Heterocyclic Building Blocks-isoxazole

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), ethyl isonipecotate (33.8 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 C19H22N2O4: 342.1580, found 342.1578.

As the paragraph descriping shows that 1136-45-4 is playing an increasingly important role.

Reference£º
Patent; Amgen Inc.; Biovitrum AB; US2008/21022; (2008); A1;,
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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

A mixture of 1 g (10 mmol) but-2-ynoyl chloride (Journal of Organic Chemistry (1981), 46(11), 2273-80), 0.625 g (5 mmol) 5-Methyl-3-phenyl-isoxazole-4-carboxylic acid (commercially available) and 1.3 g (10 mmol) AlCl3 in 10 mL dichloroethane was at room temperature for 18 h. The mixture was poured onto ice/water and the organic layer washed with Na2CO3 sat., NaCl sat. and dried with Na2SO4. After evaporation of all volatiles the residue was purified on silica eluting with a gradient of ethyl acetate and heptane affording 0.2 g (17%) of the title compound as light brown solid. (m/e): 227.1 (M+).

The synthetic route of 1136-45-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Buettelmann, Bernd; Han, Bo; Knust, Henner; Nettekoven, Matthias Heinrich; Thomas, Andrew William; US2007/66668; (2007); A1;,
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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

Step 5: To generate the acid chloride a suspension of 5-methyl-1 ,2-oxazole-4-carboxylic acid (39 mg, 0.30 mmol) in CH2CI2 (0.5 mL) at 0 C was added oxalyl chloride (50 muIota_, 1.2 mmol) and DMF (1 drop). The suspension was allowed to stir for a further 15 min at 0 C followed by 2 h at room temperature. The resulting mixture was concentrated in vacuo to give a dark oil. The oil was twice suspended in n-hexanes (2 x 1 mL) and concentrated in vacuo. A solution of 7-acetyl-10a-(4-chlorophenyl)-2,3, 10, 10a-tetrahydro-1 H,5H-imidazo[1 ,2- a]pyrrolo[1 ,2-c ]pyrazin-5-one (20 mg, 61 muetaetaomicronIota) in pyridine (0.5 mL) was added to a suspension of the acid chloride (generated as above; 0.30 mmol) in pyridine (0.5 mL) and CH2CI2 (0.5 mL) at 0 C . The resultant mixture was warmed to room temperature and stirred for 16 h. The reaction mixture was diluted with a saturated aqueous solution of NaHC03 (25 mL) and extracted with CH2CI2 containing 20% of propan-2-ol (3 x 25 mL). The organic layers were combined, dried and concentrated in vacuo to yield a crude brown residue that was partially purified using flash chromatography (Biotage SP4, 12 g cartridge, 0-10%MeOH gradient in CH2CI2) to give a mixture (10 mg) containing the desired product which was further purified by flash chromatography (2 x Biotage SP4, 12 g cartridge, C18 phase, 20-40% acetonitrile gradient in water) to give 7-acetyl-10a-(4-chlorophenyl)-1-[(5-methyl-1 ,2- oxazol-4-yl)carbonyl]-2,3, 10, 10a-tetrahydro-1 H,5H-imidazo[1 ,2-a]pyrrolo[1 ,2-c ]pyrazin-5-one (24) as a solid (3.5 mg, yield 14%).

As the paragraph descriping shows that 42831-50-5 is playing an increasingly important role.

Reference£º
Patent; BIOTA SCIENTIFIC MANAGEMENT PTY LTD; MITCHELL, Jeffrey Peter; PITT, Gary; DRAFFAN, Alistair George; MAYES, Penelope Anne; ANDRAU, Laura; ANDERSON, Kelly; WO2011/94823; (2011); A1;,
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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

5-Methylisoxazole-4-carboxylic acid (1 g, 7.86 mmol) was added to SOCl 2 (3 mL) and stirred at 50 C. After completion of the reaction, the reaction mixture was cooled and then distilled under reduced pressure to remove volatile materials to obtain crude yellow oil (96%)

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

Reference£º
Patent; Erica Hanyang University Academic Cooperation; Ha, Jung Mi; Jung, Gyung Jin; (27 pag.)KR2016/34632; (2016); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.141112-29-0,(5-Cyclopropylisoxazol-4-yl)(2-(methylsulfonyl)-4-(trifluoromethyl)phenyl)methanone,as a common compound, the synthetic route is as follows.

COMPOUND 621: 2-cyano-3-cyclopropyl-1-[2-(methylsulphonyl)-4-trifluoromethylphenyl]propan-1,3-dione, m.p. 107.5 C., starting from 5-cyclopropyl-4-[2-(methylsulphonyl)-4-trifluoromethylbenzoyl]isoxazole.

As the paragraph descriping shows that 141112-29-0 is playing an increasingly important role.

Reference£º
Patent; Rhone-Poulenc Agriculture Limited; US5804532; (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.88-14-2,Furan-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Compounds 41-70 were part of a parallel set prepared in library plate format according to General Procedure L, outlined below. ; L. General Procedure for Plate Preparation-Amide Formation XXI: Resin bound deprotected biarylphenol XVII (prepared from intermediate XII, boronates XIVd and XIVe, following general procedures D-F) was distributed into a 96 well plate, 10 mg of resin (0.013 mmol) per well. To the resin 400 mul of dichloromethane was added, followed by 100 mul of DIEA, followed by 0.13 mmol (10 equiv) of heterocyclic carboxylic acid XXa-XXn was added followed by 61 mg (0.13 mmol, 10 equiv) of PyBrop. The plate was shaken at room temperature for 24 hours, then drained and washed with dichloromethane, methanol/dichloromethane, dimethylformamide, methanol/dichloromethane and dichloromethane. The compounds were cleaved with TFA/dichloromethane (600 mul, 1:1) into a 96 deep well plate and submitted for testing without further purification. (Mass spec results obtained are shown in Table 4). Carboxylic Acids Het-COOH XX:

The synthetic route of 88-14-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Adolor Corporation; US2006/74086; (2006); A1;,
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169547-67-5, 3-(4-(Bromomethyl)phenyl)isoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (0.27 g, 0.834 mmol), prepared as described in Example 244, in DMF (4 mL), potassium carbonate (0.23 g, 1.67 mmol) and 3-(4-(bromomethyl)phenyl)isoxazole (0.248 g, 1.04 mmol) were added. The resulting mixture was heated to 65 C. After 2 h, the reaction mixture was then cooled to RT and diluted with EtOAc (200 mL). The resultant solution was then washed with water and saturated aqueous NaCl. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography eluting with hexanes/EtOAc to give the title compound, 2-(4-(isoxazol-3-yl)benzyl)-7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, as a light yellow solid. HPLC RT: 2.60 min; 1H NMR (CDCl3): delta 8.64 (d, J=1.1 Hz, 1H), 8.63 (d, J=1.7 Hz, 1H), 8.45 (d, J=1.7 Hz, 1H), 8.20 (s, 1H), 7.80 (d, J=8.2 Hz, 2H), 7.50 (d, J=8.2 Hz, 2H), 7.34 (m, 2H), 7.23 (m, 2H), 7.10 (m, 2H), 6.65 (d, J=2.2 Hz, 1H), 5.26 (s, 2H).

The synthetic route of 169547-67-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Yu, Guixue; Ewing, William R.; Mikkilineni, Amarendra B.; Pendri, Annapurna; Sher, Philip M.; Gerritz, Samuel; Ellsworth, Bruce A.; Wu, Gang; Huang, Yanting; Sun, Chongqing; Murugesan, Natesan; Gu, Zhengxiang; Wang, Ying; Sitkoff, Doree; Johnson, Stephen R.; Wu, Ximao; US2005/143381; (2005); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1188032-12-3,5-(3-Fluorophenyl)isoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 40 5-(3-Fluoro-phenyl)-isoxazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide DIPEA (153 mg, 0.2 mL, 1.18 mmol) followed by HOBT (48 mg, 0.35 mmol) and EDCI (69 mg, 0.35 mmol) were added to a stirred solution of 5-(3-Fluoro-phenyl)-isoxazole-3-carboxylic acid (69.96 mg, 0.34 mmol) (prepared according to a procedure similar to that described in synthesis procedure 3, steps 1-4-b, using 3′-Fluoro-acetophenone (Aldrich, St. Louis, Mo.) as starting material) in DMF (2 mL) at room temperature. After 2 minutes 2-Amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (prepared according to a procedure similar to that described in synthesis procedure 1, using 5-Fluoro-2-trifluoromethyl-benzoic acid (Aldrich, St. Louis, Mo.) as a starting material) (125 mg, 0.34 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and extracted with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4, concentrated under reduced pressure to afford the residue. The residue obtained was purified by recrystallisation from 10% EtOAc in Hexane to afford 45 mg (57.3%) of 5-(3-Fluoro-phenyl)-isoxazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 92.46%. 1H NMR (DMSO-d6): delta 8.72 (m, 1H), 7.86 (m, 1H), 7.78 (m, 2H), 7.44 (m, 4H), 7.38 (m, 1H), 4.1 (m, 2H), 3.4 (m, 6H), 3.0 (m, 2H).

The synthetic route of 1188032-12-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bischoff, Alexander; Subramanya, Hosahalli; Sundaresan, Kumar; Sammeta, Srinivasa Raju; Vaka, Anil Kumar; US2010/160323; (2010); A1;,
Isoxazole – Wikipedia
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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.

General procedure: The acid chloride (1 eq), ammonium thiocyanate (1.7 eq) and 1 drop of PEG-400 in DCM were stirred for 1 hour. 2-(4-Isopropylphenoxy)acetohydrazide (0.97 eq) was added and the reaction was stirred for 0.5 hours

62348-13-4 Isoxazole-5-carbonyl chloride 2736707, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Article; Lounsbury, Nicole; Eidem, Tess; Colquhoun, Jennifer; Mateo, George; Abou-Gharbia, Magid; Dunman, Paul M.; Childers, Wayne E.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 6; (2018); p. 1127 – 1131;,
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

EXAMPLE 1 Ethyl 2-amino-5-cyano-6-methyl-4-(3-phenyl-1,7-naphthyridin-5-yl)-1,4-dihydropyridine-3-carboxylate STR24 2 g (8.5 mmol) of 3-phenyl-1,7-naphthyridine-5-carboxaldehyde are suspended in 20 ml of ethanol and stirred with 0.7 ml (8.5 mmol) of 5-methylisoxazole. A solution of 196 mg of sodium in 14 ml of ethanol is added and the mixture is stirred for 2 hours at 50 C. 1.42 g of ethyl amidinoacetate hydrochloride and 0.51 ml (8.5 mmol) of acetic acid are added and the mixture is boiled for 16 hours. After cooling, 10 g of silica gel are added and the mixture is concentrated in vacuo. The residue is chromatographed on a silica gel column using toluene/ethyl acetate mixtures. After concentration of the pure fractions, the product is crystallized by trituration with ether. 2 g of crystals are obtained.

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

Reference£º
Patent; Bayer Aktiengesellschaft; US5434153; (1995); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem