Category: Isoxazoles

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%).

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

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

21169-71-1, Isoxazole-5-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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%).

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

14441-90-8, 5-Phenylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

into a 50-mL round-bottom flask, was placed a solution of 5- phenyl-1,2-oxazole-3-carboxylic acid (177.7 mg, 0.94 mmol, 1.00 eq.), 1-[1-[trans-3- aminocyclobutyl]- 1 H-pyrazol-3-yl]ethan- 1 -ol hydrochloride (246 mg, 1.13 mmol, 1.20 eq.),HATU (428.8 mg, 1.13 mmol, 1.20 eq.) and DIEA (363.9 mg, 2.82 mmol, 3.00 eq.) in DMF(10 mL). The resulting solution was stirred for 2 hours at room temperature. The reaction was then quenched by the addition of 20 mL of water. The resulting solution was extracted with ethyl acetate (3×20 mL) and the organic combined layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a Prep-TLC with ethylacetate/petroleum ether (2:1). This resulted in 189 mg (57%) of 5 -phenyl-N-[trans-3 -[3 -(1- hydroxyethyl)- 1 H-pyrazol- 1 -yl]cyclobutyl] -1 ,2-oxazole-3 -carboxamide as a off-white solid.

As the paragraph descriping shows that 14441-90-8 is playing an increasingly important role.

Reference£º
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
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 solution of 3-isoxazolecarboxylic acid (500 mg, 4.42 mmol, commercially available from e.g. Manchester Organics, Bio-Farma or APAC) in dry dichloromethane (DCM) (14.700 ml) was stirred at room temeprature under an atmosphere of argon. EDC (1017 mg, 5.31 mmol) and HOBt (339 mg, 2.21 1 mmol) were added to the stirred soltuion and the resulting solution was stirred for 3/4 hour. After this time, 1 ,1- dimethylethyl hydrazinecarboxylate (701 mg, 5.31 mmol) was added to the stirred solution and strring continued for a further 18 hours at room temperature (overnight). The reaction mixture was partitioned between DCM (~ 20 ml) and saturated sodium bicarbonate solution (~ 20 ml). The aqueous phase was extracted with DCM (2 x 20 ml) and the combined organic extracts washed with saturated brine (~ 50 ml), dried over sodium sulphate, evaporated in vacuo and dried (vacuum oven, 40 0C, 72 hr) to afford the crude product as a brown oil. This was purified via Biotage SP4 (2-20 % MeOH/DCM; 100g SNAP Biotage column; 12 CV) to afford the required product as an orange oil in 510.6 mg, which was used without further purification in the next step. LCMS: [M-Boc+H]+ m/z = 128.0; RT. = 0.62-0.63 min.

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

Reference£º
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (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.3209-71-0,Isoxazole-3-carboxylic Acid,as a common compound, the synthetic route is as follows.

A solution of isoxazole-3-carboxylic acid (10 mg, 0.084 mmol), HATU (32 mg, 0.084 mmol), triethylamine (30 ul, 0.212 mmol), 3-methyl-4-(7-methylbenzo[d]oxazol-2-yl)aniline (20 mg, 0.084) and catalytic amount of DMAP in THF (1 mL) was stirred at 65 C for 48 h. The reaction mixture was diluted with DCM, washed with saturated solution of NaHCO3 and brine. The organic solution was, dried over Na2SO4, decanted and evaporated under reduced pressure. The crude was purified by column chromatography on silica gel using 1:4 EtOAc:Hexane as mobile phase and the obtained product was triturated in hexane, filtered and dried to give N-(3-methyl-4-(7- methylbenzo[d]oxazol-2-yl)phenyl)isoxazole-3-carboxamide (3 mg, 10%). UPLC-MS (Acidic Method, 4 min): rt 2.12 min, m/z 334.1 [M+H]+ 1H NMR (400 MHz, METHANOL-d4) d ppm 7.32 (d, J=1.6 Hz, 1H), 6.63 (d, J=8.5 Hz, 1H), 6.26-6.32 (m, 2H), 6.02 (d, J=7.9 Hz, 1H), 5.71-5.77 (m, 1H), 5.65-5.69 (m, 1H), 5.40 (d, J=1.6 Hz, 1H), 1.27 (s, 3H), 1.06 (s, 3H).

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

Reference£º
Patent; JAGUAHR THERAPEUTICS PTE LTD; METE, Antonio; HITCHIN, James, R.; GRAHAM, Mark; (46 pag.)WO2020/43880; (2020); 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.4369-55-5,5-Amino-3-phenylisoxazole,as a common compound, the synthetic route is as follows.

adding 1.0 equiv. (0.2 mmol) of an oxazole ring to a schlenk tube, and adding 2 mL of analytically pure ethanol,A 1% equiv. ruthenium catalyst was reacted under green light for 24-72 hours. After the reaction is completed, the solvent is removed by a rotary evaporator, and the organic phase is extracted three times with water and dichloromethane, and the organic phase is dried over anhydrous sodium sulfate, and the solvent is evaporated and then subjected to column chromatography (dichloromethane/methanol) Amine heterocyclic propylene compound.

As the paragraph descriping shows that 4369-55-5 is playing an increasingly important role.

Reference£º
Patent; Nanjing Tech University; Jiang Yaojia; Chen Yang; Luo Deping; (7 pag.)CN110041237; (2019); A;,
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

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

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.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