Heterocyclic Building Blocks-isoxazole

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.,21169-71-1

To a flask containing 8-[5-(S)-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-1, 2, 4a, 5-tetrahydropyrazino[2, 1-c] [1, 4]benzoxazine-3(4H)-carboxylic acid phenylmethyl ester (EXAMPLE 1, 150 mg, 0.31 mmol) in methanol (5 mL) and methylene chloride (5 mL) is introduced 10% palladium on carbon (70 mg). The mixture is placed under a hydrogen balloon for 17 hours, filtered through celite, and concentrated in vacuo. The residue is dissolved in pyridine (5 mL) followed by the addition of isoxazole-5-carboxylic acid (40 mg, 0.35 mmol), 4-dimethylaminopyridine (5 mg, 0.04 mmol), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride(70 mg, 0.35 mmol). The reaction is stirred under an inert atmosphere for 17 hours, diluted with methylene chloride (20 mL), washed with 1N HCl (20 mL) and saline, dried over Na2SO4, concentrated in vacuo and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with chloroform/methanol (97/3). The appropriate fractions are combined (Rf= 0.42, TLC, chloroform/methanol, 90/10) and concentrated in vacuo to give the title compound, HRMS calcd for C21H23N5O6: 441.1648. Found: 441.1658.

The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; EP874852; (2004); 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.3209-71-0,Isoxazole-3-carboxylic Acid,as a common compound, the synthetic route is as follows.

Solid NaH (60% wt in oil) (425 mg, 10.6 mmol) was added to a THF solution (50 mL) of isoxazole-3-carboxylic acid (1.0 g, 8.8 mmol). After 15 min neat ethylchloroformate (1.0 mL, 10.6 mmol) was added. After 45 min a 7 N ammonia solution in MeOH (5.0 mL, 35 mmol) was added. After 30 min the mixture was diluted with EtOAc washed with water and brine, dried (Na2SO4) and dry packed onto silica gel. Column chromatography gave 600 mg of the title compound., 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; JANSSEN PHARMACEUTICA NV; BARBAY, J., Kent; CHAKRAVARTY, Devraj; SHOOK, Brian, Christopher; WANG, Aihua; WO2010/45006; (2010); A1;,
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%).

21169-71-1, 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2510-36-3,3,5-Dimethylisoxasole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

INTERMEDIATE 34: (S)-dibenzyl 2-(2-(2-(benzyloxy)-2-oxoethoxy)-4-(5-((((R)-2-((R)-1 – (N-((3,5-dimethylisoxazole-4- carbonyl)oxy)formamido)propyl)heptanamido)methyl)carbamoyl)furan-2- yl)benzamido)succinate DI PEA (84 muIota, 0.482 mmol) was added to a solution containing (S)-dibenzyl 2-(2-(2- (benzyloxy)-2-oxoethoxy)-4-(5-((((R)-2-((R)-1 -(N- hydroxyformamido)propyl)heptanamido)methyl)carbamoyl)furan-2-yl)benzamido)succinate (150 mg, 0.161 mmol) and 3,5-dimethylisoxazole-4-carboxylic acid (24.96 mg, 0.177 mmol), and HATU (73.4 mg, 0.193 mmol) in DMF (1072 muIota). The resulting mixture was stirred for 2 days at RT. Purification of the crude reaction mixture by reverse phase HPLC afforded the title compound as a colorless solid. (98 mg, 52 % yield). MS (m/z) 1056.6 (M+H)+

2510-36-3, The synthetic route of 2510-36-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DONATELLI, Carla A.; DOWDELL, Sarah E.; ELBAN, Mark; HILFIKER, Mark A.; HOANG, Tram H.; HOLT, Dennis Alan; MANNS, Sharada; MARCUS, Andrew; POTTEIGER, Craig; SHENJE, Raynold; WASHBURN, David G.; (364 pag.)WO2017/6296; (2017); 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.3405-77-4,5-Methylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

[00451] Step A: A mixture of 5-bromo-4-fluoro-lH-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.869 mmol, Example 1, Step H), 5-methylisoxazole-3-carboxylic acid (221 mg, 1.74 mmol) and triethylamine (606 muL, 4.35 mmol) in CH9CL (10 mL) at room temperature was treated withBOP-Cl (162 mg, 1.74 mmol). The mixture was stirred at room temperature overnight and additional BOP-Cl (81 mg, 0.87 mmol) and 5-methylisoxazole-3-carboxylic acid (110 mg, 0.87 mmol) were added. The mixture was stirred for an additional 48 hours at room temperature. Next, 2M LiOH (3 mL) was added to the mixture and stirred for 1 hour. The organic solvent was removed in vacuo, and water:CH2CL (11 mL; 10:1) were added to the aqueous residue. The solid formed was filtered, washed with additional water and dried to provide N-(5-bromo-4- fluoro-lH-pyrrolo[2,3-b]pyridin-3-yl)-5-methylisoxazole-3-carboxamide (210 mg, 71percent yield) as a solid. 1H NMR (400 MHz, (CD3^SO) delta 12.12 (s, IH), 10.22 (s, IH), 8.33 9d, IH), 7.58 (s,IH), 2.45 (s, 3H); LCMS (APCI+) m/z 338.9, 340.9 (M+H)+, Retention time = 3.16 minutes (Method 2).

3405-77-4, The synthetic route of 3405-77-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARRAY BIOPHARMA INC.; WO2009/140320; (2009); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

42831-50-5, 5-Methylisoxazole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N-(10H-Pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)-5-methyl-1,2-oxazole-4-carboxamide A solution of 520 mg of 5-methyl-1,2-oxazole-4-carboxylic acid and 0.75 ml of triethylamine in tetrahydrofuran (10 ml) was ice-cooled. After adding 0.8 ml of diethyl chlorophosphate, the resulting mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added 5 ml of a solution of 750 mg of 8-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]-benzothiazine in tetrahydrofuran and the resulting mixture was stirred at room temperature for 1.5 hours. Next, the reaction mixture was distributed into ethyl acetate and an aqueous solution of ammonium chloride. The organic layer was extracted, washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 520 mg of N-(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)-5-methyl-1,2-oxazole-4-carboxamide. Further, the product was treated by the same method as the one of Example 434 to thereby give 310 mg of the title compound as yellow crystals. 1H-NMR(DMSO-d6) delta ppm: 2.63(s, 3H), 4.23(d, J=6.3 Hz, 2H), 6.71(s, 1H), 6.72(d, J=7.5 Hz, 1H), 6.86(d, J=7.5 Hz, 1H), 7.62(s, 2H), 8.79(t, J=6.3 Hz, 1H), 8.89(s, 1H), 9.50(s, 1H)

42831-50-5, 42831-50-5 5-Methylisoxazole-4-carboxylic acid 1425240, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Eisai Co., Ltd.; US6518423; (2003); 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.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Into a 100-mL round-bottom flask, was placed a solution of [ -trans-3- aminocyclobutyl]-lH-pyrazol-3-yl]methanol (120 mg, 0.72 mmol, 1.00 eq., prepared using similar procedure as shown in example 29) in dichloromethane (5 mL). To the solution were added 5-phenyl-l ,2-oxazole-3-carboxylic acid (163 mg, 0.86 mmol, 1.20 eq.) and HCTU (360 mg, 0.87 mmol, 1.20 eq.). This was followed by the addition of DIEA (278 mg, 2.15 mmol, 3.00 eq.) dropwise with stirring. The resulting solution was stirred for 1 hour at room temperature. The reaction was then quenched by the addition of water. The resulting solution was extracted with dichloromethane (3×50 mL). The organic layers were combined, dried and concentrated under vacuum. The crude product was purified by Prep-HPLC with the following conditions (Waters): Column, Bridget Prep C18 5um OBDTM 19* 100mm; mobile phase, water with 0.05% NH4HCO3 and CH3CN (40.0% CH3CN up to 80.0% in 10 min, up to 95.0% in 1.5min, down to 40.0% in 1.5min); Detector, 254nm. This resulted in 44.7 mg (18%) of 5- phenyl-N-frara-S-fS-^ydroxymethy^-lH-pyrazol-l-ylJcyclobutylJ-l^-oxazole-S-carboxamide as a white solid. [0382] LC-MS: (M+H)+ = 339 [0383] Analytical data: lH NMR (400MHz, DMSO-i): delta 9.32-9.30 (d, J= 6.8 Hz, 1H), 7.95-7.94 (d, J = 6.0 Hz, 2H), 7.74 (s, 1H), 7.57-7.55 (m, 3H), 7.38 (s, 1H), 6.20 (s, 1H), 5.02- 4.99 (t, J= 5.6Hz, 1H), 4.96-4.95 (m, 1H), 4.71-4.65 (m, 1H), 4.44-4.42 (d, J= 6.0 Hz, 2H), 2.75-2.63 (m, 4H). [0384] HPLC purity: 98.8% at 254 nm., 14441-90-8

The synthetic route of 14441-90-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (178 pag.)WO2016/115090; (2016); A1;,
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%)., 21169-71-1

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

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

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

Example 7 Synthesis of 5-(2-hydroxyphenyl)-N-(5-methyl-3-phenylisoxazol-4-yl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamide (I-323) To a solution of 5-methyl-3-phenylisoxazole-4-carboxylic acid (29.7 mg, 0.146 mmol) in DCE (1 mL) was added a solution of TEA (14.8 mg, 0.146 mmol) in DCE (0.5 mL) at rt followed by the addition of a solution of diphenylphosphonic azide (40.2 mg, 0.146 mmol) in DCE (0.5 mL). The reaction mixture was heated at 90 C. for 2 h and then the solution was allowed to cool to rt and further to below -30 C., whereupon a solution of 2-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (35.0 mg, 0.146 mmol) in DMF (0.5 mL) was added. The mixture was shaken at rt for 16 h. The residue was partitioned between water (4 mL) and DCM (3 mL). The aqueous solution was extracted with DCM. The organic solutions were combined, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by RP-HPLC to give 5-(2-hydroxyphenyl)-N-(5-methyl-3-phenylisoxazol-4-yl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamide (5.53 mg, 8.6%). LCMS: (AAC) ES+440.3. Compounds in the following table were prepared from the appropriate starting materials in a method analogous to that of Example 7:

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; Millennium Pharmaceuticals, Inc.; US2008/171754; (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.62348-13-4,Isoxazole-5-carbonyl chloride,as a common compound, the synthetic route is as follows.

62348-13-4, To a mixture of tert-butyl 4-(4-(2-chloropyrimidin-4-yi)-lH-pyrazol-l-yl)-4- (cyanomethyl)piperidine- 1 -carboxylate (0.259 g, 0.643 mmol) in 2 mL of dioxane was added 4 M HCl in dioxane (4.0 mL). The reaction was stirred at room temperature for 30 min, then evaporated to dryness. To the resulting crude HCl salt in methylene chloride (5.0 mL) was added triethylamine (0.269 mL, 1.93 mmol) followed by isoxazole-5-carbonyl chloride (0.0744 mL, 0.771 mmol). The mixture was stirred at room temperature for 30 min, washed with saturated sodium bicarbonate, dried, and evaporated to dryness. The residue was used directly in next step (233 mg, 91%). LCMS (M+H) 398.0.

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

Reference£º
Patent; INCYTE CORPORATION; WO2009/64835; (2009); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem