Tag: M.W:100-200

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.,4677-18-3

[00107] A mixture of 2-(tetrahydro-2H-pyran-4-yl)ethanol (11.70 g, 89.9 mmol) and pyridinium chlorochromate (38.8 g, 179.8 mmol) in CH2C12 (200 mL) was stirred at 16-19 C for 17 h. TLC (petroleum ether: ethyl acetate = 3: 1) showed the reaction was complete. The mixture was filtered with Kieselguhr and the filtrate (150 mL) was used for the next step directly without further purification.

As the paragraph descriping shows that 4677-18-3 is playing an increasingly important role.

Reference£º
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; SINGH, Suresh, B.; TICE, Colin, M.; YUAN, Jing; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; (102 pag.)WO2016/61160; (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.25850-22-0,2,2-Dimethyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

(4) (2E)-3-{3-cyano-4,6-dimethyl-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4S)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide(2E)-3-{3-cyano-4,6-dimethyl-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4R)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide To a solution of (2E)-3-{3-cyano-4,6-dimethyl-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (861 mg, 2.32 mmol) in THF (8 ml) were added DMF (0.10ml) and oxalylchloride (0.243 ml, 2.79 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 (600 mg, 4.64 mmol), triethylamine (1.08 ml, 7.71 mmol) and THF (6 ml), 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 1 : 1) to separate two kinds of diastereomers. Firstly eluted diastereomer: (2E)-3-{3-cyano-4,6-dimethyl-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4S)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide yield 247 mg, yield (rate) 22.1%1H-NMR (CDCl3) delta: 1.24-1.40 (8H, m), 1.80-2.30 (6H, m), 2.59 (3H, s), 2.76 (3H, s), 2.90-3.23 (2H, m), 3.65-3.80 (2H, m), 4.19-4.24 (1H, m), 5.51 (1H, d, J = 8.0 Hz), 6.49 (1H, d, J = 7.5 Hz), 6.68-7.26 (7H, m). IR (KBr) cm-1; 3268, 2215, 1661, 1622, 1588, 1553, 1507, 1427, 1331, 1262, 1198, 735, 748. Later eluted diastereomer: (2E)-3-{3-cyano-4,6-dimethyl-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4R)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide Yield (amount) 222 mg, yield (rate) 19.8%1H-NMR (CDCl3) delta: 1.20-1.36 (8H, m), 1.76-2.29 (6H, m), 2.59 (3H, s), 2.76 (3H, s), 2.90-3.16 (2H, m), 3.65-3.80 (2H, m), 4.19-4.23 (1H, m), 5.48 (1H, d, J = 7.8 Hz), 6.50 (1H, d, J = 8.1 Hz), 6.71-7.26 (7H, m). IR (KBr) cm-1; 3268, 2215, 1661, 1620, 1588, 1549, 1507, 1449, 1427, 1368, 1331, 1262, 1198, 750, 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.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Example 3(i?)-3-(2-(Cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid, (III) Procedure BQuinine (28.7g, 88mmol) was suspended in toluene (38OmL). Cinnamyl alcohol (15.5 g, 115mmol) was added and the reaction mixture was cooled to -35 0C. The solution of 3- isobutylglutaric anhydride (15.0 g, 88 mmol) in toluene (1OmL) was added during 15 min and the reaction mixture was stirred at -35 0C for 24 hours. Toluene solution was washed with 5% HCl (250 + 5OmL), and than extracted with 2% K2CO3 solution (1000 + 25OmL). Aqueous extracts were washed with EtOAc (3x10OmL), acidified to pH 1 with cone. HCl and extracted with diisopropylether (150 + 5OmL). Combined extracts were warmed to 35 0C and (S)-alpha- phenylethylamine (9.7 g, 80 mmol) was added, followed by seed crystals (10 mg). Mixture was stirred for 4 hours at 25 C and filtered to obtain 24.8 g of (5)-alpha-phenylethylamine salt of (/?)-3-(2- (cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid. The salt was suspended in toluene (15OmL) and stirred with 3% HCl (10OmL) until clear solution was obtained. The aqueous acidic solution was separated and organic layer was washed once again with 3% HCl (30 mL). Evaporation of toluene afforded 17.3 g (66%) of monoester as viscous yellowish oil. HPLC analysis on Chiralpak AS column, hexane/EtOH/TFA=95/5/0.1 revealed 90.7 % ee., 185815-59-2

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

Reference£º
Patent; PLIVA ISTRAZIVANJE I RAZVOJ D.O.O.; MCLEISH, Nicholas, Alistair, Maxwell; WO2008/9897; (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 117 A mixture of Example B5 (66 mg, 0.508 mmol) in DCE (2 mL) was treated with oxalyl chloride (64 mg, 0.508 mmol), stirred at RT for 5 min, then warmed to 80¡ã C. for 45 min. The mixture was cooled to RT, added to a solution of DIEA (188 mg, 1.456 mmol) and Example A25 (100 mg, 0.339 mmol) in dioxane (4 mL) and stirred at RT for 3 h. The mixture was diluted with EtOAc, washed successively with satd. NaHCO3, 1N NaOH and brine, dried over Na2SO4, concentrated to dryness and purified via reverse-phase silica gel chromatography (MeCN/H2O with 0.1percent TFA). The pure fractions were partially evaporated under reduced pressure and the aqueous residue was neutralized with satd. NaHCO3 and extracted with EtOAc (3*). The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford N-((4,6-dimethyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)tetrahydro-2H-pyran-4-carboxamide (29 mg, 19percent) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 10.95 (s, 1H), 10.86 (s, 1H), 8.33 (d, J=5.7 Hz, 1H), 8.25 (s, 1H), 7.95 (s, 1H), 7.84 (s, 1H), 7.11 (d, J=2.4 Hz, 1H), 6.51 (dd, J=5.7, 2.5 Hz, 1H), 3.90-3.85 (m, 2H), 3.84 (s, 3H), 3.30-3.27 (m, 2H), 2.73-2.65 (m, 1H), 2.18 (s, 3H), 2.10 (s, 3H), 1.74-1.68 (m, 2H), 1.65-1.55 (m, 2H); MS (ESI) m/z: 451.2 (M+H+).

344329-76-6, 344329-76-6 Tetrahydro-2H-pyran-4-carboxamide 13197203, aTetrahydropyrans compound, is more and more widely used in various fields.

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

3301-94-8, 6-Butyltetrahydro-2H-pyran-2-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Delta-nonalactone (manufactured by Sigma-Aldrich, 15.6 g, 0.10 mol) and 99% ethanol (270.0 g) were charged in a 500 mL four-necked flask and stirred at 25 C. to 30 C./30 Sodium ethoxide (manufactured by Sigma-Aldrich, 21% ethanol solution, 5.5 g, 0.017 mol) is added dropwise under the conditions of 100 ml / min. After stirring overnight at room temperature, glacial acetic acid (1.0 g, 0.017 mol) was added for neutralization and concentration under reduced pressure. 15% saline (100 g) was added to the obtained residue, and the mixture was extracted with ether (100 g). The obtained organic layer was washed with 5% aqueous sodium hydrogencarbonate solution (100 g) and 15% saline (100 g) . The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give ethyl 5-hydroxynonanoate (19.8 g) as a colorless oily crude product. Crude yield 98%

3301-94-8, The synthetic route of 3301-94-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; T. Hasegawa Co., Ltd.; Kawabata, Kazuya; Kazuya, Daichi; Haraguchi, Kenji; Takaku, Hiroyasu; (16 pag.)JP2015/131773; (2015); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

65412-03-5, Production Example 18 (0329) 5-Benzyloxymethylisoxazole-3-carboxylic acid (0.35 g, 1.5 mmol), 2-(tetrahydropyran-4-yl)ethylamine (0.23 g, 1.8 mmol), and 1-hydroxybenzotriazole (0.02 g, 0.15 mmol) were added to chloroform (amylene addition product) (7.5 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.35 g, 1.8 mmol) was added to the mixture at room temperature, and the mixture was stirred overnight and then concentrated under reduced pressure. Dilute hydrochloric acid was added to the concentrate, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.43 g of N-[2-(tetrahydropyran-4-yl)ethyl]-5-benzyloxymethylisoxazol e-3-carboxamide (hereinafter, referred to as Compound of Present Invention (18)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta(ppm)): 1.31-1.34(2H, m), 1.57-1.64(5H, m), 3.36-3.39(2H, m), 3.48-3.50(2H, m), 3.95(2H, dd), 4.61(2H, s), 4.64(2H, s), 6.72(1H, s), 6.83(1H, s), 7.30-7.39(5H, m)

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

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); 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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

Step a) Intermediate 200 -[(4-Bromophenyl)sulfanyl]tetrahydro-2H-pyran To a solution of 4-bromobenzenethiol (2 g, 10.58 mmol) in DMF (20 ml) was added NaH (0.635 g, 15.87 mmol) at 0 C and the reaction stirred for 1 h. To this was added 4-bromotetrahydro-2H-pyran (1.92 g, 1 1.64 mmol) in DMF and the reaction allowed to warm to r.t. and stirred for 67 h. Reaction was quenched by addition of water and extracted with EtOAc (x 2). The organics were washed with brine (x 5), dried (MgSC>4) and concentrated under reduced pressure. The residue was purified by column chromatography (Si02; 0 -100 % DCM in petrol) to yield 4-[(4- bromophenyl)sulfanyl]tetrahydro-2H-pyran (2.18 g, 75 %). ? NMR (400 MHz, DMSO- ) 87.52 (ra, 2H), 7.35 (m, 2H), 3.73 – 3.88 (m, 2H), 3.44 – 3.56 (m, 1H), 3.39 (m, 2H), 1.84 (m, 2H), 1.49 (m, 2H)

25637-16-5, 25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; RUPRAH, Parminder, Kaur; MERCHANT, Kevin, John; WALSH, Louise, Marie; KERR, Catrina, Morven; FIELDHOUSE, Charlotte; HARRISSON, David; MAINE, Stephanie; HAZEL, Katherine; WO2013/27001; (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.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

General procedure: To the mixture of sodium ethanolate (21% solution in ethanol, 9.898 ml, 26.52 mmol) in ethanol (20 ml) at 0C 1 -(tetrahydro-2H-pyran-4-yl)ethanone (Intermediate P20, 2.000 g, 15.60 mmol) and diethyl oxalate (3.916 g, 26.52 mmol) were added consecutively. The whole was stirred for 1 hours at 0C, then for 2 hours at room temperature. The mixture was added with 30 ml of water and acidified with 6M hydrochloric acid to pH = 3. Aqueous layer was extracted with ethyl acetate ( 3 x 50 ml). Organic layer was dried over sodium sulphate. Solvent and drying agent were removed to obtain 5.056 g of the title product, which was used without purification for further reactions. MS-ESI (m/z) calculated for CnHi604Na [M+Na]+: 251.09, determined 251.1

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

Reference£º
Patent; CELON PHARMA S.A.; MOSZCZYNSKI-PETKOWSKI, Rafal; BOJARSKI, Lukasz; MAJER, Jakub; WIECZOREK, Maciej; DUBIEL, Krzysztof; LAMPARSKA-PRZYBYSZ, Monika; WO2014/24125; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

116131-44-3, 3-(Bromomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

116131-44-3, A mixture of 3- Bromomethyl Tetrahydro-2H-Pyran (24.75 g 0.138 mol), DMPU (225 ml), FeCl3 (0.75 g) and CuCl (0.3 g) was slowly added Et2Zn (106.8 ml) by drop-wise at 40~45 for 45 minutes to get the zinc-reagent. To a mixture of 4-chloro-2-(4-chlorophenyl)-thieno[2,3-d]pyridzaine-7-carboxylic acid ethyl ester, THF (810 ml) and PdCl2(dppf) (5.09 g) was added zinc-reagent mentioned above at 40~45 for 4 hours. The reaction was poured into saturated brine and filtrated after stirring for 15 minutes; the aqueous fraction was washed by THF (500 ml, 2*). The organic layer and the extract were washed with saturated brine and dried over anhydrous Na2SO4 over night. The organic layer was concentrated under reduced pressure to give 2-(4-chlorophenyl)-4-(3-tetrahydropyranmethy)-thieno[2,3-d]pyridazine-7-carboxylic acid ethyl ester (25 g). MS (ESI): 417 (M+1).

The synthetic route of 116131-44-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wu, Zhanggui; US2009/275585; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

5631-96-9, 2-(2-Chloroethoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

STEP A: 3-[1-(2-{2-tetrahydropyranyloxy}-ethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole A solution of 6.93 g of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole [described in French Pat. No. 2,362,628] dissolved at 100 C. in 70 ml of isobutyl methyl ketone admixed with 11.13 g of sodium carbonate and 14 ml of 2-(2-chloroethoxy)-tetrahydro-2H-pyran was refluxed with stirring under an inert atmosphere for 51/2 hours and was then cooled and poured into ice water. The mixture was extracted with ethyl acetate and the organic phase was washed with water, with aqueous sodium chloride solution, dried and evaporated to dryness. The 9.9 g of crystalline residue was chromatographed over silica gel and eluted with an 85-10-5 chloroform-acetonetriethylamine mixture to obtain 7.85 g of 3-[1-(2-{2-tetrahydropyranyloxy}-ethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole in the form of crystals melting at 135 C., 5631-96-9

As the paragraph descriping shows that 5631-96-9 is playing an increasingly important role.

Reference£º
Patent; Roussel Uclaf; US4324790; (1982); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics