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

a N-Methoxy-N-methyl-5-isoxazolecarboxamide A solution of isoxazole 5-carboxylic acid (2.81 g), N-methoxy-N-methylamine hydrochloride (2.49 g), EDCI (4.96 g), dimethylaminopyridine (3.15 g) and 4-methylmorpholine (2.8 ml) in dichloromethane (20 ml) was stirred for 18 h. 2M Hydrochloric acid was added and the mixture was extracted with dichloromethane (three times). The organic layers were washed with aqueous sodium hydrogen carbonate and then brine, combined, dried (magnesium sulphate), evaporated and purified by chromatography on silica eluding with petrol-ether to give the sub-title compound as a colourless oil (2.94 g, 76%). 1H NMR 300 MHz (CDCl3) 8.35 (1H, d), 6.89 (1H, d), 3.83 (3H, s), 3.39 (3H, s)., 21169-71-1

21169-71-1 Isoxazole-5-carboxylic acid 2060599, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Cheshire, David; Connolly, Stephen; Cox, David; Hamley, Peter; Mete, Antonio; Pimm, Austen; US2003/158185; (2003); A1;,
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847490-69-1,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.847490-69-1,4-Iodoisoxazole,as a common compound, the synthetic route is as follows.

[00460] Step 2: Synthesis of 3-(isoxazol-4-yl)benzaldehyde: To a mixture of 4- iodoisoxazole (1 g, 5.13 mmol), 3-formylphenylboric acid (923 mg, 6.15 mmol) and sodium carbonate in DME/H20/Toluene/EtOH (15 mL, 3/1/10/6, V/V) was added Pd(PPh3)4 (200 mg). The mixture was purged with N2 for 30 min and heated to 80 C for 3 h. The reaction mixture was cooled followed by a standard aqueous/EtOAc workup and purified by prep- TLC (EA : PE = 1 : 5) to give Intermediate 46 (12 mg, 1.5%).

847490-69-1 4-Iodoisoxazole 22274060, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; N30 PHARMACEUTICALS, LLC; SUN, Xicheng; QIU, Jian; WO2011/38204; (2011); A1;,
Isoxazole – Wikipedia
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14678-02-5, 5-Amino-3-methylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 3-methyl-1,2-oxazol-5-amine (583 mg, 5.94 mmol) and diisopropylethylamine (1.04 g, 8.08 mmol) in dichloromethane (12 mL), was added dropwise a solution of ditrichloromethyl carbonate (601 mg, 2.03 mmol) in dichloromethane (6 mL). The resulting mixture was stirred at room temperature for 20 min. A solution of 32-3 (500 mg, 1.49 mmol) in dichloromethane (2 mL) and triethylamine (902 mg, 8.91 mmol) was added and the reaction mixture was stirred at room temperature for another 5 h. Water and dichloromethane were added. The organic phase was separated, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel column with ethyl acetate/petroleum ether (1/20) as the eluent to afford the desired product (580 mg, 85% yield)., 14678-02-5

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

Reference£º
Patent; INVENTISBIO INC.; DAI, Xing; WANG, Yaolin; (187 pag.)WO2017/139414; (2017); 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.954230-39-8,Ethyl 3-(4-fluorophenyl)-5-methylisoxazole-4-carboxylate,as a common compound, the synthetic route is as follows.

954230-39-8, Step d: [3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol To a solution of 3-(4-fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (3.0 g, 12 mmol) (6.18 g, 25 mmol) in THF (320 mL) was added portionwise lithiumaluminiumhydride (528 mg, 14 mmol) at 0 C. and the reaction mixture was stirred at room temperature for 3 h. The mixture was then cooled to 0 C. and water (518 muL) added followed by sodium hydroxide (15% solution, 518 muL) and then again water (1.5 mL) and the mixture then stirred overnight at room temperature. The precipitate was then filtered off and washed with THF. The combined washings and filtrate were then evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (1.8 g, 71%) which was obtained as a white solid. MS: m/e=208.1 [M+H]+.

954230-39-8 Ethyl 3-(4-fluorophenyl)-5-methylisoxazole-4-carboxylate 22309061, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Hoffmann-La Roche Inc.; Dott, Pascal; Grassmann, Olaf; Kammerer, Michael; Manns, Joachim; Schwitter, Urs; Thomas, Andrew; Wyttenbach, Nicole; US2013/172329; (2013); A1;,
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62348-13-4,62348-13-4, Isoxazole-5-carbonyl chloride is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a stirred solution of 9f (100 mg, 0.32 mmol) in DMA (3 mL) was added 3-fluorobenzoyl chloride (43 muL, 0.36 mmol), and the mixture was stirred at room temperature overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water and brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by basic silica gel column chromatography (n-hexane/EtOAc 100:0 to 0:100) to give 10f (56 mg, 40%) as a white solid.

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

Reference£º
Article; Miyamoto, Naoki; Sakai, Nozomu; Hirayama, Takaharu; Miwa, Kazuhiro; Oguro, Yuya; Oki, Hideyuki; Okada, Kengo; Takagi, Terufumi; Iwata, Hidehisa; Awazu, Yoshiko; Yamasaki, Seiji; Takeuchi, Toshiyuki; Miki, Hiroshi; Hori, Akira; Imamura, Shinichi; Bioorganic and Medicinal Chemistry; vol. 21; 8; (2013); p. 2333 – 2345;,
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

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

Into a 500-mL round-bottom flask was placed 5-cyclopropyl-1,2-oxazole-3- carboxylic acid (6.12 g, 39.96 mmol, 1.00 equiv), tert-butyl (2R)-4-amino-2- methylpiperidine-1-carboxylate (8.57 g, 39.99 mmol, 1.00 equiv), dichloromethane (300 g), TEA (12.12 g, 120.00 mmol, 3.00 equiv) and HATU (22.8 g, 60.00 mmol, 1.50 equiv). The resulting solution was stirred for 15 h at room temperature. The resulting mixture was then washed with 2x100mL of Na2CO3 (1M, aq.). Then the organic phase was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (C18 gel, CH3CN/H2O = 1:1) to give 10.8 g diastereomeric tert- butyl 4-(5-cyclopropylisoxazole-3-carboxamido)-2-methylpiperidine-1-carboxylate. Then the purified product was separated by Prep-SFC with the following conditions (prep SFC 350): Column, CHIRALPAK AD-H SFC, 5x25cm,5um; mobile phase, CO2(50%), methanol(50%); Detector, uv 220nm. This was resulted in 7.48 g (54%) of tert-butyl (2R,4R)-4-(5-cyclopropyl-1,2-oxazole-3-amido)-2-methylpiperidine-1-carboxylate as light yellow oil. 1H-NMR (300 MHz, CDCl3): 6.86 (d, J = 6.9 Hz, 1H), 6.33 (s, 1H), 4.30-4.15 (m, 2H), 3.93-3.80(m, 1H), 3.22-3.07(m, 1H), 2.20-1.90 (m, 3H), 1.79-1.65(m, 2H), 1.46(s, 9H), 1.26(d, J = 6.9 Hz, 3H), 1.17-1.06(m, 2H), 1.06-0.94(m, 2H) ppm. LCMS (method A, ESI): RT=1.46 min, m/z =372.2 [M+H]+. And 2.52 g (18%) of tert- butyl (2R,4S)-4-(5-cyclopropyl-1,2-oxazole-3-amido)-2-methylpiperidine-1-carboxylate as a light yellow solid. 1H-NMR (300 MHz, CDCl3): 6.55 (d, J = 8.1 Hz, 1H), 6.33 (s, 1H), 4.63-4.39 (m, 1H), 4.39-4.15(m, 1H), 4.15-3.95(m, 1H), 3.0-2.85 (m, 1H), 2.15- 1.98(m, 2H), 1.92-1.78(m, 1H), 1.65-1.50 (m, 1H), 1.46(s, 9H), 1.42-1.26 (m, 1H), 1.23(d, J = 6.9 Hz, 3H), 1.17-1.06(m, 2H), 1.06-0.94(m, 2H) ppm. LCMS (method A, ESI): RT=1.46 min, m/z =372.2 [M+H]+.

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

Reference£º
Patent; EPIZYME, INC.; MITCHELL, Lorna Helen; BELL, Andrew Simon; CHESWORTH, Richard; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (375 pag.)WO2016/40515; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

19788-37-5, 4-(Chloromethyl)-3,5-dimethylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of the product of step 4 (0.15g, 0.255 mmol) in CH2Cl2 (4 mL), Huenig’s base (0.12 g, 0.9 mmol) and 4-chloromethyl-3,5-dimethyl-isoxazole (37 mg, 0.255 mmol) was stirred at RT for 3 days under N2. After completion, the reaction was diluted with CH2Cl2 (40 mL), washed with brine (30 mL, 3x), dried (Na2SO4), filtered and evaporated to give the product as a brown oil. Product was purified by flash silica gel chromatography, eluting with 5 % [(1:9)NH4OH-CH3OH] /95 % CH2Cl2 to give a yellow solid (1.4 g), m.p. 78-80 C; FABMS 35Cl[M+1] 624.2; HRMS 35Cl[M+1]+:cal’d for C33H40N5O3Cl3:624.2508; Found : 624.2506., 19788-37-5

19788-37-5 4-(Chloromethyl)-3,5-dimethylisoxazole 88246, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; SCHERING CORPORATION; EP937069; (2006); B1;,
Isoxazole – Wikipedia
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31329-64-3, 3,5-Dimethylisoxazol-4-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

31329-64-3, EXAMPLE 1 7-Methoxy-2-(tetrahydrofuran-3-yl)-benzofuran-4-carboxylic acid (3,5-dimethylisoxazol-4-yl)-amide To a stirred solution of 3,5-dimethylisoxazol-4-ylamine (88 mg) in N,N-dimethylformamide (7 ml) under an atmosphere of dry nitrogen at room temperature was added sodium bis(trimethylsilyl)amide (0.78 ml, 1.0M solution in tetrahydrofuran). The reaction was stirred for 5 minutes. 7-Methoxy-2-(tetrahydro-furan-3-yl)-benzofuran-4-carboxylic acid 4-nitrophenyl ester (200 mg) was then added and stirring continued for 15 minutes. Water (1 ml) was added and the solvent was removed in vacuo. The resulting residue was purified by column chromatography on silica eluding with 50% ethyl acetate in heptane followed by trituration with diethyl ether affording the title compound as a cream solid (52 mg). TLC Rf 0.60 (50% ethyl acetate in heptane). Mp 183.5-185.2 C.

The synthetic route of 31329-64-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Dyke, Hazel Joan; Lowe, Christopher; Montana, John Gary; US2001/31777; (2001); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

13999-39-8, 3-Amino-4,5-dimethylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 4,5-dimethylisoxazol-3-amine (4.9 g, 44 mmol, 1.0 equiv; CASNo. 13999-39-8, Org. Proc. Res. Dev. 2007, 11, 275-277) and triethylamine (6.4 mL, 46 mmol, 1.05 equiv) in acetonitrile (25 mL) was added portionwise to a 0 0C solution of phenyl chloroformate (5.8 mL, 46 mmol, 1.05 equiv) in THF (100 mL). After stirring at 0 0C for 1 h, the reaction was warmed to room temp overnight. The reaction was concentrated to about one-half the volume and partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography (20 to 40% ethyl acetate/heptane) to give the title compound as a white solid (8.39 g, 83%). m/z 233 (MH+). 1H NMR (400 MHz, DMSO-Cf6) delta ppm 10.67 (br. s., 1 H), 7.40 (t, J=8.0 Hz, 2 H), 7.17 – 7.27 (m, 3 H), 2.12 (s, 3 H), 1.82 (s, 3 H)., 13999-39-8

13999-39-8 3-Amino-4,5-dimethylisoxazole 84148, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER INC.; WO2009/127943; (2009); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem