Category: Tetrahydropyrans

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

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 250-mL 3-necked round bottom flask, was placed a solution of tetrahydropyran-4-one (5 g, 50.00 mmol, 1.00 equiv) in tetrahydrofuran (25 mL). This was followed by dropwise addition of a solution of LiAlH4 (3.8 g, 102.70 mmol, 2.00 equiv) in tetrahydrofuran (25 mL) with stirring at 0-5 C. The resulting solution was stirred for 3 h at 0-5 C. in a water/ice bath. The reaction was then quenched by the addition of 3.8 mL of water, 3.8 mL of 15% NaOH, and 11.4 mL of water. The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum to yield 5 g (96%) of product as a yellow oil., 29943-42-8

The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ardelyx, Inc.; Lewis, Jason G.; Jacobs, Jeffrey W.; Reich, Nicholas; Leadbetter, Michael R.; Bell, Noah; Chang, Han-Ting; Chen, Tao; Navre, Marc; Charmot, Dominique; Carreras, Christopher; Labonte, Eric; (323 pag.)US9301951; (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.65412-03-5,4-(2-Aminoethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.,65412-03-5

To 8-fluoro-3-(phenylsulfonyl)quinoline (300 mg), potassium carbonate (0.288 g: 2 eq) and4-amino-ethyl[2-(tetrahydro-2//-pyran-4-yl)ethyl] amine (Apollo Scientific) (0.269 g, 2 eq) inDMSO(3 ml) were added to a 5 ml microwave vial. The mixture was heated at 1800C under microwave irradiation for 1 hour. The reaction mixture was diluted with sodium hydrogen carbonate (20 ml) and extracted with ethyl acetate (3 x 20 ml). The ethyl acetate layers were combined and evaporated. The residue obtained was purified using the Flashmaster II(gradient 10-80% ethyl acetate on 50 g silica column) to give the free base of the title compound (0.255 g).NMR (400MHz, Chloroform-d6) delta 1.31-1.41 (2H, m), 1.65-1.71 (5H, m), 3.33-3.49 (4H, m), 3.94-3.97 (2H, m), 6.93 (IH, d), 7.22 (IH, d), 7.52-7.62 (4H, m), 8.00-8.03(2H, m), 8.75(IH, d), 9.07 (IH, d)LC/MS, t = 3.58min, Molecular ion observed (MH+) = 497 consistent with the molecular formula C22H24N2O3S3-(Phenylsulfonyl)-lambda^-[2-(tetrahydro-2/f-pyran-4-yl)ethyl]-8-quinolinamine (0.255g ) was taken up into methanol and treated with an excess of 2M HCl in diethyl ether to give the title compound (0.268 g)NMR (400MHz, Chloroform-d6) 1.22-1.28 (2H, m), 1.55-1.58 (2H, m), 1.07 (IH, bs), 1.85(2H, bs)3.30-3.36 (2H, m), 3.42-3.52 (2H, m), 3.88-3.92 (2H, m), 6.93 (IH, d), 7.57-7.73(4H, m), 7.85-7.87 (IH, bs), 8.04-8.10 (3H, m), 8.96 (IH, s), 9.29 (IH, s)LC/MS, t = 3.58min, Molecular ion observed (MH+) = 497 consistent with the molecular formula C22H24N2O3S

The synthetic route of 65412-03-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2008/116816; (2008); 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.344329-76-6,Tetrahydro-2H-pyran-4-carboxamide,as a common compound, the synthetic route is as follows.

Example 156 A suspension of Example B5 (0.596 g, 4.61 mmol) in dioxane (15 mL) was treated with oxalyl chloride (0.820 mL, 9.69 mmol), stirred at RT for 10 min, then heated to 80¡ã C. for 4 h. The mixture was cooled to RT, concentrated to dryness, treated with Example A13 (0.200 g, 0.703 mmol), pyridine (0.120 mL, 1.481 mmol) and THF (5 mL) and stirred at RT overnight. The mixture was concentrated to dryness, the residue suspended in MeCN and sonicated, and the resulting solid was collected via filtration, suspended in water, stirred for 15 min, then again collected via filtration. The solid was treated with MTBE, stirred for 1 h and then collected via filtration to afford N-((5-((2-(2-methylthiazol-5-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)tetrahydro-2H-pyran-4-carboxamide (110 mg, 33percent). 1H NMR (400 MHz, DMSO-d6): delta 11.06 (s, 1H), 10.89 (s, 1H), 8.41 (d, J=5.6 Hz, 1H), 8.32 (s, 1H), 8.28 (d, J=2.9 Hz, 1H), 8.09 (d, J=9.0 Hz, 1H), 7.75 (dd, J=9.0, 2.9 Hz, 1H), 7.60 (d, J=2.4 Hz, 1H), 6.82 (dd, J=5.8, 2.4 Hz, 1H), 3.88 (m, 2H), 3.34-3.25 (m, 3H), 2.65 (s, 3H), 1.72 (m, 2H), 1.62-1.59 (m, 2H); MS (ESI) m/z: 440.2 (M+H+).

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

Reference£º
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); 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.

To 75 g (0.75 mol) of tetrahydropyran-4-one in THF (150 mL) is added a suspension of 28.4 g (0.75 mol) LiAIH4 in THF (600 mL) under nitrogen atmosphere maintaining the temperature below 30 C with the aid of an ice-bath. Then the reaction is allowed to warm to RT and stirred for 5 h. The reaction is quenched by addition of sat. aq. NH4CI solution until effervescence ceased. The resulting precipitate is removed by filtration through Celite and washed with THF (150 mL). The filtrate is concentrated under reduced pressure to afford 71.1 g of tetrahydropyran-4-ol. Yield: 92%., 29943-42-8

29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; BINDER, Florian; DOODS, Henri; MUELLER, Stephan, Georg; NICHOLSON, Janet, Rachel; SAUER, Achim; WO2014/184327; (2014); 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

In 25 ml water compound is added in the bottle (J) 100 mg, EDCI67mg, dichloromethane 10 ml, reaction solution stirring 30 minutes, the compound is added (K) (in accordance with WO2012058392 method preparation) 55 mg, finally adding catalytic DMAP, reaction solution adding stirring reaction sleepovers, to splines end of the detection reaction TLC solvent, ABT-199 HPLC purified to get the pure product 98 mg, yield 65%.

1228779-96-1, As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.

Reference£º
Patent; Nanjing Acesys Pharmatech Co., Ltd; GE, MIN; XU, YUNLEI; (8 pag.)CN104370905; (2016); B;,
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.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

To a mixture of 2-chloropyrimidine-5-boronic acid (32 mg, 0.2 mmol) and N-methyl-N-tetrahydro-2H-pyran-4-ylamine (26 mu, 0.21 mmol) in EtOH (2 mL) was added triethylamine (0.070 mL, 0.5 mmol). The resulting mixture was stirred at 75 C for 5 h. Solvents were removed to give crude (2-(methyl(tetrahydro-2H-pyran-4- yl)amino)pyrimidin-5-yl)boronic acid as a light yellow solid. LCMS [M + H] 238.2. The title compound (white solid, 5.4 mg, 9%) was prepared similar to Example 29 using crude (2-(methyl(tetrahydro-2H-pyran-4-yl)amino)pyrimidin-5-yl)boronic acid (0.2 mmol) and (S)-N-(5-bromo-2-(3,4-dimethylpiperazin-l-yl)-4-fluorophenyl)-6-oxo- 4-(trifluoromethyl)-l,6-dihydropyridine-3-carboxamide (49.1 mg, 0.1 mmol). ‘H NMR (500MHz, CHLOROFORM-d) delta = 8.73 (br s, 1H), 8.57 (s, 2H), 8.52 – 8.40 (m, 1H), 7.87 (br s, 1H), 7.11 – 6.91 (m, 2H), 4.98 (br t, J=11.9 Hz, 1H), 4.11 (br dd, J=4.0, 11.4 Hz, 2H), 3.61 (br t, J=11.6 Hz, 2H), 3.11 (s, 3H), 3.05 – 2.82 (m, 4H), 2.70 – 2.55 (m, 1H), 2.38 (br s, 3H), 2.30 – 2.16 (m, 1H), 1.94 (dq, J=4.4, 12.2 Hz, 2H), 1.70 (br d, J=11.5 Hz, 2H), 1.13 (br s, 3H); LCMS [M + H]+ 604.5., 220641-87-2

The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
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,951127-25-6

12b (0.28 g, 1.2 mmol) was dissolved in dimethylacetamide (4 mL) at room temperature,Intermediate 1 (0.39 g, 1.2 mmol) and benzenesulfonic acid (0.22 g, 1.2 mmol) were added and stirred at room temperature for 1 hour.Sodium tris (acetoxy) borohydride (0.33 g, 1.4 mmol) was added to the reaction solution, and the reaction was continued at room temperature for 16 hours.After cooling to 0 C, water (30 mL) and ammonia (1 mL) were added successively to precipitate a white solid which was filtered and washed with water (10 mL x 2) and dried.The filter cake was dissolved in dichloromethane (150 mL), dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to give soil yellow solid 12c (0.30 g, yield 46.0%).

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 fields.

Reference£º
Patent; Sichuan Haisco Pharmaceutical Co.,Ltd; FAN, JIANG; CHEN, QINGPING; JIANG, WEI; ZHENG, SUXIN; YE, FEI; (128 pag.)TW2017/8221; (2017); A;,
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

A mixture of 2,2-dimethyloxan-4-one (2.00 g, 15.6 mmol), sulfur (500 mg, 15.6 mmol), cyanamide (656 mg, 15.6 mmol and pyrrolidine (13 muL¡¤, 0.156 mmol) was stirred in isopropanol (3 mL) at room temperature for 3h. The reaction mixture was filtered to remove excess sulfur and chromatographed on silica, eluting with 5% MeOH in DCM to afford the title compound as a yellow solid (2.87 g, 47 ). 1H NMR (500 MHz, CDC13) delta 4.94 (br. s., 2H), 4.64 (t, J=1.8 Hz, 2H), 2.56 (s, 2H), 1.34 – 1.30 (s, 6H)., 1194-16-7

The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); 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

KR of thiol 28 with simultaneous enantioselective synthesis of a ( ?)-Pregabalin precursor; [00120] A 20 mL reaction vial containing a stirring bar was charged with 3-isobutylglutaric anhydride (4) (102.1 mg, 0.60 mmol) and 1 8 (47.2 mg, 0.080 mmol). The reaction vial was flushed with argon and fitted with a septum. MTBE was then injected (4.0 mL, 0.2M) and the solution cooled to -30 C. 28 (0.30 mmol) was added dropwise via syringe and the resulting solution was stirred for 48 h. The mixture was the immediately loaded onto a column and the ‘slow reacting’ thiol enantiomer separated from the mixture by flash-chromatography (71 .0 mg, 0.39 mmol, 98.7% ee as determined by CSP-HPLC after derivatisation as per general procedure B). The hemithioester product (29) was suspended in aq. NH3 (3 mL) and stirred at room temperature for 4 h. The reaction was then diluted with CH2CI2 (10.0 mL) and H20 (5.0 mL) and transferred to a separating funnel. The organic and aqueous layers were separated and the aqueous layer was extracted with CH2CI2 (2 x 10.0 mL). The combined organic layers were then dried over MgS04 and the solvent removed under reduced pressure affording the ‘fast reacting’ (S)-thiol enantiomer (62.4 mg, 0.35 mmol, 95.5% ee as determined by CSP-HPLC after derivatisation as per general procedure B) after flash chromatography. Conversion = 50.8%, S Factor = 226.[00121 ] The aqueous layer was then acidified by addition of HCI (8 N) and extracted with EtOAc (5 x 15 mL). The combined organic phases were then dried over magnesium sulphate and the solvent was removed under reduced pressure to afford the desired hemiamide as a white solid (71 .2 mg, 0.38 mmol, 97.0% ee as determined by CSP-HPLC after transformation to the corresponding o-nitrophenoxy ester, as per the procedure reported below).[00122] 1H NMR spectrum of (S)-30 (400 MHz, DMSO-d6): delta 12.0 (br s, 1 H), 7.27 (s, 1 H), 6.74 (s, 1 H), 2.22-1 .91 (m, 5H), 1 .66-1 .51 (m, 1 H), 1 .09 (app t, J 6.6, 2H), 0.81 (d, J 6.6, 6H). 13C NMR (100 MHz, DMSO-d6): delta 174.3 (q), 173.9 (q), 43.6, 40.2, 39.2, 30.1 , 25.0, 23.2, 23.1. HRMS (m/z): [M+Na]+ calcd. for C9H17N03Na 210.1 106; found, 210.1 1 14.; Synthesis of Pregabalin [( ?)- 3-(aminomethyl)-5-methylhexanoic acid]; [0066] To demonstrate the potential utility of this methodology, the KR of thiol 28 (0.80 mmol) was carried out with catalyst 18 in the presence of achiral anhydride 4, which furnished (R)-28 (0.39 mmol, 99% ee) and the ring-opened product 29 (0.40 mmol) with excellent efficiency at 51 % conversion as shown in Figure 1 . Thioester 29 (as a mixture of diastereomers) was then treated with aqueous ammonia, resulting in its cleavage to afford the other thiol enantiomer (S)- 28 (96% ee, 0.35 mmol) and the aminolysed product (S)-30 (97% ee, 0.38 mmol), again with high efficiency. Hemiamide (S)-30 is a precursor which can be converted in a single step to the (R)-antipode of the anticonvulsive agent Pregabalin and thus this sequence – in addition to serving as a highly efficient KR of 28 – constitutes a rapid and convenient formal synthesis of the ‘blockbuster’ drug (marketed as ‘Lyrica’).

185815-59-2, As the paragraph descriping shows that 185815-59-2 is playing an increasingly important role.

Reference£º
Patent; THE PROVOST, FELLOWS AND SCHOLARS OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH, NEAR DUBLIN; CONNON, Stephen Joseph; PESCHIULLI, Aldo; PROCURANTI, Barbara; WO2011/70028; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics