Day: September 21, 2020

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

36958-61-9, 5-(Bromomethyl)-3-methylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation 67: 6-(5-chloro-2-{[(2,4-dimethoxyphenyl)methyl](oxan-4-yl)amino}pyrimidin- 4-yl)-2-[(3-methy 1-1 ,2-oxazol-5-yl)methyl]-2,3-dihydro-1 H-isoindol-1 -one (1591) (1592) A stirred suspension of 6-(5-chloro-2-{[(2,4-dimethoxyphenyl)methyl](oxan-4-yl)arnino}pyrimidin- 4-yl)-2,3-dihydro-1 H-isoindol-1-one (100 mg, 0.20 mmol) in THF (2 mL) was cooled to -78 C and treated with a lithium bis(trimethylsilyl)amide (1 M in THF, 0.3 mL, 0.3 mmol). The resulting suspension was stirred for 15 min before 5-(bromomethyl)-3-methylisoxazole (53 mg, 0.30 mmol) was added. The resulting suspension was allowed to reach RT and the resulting orange solution was stirred for 18 h. The mixture was treated at room temperature with more 5- (bromomethyl)-3-methylisoxazole (53 mg, 0.30 mmol) and stirred for 5 h. Lithium (1593) bis(trimethylsilyl)amide (1 M in THF, 0.15 mL, 0.15 mmol) was added and the mixture was stirred for 15 min before 5-(bromomethyl)-3-methylisoxazole (53 mg, 0.30 mmol) was added and the mixture stirred for 3 days. Brine (5 mL) was added and the mixture was extracted with ethyl acetate (3×5 mL). The combined organic phases were washed with brine (5 mL), dried (Na2S04) and concentrated. Purification by chromatography (S1O2, 10-100% ethyl acetate in iso-hexane) gave the title compound (79 mg, 67%) as a yellow foam. LC-MS: [M+H]+ =590., 36958-61-9

36958-61-9 5-(Bromomethyl)-3-methylisoxazole 10607354, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (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.42831-50-5,5-Methylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.,42831-50-5

(iv) 5-Methylisoxazol-4-yl carbonyl chloride Thionyl chloride (118 g) was added to 5-methylisoxazol-4-yl carboxylic acid (42 g) and stirred at room temperature as dimethylformamide (0.2 ml) was added. The solution was heated under reflux for 2 hours with stirring. Excess thionyl chloride was removed in vacuo at 50 C., then the residue was distilled through a 15 cm Vigreaux column at reduced pressure to give an oil, b.p. 32-34 C./0.1 mm Hg.

The synthetic route of 42831-50-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Lilly Industries Limited; US4892963; (1990); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

36958-61-9, 5-(Bromomethyl)-3-methylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

-Benzylsulfanyl-4-chloro-2H-phthalazin-1 -one (500. mg, 1 .65 mmol) in DMF (15 mL) was cooled in an ice bath, treated with sodium hydride (60% w/w) (69.35 mg, 1 .73 mmol), and the resulting mixture was stirred at ambient temperature for 1 h. 5- (Bromometh

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

Reference£º
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan; WASZKOWYCZ, Bohdan; HUTTON, Colin; WADDELL, Ian; HITCHIN, James R.; SMITH, Kate Mary; HAMILTON, Niall M.; (497 pag.)WO2016/92326; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

33282-23-4, 5-(4-Bromophenyl)isoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Preparation of 5-(4-bromophenyl)-N-methylisoxazole-3-carboxamide (121)5-(4-bromophenyl)isoxazole-3-carboxylic acid (500 mg, 1.87 mmol) and oxalyl dichloride (5 mL) were added to tetrahydrofuran (50 mL), followed by reflux for 1 hour. The solvent was removed under reduced pressure, and tetrahydrofuran (20 mL), triethylamine (Et3N, 2 mL) and methylene chloride (100 mg) were added dropwise to the reactants. After completion of the reaction was confirmed by TLC, extraction was carried out with water (20 mL) and ethyl acetate (20 mL). The organic layer was washed with water (10 mL X 2) and brine (10 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered under reduced pressure to remove ethyl acetate. The residue was purified by silica gel column chromatography using ethyl acetate and hexane as a developing solvent, thus affording the title compound 5-(4-bromophenyl)-N-methylisoxazole-3-carboxamide (121). Yield: 20%.1H NMR(CDCl3, 400MHz): 7.63(m, 4H), 6.94(s, IH), 6.80(br, IH), and 3.02(d, 3H,J=5.2Hz).

33282-23-4, 33282-23-4 5-(4-Bromophenyl)isoxazole-3-carboxylic acid 2771350, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; DONG-A PHARM. CO., LTD.; YUHAN CO., LTD.; WO2008/108602; (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.7063-99-2,Ethyl 5-phenylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

7063-99-2, Acetophenone (3 g, 25 mmol) was taken up in 30 mL of dry toluene and NaH (780 mg, 32 mmol) was then added. The resulting reaction mixture was stirred at room temperaturefor 60 minutes. A solution of diethyl oxalate (5.5 g, 37.5 mmol) in dry toluene (25 mL) was then added drop wise and stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and the resulting residue was diluted with ice water. The precipitated solids were collected by filtration and dried to afford 2.85 g of ethyl 2,4-dioxo-4-phenylbutanoate (52%yield) as a yellow solid. This material (2.85 g, 12.9 mmol) was taken up in EtOH (25 mL) along with NH2OH.HC1 (1.16 g, 16.8 mmol) and then stirred under reflux for 3 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with water and extracted with EtOAc. The combined organic layers were washed with H20, dried (Na2SO4) and concentrated under reduced pressure. Purification by silica gelchromatography (pentanes/EtOAc) afforded ethyl 5-phenylisoxazole-3 -carboxylate (2.53 g,90% yield) as a white solid. This material (2.53 g, 11.6 mmol) was taken up in THF/H20 (45 mL/5 mL) along with LiOH.H20 (1.0 g, 23.3 mmol) and the resulting reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was then concentrated under reduced pressure. Sufficient 1 N HC1 was added to the resulting residue to bring the pH toabout 5. The resulting solids were collected by filtration and dried under high vacuum to afford1.5 g of 5-phenylisoxazole-3-carboxylic acid (69%) as a white solid. 5-Phenylisoxazole-3- carboxylic acid was then coupled with (4Z,7Z,1OZ,13Z,16Z,19Z)-N-(2-(((R)-3-amino-4-((1,3- dihydroxypropan-2-yl)amino)-2-methyl-4-oxobutan-2-yl)disulfanyl)ethyl)docosa- 4,7,10,13,16,19-hexaenamide using the same general amide coupling procedure describedearlier (see example 8) to obtain N-((R)-1-((1,3-dihydroxypropan-2-yl)amino)-3-((2- ((4Z,7Z, 1 OZ, 1 3Z, 1 6Z, 1 9Z)-docosa-4,7, 10,13,16,1 9-hexaenamido)ethyl)disulfanyl)-3 -methyl-ioxobutan-2-yl)-5-phenylisoxazole-3 -carboxamide. MS (El) calc? d for C49H58N40652 778.38; found 779 [M+H].

The synthetic route of 7063-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CATABASIS PHARMACEUTICALS, INC.; VU, Chi, B.; JIROUSEK, Michael, R.; LIU, Feng; (0 pag.)WO2016/86136; (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.123770-62-7,Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

6.5. tert-Butyl 2-(3-carbamoylisoxazol-5-ylmethoxycarbonylamino)-6-azaspiro[3.4]octane-6-carboxylate A solution of 0.304 g (1.51 mmol) of 4-nitrophenyl chloroformate dissolved in 5 mL of 1,2-dichloroethane is added dropwise to a solution containing 0.284 g (1.66 mmol) of ethyl 5-hydroxymethylisoxazole-3-carboxylate and 0.39 g (3.02 mmol) of N,N-diisopropylethylamine in 10 mL of 1,2-dichloroethane, cooled to about 0 C. Stirring is continued at 0 C. for 1 hour and then at room temperature for 1 hour. 0.39 g (3.02 mmol) of N,N-diisopropylethylamine and then 0.34 g (1.51 mmol) of tert-butyl 2-amino-6-azaspiro[3.4]octane-6-carboxylate, prepared in step 6.4., are added. The reaction medium is stirred at 70 C. for 4 hours. It is allowed to cool to room temperature. Water is added to the reaction medium, the aqueous phase is separated out and extracted several times with dichloromethane, the combined organic phases are washed with aqueous sodium hydroxide solution (1N) and then with saturated aqueous ammonium chloride solution and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. 0.44 g of pure product is thus obtained in the form of an orange oil, which is used without further purification in the following step. LC-MS: M+H=424 1H NMR (DMSO) delta (ppm): 7.80 (broad s, 1H); 6.90 (s, 1H); 5.20 (s, 2H); 4.40 (q, 2H) 4.00 (m, 1H); 3.40-3.10 (m, 4H); 2.30 (m, 2H); 2.00-1.70 (m, 4H); 1.40 (s, 9H); 1.30 (t, 3H)., 123770-62-7

As the paragraph descriping shows that 123770-62-7 is playing an increasingly important role.

Reference£º
Patent; SANOFI; US2011/319381; (2011); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem