Heterocyclic Building Blocks-isoxazole

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.

Example 1. Compound of formula B, wherein R = (compound 31).To a solution of compound A (25.0 mg, 0.039 mmol), S-methylisoxazole-S-carboxylic acid (5.4 mg, 0.043 mmol) and HATU (16.2 mg, 0.043 mmol) in DMF (0.5 mL) was added diisopropylethylamine (15.0 mg, 0.116 mmol). The reaction mixture was stirred at 25 0C for 16 h and then evaporated under a positive flow of nitrogen. The residue was purified by reverse phase chromatography to give the desired product (20.8 mg, 71percent yield). MS (ESI): m/z = 755.1 [M+H]., 3405-77-4

3405-77-4 5-Methylisoxazole-3-carboxylic acid 76947, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; ENANTA PHARMACEUTICALS, INC.; WO2009/73713; (2009); 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.7063-99-2,Ethyl 5-phenylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

7063-99-2, General procedure: Sodium hydroxide (2N) was added to a solution of intermediate 2a-i (1 equiv.) in methanol at ambient temperature. The reaction mixture was stirred for 4h and the methanol was removed by rotary evaporation. The resultant mixture was adjusted to pH=5-6 with 1N HCl solution. The precipitated white solid was collected by filtration and dried to give the carboxylic acid intermediate (1a-i). 4.13.1 5-Phenylisoxazole-3-carboxylic acid(1a) (0032) Light white solid; yield: 91.5%; 1H NMR (600MHz, DMSO-d6) delta 7.95 (dd, J=7.8, 1.7Hz, 2H), 7.58-7.53 (m, 3H), 7.41 (s, 1H).

As the paragraph descriping shows that 7063-99-2 is playing an increasingly important role.

Reference£º
Article; Zhao, Shizhen; Zhang, Xiangqian; Wei, Peng; Su, Xin; Zhao, Liyu; Wu, Mengya; Hao, Chenzhou; Liu, Chunchi; Zhao, Dongmei; Cheng, Maosheng; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 96 – 107;,
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.

Dissolve the free piperazino-piperidine of Example 11, step 6 (1.7 g, 3.3 mmol) in CHCl3 (30 ml;=Stock solution A). Add 250 ul of stock solution A (0.027 mmol) to a slurry of 0.15 g (0.14 mmol ) of resin bound cardodiimide (prepared by reacting Argopore-Cl resin with 1-(3-dimethyl-aminopropyl)3-ethyl carbodiimide in DMF at 100 C. in DMF (1.5 ml) in a polyethylene SPE cartridge. To this mixture add 75 ul of a 1 M solution of 5-methyl-3-phenylisoxazole-4-carboxylic acid in DMF (0.075 mmol), and HOBT (24 ul of a 1M solution in DMF). Shake this mixture for 14 h, filter and add 0.1 g of Amberlyst-15 resin (0.47 mmol) to the filtrate. Shake for 1 to 2 h, filter and wash the resin twice with each of the following solvents THF, CH2Cl2 and CH3OH, then wash with THF and CH2Cl2. Treat the resin with 2M NH3 in CH3OH (1 time for 30 min, and 1 time for 5 min). Combine and concentrate the filtrates under reduced pressure to afford the title compound. LCMS found MH+=599.1 (calculated MW 598); TLC Rf=0.74 (CH2Cl2/CH3OH/NH4OH (95/5/0.5)).

1136-45-4, The synthetic route of 1136-45-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Schering Corporation; US6391865; (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.51677-09-9,Methyl 5-phenylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

51677-09-9, To a solution of 1-2 (1.0 g, 4.9 mmol) in MeOH (10 mL) was added sodium hydroxide solution (20 mL, 4 M). The reaction mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure to remove MeOH. The aqueous phase was acidified with aqueous HCl (1 M) till pH=3 and the mixture was extracted with EtOAc, dried with anhydrous Na2SO4, filtered and concentrated to give the crude product. The crude product was purified by silica gel chromatography eluted to give product 1-2 (0.7 g, 79.5%). MS m/z [ESI]: 190.0 [M+1].

The synthetic route of 51677-09-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUZHOU SINOVENT PHARMACEUTICALS CO., LTD.; WANG, Yonghui; ZHU, Yan; ZHOU, Juan; GAO, Yujun; WANG, Shiqun; WANG, Dong; LIU, Wandeng; SHEN, Ximing; HONG, Binbin; LIU, Tao; WU, Yaodong; LI, Chunqi; (35 pag.)US2018/271846; (2018); 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.123770-62-7,Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (0.270 g) was dissolved in absolute ethanol (4.5 ml). Methylamine (2M in THF, 3.16 ml) was added. The vial was sealed and stirred at 70C overnight. The reaction mixture was cooled to room temperature and the solvent was evaporated in vacuo. The crude product was purified via flash column chromatography (1-4% methanol in dichloromethane) affording the product as a white solid, 123770-62-7

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Dr. August Wolff GmbH & Co. KG Arzneimittel; Soeberdt, Michael; Knie, Ulrich; Abels, Christoph; EP2666766; (2013); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

78967-07-4, Mofezolac is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

78967-07-4, General procedure: N-Diisopropyl-N-ethylamine (DIEA, 0.215 mL, 1.237 mmol) andmethyl 5-aminopentanoate hydrochloride (6) (100 mg, 0.60 mmol)were solubilized in anhydrous CH2Cl2 (5 mL) and stirred at 0 C for1 h. Then, this solution was dropwise added to a stirred solution ofN,N’-dicyclohexylcarbodiimide (DCC, 170 mg, 0.825 mmol), 1-hydroxybenzotriazole monohydrate (HOBt H2O, 180 mg,1.05 mmol) and 2-[3,4-bis(4-methoxyphenyl)isoxazol-5-yl]aceticacid (mofezolac) (200 mg, 0.59 mmol) in anhydrous CH2Cl2 (20 mL)kept at 0 C. The reaction mixture was stirred for 19h at roomtemperature. Then, H2O was added and the aqueous solutionextracted with CH2Cl2. The combined organic layers were washedwith a sat. aqueous solution of K2CO3, dried over anhydrousNa2SO4, and the solvent was removed under reduced pressure.Column chromatography of the crude residue (silica gel; EtOAc/Hexane 3:7) allowed to isolated 8 (107 mg, 40% yield).

The synthetic route of 78967-07-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Perrone, Maria Grazia; Vitale, Paola; Ferorelli, Savina; Boccarelli, Angelina; Coluccia, Mauro; Pannunzio, Alessandra; Campanella, Federica; Di Mauro, Giuseppe; Bonaccorso, Carmela; Fortuna, Cosimo G.; Scilimati, Antonio; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 404 – 416;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.110256-15-0,5-Cyclopropylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of 5-cyclopropylisoxazole-3-carboxylic acid (lOOmg, 0.653mmol) in DMF (2ml) was added HATU (370 mg, 0.980 mmol). The reaction stirred at room temperature for 30 minutes and then was cooled to 0C. l-Cyclopropyl-4- methylpyrrolidin-3 -amine (109 mg, 0.781 mmol) was added followed by DIPEA (252 mg, 1.960 mmol). The reaction stirred at ambient temperature for 2 hours. After completion of the reaction the reaction mixture was poured into 50 ml of water. The aqueous phase was extracted with ethyl acetate (3 x 25ml). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated under vacuum. The material was purified using column chromatography. The product was eluted at 2% MeOH in DCM. Appropriate fractions were combined and concentrated under vacuum to get 150 mg (83.79 %) of 5-cyclopropyl-N-(l-cyclopropyl-4- methylpyrrolidin-3-yl)isoxazole-3-carboxamide as a mixture of enantiomers and diastereomers. Cis and trans isomers were seperated out by chiral preparative HPLC using 0.1% TFA in hexanes/isopropanol as mobile phase to afford 35 mg of (¡À)-cis-5- cyclopropyl-N-(l-cyclopropyl-4-methylpyrrolidin-3-yl)isoxazole-3-carboxamide (Fraction- 1) and 49 mg of (¡À)-tra/?5-5-cyclopropyl-N-(l-cyclopropyl-4-methylpyrrolidin- 3 -yl)isoxazole-3 -carboxamide (Fraction-2) . [0196] (¡À)-cz5-5-cyclopropyl-N-(l-cyclopropyl-4-methylpyrrolidin-3-yl)isoxazole-3- carboxamide: 1H NMR (400 MHz, MeOD): delta 6.41 (s, 1H), 4.33 (bs, 1H), 3.94-3.66 (m, 3H), 3.15-3.00 (m, 2H), 2.56-2.53 (m, 1H), 2.22-2.15 (m, 1H), 1.37-1.33 (d, J = 18.4 Hz, 3H), 1.23 (d, J = 6.8 Hz, 2H), 1.00-0.99 (m, 5H); LCMS: m/z = 277.23 [M+H]+. [0197] (¡À)-tra/?5-5-cyclopropyl-N-(l-cyclopropyl-4-methylpyrrolidin-3-yl)isoxazole-3- carboxamide: 1H NMR (400 MHz, MeOD): delta 6.42 (s, 1H), 4.15 (bs, 1H), 3.77-3.66 (m, 3H), 3.52-3.37 (m, 2H), 3.04 (bs, 2H), 2.62 (bS, 1H), 2.22-2.26 (m, 1H), 1.19-1.12 (m, 2H), 1.09 (d, J = 7.2 Hz, 3H), 1.01-0.98 (m, 5H), 0.97-0.90 (m, 2H); LCMS: m/z = 276.18 [M+H]+.

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

Reference£º
Patent; EPIZYME, INC.; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; HARVEY, Darren Martin; (151 pag.)WO2016/40504; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

19788-37-5, 4-(Chloromethyl)-3,5-dimethylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-Chloromethyl-3,5-dimethyl-isoxazole (1.5 eq. ) was directly added to a solution of 2-furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (0.14 mmol; see Example 1 (a) above) and Et3N (0.3 mmol) in 3 mL of CH3CN. The resulting reaction mixture was stirred at room temp for 18 hours. It was then concentrated and purified by preparative HPLC using a mixture of aqueous CH3CN that has been buffered with 0.1 % TFA. 1H NMR (DMSO-d6) delta 7.60 (d, J = 1.0 Hz, 1 H), 7.28 (br s, 2 H), 7.22 (d, J = 3.6 Hz, 1 H), 6.68 (dd, J = 3.6 Hz, 1.0 Hz, 1 H), 3.8 (br s, 2 H), 2.2-3.2 (m, 8H), 1.6 (br s, 6H). MS: m/z: 396 [M + H] +., 19788-37-5

19788-37-5 4-(Chloromethyl)-3,5-dimethylisoxazole 88246, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; BIOGEN IDEC MA INC.; WO2004/92170; (2004); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

62348-13-4,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.

Example 90 N-{[1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4- b]pyridin-5-yl]methyl}-5-isoxazolecarboxamideA solution of Intermediate 14 (20mg) in anhydrous acetonitrile (0.4ml) was treated with isoxazole-5-carbonyl chloride [e.g. available from Lancaster Synthesis Ltd.] (13mg) and DIPEA (0.016ml) and stirred at room temperature for 24 hours. The solution was blown to dryness and the residue was purified by mass directed autoprep HPLC to give Example 90 as a clear colourless gum (12mg). LCMS showed MH+ = 371; TREtau = 2.03min.

62348-13-4 Isoxazole-5-carbonyl chloride 2736707, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/36733; (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.88511-37-9,1-(Isoxazol-3-yl)ethanone,as a common compound, the synthetic route is as follows.,88511-37-9

A solution of l -(isoxazol-3-yl)ethanone (4.0 g, 36.3 mmol) in THF (200 mL) was cooled in dry ice/acetone. Lithium bis(trimethylsilyl)amide (1M in toluene, 33.8 mL, 33.8 mmol) was added over 10 min followed by 30 min of stirring at -65 to -70C. The ester pyrimidine obtained above (4.5 g, 24.2 mmol) in THF (20 mL) was dripped into the enoate solution over 5 min and stirring was continued overnight at room temperature. The solvents were removed in vacuo, then the residue was broken up under ether (100 mL) and filtered. The filter cake was washed with ether (20 mL) and air dried to leave 8.2 g crude diketo isoxazole which was carried on directly to the next reaction without further purification. LCMS (m/e) 266 (M+H).

88511-37-9 1-(Isoxazol-3-yl)ethanone 21349800, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; IRONWOOD PHARMACEUTICALS, INC.; BARDEN, Timothy Claude; SHEPPECK, James Edward; RENNIE, Glen Robert; RENHOWE, Paul Allan; PERL, Nicholas; NAKAI, Takashi; MERMERIAN, Ara; LEE, Thomas Wai-Ho; JUNG, Joon; JIA, James; IYER, Karthik; IYENGAR, Rajesh R.; IM, G-Yoon Jamie; (293 pag.)WO2016/44447; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem