Heterocyclic Building Blocks-isoxazole

59669-59-9,59669-59-9, 3-(tert-Butyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

100 mg of 5-(2-fluoropyridin-4-yl)-2-(tetrahydropyran-4-yloxy)benzonitrile are suspended in 6 ml of dioxane in a 50 ml three-necked flask under N2, 52 mg of 3-tert-butylisoxazol-5-ylamine and 79 mg of KOtBu are added The yellow solution is stirred at 80¡ã C. for 2.5 h. For work-up, the reaction mixture is evaporated in a rotary evaporator, the residue is taken up in ethyl acetate and water and extracted. The collected organic phases are dried, filtered and evaporated. The crude product is purified by preparative HPLC, giving the desired product in 46percent yield; HPLC-MS Rt. [min] 2.556; HPLC-MS [M+H] 419; [0327] 1H NMR (500 MHz, DMSO-d6) delta [ppm] 8.36 (d, J=5.7, 1H), 8.19 (d, J=2.4, 1H), 8.04 (dd, J=8.9, 2.4, 1H), 7.53 (d, J=9.1, 1H), 7.42 (dd, J=5.8, 1.6, 1H), 7.38 (s, 1H), 5.00-4.88 (m, 1H), 3.96-3.85 (m, 2H), 3.64-3.50 (m, 2H), 2.12-2.00 (m, 2H), 1.79-1.66 (m, 2H), 1.38-1.24 (s, 9H).

59669-59-9 3-(tert-Butyl)isoxazol-5-amine 2095694, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK PATENT GMBH; Hoelzemann, Guenter; Dorsch, Dieter; Eggenweiler, Hans-Michael; US2014/228340; (2014); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

42831-50-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.42831-50-5,5-Methylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

Thionylchloride (3.53 g, 0.0278 mol) was added to a solutionof 5-Methylisoxazole-4-carboxylic acid (2.7 g, 0.0185 mol) in anhydrous dichloromethane (50 ml) with catalytic drops of DMF. The reaction was heated under reflux for 12 h then followed by removing the solvent under reduced pressure. DCM (20 ml) was added and evaporated 3 times to produce a brown oil that was used directly in the next step.

As the paragraph descriping shows that 42831-50-5 is playing an increasingly important role.

Reference£º
Article; Hamdi, Abdelrahman; Said, Eman; Farahat, Abdelbasset A.; El-Bialy, Serry A.A.; Massoud, Mohammed A.M.; Letters in drug design and discovery; vol. 13; 9; (2016); p. 912 – 920;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.62348-13-4,Isoxazole-5-carbonyl chloride,as a common compound, the synthetic route is as follows.,62348-13-4

General procedure: Example 6B (0.2 g, 0.556 mmol) was dissolved in dichloromethane (2.7 ml) and pyridine (0.3 ml) and was treated dropwise with a solution of 3-methylbutanoyl chloride (0.102 ml, 0.835 mmol) in dichloromethane (0.5 ml). The reaction mixture was stirred at 25 C for 2 hours, concentrated, and purified using reverse phase HPLC (Phenomenex Luna C8(2) 5 um IotaOmicronthetaAlpha AXIA column (30mm x 75mm) run with a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B), at a flow rate of 50mL/min (0-0.5 min 10% A, 0.5-7.0 min linear gradient 10-95% A, 7.0- 10.0 min 95% A, 10.0-12.0 min linear gradient 95- 10% A) to afford the title compound.

The synthetic route of 62348-13-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBVIE INC.; SWEIS, Ramzi F.; CURTIN, Michael L.; PLIUSHCHEV, Marina A.; HANSEN, Todd M.; LONGENECKER, Kenton; WO2013/170118; (2013); 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.1136-45-4,5-Methyl-3-phenylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 1; 3-(5-Methyl-3-phenyl-isoxazol-4-yl)-imidazo[l,5-a]pyridinea) S-Methyl-S-phenyl-isoxazole-phicarboxyric acid (pyridin-2-ylmethyl)-amide A mixture of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (4.06 g, 20 mmol, commercially available) and thionyl chloride (5 mL) was heated under reflux for 3 h. Evaporation of all volatiles afforded 5-methyl-3-phenyl-isoxazole-4-carboxylic acid chloride (4.4 g, 93%) as yellow oil, which was used without further purification in the next reaction. To a mixture of an aqueous solution of 2-picolylamine (0.182 g, 1.68 mmol) in water (2 mL) and ethyl acetate (4 mL) were added sodium hydrogen carbonate (362 mg, 4.2 mmol) in one portion. Then 5-methyl-3-phenyl-isoxazole-4-carboxylic acid chloride (0.31 g, 1.4 mmol) in ethyl acetate (2 mL) was added dropwise with vigorous stirring under ice-bath cooling keeping the temperature at 0 0C. After addition, the reaction mixture was stirred at room temperature for 18 h. The resulting solution was then diluted with ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined extracts were then washed with brine, dried over sodium sulphate, and concentrated to afford the title compound (0.38 g, 93%) as a white solid. MS: m/e: 294.1 [M+H]+.

1136-45-4, 1136-45-4 5-Methyl-3-phenylisoxazole-4-carboxylic acid 14343, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; WO2007/74089; (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.13999-39-8,3-Amino-4,5-dimethylisoxazole,as a common compound, the synthetic route is as follows.

A solution of 4,5-dimethylisoxazol-3-amine (4.9 g, 44 mmol, 1.0 equiv; CASNo. 13999-39-8, Org. Proc. Res. Dev. 2007, 11, 275-277) and triethylamine (6.4 mL, 46 mmol, 1.05 equiv) in acetonitrile (25 mL) was added portionwise to a 0 0C solution of phenyl chloroformate (5.8 mL, 46 mmol, 1.05 equiv) in THF (100 mL). After stirring at 0 0C for 1 h, the reaction was warmed to room temp overnight. The reaction was concentrated to about one-half the volume and partitioned between ethyl acetate and saturated sodium 20 bicarbonate. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography (20 to 40% ethyl acetate/heptane) to give the title compound as a white solid (8.39 g, 83%). m/z 233 (MH+). 1H NMR (400 MHz, DMSO-d6) delta ppm 10.67 (br. s., 1 H), 7.40 (t, J=8.0 Hz, 2 H), 7.17 – 7.27 (m, 3 H)1 2.12 (s, 3 H), 1.82 (s, 3 H)., 13999-39-8

As the paragraph descriping shows that 13999-39-8 is playing an increasingly important role.

Reference£º
Patent; PFIZER INC.; WO2009/127944; (2009); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

91182-60-4,91182-60-4, 5-(4-Bromophenyl)-3-methylisoxazole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)-1-phenyl-ethyl ester5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (25 g, 88.7 mmol) in toluene (500 mL) was added triethylamine (18.5 mL, 133 mmol), followed by diphenylphosphoryl azide (22.1 mL, 101.9 mmol). (R)-(+)-1-Phenylethyl alcohol (11.9 mL, 97.5 mmol) was added, and the reaction was stirred at 75 C. for 2 hours. The mixture was partitioned between EtOAc and H2O and filtered through Celite. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

91182-60-4 5-(4-Bromophenyl)-3-methylisoxazole-4-carboxylic acid 56604559, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; AMIRA PHARMACEUTICALS, INC.; US2010/152257; (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.59669-59-9,3-(tert-Butyl)isoxazol-5-amine,as a common compound, the synthetic route is as follows.

59669-59-9, Step 6: Synthesis of compound B-7Activation of 55.9 g (22.3 mmol) of compound B-6 is achieved by treatment with thionyl chloride (600 mL) at 60 ¡ãC for 3 h. The reaction mixture is cooled to room temperature and excess thionyl chloride is removed under reduced pressure.The crude acid chloride is dissolved in DCM (400 mL) and added to a solution of 31.3 g (22.3 mmol) of 3-tert-Butyl-isoxazol-5-ylamine and N,N-diisopropylethylamine (194 mL) in DCM (250mL). The reaction is stirred at room temperature for 16 h. The reaction mixture is diluted with DCM (1350 mL) and washed with saturated aqueous NaHCC>3 solution (1000 mL). The organic layer is dried over Na2S04, filtered and the filtrate is concentrated under reduced pressure. The crude product is purified by dry-flash column chromatography (2 kg silica, eluent: DCM, 0-20percent ethyl acetate). The resulting solid is recrystallised from isopropanol/heptanes (1/1. 2 L), then dried under reduced pressure to afford 80 g of compound B-7 as an off-white powder. Yield 96percent; ES-MS: m/z 373 [M+H]; XH NMR (360 MHz, CHLOROFORM-d) delta ppm 1.35 (9 H, s), 1.41 – 1.55 (2 H, m), 1.74 (6 H, s), 1.82 – 1.91 (2 H, m), 2.29 – 2.52 (1 H, m), 2.92 (2 H, d, 7=6.58 Hz), 3.34 – 3.49 (2 H, m), 3.88 – 4.00 (2 H, m), 6.30 (1 H, s), 9.38 (1 H, s).

As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HICKEY, Eugene Richard; RIETHER, Doris; ERMANN, Monika; WO2012/12307; (2012); 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.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: Thionyl chloride (1.2 mL) was added at 0 C to the 3-phenylisoxazole-5-carboxylic acid 13 or the 5-phenylisoxazole-3-carboxylic acid 14 or the 5-(4-chlorophenyl)isoxazole-3-carboxylic acid 15 or the 3-(4-methylphenyl)isoxazole-5-carboxylic acid 16 (0.3 g, 1.58 mmol). The obtained suspension was stirred and heated at reflux for 16 h and then cooled at 0 C. At this temperature, a new addition of thionyl chloride (1.2 mL) was followed by another heating at reflux for 2 h. The reaction mixture was cooled at room temperature and the thionyl chloride excess was evaporated to dryness in vacuo. Anhydrous THF (2 mL) was added to the crude product. To the resulting solution, cooled at -5 C, was added dropwise a solution of appropriate amine (3.16 mmol) in dry THF (2 mL). The reaction mixture was stirred at room temperature for ca. 90 min (TLC, petroleum ether/ethyl acetate) and then the solid mass was filtered off and washed with THF. The filtrate was evaporated to dryness; the residue was treated with saturated sodium bicarbonate solution (20 mL) and extracted with dichloromethane (3¡Á15 mL). The combined organic phases were dried (Na2SO4) and evaporated to dryness to give the crude product, purified by flash-chromatography to give the desired amide.

14441-90-8, 14441-90-8 5-Phenylisoxazole-3-carboxylic acid 151916, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Article; Cosimelli, Barbara; Simorini, Francesca; Taliani, Sabrina; La Motta, Concettina; Da Settimo, Federico; Severi, Elda; Greco, Giovanni; Novellino, Ettore; Costa, Barbara; Da Pozzo, Eleonora; Bendinelli, Sara; Martini, Claudia; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4506 – 4520;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.36958-61-9,5-(Bromomethyl)-3-methylisoxazole,as a common compound, the synthetic route is as follows.

Example 13 (5RS)-2-[(3-Methyl-1,2-oxazol-5-yl)methyl]-5-(pyrrolidin-1-ylcarbonyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (Racemate) (5RS)-5-(Pyrrolidin-1-ylcarbonyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (racemate) (40.0 mg, 169 mumol) was initially charged in acetonitrile (2.0 ml). Caesium carbonate (82.7 mg, 254 mumol) and 5-(bromomethyl)-3-methyl-1,2-oxazole (32.8 mg, 186 mumol) were subsequently added. After stirring at room temperature for 2 days, the reaction mixture was admixed with water and ethyl acetate. The organic phase was removed and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and filtered, and the filtrate was concentrated. 18.6 mg (33% of theory) of the title compound were obtained. LC-MS (Method 3): Rt=0.89 min; MS (ESIpos): m/z=332 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: -0.008 (0.87), 0.008 (0.76), 1.686 (0.49), 1.709 (0.99), 1.720 (1.17), 1.732 (0.87), 1.753 (0.57), 1.772 (1.53), 1.789 (2.62), 1.806 (2.01), 1.822 (0.60), 1.892 (0.62), 1.909 (1.85), 1.925 (2.33), 1.942 (1.50), 1.959 (0.66), 1.972 (0.52), 1.983 (0.78), 1.995 (0.71), 2.004 (0.63), 2.014 (0.50), 2.019 (0.48), 2.030 (0.68), 2.039 (0.56), 2.046 (0.46), 2.055 (0.49), 2.201 (16.00), 2.215 (0.69), 2.417 (0.49), 2.523 (1.09), 2.565 (0.86), 2.580 (0.74), 2.590 (0.68), 2.602 (1.21), 2.615 (0.66), 2.643 (0.48), 3.242 (0.75), 3.254 (0.74), 3.271 (1.33), 3.288 (0.70), 3.322 (0.97), 3.339 (1.33), 3.351 (0.50), 3.357 (0.70), 3.369 (0.78), 3.454 (0.86), 3.462 (0.63), 3.471 (0.53), 3.479 (1.08), 3.496 (0.47), 3.589 (0.50), 3.606 (1.03), 3.614 (0.52), 3.623 (0.59), 3.631 (0.79), 3.703 (0.42), 4.495 (0.41), 4.510 (0.41), 4.723 (0.92), 4.732 (1.05), 4.738 (1.20), 4.747 (0.90), 4.940 (4.70), 4.982 (0.54), 6.223 (3.16).

36958-61-9, As the paragraph descriping shows that 36958-61-9 is playing an increasingly important role.

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BIBER, Nicole; BROCKSCHNIEDER, Damian; GERICKE, Kersten Matthias; KOeLLING, Florian; LUSTIG, Klemens; MEDING, Joerg; MEIER, Heinrich; NEUBAUER, Thomas; SCHAeFER, Martina; TIMMERMANN, Andreas; ZUBOV, Dmitry; TERJUNG, Carsten; LINDNER, Niels; BADOCK, Volker; MOOSMAYER, Dieter; MIYATAKE ONDOZABAL, Hideki; MOORE, Steven; SCHULZ, Alexander; (458 pag.)US2019/160048; (2019); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

3209-71-0, Isoxazole-3-carboxylic Acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 3 (24.0 g) and 16.17 g of isoxazole-3-carboxylic acid were suspended in 288 mL of acetone, 49.36 g of pyridine was added thereto and the suspension was cooled to -10C. 31.89 g of phosphorus oxychloride was poured into the suspension to react at 20 +/- 10C for about 30 minutes. The reaction mixture was cooled to 5C or below, 5.3 mL of water was added dropwise to the mixture at 20C, and 355 mL of water was poured therein. Then, 10% sodium hydroxide aqueous solution was added dropwise to the mixture until pH 4.5, and the mixture was stirred at 15 +/- 10C for about 2 hours to precipitate crystals. The crystallized slurry obtained was filtered, and the crystals were washed sequentially with 48 mL of 10% aqueous acetone, 192 mL of water, and 72 mL of 10% aqueous acetone, and dried in vacuo to afford Compound 4 (33.24 g, 91.4%).

3209-71-0, 3209-71-0 Isoxazole-3-carboxylic Acid 11286453, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; SHIONOGI & CO., LTD.; EP1408041; (2004); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem