Tag: M.W:100-200

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

Reference Example 17 Tetrahydro-2H-pyran-4-ylamine hydrochloride To a solution of tetrahydro-4H-pyran-4-one (4.30 g, 43.0 mmol) in methanol (112 ml) was added an aqueous solution (12.5 ml) of ammonium formate (25 g, 400 mmol). Insolubles were completely dissolved and then 10percent palladium carbon (5.1 g) was added thereto, which was stirred at room temperature overnight. After the insolubles were filtrated off to obtain a filtrate, which was concentrated, and to the residue was added ethanol (100 ml) and concentrated hydrochloric acid (7.5 ml). The solvent was distilled off under reduced pressure to give an objective product, which was collected by filtration and washed with ether. 1H-NMR (DMSO-d6) delta: 1.54-1.74 (2H, m), 1.82-1.98 (2H, m), 3.27-3.38 (3H, m), 3.87-3.94 (2H, m), 9.05 (3H, bs). IR (KBr) cm-1; 2966, 1377, 1163, 1088, 1015, 986, 862.

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; 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 28; One Pot Synthesis of R-CMH; To a stirred suspension of 3-isobutyl glutaric anhydride (118 mmol) and Quinidine (134 mmol) in Toluene (10 vol) at -50 C., Methanol (365 mmol) was added drop-wise. The reaction was stirred at -50 C. for 17 hours. The solution was washed with H2SO4-2N. The organic layer was filtered and extracted to NH4OH (aq.) 25% (10 vol). The aqueous solution was stirred in a closed flask at 40 C. for 24 hours and at room temperature for 48 hours. 37% HCl was added to obtain pH 3. The slurry was stirred 20 hours at room temperature and cooled to 5 C. R-CMH was filtered and dried at 55 C. under vacuum., 185815-59-2

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

Reference£º
Patent; Hedvati, Lilach; Gilboa, Eyal; Avhar-Maydan, Sharon; US2007/293694; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydro-2H-pyran-4-ol (4.5 g, 44 mmol) in DCM (200 mL) was added TEA (5.4 g, 53.5 mmol) and MeSO2C1 (3.73 mL, 50 mmol) at ice-bath temperature. The reaction mixture was stirred at rt for 16 h. The reaction was quenched with water and the organic layer was washed with brine, dried and concentrated to give 7.9 g of the title compound (100%). ?H NMR (400 MHz, CDC13): oe 1.84-1.93 (2H, m), 2.03-2.08 (2H, m), 3.05 (3H, s), 3.52-3.58 (2H, m), 3.92-3.97 (2H, m), 4.87-4.94 (1H, m)., 2081-44-9

As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; QUANTICEL PHARMACEUTICALS, INC.; KANOUNI, Toufike; STAFFORD, Jeffrey, Alan; VEAL, James, Marvin; WALLACE, Michael, Brennan; WO2014/151106; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

624734-17-4, 3-Methoxydihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

624734-17-4, To a solution of INTERMEDIATE 23 (1.79 g, 6.01 mmol), INTERMEDIATE 9 (2.35 g, 18.0 mmol), and triethylamine (0.838 mL, 6.01 mmol) in 30 mL of DCM was added sodium triacetoxyborohydride (5.10 g, 24.0 mmol) and the resulting mixture was stirred for three days. The reaction mixture was diluted with DCM and washed with saturated NaHC03 solution, then brine, dried over anhydrous MgS04, filtered, and concentrated to give 2.61 g of crude product, which was primarily a mixture of two isomers (assumed from related work to be the two cis tetrahydropyran isomers). INTERMEDIATE 24 could be used crude as a mixture of two isomers or could be purified and separated into two single isomers (see INTERMEDIATES 25A and 25B) and then carried on. ESI-MS calc. for C22H33NO4 : 375; Found: 376 (M+H).

The synthetic route of 624734-17-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; MERCK SHARP & DOHME LIMITED; WO2003/93231; (2003); A2;,
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.,220641-87-2

Step 3. 4-{ [(Furo[2,3-c]pyridine-2-carbonyl)-amino]-methyl}-benzenesulfonyl chloride (133 mg, 0.38 mmol) was added to a mixture of N-methyltetrahydro-2H-pyran-4- amine (92 mg, 0.76 mmol) and triethylamine (0.27 mL, 1.90 mmol) in DCM (1 mL). The reaction mixture was stirred at rt for 24 h and then concentrated to dryness under vacuum. The residue was purified by preparative HPLC (column: Gemini-NX, 3 x 10 cm, 10 um; detection: UV 254 nm; mobile phase A: H20 containing 0.1% NH4OH, mobile phase B: Acetonitrile; flow rate: 60 mL/min, gradient: 0-1 min 5% B, 1-10 min 5-50% B, 10-11 min 50% B, 11-11.2 min 50-95% B, 11.2-13 min 95% B, 13-13.2 min 95-5% B, 13.2-15 min. 5% B). Isolation and concentration of the appropriate fractions afforded the title compound as a white solid (34.6 mg, 21.2%). 1H NMR (400 MHz, DMSO-J6) delta 9.65 (t, J = 6.2 Hz, 1H), 9.07 (s, 1H), 8.49 (d, J = 5.0 Hz, 1H), 7.82 (dd, J = 15.2, 6.6 Hz, 3H), 7.67 (s, 1H), 7.55 (d, J = 8.1 Hz, 2H), 4.59 (d, J = 6.1 Hz, 2H), 3.95 (tt, J = 12.1, 4.3 Hz, 1H), 3.79 (dd, J = 11.5, 4.3 Hz, 2H), 3.29 (d, J = 11.7 Hz, 2H), 2.67 (s, 3H), 1.60 (qd, J = 12.2, 4.5 Hz, 2H), 1.27 – 1.13 (m, 2H). LC/MS (Method M, ESI): RT = 3.57 min, m/z = 430.2 [M + H]+.

As the paragraph descriping shows that 220641-87-2 is playing an increasingly important role.

Reference£º
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; BUCKMELTER, Alexandre, J.; CLODFELTER, Karl, H.; GUNZNER-TOSTE, Janet; HAN, Bingsong; LIN, Jian; REYNOLDS, Dominic, J.; SMITH, Chase, C.; WANG, Zhongguo; ZAK, Mark; ZHENG, Xiaozhang; ZHAO, Guiling; WO2013/130943; (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.85064-61-5,Tetrahydropyranyl-4-acetic acid,as a common compound, the synthetic route is as follows.,85064-61-5

S nthesis of Compound D6Step 1: Synthesis of Compound D2To a suspension of 0.55 g of LiAlH4 (13.9 mmol) in THF (10 mL) is added dropwise a solution of 2 g (13.9 mmol) of compound Dl in THF (10 mL) under nitrogen atmosphere (CAUTION: highly exothermic reaction.). Upon complete addition, the reaction is stirred at room temperature for 18 h. The reaction is cooled in an ice-bath and quenched with addition of 1M aqueous NH4C1 solution (2 mL). The resulting precipitate is removed by filtration through Celite and is rinsed with ethyl acetate (3 x 100 mL). The filtrate is dried over Na2S04, filtered and concentrated under reduced pressure to afford 1.63 g of compound D2 as a colorless oil. Yield: 90%; ES-MS m/z 131 [M+H]; 1H-NMR (500 MHz, CHLOROFORM-d) 5 ppm l.29 (2 H, qd, 7=12.08, 4.04 Hz), 1.50 (2 H, qd, 7=6.71, 1.37 Hz), 1.55 – 1.73 (3 H, m), 1.95 – 2.07 (1 H,m), 3.37 (2 H, t, 7=11.83 Hz), 3.66 (2 H, t, 7=6.03 Hz), 3.92 (2 H, dd, 7=11.44, 4.12 Hz)

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; ZINDELL, Renee, M.; ERMANN, Monika; WO2011/109324; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

624734-17-4, 3-Methoxydihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,624734-17-4

Step H ((3aS,5S,6aR)-5-((3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H- cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-l,6-naphthyridin-6(5H)- yl)methanone To a solution of the product of Step G (119 mg, 0.33 mmol, 1 eq) in DCM at rt was added acetic acid (0.01 mL, 0.17 mmol, 0.5 eq), 3-methoxytetrahydro-4H-pyran-4-one (131 mg, 1.0 mmol, 3 eq) and sodium triacetoxyborohydride (355 mg, 1.67 mmol, 5 eq). After stirring overnight, saturated NaHC03 was added, the solution extracted with DCM, the organics combined, dried over MgS04, and concentrated. Purification by chromatography (12 g) eluting with 4 to 8% methanol DCM with ammonia afforded the title compound of Example 1. 1H NMR (CHLOROFORM-d) delta: 8.72 (br. s., 1H), 7.70 (br. s., 1H), 4.98 – 5.14 (m, 1H), 4.70 – 4.89 (m, 2H), 3.80 – 4.18 (m, 5H), 3.25 – 3.75 (m, 8H), 3.07 – 3.24 (m, 2H), 2.53 – 2.89 (m, 1H), 2.01 – 2.48 (m, 4H), 1.39 – 1.88 (m, 5H). Calculated for C23H30F3N3O4: 470.2 (M+l); found: 470.2.

As the paragraph descriping shows that 624734-17-4 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; WINTERS, Michael P.; BRANUM, Shawn; FAWZY, Nagy E.; KANG, Fu-An; REUMAN, Michael; RUSSELL, Ronald K.; SUI, Zhihua; TELEHA, Christopher A.; WO2013/152269; (2013); 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

Example: 5(+/-)-3-(Carbamoylmethyl)-5-methylhexanoic Acid IIII An aqueous solution of ammonia (1.486 litre) was added to a solution of the anhydride VIII (667 g, 3.919 mole) in ferf-butyl methyl ether (901 ml) at 0 C. The reaction mixture was allowed to warm to room temperature, and stirred at this temperature until the reaction was complete as indicated by TLC.The aqueous layer was washed with terf-butyl methyl ether (3 chi 300 ml). The aqueous layer was cooled to 0 oC, acidified with dilute hydrochloric acid until the pH attained 2 and extracted with hot ethyl acetate (5 chi 300 ml). The extracts were combined and concentrated to give the amide II as a white solid; yield: 590 g, 80.4%., 185815-59-2

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

Reference£º
Patent; Dr. Braja Sundar Pradhan; WO2012/93411; (2012); A2;,
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.130290-79-8,(Tetrahydro-2H-pyran-4-yl)methanamine,as a common compound, the synthetic route is as follows.

To a 500 mL three-neck RB flask equipped with a mechanical stirrer were charged the 4- chloro-3-nitrobenzenesulfonamide (23.7 g, 100 mmol), DIPEA (12.9 g, 100 mmol), (tetrahydro-2H-pyran-4-yl)methanamine( 11.5 g, 100 mmol) and acetonitrile (200 mL). The reaction mixture was adjusted to an internal temperature of 80 C and agitated for no less than 12 hours. The product solution was cooled down to 40 C and agitated for no less than 1 hour until precipitation observed. The product slurry was further cooled to 20 C. Water (80 mL) was slowly charged over no less than 1 hour, and the mixture cooled to 10 C and agitated for no less than 2 hours before collected by filtration. The wet cake was washed with 1:1 mix of acetonitrile:water (40 mL). The wet cake was rinsed with water (80 mL) at 40 C for no less than 1 hour before collected by filtration. The wet cake was rinsed with water (20 mL), and dried at 75 C under vacuum to give the 3 -nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide (24.5 g, 78%) as an orange solid. ?H NMR (400 MHz, DMSO) 8.60 (t, I = 5.9 Hz, 1H), 8.48 (d, I = 2.2 Hz, 1H), 7.84 (dd, I = 9.2, 2.0 Hz, 1H), 7.54-7.18 (m, 3H), 3.86 (dd, I = 11.3, 3.2 Hz, 2H), 3.35 (s, 2H), 3.27 (t, I = 10.9 Hz, 2H), 1.92 (ddd, I = 11.2, 7.4, 3.9 Hz, 1H), 1.62 (d, I =11.4 Hz, 2H), 1.27 (qd, I = 12.3, 4.4 Hz, 2H)., 130290-79-8

The synthetic route of 130290-79-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; LOU, Yan; (108 pag.)WO2019/40550; (2019); 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.

A reaction vessel was charged with 2,2,6,6-tetramethyltetrahydropyran-4-one (CAS: 1197-66-6, 5.00 g, 32.0 mmol), ethyl cyanoacetate (CAS: 105-56-6, 3.4 ml, 32.0 mmol), morpholine (CAS: 110-91-8, 8.4 ml, 96.0 mmol) and sulfur (CAS: 7704-34-9, 1.03 g, 32.0 mmol) and solvated in ethanol (70 ml). The reaction was set to stir at RT and next heated at 80 C overnight. The reaction was allowed to cool to RT and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc and brine. The two phases were separated and the organic phase was washed with brine. The organic phase was dried over MgS04and the solvent was removed under reduced pressure. Purification by flash chromatography on silica gel (eluting with 0-40% EtOAc in isohexane) afforded ethyl 2-amino-5,5,7, 7-tetramethyl-4, 7-dihydro-5H-thieno[2,3-c]pyran-3- carboxylate as a yellow oil (7.60 g, yield 84%). The title compound was then synthesized according to the procedure described in Example 1 using ethyl 2-amino-5,5,7,7-tetramethyl-4,7- dihydro-5H-thieno[2,3-c]pyran-3-carboxylate and benzoyl chloride (CAS: 98-88-4) as starting materials (off-white solid, yield 16%).1H NMR (DMSO-d6, 400MHz): d = 13.53 (br s, 1H), 12.40 (s, 1H), 7.97 (d, J=7.5 Hz, 2H), 7.78 – 7.65 (m, 3H), 2.83 (s, 2H), 1.52 (s, 6H), 1.28 (s, 6H). LC/MS (Table 1, Method C) Rt= 2.69 min; MS m/z : 360 [M+H]+.

1197-66-6, The synthetic route of 1197-66-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ENYO PHARMA; MELDRUM, Eric; DE CHASSEY, Benoit; MACHIN, Peter; LANARO, Roberta; MACLEOD, Calum; MALAGU, Karine, Fabienne; PROISY, Nicolas; VESEY, David, Richard; WINSHIP, Paul, Colin, Michael; CHAMBERS, Mark; PAPARIN, Jean-Laurent; (150 pag.)WO2019/154949; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics