Tag: M.W:100-200

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

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.40191-32-0,Tetrahydro-2H-pyran-4-carbonyl chloride,as a common compound, the synthetic route is as follows.

Intermediate 4: [(S)-1 -(Tetrahydro-pyran-4-carbonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester; To a vigorously stirring solution of tetrahydro-2H-pyran-4-carbonyl chloride (0.455 g, 3.06 mmol) in CH2CI2 (10 mL) was added simultaneously portionwise sat. NaHC03(aq) (10 mL) and a solution of the (S)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (570 mg, 3.06 mmol) at rt. The resulting biphasic mixture was stirred vigorously at rt for 3h. The organic layer was separated by filtration through a phase separation tube, concentrated in vacuo and purified by flash chromatography on silica gel with CH2CI2 / MeOH to give [(S)-1 -(tetrahydro-pyran-4- carbonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester as a colourless gum (0.623 g, 68% yield) LCMS: [M+H]+= 299.6, Rt (7)= 0.73 min., 40191-32-0

40191-32-0 Tetrahydro-2H-pyran-4-carbonyl chloride 2795505, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo; GRAVELEAU, Nadege; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STOWASSER, Frank; STRANG, Ross; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2012/4299; (2012); 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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

To a solution of benzyloxycarbonyl-a-phosphonoglycine trimethyl ester (1.163 g, 3.52 mmol) in dry DCM (20 mL) was added DBU (0.534 g, 3.52 mmol) dropwise at 0C. Then a solution of compound cap 3a (1.8 g, 14.08 mmol) in dry DCM (20 mL) was added dropwise at 0C. The reaction mixture was stirred at 25C for 3 days. After removal of the solvent, the residue was purified using Si02 chromatography (e luting with petroleum ether/ ethyl acetate = 5: 1 to 3: 1) to providecompound cap 3b as white solid (0.15 g, 13% yield). 1H NMR (CDC13): delta 7.30-7.35 (m, 5 H), 5.11 (s, 2 H), 3.82-3.88 (m, 3 H), 3.09-3.16 (m, 2 H), 1.84 (s, 2 H), 1.48 (s, 2 H), 1194-16-7

As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; YU, Wensheng; TONG, Ling; KOZLOWSKI, Joseph A.; SELYUTIN, Oleg; CHEN, Lei; KIM, Jae-Hun; SHA, Deyou; RIZVI, Razia; SHANKAR, Bandarpalle; HU, Bin; ZHONG, Bin; WAI, Dahai; HAO, Jinglai; WEI, Wei; JI, Tao; ZAN, Shuai; WO2014/110705; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

65412-03-5,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.

Place 2- (4-FORMYLPHENOXY) thiazole-5-carboxamide (Example 12, Part D) (0.187 g, 0.755 MMOL), 2-(tetrahydropyran-4-yl)ethylamine (0.101 g, 0.831 mmol) and 3A molecular sieves in a vial. Add methanol (3.8 mL), cap and stir overnight. Add NaBH4 (0.029 g, 0.755 mmol) and stir until the gasses stop evolving. Load the reaction mixture directly onto a 25 g ISCOO pre-load column. Dry the column in a vacuum oven at room temperature. Purify by eluting through a 40 g LSCO) column with 10% (2. 0 M NH3 in methanol) in ethyl acetate over 45 minutes to give the title compound as a free base. Dissolve the compound in dichloromethane: methanol (2 : 1) (3 mL) and add 1 equivalent of 0.50 M methanesulfonic acid in dichloromethane. Stir the solution for a short time before concentrating to give the title compound: TOF MS ES+ 362.1 (M+H) +, HRMS calcd for CL8H24N303S 362. 1538 (M+H) +, found 362.1536, time 0.32 min ; HPLC [YMC- Pro pack C-18 (150 x 4.6 mm, S-5 MICRON1), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1. 0 ML/MIN, 10-20% OVER 5 min, 20-95% over 18], tR = 8. 0 min, 95. 0% purity.

65412-03-5 4-(2-Aminoethyl)tetrahydro-2H-pyran 2773198, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2004/80996; (2004); 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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

Ethyl 2,4-dioxo-3- (p-tolyl) -1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3.76 g, 13.7 mmol, 1.0 eq) was dissolved in DMF (45 mL) To this, 4- (bromomethyl) tetrahydro-2H-pyran (4.88 g, 27.4 mmol, 2.0 eq) and potassium carbonate (5.67 g, 41.1 mmol, 3.0 eq) were added. The reaction was heated to 60 C for 4 hours. After the reaction was detected by LC-MS and TLC, the temperature was lowered to room temperature, suction filtered, the filtrate was poured into water (50mL), and extracted with EA (50mL ¡Á 3). The organic phases were combined, washed with brine three times, dried, filtered, and concentrated. Silica gel column chromatography (100-200 mesh silica gel, PE / EA = 0-50%) was purified to obtain an off-white solid (1.9 g, yield: 37%)., 125552-89-8

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

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.

To a solution of dihydro-2H-pyran-3(4H)-one (100 mg, 1.0 mmol) in dry THF (10 mL) was added lithium bis(trimethylsilyl)amide (1.2 mL, 1.2 mmol, 1M in THF) at 0 C. After stirring for 5 min, i-9 (260 mg, 1.2 mmol) was added and stirred for additional 5 min. Acetic acid (1 mL) was added followed by addition of hydrazine monohydrate (1 mL, 85%). The reaction was quenched with aqueous NaHCO3 and the mixture was extracted with EtOAc. The combined organic layers were washed with saturated brine, dried over Na2SO4 and concentrated. The residue was purified by prep TLC (EtOAc/PE=1:1) to give the title compound. LCMS (ESI) calc’d for C14H13FN2O3[M+H]+: 277, found: 277., 23462-75-1

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

Reference£º
Patent; Merck Sharp & Dohme Corp.; Lapointe, Blair T.; Fuller, Peter H.; Gunaydin, Hakan; Liu, Kun; Sciammetta, Nunzio; Trotter, Benjamin Wesley; Zhang, Hongjun; Barr, Kenneth J.; Maclean, John K. F.; Molinari, Danielle F.; Simov, Vladimir; (103 pag.)US2018/16239; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

40191-32-0, Tetrahydro-2H-pyran-4-carbonyl chloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N,O-Dimethylhydroxylamine hydrochloride (1.23 g, 12.7 mmol) and N-methylmorpholine (3.80 mL, 34.5 mmol) were dissolved in DCM (20 mL) and a solution of oxane-4-carbonyl chloride (1.71 g, 11.5 mmol) in DCM (20 mL) was added drop-wise. The reaction mixture was stirred for 2 h, then diluted to 200 mL with DCM, washed with 1 M aq HCl (2*100 mL), 1M aq Na2CO3 (100 mL) and water (100 mL), dried (MgSO4) and concentrated in vacuo to give the crude title compound as a yellow oil (1.87 g, 94%). LCMS (ES+): 174.1 (M+H)+.

40191-32-0, As the paragraph descriping shows that 40191-32-0 is playing an increasingly important role.

Reference£º
Patent; PROXIMAGEN LIMITED; Evans, David; Carley, Allison; Stewart, Alison; Higginbottom, Michael; Savory, Edward; Simpson, Iain; Nilsson, Marianne; Haraldsson, Martin; Nordling, Erik; Koolmeister, Tobias; US2013/102587; (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.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Experimental ProceduresDesymmetrisation of 3-/sobutylglutaric anhydride by thiolysis using catalyst C2 at ambient temperature:[0099] A 60 ml. reaction vial, charged with 3-/sobutylglutaric anhydride (102.1 mg, 0.60 mmol) and C2 (7.1 mg, 0.012 mmol), was fitted with a septum and flushed with argon. MTBE (40 ml.) was added followed by cyclohexyl mercaptan (368 mul_, 3.0 mmol) in a dropwise manner via syringe. After 72 h stirring at room temperature, volatiles were removed under reduced pressure and the desired product (Vl) obtained, after purification by flash chromatography, in 100% yield(164.0 mg) as a colourless oil. [alpha]D20 = -5.9 (c 1.64, acetone).[0100] deltaH (400 MHz, CDCI3): 0.92 (app. d, J 6.5, 6H), 1.18-1.34 (m, 3H), 1.36-1.50 (m, 4H),1.56-1.78 (m, 4H), 1.88-1.98 (m, 2H), 2.34-2.52 (m, 3H), 2.56-2.64 (m, 2H), 3.48-3.59 (m, 1 H). deltac (100 MHz, CDCI3): 22.0, 22.1 , 24.7, 25.0, 25.5, 30.0, 32.5, 32.6, 37.6, 41.9, 42.7, 47.5, 176.7,198.2. HRMS (ESI): Found 285.1522 (M – H+) Ci5H25O3S requires 285.1524., 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; MARKEY, Lyn; WO2010/86429; (2010); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics