Category: Isoxazoles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33282-16-5,5-(4-Methoxyphenyl)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.

The synthetic route of 33282-16-5 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19788-37-5,4-(Chloromethyl)-3,5-dimethylisoxazole,as a common compound, the synthetic route is as follows.

General procedure: Intermediate 22: N-{1-[(6-methyl-2-pyridinyl)methyl]-1H-pyrazol-3-yl}acetamide Intermediate 1 (97 mg, 0.774 mmol) was dissolved in 8 mL of THF (anh), at 0 C. NaH (ALDRICH, 31 mg, 0.774 mmol) was added, and mixture of reaction was stirred at 0 C. for 30 minutes. A solution of Intermediate 11 (144 mg, 0.774 mmol) in 2 mL THF (anh) was added to the mixture. Reaction was heated at 75 C. overnight. Mixture of reaction was partitioned between distilled water, EtOAc (*3) and DCM. Organic layers were dried over MgSO4 (anh) and filtered. Solvent was evaporated under vacuum. Residue was purified by silica chromatography column using a linear gradient of DCM/MeOH as eluents to give the title compound (133 mg, 0.578 mmol, 75% yield). 1H NMR (300 MHz, DMSO-d6) delta ppm: 10.40 (br s, 1H), 7.72 (d, 1H), 7.60-7.66 (m, 1H), 7.17-7.16 (m, 1H), 6.74-6.77 (m, 1H), 6.49 (d, 1H), 5.24 (s, 2H), 2.44 (s, 3H), 1.95 (s, 3H). [ES+MS] m/z 231 (MH+). The Intermediates 23-39 were prepared by methods analoguous to that described for Intermediate 22 but replacing the benzyl halide (Intermediate 11) with that indicated in Table 3. Modifications are also indicated. Reaction times varied from 2 h to 3 h.

As the paragraph descriping shows that 19788-37-5 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; Castro Pichel, Julia; Fernandez Menendez, Raquel; Fernandez Velando, Esther Pilar; Gonzalez Del Valle, Silvia; Mallo-Rubio, Araceli; US2013/203802; (2013); A1;,
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Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108655-63-6,3-(Trifluoromethyl)isoxazol-5-amine,as a common compound, the synthetic route is as follows.

To a solution of 3- (trifluoromethyl) isoxazol-5-amine (1.0 g, 6.57 mmol) in CH2C12 (15 ml) is added dropwise, phenyl CHLOROFORMATE (1.8 ml, 14.45 mmol) and pyridine (1.0 ml, 13.14 mmol) at 0oC. The reaction mixture is stirred at 0oC for 30 min. The reaction mixture is washed with H20 and 1% HCI. To the combined organic layers are added pyridine (1.0 ml, 6.57 mmol), HA0 (1.0 ml), AND CH2CL2 (20 ml), and the mixture is stirred at RT for 3 hours. The reaction mixture is washed with 0. 1N HC1 and brine, dried (Na2SO4), and concentrated. The residue is recrystallized from n-hexanes to give phenyl 3- (trifluoromethyl) isoxazol-5-ylcarbamate as an off white solid 1.3 g (73%). MS (ESI-) for CLLH7F3N203 ONLY 271.0 (M-H)-.

The synthetic route of 108655-63-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/85433; (2004); A2;,
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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.

To a solution of 5-phenylisoxazole-3-carboxylic acid (117 mg, 0.620 mmol) in dichloromethane (2 mL) at 20 C. was added oxalyl chloride (1 mL). The reaction mixture was stirred at room temperature for 0.5 h. The volatiles were removed in vacuo. The crude residue was dissolved in dichloromethane (2 mL) and added to a mixture of 1-((4-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrazol-4-amine (0.150 g, 0.620 mmol) and triethylamine (0.188 g, 1.86 mmol) in dichloromethane (5 mL) dropwise. The reaction mixture was stirred for 0.5 h and purified by prep-HPLC (the crude sample was dissolved in N,N-dimethylformamide and loaded onto Boston C18 21¡Á250 mm 10 mum column. The mobile phases were acetonitrile/0.01% aqueous trifluoroacetic acid) to offer 5-phenyl-N-(1-((4-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrazol-4-yl)isoxazole-3-carboxamide (65.5 mg, 0.158 mmol, 25%) as a white solid. 1H NMR (500 MHz, Dimethylsulfoxide-d6) delta 11.09 (s, 1H), 8.81 (d, J=5.0 Hz, 1H), 8.34 (s, 1H), 8.29 (s, 1H), 7.98 (dd, J=7.6, 1.6 Hz, 2H), 7.80 (d, J=5.0 Hz, 1H), 7.75 (s, 1H), 7.59-7.56 (m, 3H), 7.47 (s, 1H), 5.61 (s, 2H); LCMS (ESI) m/z: 414.1 [M+H]+.

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

Reference£º
Patent; Yumanity Therapeutics, Inc.; WRONA, Iwona; TIVITMAHAISOON, Parcharee; TARDIFF, Daniel; PANDYA, Bhaumik; OZBOYA, Kerem; LUCAS, Matthew; BOURDONNEC, Bertrand Le; (259 pag.)US2019/330198; (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.

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

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;,
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Isoxazole | C3H3NO – PubChem

63366-79-0, Ethyl 3-methylisoxazole-5-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A round bottom flask with magnetic stirrer was charged with 3-methyl-isoxazole-5- carboxylic acid ethyl ester (900 mg, 5.8 mmol) in tetrahydrofuran (2.0 mL). To the reaction was added a solution of sodium hydroxide (465 mg, 11.6 mmol) in water (2 mL), followed by methanol (4 mL). The reaction was stirred at room temperature for 18 – 20 hours under an argon atmosphere. The reaction was transferred to a separatory funnel and the pH adjusted to 2 via addition of IN hydrochloric acid. The mixture was extracted with ethyl acetate (3 x 35 mL) and the combined extractions were washed with brine (1 x 50 mL), dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to yield S-methyl-isoxazole-S-carboxylic acid as a white solid (660 mg, 90%). The solid was used without purification in the next reaction.

63366-79-0 Ethyl 3-methylisoxazole-5-carboxylate 10329487, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2006/91674; (2006); A1;,
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Isoxazole | C3H3NO – PubChem

13999-39-8, 3-Amino-4,5-dimethylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A. 2-Bromo-N-(4,5-dimethyl-3-isoxazolyl)benzenesulfonamide To 4,5-dimethyl-3-isoxazolamine (1.62 g, 13.00 mmol, prepared as described in T. Konoike et al., Tetrahedron Letters, 37, 3339 (1996)) and 4-dimethylaminopyridine (159 mg, 1.3 mmol) in 6.5 ml pyridine at 0 C., 2-bromobenzenesulphonyl chloride (3.65 g, 14.3 mmol) was added in portions over 10 minutes. After stirring at room temperature overnight, the mixture was added dropwise to 40 ml 6N HCl at 0 C. The mixture was extracted with 3*50 ml EtOAc. The combined organic extracts were washed with 30 ml each of 1N HCl and brine and dried and concentrated. The residue was dissolved in 160 ml MeOH and 160 ml 3% aqueous NaHCO3 solution was added and the mixture was concentrated in vacuo to remove most of the MeOH. The solid was filtered off and the aqueous filtrate was acidified to pH 2 with solid NaHSO4, and extracted with 3*100 ml of EtOAc. The extracts were washed with brine, dried and concentrated to give the title compound of this step (3.0 g, 70%). Rf=0.57, silica gel, 1:1 hexane/EtOAc.

13999-39-8 3-Amino-4,5-dimethylisoxazole 84148, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; Bristol-Myers Squibb Company; US5780473; (1998); A;,
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Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.78967-07-4,Mofezolac,as a common compound, the synthetic route is as follows.

Diisopropyl ethylamine (DIEA, 0.215 mL, 1.237 mmol) and methyl 5-aminopentanoate hydrochloride (100 mg, 0.60 mmol) were solubilized in dry CH2Cl2 (5 mL) and stirred at 0 C for 1h. Then, this solution was dropwise added to a stirred solution of N,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]acetic acid (mofezolac) (200 mg, 0.59 mmol) in dry CH2Cl2 (20 mL) kept at 0 C. The reaction was stirred for 19h at room temperature. Then, H2O was added and the aqueous solution extracted with CH2Cl2. The combined organic layers were washed with a sat. solution of K2CO3, dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. Column chromatography of the crude residue (silica gel; EtOAc/Hexane = 3:7) afforded the product as a solid (107 mg, 40% yield). FT- IR (KBr): 3458, 3089, 2987, 2948, 1737, 1652, 1609, 1562, 1516, 1455, 1441, 1426, 1253, 1233, 1175, 1108, 1029, 1019, 949, 831, 729 cnf1. NMR (300 MHz, CDCl3, delta) : 7.41-7.37 (m, 2H, aromatic protons), 7.17-7.14 (m, 2H, aromatic protons), 6.92-6.89 (m, 4H, aromatic protons), 5.9 (bs, 1H, NJJ: exchanges with D2O) , 3.83 (s, 3H, OCH3) , 3.80 (s, 3H, OCH3) , 3.67 (s, 2H, CJJ2CONH) , 3.65 (s, 3H, OCH3) , 3.27 (q, 2H, J= 6.9 Hz, NHCJJ2), 2.33 (t, 2H, J= 6.9 Hz, CJJ2CO2), 1.65-1.50 (m, 4H, CH2CH2). 13C NMR (75 MHz, CDC13, delta) : 174.1, 166.8, 162.8, 161.4, 160.8, 159.7, 131.2, 130.0, 121.6, 121.2, 117.8, 114.6, 114.2, 55.5, 55.4, 39.7, 34.4, 33.6, 29.0, 22.2. ESI-MS: m/z (%) : C25H28 206 (M + Na) +: 475.

As the paragraph descriping shows that 78967-07-4 is playing an increasingly important role.

Reference£º
Patent; UNIVERSITA’ DEGLI STUDI DI BARI “ALDO MORO”; SCILIMATI, Antonio; PERRONE, Maria Grazia; VITALE, Paola; (114 pag.)WO2017/187352; (2017); A1;,
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Isoxazole | C3H3NO – PubChem

100499-66-9, 5-Methylisoxazol-4-amine hydrochloride is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Method 73; N-(5-Methyl- 1 ,2-oxazol-4-yl)cyclobutanecarboxamide; Cyclobutyl carbonyl chloride (26.7 ml) was added dropwise to a stirred solution of 5- methyl-l,2-oxazol-4-amine hydrochloride (30g) and TEA (80 ml) in DCM (450 ml) at EPO ambient temperature. The reaction mixture was stirred for 30 min then washed with water (150 ml), 10% aq. citric acid (2 x 100 ml), sat. aq. NaHCO3 (2 x 100 ml). The aqueous layers were re-extracted with DCM (2 x 100 ml), the combined organic extracts dried (Na2SO4), filtered and concentrated in vacuo. The residue was triturated with ether (250 ml), filtered and dried to give the title compound as a beige solid (35.3 g). NMR (300.072 MHz, CDCl3) 8.52 (s, IH), 6.60 (br.s, IH), 3.14 (quintet, IH), 2.45-2.16 (m, 5H), 2.11-1.84 (m, 2H); m/z 181.

100499-66-9 5-Methylisoxazol-4-amine hydrochloride 13033203, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/15064; (2007); A1;,
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Isoxazole | C3H3NO – PubChem

946426-89-7, 5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazole-4-methanol is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Thionylchloride (62 ml, 0.52 mol) was added slowly to a solution of (5-cyclopropyl-3- (2,6-dichlorophenyl)isoxazol-4-yl)methanol (1.5 g, 5.3 mmol) in dichloromethane (100 ml) at 0-5 C and the resulting mixture allowed to warm to room temperature. After 2 h the reaction mixture was concentrated under reduced pressure and dissolved in DMF (15 ml). 4-(2-(4- Bromophenyl)cyclopropyl)-3-chlorophenol (1.8 g, 5.80 mmol), potassium carbonate (4.7 g, 34.33 mmol) and sodium iodide (800 mg, 5.33 mmol) were then added and the reaction mixture heated at 60-65 C. After 16 h the reaction was poured into water, extracted with ethyl acetate, the organic layer washed with water, brine, dried over anhydrous Na2S04, filtered, concentrated under reduced pressure and purified using silica gel column chromatography, eluting with 20% EtOAc in petroleum ether to give the titled compound (710 mg, 23 %) as a solid. LC-MS: 2.76 mins, [M+H]+ 588

The synthetic route of 946426-89-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; INORBIT THERAPEUTICS AB; SHARMA, Rajiv; BENTHEM, Lambertus; JUDKINS, Robert; (69 pag.)WO2020/33382; (2020); A1;,
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Isoxazole | C3H3NO – PubChem