Heterocyclic Building Blocks-isoxazole

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.

Ethyl chlorooximidoacetate (10 g, 66 mmol) in CHCl3 (80 mL) is slowly added to propargyl alcohol (4.7 mL, 81 mmol) and K2CO3 (27 g, 198 mmol) in CHCl3 (80 mL). The addition is accompanied by an exothermic reaction which causes the chloroform to reflux. After being allowed to cool to RT, the mixture is stirred overnight. The reaction mixture is filtered and the residue is rinsed with chloroform and concentrated in vacuo. The crude product is purified by chromatohraphy (Biotage 40M, EtOAc/Hex:20/80) to yield 3.23 g (29% yield) of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate as an oil. 1H NMR (400 MHz, CDCl3) delta 6.69, 4.86, 4.45, 4.42. A solution of diethylaminosulfur trifluoride (DAST) (2.8 mL, 21 mmol) in 30 mL CH2Cl2 is added dropwise to a solution of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (3.0 g, 18 mmol) in 30 mL CH2Cl2 at -78 C. The mixture is stirred at -78 C. for 1 h and then warmed to RT over 3 h. Water (10 mL) and 30 mL of 2.5% aqueous sodium bicarbonate solution are added successively and the organic layer is separated, dried (MgSO4) and evaporated in vacuo. The residue is purified by chromatography (Biotage 40M, EtOAc/Hex:20/80) to give 1.83 g (60% yield) of ethyl 5-(fluoromethyl)isoxazole-3-carboxylate as an oil. 1H NMR (400 MHz, CDCl3) delta 6.82, 5.54, 5.42, 4.47, 1.43. 10% Aqueous sodium hydroxide solution (5 mL) is added to a solution of ethyl 5-(fluoromethyl)isoxazole-3-carboxylate (1.82 g, 10 mmol) in ethanol (30 mL) at RT. The mixture is stirred for 2 h and the solvents are evaporated in vacuo. The residue is dissolved in water and acidified to pH 1 with 35% HCl. Ethanol is added, solvents are evaporated in vacuo and the residue is azeotroped with ethanol. Ethanol is added and the mixture filtered to remove inorganic solids. Evaporation in vacuo of the filtrate gives 0.95 g (63% yield) of 5-(fluoromethyl)isoxazole-3-carboxylic acid as a tan solid. 1H NMR (400 MHz, DMSO-d6) delta 7.05, 5.67, 5.56. Oxalyl chloride (0.85 mL, 9.8 mmol) is added dropwise to a suspension of 5-(fluoromethyl)isoxazole-3-carboxylic acid (0.94 g, 6.5 mmol) and a catalytic amount of DMF in 20 mL CH2Cl2. After 1 h, the volatiles are removed in vacuo and the remaining residue is dissolved in acetone. To this solution is added an aqueous solution of sodium azide (0.59 g, 9.1 mmol) at 0 C. with vigorous stirring. Volatiles are removed in vacuo and the residue washed with water and dried under nitrogen to yield 0.57 g (51% yield) of 5-(fluoromethyl)isoxazole-3-carbonyl azide as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 7.21, 5.71, 5.59. Example 605 is prepared according to Method F, making non-critical modifications. Yield 37%. HRMS (ESI) calcd for Cl3H13ClFN3O4+H 330.0657 found 330.0649

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

Reference£º
Patent; Piotrowski, David W.; Rogers, Bruce N.; McWhorter JR., William W.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Groppi JR., Vincent E.; Rudmann, Daniel G.; US2003/236287; (2003); 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.

4- [2- (4-BENZO [d] isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine was diluted to 0.20 M with anhydrous DICHLOROMETHANE, then delivered to an 8 mL vial via pipette (0.20 MMOL). To the amine solution was added base (0.4 M triethylamine in DICHLOROMETHANE, 0.40 mmol). Isoxazole-5- carbonyl chloride was diluted to 0.20 M with DICHLOROMETHANE, and added at rt (0.40 MMOL). The solution was shaken overnight at rt. Polyamine scavenging resin was added (0.5 mmol). The solution was shaken overnight at rt, then filtered into an 8 mL vial. The filtrate was evaluated by MS, then concentrated using an HT-12 GeneVac. Crude was purified by HPLC (30×100 mm ODS-A C (18) 5u COLUMN). 4- [2- (4-BENZO [d] ISOTHIAZOL- 3-YL-PIPERAZIN-1-YL)-ETHYL]-PHENYLAMINE was isolated in 94.5% purity @ 254 nm, LCMS (APCI) : 434 [M+H] +.

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

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/41793; (2004); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

110256-15-0, 5-Cyclopropylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 24 5-Cyclopropyl-isoxazole-3-carboxylic acid (1-{4-[3-chloro-2-(2-methyl-2H-tetrazol-5-yl)-indol-1-yl]-benzylcarbamoyl}-cyclopropyl)-amide A mixture of 23.0 mg (0.15 mmol) of 5-cyclopropyl-isoxazole-3-carboxylic acid, 30 mul (0.21 mmol) of triethylamine, 63.2 mg (0.18 mmol) of 1-amino-cyclopropanecarboxylic acid 4-[3-chloro-2-(2-methyl-2H-tetrazol-5-yl)-indol-1-yl]-benzylamide (Reference Example 4) 60.0 mg (0.16 mmol) of HATU and 1 mL of N,N-dimethylformamide was stirred at room temperature for 24 h. The reaction mixture was purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and hexane:ethyl acetate=4:1 as eluent to yield 26 mg (31%) of the title compound. MS (EI) 557.2 (MH+).

The synthetic route of 110256-15-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Richter Gedeon Nyrt.; Beke, Gyula; Benyei, Gyula Attila; Borza, Istvan; Bozo, Eva; Farkas, Sandor; Hornok, Katalin; Papp, Andrea; Vago, Istvan; Vastag, Monika; US2013/217702; (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.946426-89-7,5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazole-4-methanol,as a common compound, the synthetic route is as follows.

Thionylchloride (62 ml, 0.52 mol) was added slowly to a solution of (5 -cyclopropyl-3 – (2,6-dichlorophenyl)isoxazol-4-yl)methanol (21 g, 0.073 mol) in dichloromethane (100 ml) at 0-5 C. The reaction mixture was then allowed to warm to 25-30 C and stirred for a further 2 h before being concentrated under reduced pressure. The crude product was then added to a mixture of bromo-3-chloro-phenol (16.2 g 0.081 mol), potassium carbonate (67 g 0.48 mol) and sodium iodide (19 g 0.12 mol) in DMF (100 ml). The mixture was heated at 60-65 C for 16 h, poured into water (500 ml) and extracted with ethyl acetate (600 ml). The organic layers were washed with water, brine, dried, concentrated under reduced pressure and the crude product purified by chromatography on silica gel eluting with 20% EtOAc in petroleum ether to afford the titled compound as a solid (18 g, 60 %). LC-MS: 2.63mins, [M+H]+ 472

As the paragraph descriping shows that 946426-89-7 is playing an increasingly important role.

Reference£º
Patent; INORBIT THERAPEUTICS AB; SHARMA, Rajiv; BENTHEM, Lambertus; JUDKINS, Robert; (69 pag.)WO2020/33382; (2020); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

1750-42-1, Isoxazol-3-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 64 Preparation of 2-{3-[2-(4-chlorophenyl)ethyl]-5-oxo-1-phenyl-2-sulfanylideneimidazolidin-4-yl}-N-(1,2-oxazol-3-yl)acetamide. Oxalyl chloride (44.8 muL; 0.51 mmol; 2 eq) and dimethylformamide (0.3 mL) were added to a solution of 2-{3-[2-(4-chlorophenyl)ethyl]-5-oxo-1-phenyl-2-sulfanylideneimidazolidin-4-yl}acetic acid (1-3) (100 mg; 0.26 mmol; 1 eq) in dichloromethane (6 mL). The reaction mixture was stirred at room temperature for 3 hours. Then, pyridine (62 muL; 0.77 mmol; 3 eq) and 1,2-oxazol-3-amine (38 muL; 0.51 mmol; 2 eq) were added. The mixture was stirred at room temperature over the week-end. Saturated ammonium chloride (30 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with saturated sodium chloride (3 x 30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified on silica gel using dichloromethane/ethyl acetate (95/5 to 50/50) as an eluent. After trituration in diethyl ether and lyophilisation, the title compound 2- {3-[2-(4-chlorophenyl)ethyl]-5-oxo-1-phenyl-2-sulfanylideneimidazolidin-4-yl}-N-(1,2-oxazol-3-yl)acetamide was obtained in 25% yield (29.25 mg) as a white powder. 1H-NMR (DMSO-d6): delta (ppm) 2.89 (m, 1H), 3.03 (m, 1H), 3.18 (m, 1H), 3.39 (m, 1H), 3.71 (m, 1H), 4.17 (m, 1H), 4.8 (t, 1H), 6.9 (d, 1H), 7.32 (m, 4H), 7.38 (m, 2H), 7.48 (m, 3H), 8.81 (d, 1H), 11.34 (s, 1H); MS (ESI+): m/z = 454.8, 456.8 [M+H]+.

As the paragraph descriping shows that 1750-42-1 is playing an increasingly important role.

Reference£º
Patent; Vivalis; Guedat, Philippe; Berecibar, Amaya; Ciapetti, Paola; Venkata Pithani ,Subhash; Trouche, Nathalie; EP2664616; (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.110256-15-0,5-Cyclopropylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

A mixture of 23.0 mg (0.15 mmol) of 5-cyclopropyl-isoxazole-3-carboxylic acid, 30 mu (0.21 mmol) of triethylamine, 63.2 mg (0.18 mmol) of 1-amino- cyclopropanecarboxylic acid 4-[3-chloro-2-(2-methyl-2H-tetrazol-5-yl)-indol-l -yl]- benzylamide (Reference Example 4) 60.0 mg (0.16 mmol) of HATU and 1 mL of N,N- dimethylformamide was stirred at room temperature for 24 h. The reaction mixture was purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and hexane:ethyl acetate = 4: 1 as eluent to yield 26 mg (31 %) of the title compound. MS (EI) 557.2 (MH+).

As the paragraph descriping shows that 110256-15-0 is playing an increasingly important role.

Reference£º
Patent; RICHTER GEDEON NYRT.; BEKE, Gyula; BENYEI, Gyula Attila; BORZA, Istvan; BOZO, Eva; FARKAS, Sandor; HORNOK, Katalin; PAPP, Andrea; VAGO, Istvan; VASTAG, Monika; WO2012/59776; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

123770-62-7, Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Production Example 199 (0842) Ethyl 5-hydroxymethylisoxazole-3-carboxylate (0.29 g, 1.7 mmol) was dissolved in tetrahydrofuran (10 mL), and 3-fluoro-2-naphthylmethyl bromide (0.48 g, 2.0 mmol) and 18-crown-6 (0.05 g, 0.2 mmol) were added thereto. Sodium hydride (60% oil-based) (0.14 g, 3.4 mmol) was slowly added thereto at room temperature, and the mixture was stirred at room temperature overnight. Then, dilute hydrochloric acid was added thereto, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was dissolved in ethanol (4 mL), and an aqueous solution obtained by dissolving potassium hydroxide (0.56 g, 10 mmol) in water (2 mL) was added thereto at room temperature, and then the mixture was stirred at 80C for 3 hours. Water was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Tert-butyl methyl ether was added to the concentrate, and the aqueous layer was fractionated. Dilute hydrochloric acid was added to the resulting aqueous layer, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 0.48 g of 5-(3-fluoro-2-naphthylmethoxymethyl)isoxazole-3-carboxylic acid represented by the following formula. The product was subjected to a next reaction without purification

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

78967-07-4, Mofezolac is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation of 3,4-bis(4-methoxyphenyl)-5-hydroxyethylisoxazole (X) To a solution of mofezolac (VII) (200 mg, 0.589 mmol), in anhydrous THF (2 mL) kept at 0 C by a bath of ice, 1M BMS in THF (1.16 mL, 1.16 mmol) was added dropwise, and the mixture was stirred overnight at room temperature to give a pale yellow homogeneous solution. Distilled water (1 mL), 20% NaOH (I mL) and 35% H202 (1 mL) were added and the obtained reaction mixture was stirred for 1 hour. Then, the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous Na2S04 and the solvent removed under reduced pressure. The product (X) was isolated as a white solid (68% yield) by flash chromatography on silica gel (hexane/ethyl acetate 6:4) of the reaction crude, the NMR (400 MHZ, CDC13, delta): 3.81 (s, 3H, CH3), 3.85 (s, 3H, CH3); 4.44 (t, 2H, J- 6.6 Hz CH2), 4.26 (t, 2H, J= 6.6 Hz CH2 6.85 (d, 2H, J= 9.0 Hz, ArH), 6.95 (d, 2H, J= 9.0 Hz, ArH), 7.21 (d, 2H, J= 9.0 Hz, ArH); 7.39 (d, 2H, J= 9.0 Hz, ArH). ESI-MS: m/z (%): C18H20NO4 (M)+, 325.

The synthetic route of 78967-07-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITA’ DEGLI STUDI DI BARI; SCILIMATI, Antonio; PERRONE, Maria, Grazia; VITALE, Paola; WO2014/115020; (2014); A1;,
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

5-Methyl-3-phenylisooxazole-4-carboxylic acid (40 mg, 0.197 mmol), 3-(pyrrolidin-2-ylmethyl)pyridine (50.5 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 (1.0 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 C21H21N3O2: 349.1426, found 349.1693.

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;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108655-63-6,3-(Trifluoromethyl)isoxazol-5-amine,as a common compound, the synthetic route is as follows.

Example 1 3-Trifluoromethyl-5-hydroxyisoxazole A solution of 36 % HCl (9.12 g, 15 eq.) and n-propanol (9.0 ml) was added to 5-amino-3-trifluoromethyl-isoxazole (0.91 g, 6.0 mmole) from Preparation 1 and heated at reflux for 23 hours. The reaction mixture was cooled, extracted with methylene chloride and distilled under reduced pressure to give 0.006 g (0.7 %) of the titled compound as a cololess liquid, b.p. 35 – 37C/1.4 mmHg.

108655-63-6 3-(Trifluoromethyl)isoxazol-5-amine 13913996, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; SHIONOGI & CO., LTD.; EP220025; (1991); B1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem