Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14678-02-5,5-Amino-3-methylisoxazole,as a common compound, the synthetic route is as follows.

Prepared by following a methodology reported by M. Ohkubo et al. in Chem Pharm Bull. 1995, 43 (9), 1497-1504.To a solution of 5-amino-3-methylisoxazole (0.165 g, 1.67 mmol) in anhydrous toluene (6.5 ml) and anhydrous pyridine (0.18 ml, 2.0 mmol) cooled in an ice/water bath (T=10 C.) was slowly added bromoacetyl bromide (0.402 g, 2.0 mmol). The reaction mixture was stirred for 1.5 h under argon, then poured into water (20 ml), and extracted with ethyl acetate (2¡Á40 ml). The combined organics were washed with water (30 ml), brine (30 ml), dried (Na2SO4), and concentrated in vacuo. The residue was triturated with diethyl ether, the precipitate was removed by filtration, and the filtrate was concentrated in vacuo to afford the title compound as a white solid (0.200 g, 55%); 1H-NMR (500 MHz, DMSO-d6) 2.18 (s, 3H, CH3), 4.08 (s, 2H, CH2Br), 6.15 (s, 1H, isoxazole C-H), 11.94 (s, 1H, CONH);LC (Method B)-MS (ESI, m/z): Rt=2.92 min-219, 221 [(M+H)+, Br isotopic pattern]., 14678-02-5

As the paragraph descriping shows that 14678-02-5 is playing an increasingly important role.

Reference£º
Patent; THE INSTITUTE OF CANCER RESEARCH; US2009/247507; (2009); 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.354795-62-3,3-Methylisoxazol-4-amine,as a common compound, the synthetic route is as follows.

Example 165-Bromo-2-{[(4-fluorophenyl)methyl]oxy}- V-(3-methyl-4-isoxazolyl)-4-(4- morpholinylmethyl)benzamide (E16)To a solution of 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acid (may be prepared as described in Description 20; 150 mg, 0.35 mmol) in N,N- dimethylformamide (4 ml) was added 3-methyl-4-isoxazolamine (41.6 mg, 0.42 mmol), diisopropylethylamine (0.12 ml, 0.71 mmol), 1 -hydroxy- 7-azabenzotriazole (57.7 mg, 0.42 mmol) and EDC (102 mg, 0.53 mmol). The mixture was stirred for 18 hours, then the solvent removed in vacuo to give a residue. The residue was purified by column chromatography (10% 7M NH3 in methanol/dichloromethane) to yield the title compound as a solid. 178 mg. MS (electrospray): m/z, [M+H]+ = 504/506

354795-62-3, 354795-62-3 3-Methylisoxazol-4-amine 13804284, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXO GROUP LIMITED; ANDREOTTI, Daniele; DAI, Xuedong; EATHERTON, Andrew John; JANDU, Karamjit Singh; LIU, Qian; PHILPS, Oliver James; WO2012/28629; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

108655-63-6, 3-(Trifluoromethyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Pyridine (5.4 mL, 0.067 mol) is added dropwise to 5-chloro-2,4-dimethoxyaniline (10.45 g, 0.056 mol) and phenyl chloroformate (8.4 mL, 0.067 mol) in CH2Cl2 (500 mL) at 0 C. The reaction is stirred for 1.5 h and diluted with 0.1M HCl (100 mL). The organics are separated, washed w/5% NaHCO3 (100 mL) and brine (150 mL), dried (MgSO4), and the solvent is removed. The resulting solid is recrystallized (EtOAc/hexanes) to give phenyl 5-chloro-2,4-dimethoxyphenylcarbamate (16.72 g, 97% yield) as a purple solid. Sodium hydride(1.82 g, 0.046 mol, 60% oil disp.) is added to 3-(trifluoromethyl)isoxazole-5-amine (6.93 g, 0.046 mol) in DMF (350 mL) at RT. After 0.5 h, a DMF solution (100 mL) of phenyl 5-chloro-2,4-dimethoxyphenylcarbamate (14.0 g, 0.046 mol) is added and the reaction warmed to RT. The reaction is heated at 50 C. for 1 h, cooled to RT and the solvent is removed. The residue is dissolved in EtOAc (150 mL), washed with 1M HCl (150 mL), H2O (150 mL), and brine (150 mL). The organics are separated, dried (MgSO4) and the solvent is removed under reduced pressure. The dark solid is dissolved in EtOH (500 mL) and stirred with Darco activated carbon (15) for 4 h. The mixture is filtered over Celite and the solvent is removed to give a solid, which is recrystallized (EtOAc/hexanes) to give Example 500 as a tan solid (10.47 g, 63% yield). HRMS (ESI) calcd for C13H11ClF3N3O4+H 366.0468 found 366.0475., 108655-63-6

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

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

62348-13-4, Isoxazole-5-carbonyl chloride is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

62348-13-4, EXAMPLE 2 6.52 parts of 2-methylpyridine were added to a stirred mixture of 15.7 parts of 7-chloro-5-nitro-8-hydroxyquinoline in 190 parts of 1,2-dichloroethane at 25 C. in the course of 5 minutes, and the mixture was stirred for 5 minutes. 9.2 parts of isoxazole-5-carbonyl chloride were then added at from 20 to 25 C. in the course of 10 minutes, while stirring, and stirring was continued for 3 hours at 55 C. The reaction mixture was evaporated to dryness under reduced pressure, and the residue was stirred in 200 parts of 0.5N hydrochloric acid for 5 minutes. The precipitate was filtered off under suction, washed with water and stirred for 10 minutes in 200 parts of dilute sodium carbonate solution. Filtration under suction, washing with water at 60 C. and drying gave 17.5 parts of 7-chloro-5-nitro-8-(isoxazole-5′-carbonyl)-oxyquinoline of melting point 132-134 C.

As the paragraph descriping shows that 62348-13-4 is playing an increasingly important role.

Reference£º
Patent; BASF Aktiengesellschaft; US4829072; (1989); A;,
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

The ethyl 5-phenyl-isoxazole-3-carboxylate (1g, 4.6mmol) and hydrazine hydrate (0.69g, 13.8mmol) was dissolved in 20mL of ethanol and refluxed overnight.The solid was precipitated by cooling to room temperature, suction filtered, and dried to give a solid, about 0.63 g, yield: 69%.

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

Reference£º
Patent; China Pharmaceutical University; Wang Jinxin; Shang Yanguo; Song Meng; (13 pag.)CN110156708; (2019); A;,
Isoxazole – Wikipedia
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

a) 2-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-isoindole-1,3-dione To a solution of [3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol (5.0 g, 24 mmol) in THF (290 mL) was added phthalimide (4.7 g, 32 mmol) and triphenylphosphine (8.4 g, 32 mmol) at ambient temperature under an argon atmosphere. Then a solution of diethyl azodicarboxylate (40% in toluene, 12.5 mL, 32 mmol) was added and the reaction mixture was stirred for 1 h at room temperature. Concentration and repeated trituration and then purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (6.0 g, 74%) as a white solid. MS: m/e=337.1 [M+H]+.

1018297-63-6, 1018297-63-6 (3-(4-Fluorophenyl)-5-methylisoxazol-4-yl)methanol 28473136, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Buettelmann, Bernd; Jakob-Roetne, Roland; Knust, Henner; Thomas, Andrew; US2009/143385; (2009); 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

Intermediate 10: 3-Amino-4-chloroisooxazole.; To a 50 ml_ round-bottomed flask were added a stirbar, 506 mg (6.01 mmol) 3-aminoisoxazole, 15 ml_ DMF and 1.04 g (7.75 mmol) N-chlorosuccinimide. The flask was purged with nitrogen and heated at 50 0C for 48 h. The reaction mixture was then concentrated to dryness in vacuo, the residue taken up in DCM and washed with 1 N NaOH containing Na2S2O3. The organic layer was dried over MgSO4, filtered and evaporated to dryness to give a brown oil. Subjecting the residue to FCC (0-5% 2 N NH3 in MeOH/DCM) gave the pure product as a pale- yellow solid (335.4 mg, 47%). MS (ESI+): Calcd for C3H3N2OCI [M+H]+, m/z 117.99, found 119.0 (M + H)+. 1H NMR (500 MHz, CDCI3): 8.10 (s, 1 H), 4.26 (br s, 2H)., 1750-42-1

The synthetic route of 1750-42-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; BREITENBUCHER, J., Guy; KEITH, John, M.; TICHENOR, Mark, S.; CHAMBERS, Alison, L.; JONES, William, M.; HAWRYLUK, Natalie, A.; TIMMONS, Amy, K.; MERIT, Jeffrey, E.; SEIERSTAD, Mark, J.; WO2010/68453; (2010); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

946426-89-7, 5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazole-4-methanol is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation of compound A6e: [Show Image] To the solution of benzotrizole (17.85 g, 194.3 mmol) in 100 mL of dry DCM was added SOCl2 (23.09 g, 73.7 mmol) at 0C, and stirred at room temperature for 1 hour. The resulting mixture was added to the solution of compound A5e (55 g, 194.3 mmol) in 500 mL of dry DCM at room temperature and stirred for 1.5 h. 120 mL of water was added to the mixture for quench, and the mixture was extracted with DCM. The organic layer was washed with 1 N aq. NaOH solution, dried over Na2SO4, filtered, concentrated and purified by chromatography on silica gel (eluent: PE/EtOAc = 10/1) to give 47.4 g of compound A6e as a white solid (Yield: 81 %). 1H NMR (400 MHz, CDCl3): delta 1.23-1.33 (m, 4H), 2.14 (m, 1H), 4.40 (s, 2H), 8.31 (s, 2H)., 946426-89-7

946426-89-7 5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazole-4-methanol 45790382, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Phenex Pharmaceuticals AG; EP2289883; (2011); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

14678-02-5, 5-Amino-3-methylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3-Methylisoxazol-5-amine (2.9 g) and potassium carbonate (9.8 g) were suspended in dichloromethane (100 mL) at room temperature 2-bromoacetyl bromide (6 g) was added dropwise. The mixture was allowed to stir overnight. Water (0.3 mL) was added together with a further quantity of potassium carbonate (3 g) and the reaction stirred for a further 30 minutes. The reaction mixture was poured into water (100 mL) and extracted with dichloromethane (2 x 50 mL). The combined organic extracts were dried over Magnesium Sulfate and then evaporated in vacuo. The crude product was purifed by column chromatography on silica eluting with ethyl actetate / isohsxane (50:50) to give sub-titled compound (4.8 g).1H NMR (299.946 MHz, CDCl3) delta 11.97 (s, IH)5 6.16 (s, IH), 4.09 (s, 2H), 2.19 (s, 3H).

14678-02-5, The synthetic route of 14678-02-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/59245; (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.25742-00-1,(3-Bromoisoxazol-5-yl)methanol,as a common compound, the synthetic route is as follows.

To a chilled (O0C) solution of 3-bromo-isoxazol-5-yl)-methanol (560 mg, 3.15 mmol) in CH2Cl2 (31 niL) was added Dess-Martin periodinane (2.00 g, 4.72 mmol) in 3 portions and the mixture was warmed to room temperature. After 4 hours, the mixture was diluted with Et2O (40 mL) and 1:1 mixture of aqueous solution of saturated aqueous NaHCO3 (20 mL) and saturated aqueous Na2S2O3 (20 mL) was added. After 15 hours, the aqueous layer was separated and extracted with Et2O (2 x) and EtOAc (2 x). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford S-bromo-isoxazole-S-carbaldehyde as a yellowish/orange solid. MS m/z 194.00 (M+ H2O); 195.97 (M+2).

25742-00-1, 25742-00-1 (3-Bromoisoxazol-5-yl)methanol 2763220, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; DISALVO, Darren; FANDRICK, Daniel Robert; HARCKEN, Christian; KUZMICH, Daniel; LEE, Thomas Wai-Ho; LIU, Pingrong; LORD, John; MAO, Can; NEU, Jochen; RAUDENBUSH, Brian Christopher; RAZAVI, Hossein; REEVES, Jonathan Timothy; SONG, Jinhua, J.; SWINAMER, Alan, David; TAN, Zhulin; WO2010/36632; (2010); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem