Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5765-44-6,5-Methylisoxazole,as a common compound, the synthetic route is as follows.

5765-44-6, Example 11A Sodium 1-cyanoprop-1-en-2-olate Sodium (7.69 g, 335 mmol) is introduced in portions into 350 ml of anhydrous methanol. After the reaction mixture has been cooled to 25 C., 5-methylisoxazole (27.8 g, 335 mmol) is slowly added in portions (exothermic reaction). After the addition is complete, the mixture is stirred at RT for 4 h and then concentrated. The residue is washed with a little diethyl ether, filtered off with suction and dried under oil pump vacuum. 32.0 g (91% of theory) of the title compound are obtained. 1H-NMR (400 MHz, DMSO-d6): delta=3.18 (s, 1H), 1.51 (s, 3H).

5765-44-6 5-Methylisoxazole 79833, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/305052; (2010); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3405-77-4,5-Methylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

(2R,6S,13aS,14aR,16aS,Z)-ethyl 6-(5-methylisoxazole-3-carboxamido)-2-(4- nitrobenzoyloxy)-5,16-dioxo-l,2,3,5,6,7,8,9,10,l l,13a,14,14a,15, 16,16a- hexadecahydrocyclopropa[e]pyrrolo[l,2-a][l,4]diazacyclopentadecine-14a-carboxylate; To a solution of (2R,6S,13aS,14aR,16aS,Z)-14a-(ethoxycarbonyl)-2-(4-nitrobenzoyloxy)- 5,16-dioxo-l,2,3,5,6,7,8,9,10,l l,13a,14,14a,15,16,16a- hexadecahydrocyclopropa[e]pyrrolo[l,2-a][l,4]diazacyclopentadecin-6-aminium 4- methylbenzenesulfonate (9.95 g), 5-methylisoxazole-3-carboxylic acid (2.12 g), and NMP (30.0 g) at 5 ¡ãC was added diisopropylethylamine (6.5 g). Propanephosphonic acid anhydride (5.3 g) was charged as a solution in EtOAc (5.3 g) and NMP (10 mL) to the reaction mixture. The reaction was warmed to rt over 14 h. The reaction solution was diluted with 2-Me-THF (150 mL). The diluted reaction solution was washed with water (150 mL), a 1.0 M aqueous solution of H3PO4 (2 x 50 mL), water (50 mL), a 5percent aqueous solution of NaHC03 (50 mL), and then a 10percent aqueous solution of NaCl (2 x 50 mL). The organic solution was dried over MgS04, filtered, and then concentrated under reduced pressure, and then co-distilled with THF (200 mL). THF was added and the product-containing solution was filtered and evaporated to an oil (8.5 g, 93percent yield).

3405-77-4, The synthetic route of 3405-77-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBOTT LABORATORIES; ENANTA PHARMACEUTICALS, INC.; CHEN, Hui-ju; MCDANIEL, Keith, F.; GREEN, Brian, E.; SHANLEY, Jason, P.; KRUGER, Albert, W.; GANDARILLA, Jorge; WELCH, Dennie, S.; CINK, Russell, D.; GAI, Yonghua; WANG, Guoqiang; OR, Yat, Sun; WO2011/156337; (2011); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

3405-77-4, 5-Methylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 5-methylisoxazole-3-carboxylic acid (284.0 mg, 2236.0 mumol) dissolved in DCM(lO.OmL) was added HATU (1020.0 mg, 2683.0 mumol) followed by DIEA(586mul, 3353 mumol). The solution was stirred at room temperature for 5 minutes. 4-amino-2-(l- methyl-lH-pyrazol-5-yl)phenol (500.00 mg, 2236 mumol) was added and the reaction mixture was stirred at 25¡ãC for 15 hours. The reaction mixture was subjected to purification by column chromatography (ethyl acetate rhexane 50:50) to afford the title compound as an off- white solid in 59.0percent yield. LCMS m/z = 333.2 (M+H), 1H NMR (400 MHz5 OMSO-d) delta ppm 2.69 (s, 3H), 3.66 (s, 3 H), 6.64 (s, 1 H), 7.00 (d, /=8.84 Hz, 1 H), 7.61 (s, 1 H), 7.64 (d, /=2.53 Hz, 1 H), 7.73 (dd, /=8.84, 2.53 Hz, 1 H), 10.04 (s, 1 H), 10.60 (s, 1 H).

3405-77-4, The synthetic route of 3405-77-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; WO2007/136703; (2007); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.21169-71-1,Isoxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: Compounds were synthesized in solution phase using Boc-protected amino acids on 100-200mg scale. Firstly, the amino acid (1.2-1.5equiv) was activated with HBTU (1.5equiv) and DIPEA (1.5equiv) as 0.2-0.5M solution in DMF for 10min. Then the solution was added to an amino group bearing C-terminal moiety (R1R2NH) and the mixture was stirred for a minimum of 1h at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (2¡Á). The organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude product was then treated with 20% TFA in DCM and stirred for 1-2h to remove the Boc group. TFA was removed by evaporating the reaction mixture under a stream of N2. The residue was dissolved in DCM and washed with saturated NaHCO3 (2¡Á). DCM phase was dried with MgSO4, filtered and evaporated in vacuo. Subsequent N-Boc-amino acids and amines were sequentially coupled under the same conditions. Each coupling reaction was monitored by ESMS, with most reactions going to completion overnight. All final compounds were purified on rpHPLC (97% by analytical HPLC) and fully characterized by NMR and HRMS (yields between 30% and 40%).

21169-71-1, The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Yau, Mei-Kwan; Liu, Ligong; Lim, Junxian; Lohman, Rink-Jan; Cotterell, Adam J.; Suen, Jacky Y.; Vesey, David A.; Reid, Robert C.; Fairlie, David P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 986 – 991;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14678-02-5,5-Amino-3-methylisoxazole,as a common compound, the synthetic route is as follows.

General procedure: A solution of 2-(chloroseleno)benzoyl chloride (1 mmol) in dryether (10 mL) was added dropwise over 30 min to a stirred solution ofthe appropriate amine (1.2 mmol) and triethylamine (3.5 mmol) in dryDCM (10 mL) at 0 C. The reaction mixture was stirred at room temperatureovernight. The solvent was removed under reduced pressureand the residue was washed with water (20 mL), and extracted withDCM (3¡Á10 mL). The combined organic extracts were dried over anhydrousMgSO4, the solvent removed was under reduced pressure, andthe crude product was purified by flash column chromatography onsilica gel (eluents: 10-50% ethyl acetate in petroleum gradient) [31].All EB analogues except 4c and 4e have been reported., 14678-02-5

The synthetic route of 14678-02-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Chen, Cheng; Yang, Kewu; Bioorganic Chemistry; vol. 93; (2019);,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

110256-15-0, 5-Cyclopropylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of 5-cyclopropylisoxazole-3-carboxylic acid (50 mg, 0.32 mmol) in DMF (1 mL) was added HATU (120 mg, 0.32 mmol) under N2, the mixture was stirred for 30 mm, then c/s-i[5 -[3 -(trifluoromethoxy)cyclobutylj -1,3 ,4-oxadiazol-2-yl Ibicyclo [1.1.1 jpentan-3 -amine hydrochloride (8:1 to 10:1 favoring the cis- diastereomer) (89 mg, 0.27 mmol) and DIEA (140 mg, 1.1 mmol) were added to the solution at 0 C. The reaction mixture was stirred at 20 C for 12 h. The reaction mixture was quenched by addition of H20 (10 mL) at 0 C and extracted with EtOAc (3 x 10 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The cmde reaction mixture was purified employing reverse- phase HPLC. LC-MS, mlz = 425.3 [M+Hfb. ?H-NMR (400 MHz, CDC13): 7.25 (s, 1H), 6.32 (s, 1H), 4.71 (quin, J= 7.56 Hz, 1H), 3.40-3.26 (m, 1H), 2.94-2.81 (m, 2H), 2.74-2.69 (m, 2H), 2.686H), 2.15-2.03 (m, 1H), 1.19-1.08 (m, 2H), 1.03-0.94 (m, 2H).

110256-15-0, As the paragraph descriping shows that 110256-15-0 is playing an increasingly important role.

Reference£º
Patent; DENALI THERAPEUTICS INC.; CRAIG, Robert A., II; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian; HALE, Christopher R. H.; LEXA, Katrina W.; OSIPOV, Maksim; REMARCHUCK, Travis; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (187 pag.)WO2019/32743; (2019); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

31329-64-3, 3,5-Dimethylisoxazol-4-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 1 4-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (3,5-dimethylisoxazole-4-yl)-amide Oxalyl chloride (0.2 ml) was added to a suspension of 4-difluoromethoxy-2-(piperidin-1-yl)-benzooxazole-7-carboxylic acid (0.3 g) in dichloromethane (20 ml) at room temperature under an atmosphere of nitrogen. Three drops of N,N-dimethylformamide were added, and the mixture stirred for 18 hours. The solvent was removed in vacuo and the residue dissolved in dichloromethane (20 ml). The resulting solution was added to a mixture of 3,5-dimethylisoxazol-4-ylamine (0.16 g) and triethylamine (0.2 ml) in dichloromethane (20 ml) at room temperature under an atmosphere of nitrogen. The mixture was stirred for 2 hours, then washed with aqueous sodium bicarbonate (2*20 ml) and water (20 ml). The organics were dried over magnesium sulphate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluding with 50% ethyl acetate in heptane afforded the title compound as a white solid (0.29 g). TLC Rf 0.65 (ethyl acetate). Mass spectrum m/z 350 (M-1), 31329-64-3

As the paragraph descriping shows that 31329-64-3 is playing an increasingly important role.

Reference£º
Patent; Darwin Discovery, Ltd.; US6403791; (2002); B1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33282-23-4,5-(4-Bromophenyl)isoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: A solution of isoxazole acid derivative 1 (1mmol), EDCI (1.1mmol), and HOBt (1mmol) in dry acetonitrile (10mL) was stirred at room temperature for 30min. Then, 3-picolylamine 2a or 4-picolylamine 2b (1mmol) was added drop wise to the mixture and the reaction was continued at room temperature for 24h. After completion of the reaction, the solvent was reduced under vacuum and the residue was dissolved in dichloromethane and washed with sodium carbonate (10%, 3¡Á20). The organic phase was dried over Na2SO4 and the solvent was evaporated under vacuum to give compound 3 which was completely pure. Finally, the mixture of compound 3 (1mmol) and benzyl halide derivative 4 (1.2mmol) in dry acetonitrile (10mL) was heated at reflux for 10-15h. After completion of the reaction which was monitored by TLC, the mixture was allowed to be cool and the precipitates were filtered off to afford products 5a-q in good yields., 33282-23-4

The synthetic route of 33282-23-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Vafadarnejad, Fahimeh; Karimpour-Razkenari, Elahe; Sameem, Bilqees; Saeedi, Mina; Firuzi, Omidreza; Edraki, Najmeh; Mahdavi, Mohammad; Akbarzadeh, Tahmineh; Bioorganic Chemistry; vol. 92; (2019);,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

33282-15-4, 5-(4-Hydroxyphenyl)isoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of oximic acid (4a-k, 3.6 mmol in 50 mL THF) was added HOBt (3.6 mmol) in an ice-cooled bath. Next, a mixture of cystamine dihydrochloride (1.8 mmol) and TEA (1 mL) in DMSO (6 mL) were added, followed by the addition of EDCI (4.0 mmol). After stirring for 24 h at room temperature, the reaction was quenched with water and extracted with EtOAc (60 mL ¡Á 3). The combined organic extracts were washed with brine (50 mL), dried over MgSO4 and then evaporated. The resulting residue was then purified by column chromatography on silica gel as indicated., 33282-15-4

The synthetic route of 33282-15-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wen, Jiachen; Bao, Yu; Niu, Qun; Liu, Jiang; Yang, Jinyu; Wang, Wanqiao; Jiang, Tao; Fan, Yinbo; Li, Kun; Wang, Jian; Zhao, Linxiang; Liu, Dan; Bioorganic and Medicinal Chemistry Letters; vol. 26; 17; (2016); p. 4372 – 4376;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

3356-89-6, 5-Chloro-3-phenylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of 5-chloro-3-phenylisoxazole (2) (5 mmol), thiol (10 mmol) and K2CO3 (15 mmol) in DMF (25 mL) was stirred for 36 h at r.t. The reaction mixture was diluted with H2O (40 mL) and extracted with CH2Cl2 (3 ¡Á 20 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel using hexane-EtOAc as the eluent to give the desired compound. 3-Phenyl-5-[(2,2,2-trifluoroethyl)sulfanyl]isoxazole (6a) Yield: 1.28 g (99%); colorless oil. 1H NMR (400 MHz, CDCl3): delta = 7.85-7.75 (m, 2 H), 7.54-7.44 (m, 3 H), 6.69 (s, 1 H), 3.66 (q, J = 9.3 Hz, 2 H). 13 NMR (100 MHz, CDCl3): delta = 163.5, 162.3, 130.4, 129.0, 128.3, 126.8, 124.5 (q, J = 277 Hz), 105.0, 35.3 (q, J = 34.4 Hz). HRMS (ESI): m/z [M + H]+ calcd for C11H9F3NOS: 260.0351; found: 260.0355., 3356-89-6

The synthetic route of 3356-89-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Rostovskii, Nikolai V.; Agafonova, Anastasiya V.; Smetanin, Ilia A.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; Ruvinskaya, Julia O.; Starova, Galina L.; Synthesis; vol. 49; 19; (2017); p. 4478 – 4488;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem