred at room temperature for 20 h. The mixture was partitioned with EtOAc (20 mL) and 1M HCl (3*20 mL) and the organic layer was washed with 1M K2CO3 (3*20mL). The acidic aqueous layer was extracted with EtOAc (20 mL) and the combined organic layer was washed with brine (10 mL), dried (MgSO4), filtered, and concentrated under vacuum. The crude material was purified as indicated.

The synthetic route of 85064-61-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Shouksmith, Andrew E.; Evans, Laura E.; Tweddle, Deborah A.; Miller, Duncan C.; Willmore, Elaine; Newell, David R.; Golding, Bernard T.; Griffin, Roger J.; Australian Journal of Chemistry; vol. 68; 4; (2015); p. 660 – 679;,
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 14: Preparation of GRV5-methyl-3-f2-oxo-2(r(lR)-l-rhohenylethvnamino>ethvD hexanoic acid compound (24); [0088] A three-necked flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer, was charged with ethanol (100 ml), (R)-(+)- phenylethylamine (35.58 g, 0.147mole) and 4-dimethylaminopyridine (0.18 g, 0.00147 mole). The mixture was cooled to a temperature of 0-5 C, followed by addition of a solution of 3-isobutyl glutaric anhydride (25 g, 0.147 mole) in ethanol (25 ml), over a period of 15-20 minutes, and stirring for additional 1.5-2 hours, at a temperature of 0-50C. The solvent was stripped off and the residue was extracted with 2.5-3 percent aqueous solution of NaOH solution (500 ml), and diluted with water (1000 ml) followed by washing the aqueous phase with toluene (1 x 100 ml and 1 x 50 ml). The pH of the aqueous phase was adjusted to 2-2.5 by adding a 1-12N solution of hydrochloric acid. The aqueous phase was further extracted with ethyl acetate (1 x 150 ml and 1 x 50 ml), followed by drying the combined ethyl acetates extracts over anhydrous sodium sulfate, and stripping off the solvents, to obtain a residue. The residue was crystallized from ethyl acetate and toluene mixture to get 22.7 g (53.09 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 99.17 percent, as measured by chiral HPLC.

The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2007/35789; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics