Heterocyclic Building Blocks-isoxazole

1136-45-4, 5-Methyl-3-phenylisoxazole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 5-methyl-3-phenylisoxazole-4-carboxylic acid (1.01 g, 4.97 mmol) and DMF (25 mL) was cooled to 0-10 C. N-(4-Chlorophenyl)-4-methyl-4,5-dihydrothiazol-2-amine (1.12 g, 4.94 mmol) and O-ibenzotriazol- l-y^-N.N.N’.N’-tetramethyluronium tetrafluoroborate (TBTU, 1.90 g, 5.92 mmol) were added to the reaction mixture and the mixture stirred at 0-10 C for 10 min. DIPEA (0.78 g, 6.04 mmol) was slowly added to the reaction mixture and the mixture stirred at 0-10 C for 4 h. The cooling bath was removed and the mixture was stirred for further 50 min allowing it to warm up to rt. EtOAc (40 mL) and an 10% aqueous NaHC03- solution (35 mL) were added to the reaction mixture and the mixture was stirred at rt for 5 min. The layers were separated and the organic layer was washed with water (3 x 30 mL) and brine (15 mL). The organic layer was dried with Na2S04, the drying agent was filtered off and the solvents were evaporated in vacuo to give the crude product. It was dissolved in EtOAc (10- 12 mL) at rt and the solution was stirred for 15 min, during the time the product started to crystallize out of the solution. n-Heptane (20 mL) was added and the mixture was stirred at rt for 15 min, during the time more product precipitated. The precipitated product was filtered off, it was washed with n- heptane and dried in vacuo at 50 C overnight to give the product as a white powder (1.53, 75%). 1H NMR (200 MHz, CDC13): delta .6-1 A (m, 5H, arom.), 7.2-7.1 (m, 2H, arom.), 6.4- 6.3 (m, 2H arom.), 4.6-3.5 (broad m, 2H, thiazole CH2), 3.5 (m, 1H, thiazole CH), 2.6 (s, 3H, Me), 1.4 (d, 3H, thiazole Me) ppm.

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

Reference£º
Patent; UNIVERSITY OF HELSINKI; UNIVERSITY OF OULU; KINNUNEN, Sini; TOeLLI, Marja; VAeLIMAeKI, Mika; JUMPPANEN, Mikael; BOIJE AF GENNAeS, Gustav; YLI-KAUHALUOMA, Jari; RUSKOAHO, Heikki; (75 pag.)WO2018/55235; (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.354795-62-3,3-Methylisoxazol-4-amine,as a common compound, the synthetic route is as follows.

Example 25H-pyrazol-4-yl)-4-(4-morpholinylcarbonyl)-2-To a solution of 5-(1 -methyl- 1 H-pyrazol-4-yl)-4-(4-morpholinylcarbonyl)-2- [(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 26; 44 mg, 0.10 mmol) in N,N-dimethylformamide (5 ml) was added diisopropylethylamine (0.04 ml, 0.21 mmol), 3-methyl-4-isoxazolamine (20.48 mg, 0.21 mmol), 1-hydroxy-7-azabenzotriazole (21.32 mg, 0.16 mmol) and EDC (34.0 mg, 0.18 mmol). The reaction was stirred for 18 hours and then the solvent was removed in vacuo. The residue was purified by MDAP to yield the title compound as a white solid. 43 mg.MS (electrospray): m/z, [M+H]+ = 5021 H NMR (400 MHz, DMSO-d6); 1.92 (s, 3 H), 2.80 – 3.13 (m, 3 H), 3.35 – 3.72 (m, 5 H), 3.92 (s, 3 H), 5.13 – 5.41 (m, 2 H), 7.24 (s, 1 H), 7.33 – 7.45 (m, 3 H), 7.47 – 7.62 (m, 3 H), 7.85 (d, J=3.01 Hz, 2 H), 9.16 (s, 1 H), 9.90 (s, 1 H).

The synthetic route of 354795-62-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; ANDREOTTI, Daniele; DAI, Xuedong; EATHERTON, Andrew John; JANDU, Karamjit Singh; LIU, Qian; PHILPS, Oliver James; WO2012/28629; (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.21169-71-1,Isoxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of (R)-methyl l-((l-(tert-butoxycarbonyl)pyrrolidin-2-yl)methyl)-2-imino- 2,3-dihydro-lH-benzo[d]imidazole-5-carboxylate (1 120 mg, 2.99 mmol) (Intermediate 13, Step 3), isoxazole-5-carboxylic acid (507.3 mg, 4.49 mmol), and DIPEA (1.03 mL, 5.9 8mmol) in DMF (6 mL)) was added HATU (1705 mg, 4.49 mmol). The resultant mixture was stirred at rt for 2 hours. The reaction mixture was evaporated, then the crude mixture was diluted with DCM and washed with brine. The organic layers were separated and dried with MgS04, filtered and concentrated to crude oil. This crude oil was purified by chromatography to obtain 1380 mg of (R)-methyl l-((l-(tert-butoxycarbonyl)pyrrolidin-2-yl)methyl)-2-(isoxazole-5-carboxamido)-lH- benzo[d]imidazole-5-carboxylate.

21169-71-1 Isoxazole-5-carboxylic acid 2060599, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; PRINCIPIA BIOPHARMA INC.; BRAMELD, Kenneth, A.; OWENS, Tim, A.; WO2014/36016; (2014); 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.14678-05-8,Isoxazol-5-amine,as a common compound, the synthetic route is as follows.

Example 37 Synthesis of ethyl 2-(2,4,5-trifluorobenzoyl)-3-(isoxazol-5-ylamino)acrylate (Compound No. 87) Ethyl 2,4,5-trifluorobenzoylacetate (1.50 g), 1.36 g of ethyl orthoformate and 2.80 g of acetic anhydride were combined, followed by heating at 130C for 3 hours. Excess ethyl orthoformate and acetic anhydride were distilled off. The residue was dissolved in 30 ml of chloroform. To the resulting solution, a solution of 512 mg of 5-aminoisoxazole in 30 ml of methanol was added, followed by stirring at room temperature for 3 hours. The solvent was distilled off. The residue was purified using a silica gel column (hexane:chloroform = 1:1), whereby 1.74 g of the title compound was obtained as a colorless solid.

14678-05-8 Isoxazol-5-amine 84591, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; WAKUNAGA SEIYAKU KABUSHIKI KAISHA; FUJISAWA PHARMACEUTICAL CO., LTD.; EP700912; (1996); 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.10557-85-4,3,5-Dimethyl-4-iodoisoxazole,as a common compound, the synthetic route is as follows.

To a solution of 4-iodo-3,5-dimethylisoxazole (2 g, 8.97 mmol, Eq: 1.00) and ethynyltrimethylsilane (1.06 g, 1.51 ml, 10.8 mmol, Eq: 1.2) in triethylamine (3.63 g, 5.00 ml, 35.9 mmol, Eq: 4) and DMF (17.9 ml) was added bis(triphenylphosphine)palladium (II) chloride (315 mg, 448 mumol, Eq: 0.05) and copper (I) iodide (40.2 mg, 448 mumol, Eq: 0.05). The mixture was heated to 75 C. for 2 hrs, diluted ether, washed with brine (2*), and dried over MgSO4. Concentration of the organic layer onto silica gel and purification by flash chromatography (5-18% ethyl acetate/hexane gradient) gave 3,5-dimethyl-4-((trimethylsilyl)ethynyl)isoxazole (1.07 g, 5.53 mmol, 61.7% yield) as a brown oil.

As the paragraph descriping shows that 10557-85-4 is playing an increasingly important role.

Reference£º
Patent; Hoffmann-La Roche Inc.; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Bhagirath, Niala; Kennedy-Smith, Joshua; Wilhelm, Robert Stephen; US2013/158049; (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.36958-61-9,5-(Bromomethyl)-3-methylisoxazole,as a common compound, the synthetic route is as follows.

A mixture of 2-( morpholin-4-yl)-8-[1-(tetrahyd ro-2H-pyran-2-yl )-1H-pyrazol-5-yl]-1,7-naphthy- ridin-4-ol (283 mg, 0.47 mmol), 5-(bromomethyl)-3-methyl-1,2-oxazole (123 mg, 0.70 mmol) andCaesiumcarbonate (197 mg, 0.61 mmol) in DMF (1.78 ml) was heated in a sealed tube in the microwave at 100C for one hour. The reaction mixture was allowed to cool to ambient temperature, a solution of concentrated aqueous HCI (0.7 ml) was added and the reaction was stirred at this temperature for two hours. The solvent was evaporated under reduced pressure,the residue was taken up in dichloromethane (10 ml) and water (10 ml). The layers were separated and the aqueous layer was extracted with dichloromethane (2x10m1). The combined organic layers were dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by HPLC chromatography (acidic conditions). The title compound was obtained in 3 % yield (6 mg). ?H-NMR (400 MHz, DMSO): 6 [ppm] = 2.27 (3H), 3.76 (8H), 5.57 (2H),6.65 (1H), 7.06 (1H), 7.36 (1H), 7.61 (1H), 7.69 (1H), 8.32 (1H), 13.35 (1H).

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

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WORTMANN, Lars; LUeCKING, Ulrich; LEFRANC, Julien; BRIEM, Hans; KOPPITZ, Marcus; EIS, Knut; VON NUSSBAUM, Franz; BADER, Benjamin; WENGNER, Antje Margret; SIEMEISTER, Gerhard; BONE, Wilhelm; LIENAU, Philip; GRUDZINSKA-GOEBEL, Joanna; MOOSMAYER, Dieter; EBERSPAeCHER, Uwe; SCHICK, Hans; (509 pag.)WO2016/20320; (2016); 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.3209-71-0,Isoxazole-3-carboxylic Acid,as a common compound, the synthetic route is as follows.

a) Ethyl 5-(isoxazol-3-yl)-l,2,4-oxadiazole-3-carboxylate Ethyl aminohydroxyiminoacetate (3.78 mmol, 0.5 g), 3-isoxazolecarboxylic acid (3.78 mmol, 0.428 g) and 1,3-diisopropylcarbodiimide (4.16 mmol, 0.525 g) were dissolved in DCM (70 ml) under nitrogen atmosphere. The mixture was stirred at RT for a day. The solvent was evaporated to dryness and the residue was dissolved in pyridine and refluxed for 6 h and overnight at RT. Pyridine was evaporated and the residue was diluted with DCM and water. The aqueous phase was extracted four times with DCM. The combined organics were washed with aqueous HC1 solution, saturated NaHC03, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.396 g of the title compound was obtained. Rotamers were obtained in 1 H-NMR and analysis was repeated at elevated temperature. 1 H-NMR (400 MHz, DMSO-c?, +60C): 5 1.38 (t, 3H), 4.49 (q, 2H), 7.21 (d, 1H), 9.05 (d, 1H).

As the paragraph descriping shows that 3209-71-0 is playing an increasingly important role.

Reference£º
Patent; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

1136-45-4, 5-Methyl-3-phenylisoxazole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-Methyl-3-phenylisooxazole-4-carboxylic acid (40 mg, 0.197 mmol), 3-(teroom temperature-Butoxycarbonylamino)pyrrolidine (40 mg, 0.215 mmol), O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (86.2 mg, 0.268 mmol) and diisopropylethylamine (25.4 mg, 0.197 mmol) were mixed in dimethylformamide (1.5 mL) and stirred at room temperature. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The combined fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C20H25N3O4: 371.1845, found 371.1851.

As the paragraph descriping shows that 1136-45-4 is playing an increasingly important role.

Reference£º
Patent; Amgen Inc.; Biovitrum AB; US2008/21022; (2008); 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.

To a 100 mL round-bottomed flask was added, in sequence, isoxazole-5-carboxylic acid (0.34 g, 3.0 mmol), HATU (1.4 g, 3.6 mmol), TEA (0.92 g, 9.1 mmol), DCM (40 mL), and 2-ethoxy-4-fluoroanaline (0.60 g, 3.9 mmol) at 0 C. The reaction mixture was warmed to rt and stirred for 15 h. The reaction mixture was concentrated to dryness and the residue was purified by FCC to give the title compound (0.32 g, 43% yield) as a yellow solid. MS (ESI): mass calcd. for C12H11FN2O3 250.1, m/z found 251.1 [M+H]+.

As the paragraph descriping shows that 21169-71-1 is playing an increasingly important role.

Reference£º
Patent; Janssen Pharmaceutica NV; Bacani, Genesis M.; Chai, Wenying; Edwards, James P.; Smith, Russell C.; Tichenor, Mark S.; Venable, Jennifer D.; Wei, Jianmei; (64 pag.)US2018/289706; (2018); 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

[00226] Isooxazole-3 -carboxylic acid ((8′), 92 wt % assay based on 1H-NMR, 3.86 kg, 34.1 mol, 1.0 equiv), toluene (19.3 L) and DMF (0.131 L, 1.69 mol, 0.05 equiv) were mixed in a 30 L jacketed reaction vessel equipped with a nitrogen inlet-outlet, overhead stirrer, a thermocouple and an addition funnel. The resulting slurry was heated to 45 to 55 C. Oxalyl chloride (4.80 kg, 37.8 mol, 1.11 equiv) was charged via the addition funnel over the course of 4 hours 30 minutes, while maintaining the reaction temperature between 45 to 55 C. Vigorous gas evolution was observed. A brown mixture was obtained after the addition. The brown mixture was held at 45 to 55 C for 30 minutes, then heated to 85 to 95 C and stirred at 85 to 95 C for 1 hour. During heating, the brown mixture turned into a black mixture. The black mixture was cooled to 20 to 25 C, over 4 hours and held at 20 to 25 C for a minimum of 16 hours. The reaction was monitored by quenching a portion of the reaction mixture into piperidine and monitoring the formation of the piperidine amide by HPLC ((8′) : piperidine amide area:area % was < 1.9). After the reaction was complete by HPLC the dark mixture was in-line filtered via gas a dispersion tube (coarse frit) into a 20 L rotavapor flask. Toluene (3.9 L) was used to rinse the reactor and the rinse was in-line filtered into the 20 L rotavapor flask. The filtered reaction mixture was concentrated under reduced pressure until no more distillate was seen coming off. As the paragraph descriping shows that 3209-71-0 is playing an increasingly important role. Reference£º
Patent; CYCLERION THERAPEUTICS, INC.; WALLACE, Debra Jane; ZHOU, Fenger; WANG, Yuguang; NAKAI, Takashi; KARNATI, Vishnu Vardhan Reddy; SCHAIRER, Wayne C.; KISSEL, Willaim; XUE, Song; HASHASH, Ahmad; (263 pag.)WO2019/140095; (2019); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem