Heterocyclic Building Blocks-Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1240390-36-6,tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Step 5 {(3R,4R)-4-[7-(Thiazolo[4,5-b]pyridine-2-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester To a solution of 2-chloro-N-(thiazolo[4,5-b]pyridin-2-yl)thieno[3,2-d]pyrimidine-7-carboxamide (0.162 g, 0.466 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.151 g, 0.699 mmol) in dioxane (4 mL) was added diisopropylethylamine (0.244 mL, 1.4 mmol). The reaction mixture was heated at 120 C. overnight. The reaction mixture was cooled and then diluted with dichloromethane, washed with aqueous sodium carbonate, then brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was then purified by chromatography (silica, 40 g, 0 to 15% MeOH in dichloromethane) to give {(3R,4R)-4-[7-(thiazolo[4,5-b]pyridine-2-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (0.118 g, 0.224 mmol, 48%) as a yellow solid. LCMS m/z [M+H]=528.

1240390-36-6, As the paragraph descriping shows that 1240390-36-6 is playing an increasingly important role.

Reference£º
Patent; Hoffmann-La Roche Inc.; Chen, Shaoqing; Hermann, Johannes Cornelius; Le, Nam T.; Lucas, Matthew C.; Padilla, Fernando; US2013/178460; (2013); 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.

Into a 8-mL round-bottom flask, was placed 4-(4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex -l-en-l-yl]methyl]piperazin-l-yl)-2- [l2,l2-difluoro-l4-oxa-2,4,l0-triazatricyclo[7.5.0.0A[3,7]]tetradeca-l(9),2,5,7-tetraen-l0- yl]benzoic acid (20.00 mg, 0.030 mmol, 1.00 equiv), 3-nitro-4-[[(oxan-4-yl)methyl]amino] benzene- l-sulfonamide (11.43 mg, 0.036 mmol, 1.2 equiv), DCM (3 mL), DMAP (14.76 mg, 0.121 mmol, 4 equiv), EDCI (11.58 mg, 0.060 mmol, 2 equiv). The resulting solution was stirred for 12 h at room temperature. 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% NH4HCO3 & NH4OH) and CH3CN (32% CH3CN up to 52% in 6 min); Detector, UV 254 nm. This resulted in 11.5 mg (39.68%) of 4-(4-[[2-(4- chlorophenyl)-4,4-dimethylcyclohex- l-en- l-yl]methyl]piperazin- l-yl)-2-[l2, 12- difluoro- l4-oxa-2,4,l0-triazatricyclo[7.5.0.0A[3,7]]tetradeca-l(9),2,5,7-tetraen-l0-yl]-N-(3-nitro-4- [[(oxan-4-yl)methyl]amino]benzenesulfonyl)benzamide as a white solid. LC-MS-0: (ES, m/z) M+l=96l.47. 1H-NMR-0(300MHz, d-DMSO, ppm): 511.01 (s, 1H), 8.34-8.33 (d, / =3.0 Hz, 1H), 7.47-7.45 (m, 2H), 7.38-7.35 (m, 2H), 6.82-6.80 (m, 3H), 6.02 (s, 1H), 3.86- 3.51 (m, 7H), 3.39-3.17 (m, 5H), 2.77-2.73 (m, 2H), 2.24-2.20 (m, 6H), 2.00 (s, 2H), 1.42 (m, 2H), 1.30 (s, 1H), 0.95 (s, 6H)., 1228779-96-1

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

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,101691-94-5

A solution of 4-(iodomethyl)tetrahydro-2H-pyran ([101691-94-5], 565 mg, 3 mmol) in LiC1 solution (0.5 M in THF, 5 mL, 3 mmol) was pumped using the R2 + R4 through a column containing activated Zn (12 g) at 0.5 mL/min at 60 C. Titration with 12/LiC1 showed a concentration of organozinc reagent of 0.28 M. The solution was used in the next step without further purification.

As the paragraph descriping shows that 101691-94-5 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; VOS, Ann, Marleen; OEHLRICH, Daniel; GIJSEN, Henricus, Jacobus, Maria; WATTS, Karl, Shawn; BHAT, Sathesh, Pangala; BUIJNSTERS, Peter, Jacobus, Johannes, Antonius; VAN BRANDT, Sven, Franciscus, Anna; ALCAZAR-VACA, Manuel, Jesus; (57 pag.)WO2018/162444; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

65412-03-5,65412-03-5, 4-(2-Aminoethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2,4,6-Trichlorophenyl 1-benzyl-5-(methylcarbamoyl)-6-oxo- 1,6-dihyd ropyrid ine-3- carboxylate (61 mg, 0.13 1 mmol), 2-(tetrahydro-2H-pyran-4-yl)ethanamine (33.8 mg, 0.262 mmol), N,N-dimethylpyridin-4-amine (4 mg, 0.033 mmol),triethylamine (0.05 mL, 0.359 mmol) and THF (1mL) were stirred at 45 C for 4 h. A white precipitate formed which was filtered to give 31 mg of a white solid. This was purified by chromatography on Si02 (Biotage SNAP 10 g cartridge, eluting with O-100% ethyl acetate/(25% ethanol in ethyl acetate)). The appropriate fractions were collected and concentrated to give 1-benzyl-N3-methyl-2-oxo-N5-(2-(tetrahydro-2H-pyran-4-yl)ethyl)- 1,2- dihydropyridine-3,5-dicarboxamide (9 mg, 0.020 mmol, 15.56 % yield) as a white solidLCMS (2mm Formic): Rt=0.89 mi [MH] = 398.

As the paragraph descriping shows that 65412-03-5 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; HOUSE, David; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (141 pag.)WO2017/50714; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

25850-22-0, 2,2-Dimethyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(4) (2E)-3-{1-[bis(4-fluorophenyl)methyl]-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-(2,2-dimethyltetrahydro-2H-pyran-4-yl)prop-2-enamide To a solution of (2E)-3-{1-[bis(4-fluorophenyl)methyl]-3-cyano-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (300 mg, 0.677 mmol) in THF (3 ml) were added DMF (0.03ml) and oxalylchloride (0.071 ml, 0.813 mmol), the mixture was stirred at room temperature for 1 hour and the solvent was distilled off under reduced pressure. The residue was added under ice-cooling to a solution of 2,2-dimethyltetrahydro-2H-pyran-4-ylamine (175 mg, 1.35 mmol), triethylamine (0.313 ml, 2.25 mmol) and THF (2 ml), and the mixture was stirred under ice-cooling for 2 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to give the objective product as a solid material. Yield (amount) 177 mg, yield (rate) 47.1% 1H-NMR (CDCl3) delta: 1.18-1.40 (8H, m), 1.80-1.90 (2H, m), 2.56 (3H, s), 2.75 (3H, s), 3.69-3.77 (2H, m), 4.16-4.21 (1H, m), 5.49 (1H, d, J = 7.6 Hz), 6.78 (1H, d, J = 15.8 Hz), 6.92-7.26 (9H, m), 7.44 (1H, d, J = 15.8 Hz), 7.94 (1H, s). IR (KBr) cm-1; 3289, 2216, 1661, 1607, 1510, 1333, 1231, 1159, 733., 25850-22-0

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

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1535922; (2005); 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.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

Add in a 50mL single-mouth bottle2-(5-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine (0.11 g, 0.30 Mm),1-(tetrahydro-2H-pyran-4-yl)ethanone (0.050 g, 0.39 mmol) and methanol (10 mL),Acetic acid (0.17 mL, 3.0 mmol) was added at 0 C.After stirring at room temperature for 1 hour and then cooled to 0 C, sodium cyanoborohydride (0.094 g, 1.5 mmol) was added.It was then stirred at room temperature overnight.Evaporation of the solvent, EtOAc (EtOAc)The organic phase was washed with water (30 mL) and brine (30 mL)The residue was purified by silica gel column chromatography (dichloromethane/methanol (v/v) = 80/1, 0.5% triethylamine)A pale yellow solid (0.036 g, 25.0%)., 137052-08-5

137052-08-5 1-(Tetrahydro-2H-pyran-4-yl)ethanone 9877365, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Wang Xiaojun; Zuo Yinglin; Yu Chuan; Yang Chuanwen; Wang Jiancheng; Li Jing; Cao Shengtian; Wu Fangyuan; Zhang Yingjun; S ¡¤geerdeman; (79 pag.)CN108690016; (2018); A;,
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

Intermediate 077 N-(2,4-Dimethoxybenzyl)-5-nitro-2-(tetrahydro-2H-pyran-4- ylmethoxy)benzenesulfonamide 2-Chloro-N-(2,4-dimethoxybenzyl)-5-nitrobenzenesulfonamide (2.00 g, 5.17 mmol) was dissolved in dimethylformamide (10 mL), treated with tetrahydro-2H-pyran-4-ylmethanol (901 mg, 7.76 mmol) and sodium hydride (1.58 g, 36.2 mmoL) and was stirred for 2 hours at room temperature. It was quenched under ice cooling with water/ethyl acetate. The phases were separated, the aqueous phase was three times reextracted with ethyl acetate and all organic phases were combined, dried and concentrated in vacuo. It was tehn stirres with ethyl acetate/methyl tert.-butyl ether (1/2) until a white solid precipitated. Filtration led to N-(2,4-dimethoxybenzyl)-5-nitro-2-(tetrahydro-2H-pyran-4- ylmethoxy)benzenesulfonamide (2.20 g, 4.75 mmol, 91% yield, 95% purity) LC-MS (Method A): Rt = 1.16 min MS (ESIneg): m/z = 465 (M-H)+ 1H-NMR (400MHz, DMSO-d6) [ppm]: 1.23 – 1.36 (m, 2H), 1.70 – 1.77 (m, 2H), 2.09 – 2.23 (m, 1H), 3.29 – 3.39 (m, 2H), 3.59 (s, 3H), 3.65 (s, 3H), 3.89 (dd, 2H), 3.99 (d, 2H), 4.08 (s, 2H), 6.21 (d, 1H), 6.30 (dd, 1H), 7.01 (d, 1H), 7.25 (d, 1H), 7.42 (s, 1H), 8.23 (d, 1H), 8.31 (dd, 1H)., 14774-37-9

As the paragraph descriping shows that 14774-37-9 is playing an increasingly important role.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WERNER, Stefan; MESCH, Stefanie; BRAeUER, Nico; POOK, Elisabeth; DAHLLOeF, Henrik; NUBBEMEYER, Reinhard; OSMERS, Maren; KALTHOF, Bernd; (386 pag.)WO2016/198374; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

2-(2,6-dichlorophenyl)-1 -[(1 S)-4-iodo-1-methyl-1 ,3-dihydro-2H-isoindol-2-yl]ethanone a48(100 mg, 0.22 mmol), sodium metabisulfite (87 mg, 0.45 mmol), tetrabutylammonium bromide (80 mg, 0.25 mmol), sodium formate (34 mg, 0.49 mmol), palladium(Il) acetate (5mg, 0.02 mmol), 1,10-phenanthroline (12 mg, 0.07 mmol) and triphenylphosphine (18 mg, 0.07 mmol) were mixed in DMSO (2 mL). The mixture was stirred at 70 C for 2 h. The reaction mixture was cooled to rt, then 4-(iodomethyl)tetrahydro-2H-pyran (100 mg, 0.44mmol) was added. The mixture was stirred at ft for 16 h, then diluted with DCM (50 mL) and successively washed with water (50 mL) and brine (50 mL). The organic layer was dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by reverse phase chromatography (basic mode, LCMS prep) to yield 12 mg of 2-(2,6- dichlorophenyl)-1 -{(1 S)-1 -methyl-4-[(tetrahydro-2H-pyran-4-ylmethyl)sulfonyl]- 1 ,3-dihydro-2H-isoindol-2-yl}ethanone 42 as a white solid.Yield: 10%.LCMS (ES) 482/484/486 (M-?-H), 96.78 % purity.

101691-94-5, As the paragraph descriping shows that 101691-94-5 is playing an increasingly important role.

Reference£º
Patent; UCB BIOPHARMA SPRL; SKOLC, David; ATES, Ali; JNOFF, Eric; VALADE, Anne; (99 pag.)WO2016/55482; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

7525-64-6, 4-Methyltetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7525-64-6, Step 1. Preparation of (4-methyltetrahydropyran-4-yl)-(4-nitrophenyl)-carbonate In a flame-dried round bottomed flask equipped with a magnetic stirrer, 4-methyltetrahydropyran-4-ol (1.5 g, 12.9 mmol), prepared as described in patent application WO2004/041161, was dissolved in CH2Cl2 (30 mL). The mixture was chilled to 0 C. then pyridine (2.04 mL, 25.82 mmol, 2 eq) and p-nitrophenylchloroformate (3.38 g, 16.78 mmol) solution in CH2Cl2 (10 mL) were slowly added. A white precipitate almost immediately appeared and the mixture was stirred overnight at rt. The crude mixture was then diluted with CH2Cl2, washed with 1M HCl solution, saturated NaHCO3 solution and finally with brine. The two phases were separated and the organic one was dried over Na2SO4. Removal of the organics under reduced pressure gave a crude yellow solid (3.8 g), as a 1:1 mixture of desired product and p-nitrophenylchloroformate, which was used in the next step without further purification. 1H NMR (CDCl3): delta 1.67 (s, 3H), 1.87 (m, 2H), 2.23 (m, 2H), 3.78 (m, 4H), 7.39 (d, J=9.0 Hz, 2H), 8.29 (d, J=9.0 Hz, 2H)

The synthetic route of 7525-64-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; The Regents of the University of California; Fondazione Istituto Italiano Di Technologia; Universita Degli Studi Di Parma; Universita Degli Studi Di Urbino ?Carlo Bo?; Piomelli, Daniele; Bandiera, Tiziano; Mor, Marco; Tarzia, Giorgio; Bertozzi, Fabio; Ponzano, Stefano; (102 pag.)US9353075; (2016); 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.4677-18-3,2-(Tetrahydro-2H-pyran-4-yl)ethanol,as a common compound, the synthetic route is as follows.

To an ice-cold solution of 2-(tetrahydro-2H-pyran-4-yl)ethanol (1.00 g) in pyridine (6.5 mL) was added p-toluenesulfonyl chloride (1.5 g), followed by stirring at the same temperature for 30 minutes, and at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and then diluted aqueous hydrochloric acid (20 mL) was added to the residue, followed by twice extractions with ethyl acetate (20 mL). The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=80/20-50/50) to obtain p-toluenesulfonic acid 2-(tetrahydro-2H-pyran-4-yl)ethyl ester (450 mg)., 4677-18-3

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

Reference£º
Patent; Astellas Pharma Inc.; EP2194044; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics