Category: 3405-77-4

Analyzing the synthesis route of 3405-77-4

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

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
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Some tips on 3405-77-4

3405-77-4 5-Methylisoxazole-3-carboxylic acid 76947, aIsoxazoles compound, is more and more widely used in various fields.

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.

General procedure: To a solution of 2a (3.0g, 6.7mmol) in anhydrous DCM (30mL) was added CF3COOH (5.0mL, 67mmol) slowly at 0¡ãC. Then, the reaction mixture was stirred at RT for 2h and then concentrated. To a solution of the residue obtained in DCM (40mL) was added Et3N drop-wise to adjust the pH to 7.0at 0¡ãC, and then butyric acid (0.60g, 6.7mmol), EDCI (1.53g, 8.0mmol) and HOBt (1.08g, 8.0mmol) were sequentially added. After 20min, Et3N (3.8mL, 26.8mmol) was added drop-wise. Then, the reaction mixture was stirred at RT for 3h, followed by washing with H2O (50mL¡Á2), saturated citric acid solution (50mL¡Á2), saturated NaHCO3 solution (50mL¡Á2) and brine (50mL¡Á2). The organic phase was dried over Na2SO4 and concentrated, and the residue was purified by column chromatography (EtOAc: petroleum ether, 4: 1 v/v) to afford the pure product as a light yellow oil 3f (2.4g, 5.69mmol, 85percent)., 3405-77-4

3405-77-4 5-Methylisoxazole-3-carboxylic acid 76947, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Article; Zhai, Yangyang; Ma, Yuying; Ma, Fei; Nie, Quandeng; Ren, Xuejiao; Wang, Yaxin; Shang, Luqing; Yin, Zheng; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 559 – 573;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

New learning discoveries about 3405-77-4

As the paragraph descriping shows that 3405-77-4 is playing an increasingly important role.

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.

To a solution of the product from step 2 (57 mg, 0.17 mmol) and 5-methylisoxazole-3-carboxylicacid (23 mg, 0.18 mmol) in CH2C12 (2 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimidehydrochloride (38 mg, 0.20 mmol) and HOBTH2O (2.5 mg, 0.017 mmol) and the solution stirred at RT for 20 h. 5-Methylisoxazole-3-carboxylic acid (23 mg, 0.18 mmol) and 1-ethyl-3-(3-dimethylamino- propyl)carbodiimide hydrochloride (38 mg, 0.20 mmol) were added and the solution stirred at RT for 3 days. Water (2 mL) was added then the aqueous extracted with CH2C12 (2 mL). The combined organicswere passed through a hydrophobic fit and concentrated in vacuo to leave a colourless residue. Flash chromatography (10-45percent EtOAc-cyclohexane) gave a clear gum (62 mg). Freeze-drying from acetonitrile-water (1:1, 3 mL) left a white solid (56 mg). 1H NMR (400 MHz, DMSO-d6) -3:1 ratio rotamers: 1H NMR (400 MHz, CDC13) 7.42 – 7.35 (2H, m), 7.03 (2H, dd, J=8.0, 8.0 Hz), 6.56 (1H, s), 4.47 (1H, d, J=14.3 Hz), 4.21 – 3.91 (3H, m), 2.97 (1H, d, J=4.0 Hz), 2.36 – 2.34 (6H, m), 1.37 – 1.23 (7H,m), 0.70 (3H, s); MS (ESI): [M+H] 453.2., 3405-77-4

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Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; CRAWFORD, James J.; BRONNER, Sarah M.; BODIL VAN NIEL, Monique; CRIDLAND, Andrew; GANCIA, Emanuela; HURLEY, Christopher; KILLEN, Jonathan; WARD, Stuart; (108 pag.)WO2016/177760; (2016); A1;,
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Brief introduction of 3405-77-4

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

3405-77-4, 5-Methylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 5-methylisoxazole-3-carboxylic acid (3.81 g, 0.03 mol) in 150 mL of toluene was dried via azeotropic distillation of some of the toluene into a two-neck 500 mL round bottom flask fitted with a Dean-Stark trap and a magnetic stirrer. The mixture was allowed to cool to about 90 C, and dimethylformamide, 1 mL, was added. Thionyl chloride (4.8 g, 0.04 mol) was added dropwise over 15 min and the mixture was refluxed for 5 h with continuous stirring. The reaction was allowed to cool to room temperature, and then the solvent was evaporated in vacuo to yield the product, a dark-brown oil, 80%, which crystallized on standing. It was kept under vacuum until further use.

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

Reference£º
Article; Jackson, Patrice L.; Hanson, Clive D.; Farrell, Alanna K.; Butcher, Raymond J.; Stables, James P.; Eddington, Natalie D.; Scott; European Journal of Medicinal Chemistry; vol. 51; (2012); p. 42 – 51;,
Isoxazole – Wikipedia
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Analyzing the synthesis route of 3405-77-4

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

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.

Example 19b A mixture of the product of Example 19a (30 mg, 0.039 mmol), 5-methylisoxazole-3-carboxylic acid (5.0 mg, 0.039 mmol), N-ethyl-N-isopropylpropan-2-amine (15.2 mg, 0.118 mmol), and HATU (17.9 mg, 0.047 mmol) in dichloromethane (0.5 mL) was stirred at mom temperature for one hour and then evaporated. Purification of the crude material via reverse phase chromatography eluting with acetonitrile/water/TFA provided the title compound (18 mg, 53percent yield). MS (ESI): m/z=837.9[M+H].

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; AbbVie Inc.; Enanta Pharmaceuticals, Inc.; Ku, Yiyin; McDaniel, Keith F.; Chen, Hui-Ju; Shanley, Jason P.; Kempf, Dale J.; Grampovnik, David J.; Sun, Ying; Liu, Dong; Gai, Yonghua; Or, Yat Sun; Wagaw, Seble H.; Engstrom, Kenneth; Grieme, Tim; Sheikh, Ahmad; Mei, Jianzhang; (46 pag.)US9309279; (2016); B2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

New learning discoveries about 3405-77-4

As the paragraph descriping shows that 3405-77-4 is playing an increasingly important role.

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.

3405-77-4, Step 1 : 5-methylisoxazole-3-carboxylic acid (20 mg, 0.15 mmol) and teri-butyl (5)-2- methylpiperazine-l-carboxylate (40.1 mg, 0.20 mmol, 1.33 equiv) were dissolved in N,N- dimethylformamide (10 mL) before HATU (190 mg, 0.5 mmol, 3.33 equiv), N,N- diisopropylethylamine (0.35 mL, 2.0 mmol, 13.3 equiv) and 4-dimethylaminopyridine (1 mg) were added. The mixture was stirred for 4 h at room temperature before adding brine and extracting with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give teri-butyl (5)-2-methyl-4-(5-methylisoxazole-3- carbonyl)piperazine-l-carboxylate.

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Reference£º
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; FOO, Klement Jihao; POULSEN, Anders; KELLER, Thomas Hugo; LIEW, Si Si; CHIA, Cheng San Brian; ANG, Jin Yan Melgious; HUANG, Chuhui; (367 pag.)WO2017/61957; (2017); A1;,
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Isoxazole | C3H3NO – PubChem

New learning discoveries about 3405-77-4

As the paragraph descriping shows that 3405-77-4 is playing an increasingly important role.

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.

General procedure: To the appropriate acid derivative 7, (Jackson et al., 2012) 10 (0.021 mol) in 20 ml of THF, 3.6 g of N,N’-carbonyldiimidazol (CDI) was slowly added under stirring. After addition was complete, the solution was first magnetically stirred for 30 min at room temperature and then heated to 60 ¡ãC for 1 h. The reaction mixture was cooled to room temperature and treated with 2.3 g of MgCl2 and 4.5 g of ethyl potassium malonate. After stirring (r.t.) for 3 h 15 ml of water followed by 5 ml of HCl 6 N was added. The mixture was then concentrated under reduced pressure, and the obtained white solid was collected by filtration, washed with water, and dried. Spectroscopical and physical data of compound 11a are in accordance with those reported in the literature (Takagi et al., 2008)., 3405-77-4

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Reference£º
Article; Cascioferro, Stella; Maggio, Benedetta; Raffa, Demetrio; Raimondi, Maria Valeria; Cusimano, Maria Grazia; Schillaci, Domenico; Manachini, Barbara; Leonchiks, Ainars; Daidone, Giuseppe; Medicinal Chemistry Research; vol. 25; 5; (2016); p. 870 – 878;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

New learning discoveries about 3405-77-4

As the paragraph descriping shows that 3405-77-4 is playing an increasingly important role.

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.

a 5-Methyl-3-isoxazolecarboxylic Acid 2-(Pyrido[3,4-d]pyridazin-4(3H)-one-1-yl)hydrazide 1-Hydrazinopyrido[3,4-d]pyridazin-3(4H)-one [prepared by the method of K. Kormendy, T. Kovacs, F. Ruff and I. Kovesdi, Acta Chim. Hung., 1983, 112(4), 487] (1.72 g, 9.7 mmol), triethylamine (1.36 ml, 9.7 mmol), 5-methylisoxazole-3-carboxylic acid (1.23 g, 9.7 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic acid (2.48 g, 9.7 mmol) in 1,2-dichloroethane (60 ml) were heated at reflux under nitrogen for 18 h. The mixture was allowed to cool and diluted with water (20 ml). The precipitate was filtered off and washed successively with water (2*50 ml) and diethyl ether (2*50 ml) to give the title compound (2.2 g, 79percent), 1H NMR (400 MHz, d6 DMSO) delta 2.50 (3H, s, Ar-CH3), 6.62 (1H, s, Ar-H), 8.04 (1H, d, J=5.5 Hz, Ar-H), 9.10 (1H, d, J=5.5 Hz, Ar-H), 9.11 (1H, s, Ar-H), 9.45 (1H, s, NH), 10.62 (1H, s, NH), 12.08 (1H, s, NH).

As the paragraph descriping shows that 3405-77-4 is playing an increasingly important role.

Reference£º
Patent; Merck Sharp & Dohme Ltd.; US6613766; (2003); B1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Downstream synthetic route of 3405-77-4

As the paragraph descriping shows that 3405-77-4 is playing an increasingly important role.

3405-77-4, 5-Methylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[00261] Isobutyl chloroformate (0.281 g, 2.06 mmcl) was added dropwise to a solution of 5-methylisooxazole-3-carboxylic acid (0.25 g, 1 .7 mmol) in THE (2.5 mL), followed by addition of N-methylmorpholine (0.208 g, 2.06 mmol). The reaction mixture was stirred at rt for 30 mm and then filtered to remove solids. In a separate flask, a solution of LHMDS (1 .3 M in THE, 2.6 mL, 3.4 mmol) was added dropwise to a solution of tert-butyl (S)-2-methyl-4-oxopiperidine-1- carboxylate (0.37 g, 1 .7 mmol) in THE (2.5 mL) at 0 00 under a nitrogen atmosphere. The reaction was stirred at 0 00 for 1 0 mm and then cooled to -78 00. To this reaction mixture, the filtrate containing the mixed anhydride from the first flask was added dropwise at -78 00. After the addition was complete, the reaction mixture was stirred at rt for 2 h. The reaction mixture was then acidified with aqueous 1 N HCI. The mixture was extracted with EtOAc (twice). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give a mixture of crude tert-butyl (2S)-2-methyl-5-(5-methylisoxazole-3-carbonyl)-4-oxopiperidine- 1- carboxylate and tert-butyl (2S) -2-methyl-3-(5-methylisoxazole-3-carbonyl)-4-oxopiperidine- 1- carboxylate (0.43 g) which was used without further purification. MS m/z 323.5 (M+H).

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Reference£º
Patent; NOVARTIS AG; FU, Jiping; LINDVALL, Mika; MANNING, James R.; MCENROE, Glenn; (103 pag.)WO2019/97479; (2019); A1;,
Isoxazole – Wikipedia
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Simple exploration of 3405-77-4

3405-77-4 5-Methylisoxazole-3-carboxylic acid 76947, aIsoxazoles compound, is more and more widely used in various.

3405-77-4, 5-Methylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-methylisoxazole-3-carboxylic acid (1.5 g, 12.04 mmol) was added to a mixture of potassium nitrate (1.83 g, 18.06 mmol) and sulfuric acid (5 ml) at room temperature. After complete dissolution, the mixture was warmed to 50¡ãC and stirred for 4 hours. The mixture was then cooled to 0¡ãC, ice was added, and the solution was neutralized with sodium bicarbonate. The mixture was extracted with ethyl acetate (3 x 30 ml), dried over sodium sulfate, filtered and concentrated to give 1.45 g of 4 as a white solid (8.43 mmol, 70percent). The product could be further recrystallized from dichloromethane.

3405-77-4 5-Methylisoxazole-3-carboxylic acid 76947, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Article; Wei?wer, Michel; Bittker, Joshua A.; Lewis, Timothy A.; Shimada, Kenichi; Yang, Wan Seok; MacPherson, Lawrence; Dandapani, Sivaraman; Palmer, Michelle; Stockwell, Brent R.; Schreiber, Stuart L.; Munoz, Benito; Bioorganic and Medicinal Chemistry Letters; vol. 22; 4; (2012); p. 1822 – 1826;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem