Heterocyclic Building Blocks-Tetrahydropyrans

4677-18-3, 2-(Tetrahydro-2H-pyran-4-yl)ethanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 33: 2-(Tetrahydro-2/-/-pyran-4-yl)ethyl methanesulfonate To 2-(tetrahydro-2H-pyran-4-yl)ethanol (3,3g) in dry dichloromethane (100 ml) at O0C and under nitrogen was added triethylamine (4.6 ml), followed by methanesulphonyl chloride (2.6 ml) dropwise over 5 minutes. The reaction was stirred until the ice in the bath melted and left overnight at room temperature. The reaction was washed with saturated aqueous sodium bicarbonate (40 ml). The organic layer was dried by passing through a hydrophobic frit and concentrated in vacuo to yield the title compound as a yellow oil (5.4g).1 H NMR (DMSO): 4.24 (2H, t), 3.82 (2H, m), 3.80 (3H, s), 3.27 (2H, m), 2.50 (5H, m), 1.60 (2H, m).

4677-18-3 2-(Tetrahydro-2H-pyran-4-yl)ethanol 17750944, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/101867; (2008); 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

Example 1: N-[6-(4-Morpholinyl)-3-pyridinyl]-2-(tetrahydro-2H-pyran-4-yl)-N-[(1-(at)[4- (trifluoromethyl)phenyl]methyl)-4-piperidinyl)methyl]acetamide; Oxalyl chloride (0.27ml, 3.05mmol) was added to a stirred solution of tetrahydro-2H- pyran-4-ylacetic acid (0.2g, 1.38mmol) in DCM (10ml). DMF (1 drop) was added and the reaction mixture stirred at room temperature for 1.5h then evaporated in vacuo to afford a colourless oil (1.17g). The crude acid chloride was dissolved in DCM (10ml) and added to a stirred solution of 6-(4-morpholinyl)-N-[(1-{[4-(trifluoromethyl)phenyl]methyl)-4- piperidinyl) methyl]-3-pyridinamine D5 (0.45g, 1.03mmol) and triethylamine (0.58ml, 4.12mmol) in DCM (10ml). After 24h the mixture was washed with saturated sodium hydrogen carbonate, the organic layer separated by passage through a phase separation cartridge and evaporated in vacuo. Chromatography on silica gel eluting with 50-100% ethyl acetate in pentane gradient afforded the title compound as an orange gum (0.47g). A 70mg portion was dissolved in 1:1 DMSO/MeCN (0.9ml) and purified by mass directed autoprep hplc on a Waters C18 5muM column 8(id 19 x 100mm) eluting with 5 – 99% MeCN in water gradient containing 0.1 % formic acid. Fractions containing the desired material were passed through a 2g SCX column, the column washed with methanol (30ml) and eluted with 1 N ammonia in methanol to afford the title compound as a colourless gum (0.05g). Mass Spectrum (AP+): Found 561 (MH+). C30H39F3N403 requires 560.

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

Reference£º
Patent; GLAXO GROUP LIMITED; WO2005/103038; (2005); 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

Into a 8-mL round-bottom flask, was placed a solution of 4-(4-[[2-(4-chlorophenyl)- 4,4-dimethylcyclohex-l-en-l-yl]methyl]piperazin- l-yl)-2-[l3-oxa-2,4,l0- triazatricyclo[7.4.0.0A[3,7]]trideca-l,3(7),5,8-tetraen-l0-yl]benzoic acid (35 mg, 0.06 mmol, 1.00 equiv) in dichloromethane (5 mL), 4-dimethylaminopyridine (27.8 mg, 0.23 mmol, 4.00 equiv), 3-nitro-4-[(oxan-4-ylmethyl)amino]benzene-l-sulfonamide (21.7 mg, 0.07 mmol, 1.20 equiv), EDCI (22 mg, 0.11 mmol, 2.00 equiv). The resulting solution was stirred for overnight at room temperature. The resulting mixture was concentrated under vacuum. The crude product was purified by Prep-HPLC with the following conditions (Waters-2767): Column, X-bridge RP18, 5um, l9* l00mm; mobile phase, 0.03% ammonia in water (0.03% NH4HC03 & NH40H ) and CH3CN (32% CH3CN up to 52% in 6 min); Detector, UV 254 nm. This resulted in 28.3 mg (54%) of 4-(4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-l-en- l-yl]methyl]piperazin-l-yl)-N-([3-nitro-4-[(oxan-4-ylmethyl)amino]benzene]sulfonyl)-2-[l3- oxa-2,4,l0-triazatricyclo[7.4.0.0A[3,7]]trideca-l,3(7),5,8-tetraen-l0-yl]benzamide as a yellow solid. LC-MS-: (ES, m/z ): (ES, m/z): M+l=909, R.T= 1.52 min. The measurements of the retention were done with a reversed phase column (C18). Shimadzu LCMS 2020; 50*3.0 Kinetex 2.6u XB-C18 , 2.6 microm; Eluent A: water (0.05 % TFA); Eluent B: Acetonitrile; linear gradient. H-NMR: (CDCl3, 300 MHz) d: 8.70 (s, 1H), 8.46 (m, 2 H), 8.10-8.06 (m, 1 H), 7.89-7.60 (m, 1 H), 7.10 (s, 1 H), 6.94-6.71 (m, 5 H), 6.49 (s, 1 H), 6.16 (s, 1 H), 4.70- 4.65 (m, 2 H), 4.00-4.10 (m, 2 H), 3.67-3. l9(m, 7 H), 3.20-3.00(m, 4 H), 2.78(s, 1 H), 2.58- 2.52(m, 2 H), 2.27-2. l7(m, 3 H), 2.05-l.98(m, 4 H), 1.74-1.70 (m, 3 H), 1.55-1.40 (m, 3H), 0.98 (s, 6H).The measurements of the NMR spectra were done with BrukerAvancelll HD 300MHzwith a probe head of BBOF

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

Reference£º
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (475 pag.)WO2020/41406; (2020); 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.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.

Step 3. 2,2,6,6-Tetramethyl-4-trimethylsilanylethynyl-tetrahydro-pyran-4-ol To a solution of ethynyl-trimethyl-silane (5.5 mL, 38.4 mmol) in dry THF (25 mL) was added n-BuLi (32 mL, 38.4 mmol) at -78 C. and the mixture was stirred at that temperature for 45 min followed by addition of 2,2,6,6-tetramethyl-tetrahydro-pyran-4-one (5.0 g, 32 mmol) in dry THF (25 mL) at -78 C. The mixture was stirred for 1 h and then quenched with saturated NH4Cl solution and extracted with ethyl acetate (3*100 mL). The combined organic extract was washed with water and brine solution, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the product as sticky white solid. Crude product was forwarded for next stage without purification. Yield: 8.0 g, crude.

1197-66-6 2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one 11829691, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Janssen Pharmaceutica NV; Ahmad, Ishtiyaque; Bakthavatchalam, Rajagopal; Battula, Sivaramakrishna; Gijsen, Henricus Jacobus, Maria; Wall, Mark; US2015/51225; (2015); A1;,
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

A 100 ml three-necked round-bottom flask, under nitrogen atmosphere, is added with 98% hydrazine hydrate (19.5 g, 0.382 mols), sodium hydroxide (12.4 g, 0.309 mol) in water (150 ml) and the solution is cooled to a temperature of -5C. 3-Isobutyl-glutaric anhydride (183.0 g, 1.075 mol) is dropped therein in about 1-2h, keeping the temperature below 0-5C and the mixture is reacted for about 1h. 35-37% Hydrochloric acid (450 ml) and toluene (400 ml) are added. Keeping a temperature of -5C, a solution of sodium nitrite (160.0 g, 2.026 mol) in water (320 ml) is added dropwise, keeping the temperature below 10-15C. After completion of the addition, the mixture is reacted for 15-20 minutes, afterwards the phases are separated and the aqueous phase is extracted with toluene (250 ml). The cooled combined organic phases are dropped into isopropanol (800 ml) under reflux in about 1 hour. The mixture is refluxed for about 30 minutes and the solution is concentrated to small volume. The resulting oil is taken up into hexane (500 ml) and left under strong stirring for 2-3 hours, the solid is filtered and dried at 50C for 16-18 hours. 205 g of a white solid are obtained, in a 78% yield. 1H-NMR (300 MHz, D2O, 28C): delta 7.00 (broad, 1H exchange with D2O); 4.70 (m, 1H); 3.00 (m, 1H); 2.80 (m, 1H); 2.10 (m, 2H); 1.95 (m, 1H); 1.60 (m, 1H); 1.20-1.00 (m, 8H); 0.80 (d, 6H).

185815-59-2 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Dipharma Francis S.r.l.; EP2067768; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(0127) To a suspension of hexane-washed NaH (0.72 g, 60% in mineral oil) in tetrahydrofuran (30 ml) was added a solution of 2,2-dimethyldihydro-2H-pyran-4(3H)-one (2.0 g) in tetrahydrofuran (20 ml). The suspension was stirred at room temperature for 30 minutes. The dimethylcarbonate (6.31 ml) was added dropwise by syringe. The mixture was heated to reflux for 4 h. LC/MS showed the expected product as the major product. The mixture was acidified with 5% HCl and extracted with dichloromethane (100 ml¡Á3) and washed with water, brine and dried over Na2SO4. After evaporation, the crude product was loaded on a column and eluted with 10% ethyl acetate in hexane to give the product.

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; AbbVie Inc.; Catron, Nathaniel; Lindley, David; Miller, Jonathan M.; Schmitt, Eric A.; Tong, Ping; US10213433; (2019); B2;,
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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

EXAMPLE 85c; Preparation of intermediate 5-chloro-2-(tetrahydro-pyran-4-yl-methoxy)-benzaldehyde; A mixture of 5-chlorosalicylaldehyde (5.0 g, 32 mmol), toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester (8.6 g, 32 mmol) and K2CO3 (9.5 g, 68.8 mmol) in DMF (50 mL) was heated at 75 C. overnight. After cooled to room temperature, the mixture was poured into water. The aqueous phase was extracted with EtOAc twice. The combined organic phases were washed with water and brine, dried and concentrated. The residue was purified by column chromatography to give the title compound (7.0 g).

As the paragraph descriping shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

It was added 18.0 parts of ethanol 90 parts of the compound represented by formula (I-7-a), and stirred for 1 hour at 23 C. To the resulting mixed solution, after addition of 4.33 parts of sodium hydroxide, 23 After stirring for 1 hour at C, over 30 minutes compound 13.05 parts of the formula (I-7-b) It dropped, and 25 hours reflux and stirred at 75 C. The resulting reaction mass was concentrated, added to 90 parts of chloroform and 30 parts of ion exchange water and stirred for 30 min at 23 C, the organic layer was removed by liquid separation. This operation was repeated five times. The recovered organic layer was filtered and concentrated the filtrate to give the compound 18.97 parts of the formula (I-7-c).

1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; ADACHI, YUKAKO; YAMAMOTO, SATOSHI; ICHIKAWA, KOJI; (81 pag.)JP2015/27994; (2015); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

287193-07-1, Ethyl 4-oxotetrahydro-2H-pyran-2-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 30 2-(Oxalyl-amino)-5-phenylcarbamoyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3 carboxylic acid; A solution of glyoxylic acid ethyl ester, polymer form (2.02 g, 8.9 mmol) and (3-methoxy-1-methylene-allyloxy)-trimethyl-silane (1.9 ml, 8.9 mmol, Danishefsky’s diene) in benzene (12 ml) was placed under nitrogen. Zinc chloride (0.5N in tetrahydrofuran, 8.9 ml, 4.45 mmol) was added and the reaction stirred at ambient temperature for 72 h. The mixture was concentrated in vacuo, diluted with ethyl acetate (100 ml) and washed with 1 N hydrochloric acid (20 ml), saturated sodium bicarbonate (20 ml), and brine (20 ml). The organic layer was dried (Na2SO4), filtered, and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using a mixture of ethyl acetate/hexane (1:2) as eluant. Pure fractions were collected and the solvent evaporated in vacuo which afforded 1.2 g (75%) of 4-oxo-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester as an oil.1H NMR (400 MHz, CDCl3) delta 7.40 (d, J=6, 1H), 5.48 (d, J=6, 1H), 5.01 (t, J=8, 1H), 4.28 (q, J=7, 2H), 2.85 (d, J=8, 2H), 1.29 (t, J=7, 3H).To a solution of the above of 4-oxo-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester (1.0 g, 5.9 mmol) in ethyl acetate (12 ml) was added 10% palladium on activated carbon (0.15 g). The reaction was shaken on a Parr hydrogenator under a hydrogen atmosphere (30 psi) for 1.5 h. The mixture was filtered through celite and concentrated in vacuo. The residue was purified by silica gel chromatography sing diethyl ether as eluant. Pure fractions were collected and the solvent evaporated in vacuo which affording 0.6 g (60%) of 4-oxo-tetrahydro-2H-pyran-2-carboxylic acid ethyl as an oil.1H NMR (300 MHz, CDCl3) delta 4.41-4.35 (m, 1H), 4.26 (q, J=7, 2H), 3.81-3.70 (m, 1H), 2.73-2.58 (m, 3H), 2.44-2.36 (m, 1H), 1.29 (t, J=7, 3H).To a solution of 4-oxo-tetrahydro-2H-pyran-2-carboxylic acid ethyl (0.6 g, 3.5 mmol) in absolute ethanol (6 ml) was added sulfur (0.12 g, 3.85 mmol) and tert-butyl cyanoacetate (0.64 g, 4.55 mmol). The solution was stirred under nitrogen in a 50 C. oil bath and morpholin (0.61 ml, 7.0 mmol) was added. The reaction was stirred for 18 h. and then cooled to ambient temperature and excess sulfur removed by filtration. The filtrate was concentrated in vacuo and reconstituted in ethyl acetate (50 ml). The organic phase was washed with brine (2¡Á10 ml), dried (Na2SO4), filtered, and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using a gradient of ethyl acetate/hexane (20 to 25% gradient) as eluant. Pure fraction of the two isomers were collected and the solvent evaporated in vacuo which afforded 0.47 g of 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3,5-dicarboxylic acid 3-tert-butyl ester 5-ethyl ester (A) and 0.3 g of 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3,7-dicarboxylic acid 3-tert-butyl ester 7-ethyl ester (B) in 62% combined yield.(A)1H NMR (300 MHz, CDCl3) delta 5.96 (bs, 2H), 4.77-4.61 (m, 2H), 4.32-4.18 (m, 3H), 3.19-3.12 (m, 1H), 2.90-2.80 (m, 1H), 1.52 (s, 9H), 1.29 (t, J=7, 3H).APCI-MS: [M+H]+=272.4 (loss of t-butyl)(B)1H NMR (300 MHz, CDCl3) delta5.10 (s, 1H), 4.28-4.13 (m, 3H), 3.98-3.91 (m, 1H), 2.82-2.76 (m, 2H), 1.51 (s, 9H), 1.31 (t, J=7, 3H).APCI-MS: [M+H]+=272.4 (loss of t-butyl)The above 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3,5-dicarboxylic acid 3-tert-butyl ester 5-ethyl ester (275 mg, 0.84 mmol) was dissolved in a mixture of ethanol (4 ml) and tetrahydrofuran (1 ml). Sodium hydroxide (1N, 1.6 ml, 1.68 mmol) was added and the reaction stirred at ambient temperature for 5 h. after which TLC analysis indicated that the reaction was complete. The reaction was monitored with a pH meter and neutralized with 1N hydrochloric acid until pH=6.9. The solution was concentrated in vacuo to give 2-amino-4+/-7-dihydro-5H-thieno[2,3-c]pyran-3,5-dicarboxylic acid 3-tert-butyl ester as a solid. Sodium chloride remained as an impurity.1H NMR (300 MHz, CD3OD) delta 4.67-4.54 (m, 2H), 4.00-3.95 (m, 1H), 3.20-3.12 (m, 1H), 2.74-2.63 (m, 1H), 1.54 (s, 9H).APCI-MS: [M+H]+=300.0To a solution of the above 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3,5-dicarboxylic acid 3-tert-butyl ester (94 mg, 0.31 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (72 mg, 0.37 mmol) in distilled dichloromethane (4 ml) under nitrogen was added aniline (32 mul, 0.34 mmol) followed by 2,6-lutidine (0.11 ml, 0.93 mmol). The reaction was stirred for 72 h., concentrated in vacuo and reconstituted in ethyl acetate (30 ml). The organic layer was washed with 1% hydrochloric acid (10 ml), saturated sodium bicarbonate (10 ml), brine (10 ml), dried (Na2SO4), filtered, and the solvent evaporated in vacuo to give 51 mg (45%) of 2-amino-5-phenylcarbamoyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as a solid.1H NMR (400 MHz, CDCl3) delta 8.40 (s, 1H), 7.60 (d, 1H, J=7), 7.49 (d, 1H, =8), 7.34 (t, 1H, J=8), 7.32 (t, 1H, J=8), 7.13 (t, 1H, J=7)…

The synthetic route of 287193-07-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Novo Nordisk A/S; US7115624; (2006); B1;,
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.5631-96-9,2-(2-Chloroethoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

(1) 13.4 g of 4-acetamido-2-methoxyphenol are dissolved in 80 ml of dimethylsulfoxide under nitrogen atmosphere, and 2.96 g of powdery sodium hydroxide are added thereto. The mixture is stirred at 50 C. to 55 C. for 3 hours. A solution of 10 g of 2-chloro-1-(tetrahydropyran-2-yl-oxy)ethane in 20 ml of dimethylsulfoxide is added dropwise to the mixture, and said mixture is stirred at 100 C. for one hour. After the reaction, the mixture is poured into ice-water, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water and an aqueous saturated sodium chloride solution, successively. Said extract is dried and then evaporated under reduced pressure to remove the solvent. The residue is recrystallized from a mixture of ethyl acetate and n-hexane, whereby 15.5 g of 1-(4-acetamido-2-methoxyphenoxy)-2-(tetrahydropyran-2-yl-oxy)ethane are obtained as colorless needles. Yield: 82.5% M.p. 88 C.-90 C.

The synthetic route of 5631-96-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Tanabe Seiyaku Co., Ltd.; US4413006; (1983); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics