Heterocyclic Building Blocks-isoxazole

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

Example L Isoxazole-5-carboxylic acid [2-(2-o-tolyl-chroman-6-yloxy)-thiazol-5-ylmethyl]-amide To a solution of [2-(2-o-tolyl-chroman-6-yloxy)-thiazol-5-ylmethyl]amine (150 mg, 0.43 mmol) in DMF (2 ml), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (114 mg, 0.60 mmol, 1.4 eq), 1-hydroxy-benzotriazole (81 mg, 0.60 mmol, 1.4 eq) and N-methylmorpholine (107 mg, 1.07 mmol, 2.5 eq) and isoxazole-5-carboxylic acid (72 mg, 0.64 mmol, 1.5 eq) were added. The mixture was stirred for 16 h, then diluted with water, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with a diluted aqueous solution of sodium carbonate and brine, dried over sodium sulfate and filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, ethyl acetate/methanol gradient). Isoxazole-5-carboxylic acid [2-(2-o-tolyl-chroman-6-yloxy)-thiazol-5-ylmethyl]-amide (112 mg, 59%) was obtained as a white solid., 21169-71-1

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

Reference£º
Patent; SANOFI; CZECHTIZKY, Werngard; WESTON, John; RACKELMANN, Nils; PODESCHWA, Michael; ARNDT, Petra; WIRTH, Klaus; GOEGELEIN, Heinz; RITZELER, Olaf; KRAFT, Volker; BELLEVERGUE, Patrice; MCCORT, Gary; US2013/65859; (2013); 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.87988-94-1,5-Methylisoxazol-4-amine,as a common compound, the synthetic route is as follows.,87988-94-1

Example 8(a) 5-Acetyl-l-(tetrahydro-2H-pyran-4-yl)- 2-trifluoromethyl-lH-imidazole; 5-Methyl-4-amino-isoxazole (1.7 g, 17.25 mmol) and acetic acid (1.1 g, 19 mmol) were dissolved in methanol (50 mL). Tetrahydro-2H-pyran-4-one (1.9 g, 19 mmol) was added and the mixture was cooled to 0 – (-5) 0C and stirred for 1 h. Sodium cyanoborohydride (0.812 g, 12.9 mmol) was added in portions to the reaction mixture at -5 C, causing weak exothermic and gas evolution. The cooling bath was removed and the mixture was stirred at r.t. for 2 h followed by addition of water (20 mL). The methanol was removed from the reaction mixture, and the intermediate amine was extracted with ethyl acetate (3×80 mL). The combined organic layers were dried (Na2SO4), concentrated to dryness, dissolved in toluene and re-concentrated. The crude intermediate amine, was dissolved in CH2Cl2 (20 mL) and pyridine (2 mL, 26 mmol) was added. The mixture was cooled to 0C and trifluoroacetic anhydride (4.35 g, 20.7 mmol) was added dropwise. The mixture was continued stirring for 2 h at r.t. and was then washed with water and saturated NaHCO3. The aqueous layer was extracted with CH2Cl2 (2×30 mL), the organic extracts were dried (Na2SO4) and concentrated to dryness to give a second crude intermediate, 4-[N- (tetrahydro-2H-pyran-4-yl)]-N-trifluoroacetyl-amino-5-methylisoxazole. MS (ES) m/z 279 (M++.). The title compound was prepared in accordance with the general method of Example 6 (b) using the intermediate 4-[N-(tetrahydro-2H-pyran-4-yl)]-N-trifluoroacetyl- amino-5-methylisoxazole (max 17.25 mmol), with the exception that the product was purified by flash chromatography (heptane/EtOAc 3:2), giving the title compound (3.03 g, 67%).1H nuMR (CDCl3, 300 MHz) delta 7.85 (s, 1 H), 4.89-4.75 (m, 1 H), 4.17-4.07 (m, 2 H), 3.54- 3.44 (m, 2 H), 2.75-2.60 (m, 2 H), 2.56 (s, 3 H), 1.72-1.63 (m, 2 H); MS (ES) m/z 263 (M+l).

87988-94-1 5-Methylisoxazol-4-amine 13033202, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; WO2008/2244; (2008); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.354795-62-3,3-Methylisoxazol-4-amine,as a common compound, the synthetic route is as follows.

A mixture of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 0.12 g, 0.36 mmol), EDC (0.14 g, 0.72 mmol) and HOBT (0.11 g, 0.72 mmol) in Nu,Nu-dimethylformamide (2 ml) was stirred in air at room temperature for 1 h, then 3-methyl-4-isoxazolamine (may be prepared as described in Description 91; 100 mg, 1.02 mmol) was added in one charge. The reaction mixture was stirred at 25 C overnight. The reaction mixture was diluted with water (25 ml). The solid was filtered, washed with water (30 ml) and methanol (5 ml x 2), and dried in vacuo to yield the title compound as a grey solid. 72 mg.1HNMR (400 MHz, DMSO- /6): 9.97 (s, 1 H), 9.19 (s, 1 H), 8.63 (d, 2H, J=6.0), 8.18 (d, 1 H, J=2.4), 8.04 (dd, H, J=2.4, J=8.8), 7.75 (d, 2H, J=6.0), 7.56 (d, 2H, J=6.8),7.49-7.38 (m, 4H), 5.34 (s, 2H), 1.95 (s, 3H).MS (electrospray): m/z [M+H]+ = 386.00, 354795-62-3

The synthetic route of 354795-62-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); 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.1121-13-7,4-Nitroisoxazole,as a common compound, the synthetic route is as follows.

To a solution of 4b (200mg, 1.75mmol) in con. HCl (9mL) was added SnCl2.2H2O (1.98g, 8.77mmol). The mixture was stirred at rt for 1.5h, then adjusted by SaLNa2CO3 to pH=8~9 and filtered. The water phase was extracted with EA (30×4) and the combined extract was dried over anhydrous Na2SO4 and filtered. 5OmL of HClZEt2O solution was added to the filtrate and stirred for 30 min then evaporated to dryness to give 4c (125mg, 59%)., 1121-13-7

1121-13-7 4-Nitroisoxazole 11332437, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; XCOVERY, INC.; WO2009/154769; (2009); A1;,
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Isoxazole | C3H3NO – PubChem

1018297-63-6, (3-(4-Fluorophenyl)-5-methylisoxazol-4-yl)methanol is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Alternative 2: Telescoped process To as suspension of sodium hydride (60% in mineral oil, 3.95 g, 99 mmol, 1.6 eq.) in THF (120 mL) was added within 120 minutes at 25-32C a solution of [3-(4-Fluorophenyl)-5-methyl- isoxazol-4-yl] -methanol (12.50 g, 60 mmol) and 6-chloronicotinonitrile (8.36 g, 60 mmol) in THF (60 mL) and the resulting mixture was stirred for one hour at approx. 30C. The mixture was then treated drop wise at room temperature with water (100 mL). THF was distilled off under reduced pressure (200-70 mbar) with a jacket temperature of 50C. The residue was diluted with ethanol (90 mL) and subsequently treated at 20 to 35C with 28% sodium hydroxide solution (69.6 g, 487 mmol). The mixture was heated to 50-55C and subsequently stirred at this temperature for 15 hour. The reaction mixture was treated with toluene (150 mL) and the resulting biphasic mixture was stirred for 15 minutes and the layers were then allowed to separate for 30 minutes. The lower product-containing aqueous layer was separated and the toluene layer was extracted at 30C with water (1×50 mL). The combined aqueous layers were acidified with 20% sulfuric acid (approx. 150 g) until a pH of 3.0-3.3 was obtained. The suspension was treated with THF (120 mL) and the resulting biphasic mixture was stirred for 15 minutes and the layers were then allowed to separate for 30 minutes. The lower aqueous layer was removed and the product-containing organic layer was diluted with toluene (150 mL) to afford a biphasic mixture from which the lower aqueous layer was separated. The aqueous layer was removed and the organic layer was washed with water (2×30 mL). From the organic layer THF, Ethanol and water were then completely distilled off under reduced pressure and at a jacket temperature of 40-80C and continuously replaced by toluene (250 mL in total). At the end of the distillation a volume of approx. 300 mL was adjusted in the reactor. The partly precipitated product was completely re-dissolved by heating the suspension to 100-105C. The clear solution was cooled to 15-20C within 5-10 hours whereupon crystallization occurred. The crystals were filtered off, washed with toluene (100 mL) and subsequently dried at 55C/

1018297-63-6, As the paragraph descriping shows that 1018297-63-6 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; DOTT, Pascal; HANLON, Steven Paul; HILDBRAND, Stefan; IDING, Hans; THOMAS, Andrew; WALDMEIER, Pius; WO2013/57123; (2013); 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.1202769-66-1,2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol,as a common compound, the synthetic route is as follows.

Step 4: Synthesis of 4-[1-(2-aminopyrimidin-4-yl)-2-[[1-(2-hydroxyethyl)azetidin-3-yl]oxy]-1H-1,3-benzodiazol-6-yl]-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol A mixture of 2-(3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]azetidin-1-yl)ethan-1-ol (80 mg, 0.20 mmol), 2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol (160 mg, 1.06 mmol), bis(triphenylphosphine)palladium(II) dichloride (160 mg, 0.23 mmol) and triethylamine (1 mL) in dimethylsulfoxide (2 mL) was stirred under nitrogen for 2 hr at 70 C. The reaction mixture was cooled to room temperature then filtered through a frit filter to remove the catalyst. The filtrate was purified by preparative HPLC to give 7 mg (7%) of 4-[1-(2-aminopyrimidin-4-yl)-2-[[1-(2-hydroxyethyl)azetidin-3-yl]oxy]-1H-1,3-benzodiazol-6-yl]-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol as a white solid: 1H NMR (400 MHz, DMSO) delta 8.41 (d, J=5.6 Hz, 1H), 8.17 (s, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 7.10 (s, 2H), 7.01 (d, J=5.6 Hz, 1H), 6.45 (s, 1H), 6.37 (s, 1H), 5.37 (t, J=5.2 Hz, 1H), 4.44 (t, J=5.4 Hz, 1H), 3.75 (t, J=7.2 Hz, 2H), 3.41 (t, J=6.0 Hz, 2H), 3.28 (t, J=6.8 Hz, 2H), 2.57 (s, 2H), 2.41 (s, 3H), 1.81 (s, 3H); LC-MS: m/z=+476 (M+H)+., 1202769-66-1

1202769-66-1 2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol 58221759, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Genentech, Inc.; US2012/214762; (2012); 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

To a solution of hydrochloride salt of N-{3-[4-(3-aza-bicyclo[3.1.0]hex-l-yl)-phenyl]-2-oxo- oxazolidin-5(5)-yl-methyl}-acetamide (Intermediate IV) (200 mg, 0.57 mmol), in DMF (10 mL), were added isoxazole-S-carboxylic acid (71 mg, 0.63 mmol), EDC (130 mg, 0.68 mmol), HOBt (89 mg, 0.68 mmol) and NMM (0.19 mL, 1.71 mmol) at 0 C. The reaction mixture was stirred at r.t. and progress of the reaction was monitored by TLC. On completion, DMF was evaporated in vacuo and residue was dissolved in chloroform (50 mL). The organic layer was washed with water (25 mL), brine (25 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0.4: 9.6 MeOH: CHCl3) to provide the title compound (156 mg, 67%) as white solid.1H NMR (400 MHz, CDCl3): delta 0.80-0.90 (m, IH), 1.15-1.25 (m, IH), 1.85-2.02 (m, IH), 2.03 (s, 3H), 3.55-3.65 (m, IH), 3.65-3.75 (m, IH), 3.75-3.85 (m, 2H), 4.07 (t, J= 9.0 Hz, IH), 4.08- 4.20 (m, IH), 4.23 (dd, J = 9.1 and 17.6Hz, IH), 4.46 (dd, J = 9.1 and 16.9 Hz, IH), 4.70-4.85 (m, IH), 6.00-6.15 (bs, IH), 6.91 (d, J = 1.7 Hz, IH), 7.15-7.25 (m, 2H), 7.48 (d, J = 8.7 Hz, 2H), 8.33 (t, J= 1.8 Hz, IH) ESIMS (m/z): 411.3 (M+l), 21169-71-1

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

Reference£º
Patent; PANACEA BIOTEC LTD.; JAIN, Rajesh; TREHAN, Sanjay; DAS, Jagattaran; KAUR, Gurmeet; KANWAR, Sandeep; SINGH, Nishan; NANDA, Gurmeet Kaur; MAGADI, Sitaram Kumar; SHARMA, Sudhir Kumar; WO2010/150281; (2010); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1136-45-4,5-Methyl-3-phenylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

5-Methyl-3-phenylisooxazole-4-carboxylic acid (40 mg, 0.197 mmol), 3-phenyl-pyrrolidine (31.6 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 C21H20N2O2: 332.1525, found 332.1539.

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; Amgen Inc.; Biovitrum AB; US2008/21022; (2008); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

7063-99-2, Ethyl 5-phenylisoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7063-99-2

A mixture of ethyl 5-phenylisoxazole-3-carboxylate (406 mg, 1.87 mmol) and N-iodosuccinimide (505 mg, 2.24 mmol) in trifluoroacetic acid (10 mL) was stirred at room temperature for 1.5 h. The volatiles were removed under reduced pressure, and the residue was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with a IN aqueous solution of sodium hydroxide (50 mL), washed with a 2.5% aqueous solution of sodium bisulfite (50 mL), washed with brine (50 mL), and dried over anhydrous magnesium sulfate. Concentration under reduced pressure afforded ethyl 4-iodo-5-phenylisoxazole-3-carboxylate (641 mg, 1.87 mmol, 100% yield) as a light yellow oil. The compound had an HPLC retention time = 3.36 minutes (YMC-Combi 4.6 x 50 mm S-5 ODS column) eluting with 10-90% aqueous methanol + 0.2% phosphoric acid over a 4 minute gradient. MS:(M+H) = 343.97. XH-NMR (400 MHz, CDC13) delta ppm 1.47 (t, J=7.1 Hz, 3H), 4.50 (q, J=7.0Hz, 2H), 7.52-7.56 (m, 3H), and 8.05 (m, 2H).

As the paragraph descriping shows that 7063-99-2 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Robert J.; ZHANG, Yanlei; WO2011/133734; (2011); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

5765-44-6, 5-Methylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,5765-44-6

Sodium (7.36 g, 320 mmol) was reacted with ethanol (368 ml) and then 5-methylisoxazole (26.56 g, 320 mmol) was added to the mixture at 20 C. The mixture wasstirred at 20 oc for 1.5 h and at 0 oc for 1.5h. The white solid was collected by filtration,washed with ether, dried in vacuo to provide the titled compound (1 0.168 g, 30%) as awhite solid.

As the paragraph descriping shows that 5765-44-6 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE LLC; LIN, Hong; MOORE, Michael Lee; QU, Junya; RIVERO, Ralph A.; TEDESCO, Rosanna; YU, Hongyi; LUENGO, Juan Ignacio; WO2013/28263; (2013); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem