Category: 1750-42-1

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1750-42-1,Isoxazol-3-amine,as a common compound, the synthetic route is as follows.

General procedure: The heterocyclic amines (1a-h, 10 mmol) were dissolved in 10 mL water followed by addition of 40 mL of 6M HCl and the systems were cooled in the ice-salt bath down to -10C. Afterwards, an aqueous solution of NaNO2 (10 mmol, 0.7g/5 mL H2O) was added slowly drop by drop and stirred vigorously on a magnetic stirrer. After 15 min, fresh solution of 4-hydroxycoumarin (3, 10 mmol, 1.62 g) in 10 mL NaOH (10 wt.) was added. Intensively colored and voluminous precipitates (4a-h) were obtained immediately which were stirred 15 min. in the bath and 30 min. on room temperature. Finally, they were filtrated by vacuum, washed 3 times with distilled water and dried on air. The purification was carried out by the technique of recrystallization using ethanol as solvent.

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

Reference£º
Article; Jashari, Ahmed; Imeri, Faik; Ballazhi, Lulzime; Shabani, Agim; Mikhova, Bozhana; Draeger, Gerald; Popovski, Emil; Huwiler, Andrea; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2655 – 2661;,
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

A solution of 3-(l-(2,4-difluorophenyl)-7-ethyl-6-oxo-6,7-dihydro-lH-pyrazolo[4,3- b]pyrazin-5-yl)-5-fluoro-4-methylbenzoic acid (360 mg, 0.84 mmol) in 5.0 mL of DCM was treated with oxalyl chloride (0.84 mL of 2.0 M in DCM solution, 1.68 mmol) followed by two drops of DMF while cooling in an ice bath at 00C. It was stirred at this temperature for 15 min then allowed to stir at RT for 45 min. The reaction mixture was then concentrated under reduce pressure to remove the excess oxalyl chloride. The residue was dissolved in 5.0 mL of DCM, treated with 3-aminoisoxazole (212 mg, 2.52 mmol) followed by Et3N (0.18 mL, 1.26 mmol) and stirred for 18 h. The reaction mixture was treated with 15 mL saturated NaHCO3 and extracted with DCM (2 x 15 mL). The combined DCM layers were dried over MgSCv Purification on the ISCO (12 g column, 20-70% EtOAc in hexanes) afforded 3-(l-(2,4-difluorophenyl)-7-ethyl-6-oxo-6,7- dihydro-lH-pyrazolo[4,3-b]pyrazin-5-yl)-5-fluoro-N-(isoxazol-3-yl)-4-methylbenzamide as a light yellow amorphous solid. MS (ES+): 495.1 (M+H)+.

1750-42-1, Big data shows that 1750-42-1 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; WO2009/117156; (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

A solution of 3-aminoisoxazole (0.041 ml, 0.548 mmol) and 1-(5-bromo-4-chloro-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonyl chloride (0.254 g, 0.548 mmol) in THF (5.48 ml) was cooled to 0 C., at which point LiHMDS, 1.0M in THF (1.152 ml, 1.152 mmol) was added drop wise. After 40 minutes in the ice bath, the reaction was complete and ammonium chloride (sat aq) was added and the product was extracted with ethyl acetate (*3). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified via MPLC, eluting with 0-100% ethyl acetate in heptane to yield 1-(5-bromo-4-chloro-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.096 g, 0.188 mmol, 34.3% yield) as a light-yellow solid. m/z (ESI) 510.0 (M+H)+., 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; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1750-42-1,Isoxazol-3-amine,as a common compound, the synthetic route is as follows.

(E)-Ethyl 3-(5-(benzylthio)-2-iodophenyl)acrylate (0.225 g, 0.265 mmol) was added to a vial and dissolved in acetonitrile (2.494 ml). Acetic acid (0.095 ml) and water (0.062 ml) were added and the vial was cooled to 0 C. 1,3-dichloro-5,5-dimethylhydantoin (0.057 g, 0.292 mmol) was then added as a solid in one portion while 0 C. was maintained. After 20 min. LC/MS showed mass corresponding to sulfoxide (mono-oxidation) along with sulfonyl chloride. After 1 hr. an additional 0.2 equiv (10 mg) of hydantoin was added. After an additional 20 min. the oxidation was complete. Solid sodium bisulfite was added and the reaction was diluted with EtOAc and water and stirred for 5 min. The organic layer was separated, the aq. re-extracted 2* with EtOAc, and the organic layers combined. After washing with brine, drying with Na2SO4, and concentrating, the crude residue was brought up in 1.5 mL of DCM and treated with 3-aminoisoxazole (0.039 ml, 0.530 mmol) and pyridine (0.107 ml, 1.326 mmol) After 45 min, the reaction was poured into 1N HCl and extracted 2* with EtOAc. The combined organics were washed with brine, dried over Na2SO4, and concentrated to give an orange solid that was purified by MPLC (25 g puriflash, 25-85% EtOAC:Heptanes) to give (E)-ethyl 3-(2-iodo-5-(N-(isoxazol-3-yl)sulfamoyl)phenyl)acrylate (0.043 g, 0.096 mmol, 36.2% yield) as a white solid. m/z (ESI) 447.0 (M-H)-.

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

Reference£º
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1750-42-1,Isoxazol-3-amine,as a common compound, the synthetic route is as follows.

To a solution of isoxazol-3-amine (313 mg, 3.729 mmol) and imidazole (761 mg, 11.19 mmol) in DCM (9 mL) at -78 C was added SO2Cl2 (503 mg, 3.729 mmol) dropwise. The mixture was warmed to room temperature and stirred for 30 min.1-[5-fluoro-2-methoxy-4-[3-(trifluoromethyl)phenyl]phenyl]- 3,4,4a,5,6,7,8,8a-octahydro-1,6-naphthyridin-2-one (315 mg, 0.7457 mmol) in DCM (1 mL) was then added. The mixture was heated at 80 C for 30 min. The reaction was quenched with water, extracted with DCM (3x). The combined organics were dried (Na2SO4), filtered and concentrated. The crude product was purified by silica flash chromatography (0-10% MeOH/DCM) to give the title compound (235 mg, 55%) as yellow oil. LCMS (ESI) m/z 569 [M+H]+., 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; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; MCKERRALL, Steven; SAFINA, Brian Salvatore; KOLESNIKOV, Aleksandr; ZHANG, Birong; LIU, Wenfeng; LAI, Kwong Wah; (110 pag.)WO2019/191702; (2019); 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.1750-42-1,Isoxazol-3-amine,as a common compound, the synthetic route is as follows.

EXAMPLE 305 Synthesis of (f?)-3-chloro-/V-(isoxazol-3-yl)-4-((1-(1-phenylethyl)piperidin-4- yl)oxy)benzenesulfonamide formate Step 1. Preparation of 3-chloro-4-fluoro-/V-(isoxazol-3-yl)benzenesulfonamide To a mixture of isoxazol-3-amine (0.500 g, 5.95 mmol), 4- dimethylaminopyridine (0.0727 g, 0.595 mmol) and pyridine (0.941 g, 1 1.9 mmol) in dichloromethane (2 mL) was added a solution of 3-chloro-4-fluoro-benzene-1-sulfonyl chloride (1.64 g, 7.14 mmol) in dichloromethane (1 mL) at 0 C. The mixture was stirred at ambient temperature for 12 h and was then diluted with water (20 mL) and extracted with dichloromethane (2 chi 30 mL). The combined organic extracts were washed with water (20 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo and purification of the residue by preparative reverse phase HPLC, using acetonitrile in water containing 0.1 % of formic acid as eluent, afforded the title compound as a colorless solid (0.250 g, 15% yield): H NMR (400 MHz, CDCIs) 8.31 (d, J = 1.8 Hz, 1 H), 7.92-7.90 (m, 1 H), 7.76-7.74 (m, 1 H), 7.22 (t, J = 8.5 Hz, 1 H), 6.62 (s, 1 H), NH not observed; MS (ES+) m/z 276.9 (M + 1)., 1750-42-1

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

Reference£º
Patent; XENON PHARMACEUTICALS INC.; ANDREZ, Jean-Christophe; BURFORD, Kristen, Nicole; CHOWDHURY, Sultan; COHEN, Charles, Jay; DEHNHARDT, Christoph, Martin; DEVITA, Robert, Joseph; EMPFIELD, James, Roy; FOCKEN, Thilo; GRIMWOOD, Michael, Edward; HASAN, Syed, Abid; JOHNSON, James, Philip, Jr.; ZENOVA, Alla, Yurevna; (493 pag.)WO2017/201468; (2017); 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

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

To a stirred solution of bromoacetylbromide (5.36 ml, 61.6 mmol) in diethylether (100 ml) at -40 0C is added, dropwise over 20 minutes, a solution of 3-aminoisoxazol (5.0 ml, 67.0 mmol) and triethylamine (8.5 ml, 61.4 mmol) in diethylether (20 ml). Additional diethylether (50 ml) is added and stirring continued for 3 hours. The reaction mixture is filtered and the solution then washed with 1 M sodium carbonate solution, 1 M hydrochloric acid and brine. Concentration followed by purification by flash silica column chromatography (ethyl acetate/ iso-hexane 4:7) gives the title compound as a white solid., 1750-42-1

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

Reference£º
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/66929; (2006); 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

General procedure: To a solution of compounds 1a-1e or methyl 4-aminobenzoate (1.0 mmol) in pyridine (3.0 mL), the corresponding sulfonyl chloride (1.3 mmol) in pyridine (3.0 mL)were added dropwise under nitrogen atmosphere at 0 C, then the reaction mixture was stirred at room temperature overnight. The reaction was then acidified to pH=1 with 4NHCl(aq) and the resulting solid was collected by filtration. The crude product was purified by flash column chromatography (ethyl acetate-petroleum ether = 1:2) to give the title compounds 2a-2i., 1750-42-1

Big data shows that 1750-42-1 is playing an increasingly important role.

Reference£º
Article; Zhang, Jiankang; Shen, Luqing; Wang, Jincheng; Luo, Peihua; Hu, Yongzhou; Medicinal Chemistry; vol. 10; 1; (2014); p. 38 – 45;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1750-42-1,Isoxazol-3-amine,as a common compound, the synthetic route is as follows.

A 40-mL vial was charged with imidazole (922 mg, 13.6 mmol) and 3-aminoisoxazole (320 |xL, 4.34 mmol) then purged with nitrogen. CH2C12 (10 mL) was introduced and the reaction mixture was cooled to -78 C in a dry ice-acetone bath. Sulfuryl chloride (352.0 |xL, 4.32 mmol) was added dropwise via syringe to the reaction mixture. Following addition, the cold bath was removed and the resultant mixture was allowed to warm to ambient temperature. After 30 minutes, (Rac)-1 -(4-bromo-5 -fluoro-2-methoxyphenyl)-5,6,7,8-tetrahydro-l,6-naphthyridin-2(lH)-one (See Preparation 8a, step 1, 957 mg, 2.71 mmol) was introduced in a single portion followed by CH2C12 (10.0 mL). The vial was sealed with a PTFE lined cap and the reaction mixture was warmed to 80 C. After 30 min, the reaction mixture was cooled to ambient temperature and diluted with an aqueous solution of citric acid (1.0 M, 25 mL), brine (25 mL) and EtOAc (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3 x 25 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure and purified (100-g silica gel SNAP Ultra column, 0 to 50% 3:1 EtOAc/EtOH in heptane with DCM as a 10% additive) to afford (rac)-1-(4-bromo-5-fluoro-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-sulfonamide (1.01 g, 2.023 mmol, 74.7 % yield) as a yellow solid.

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; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem