Heterocyclic Building Blocks-isoxazole

832740-73-5, 4-(Isoxazol-5-yl)aniline is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

832740-73-5, Example 18 5-((1R,2R)-2-amino-3,3-difluorocyclohexylamino)-3-(4-(isoxazol-5-yl)phenylamino)pyrazine-2-carboxamide A mixture of 5-((1R,2R)-2-amino-3,3-difluorocyclohexylamino)-3-chloropyrazine-2-carbonitrile (74 mg, 0.257 mmol), 4-(isoxazol-5-yl)aniline (60 mg, 0.375 mmol), K2CO3 (80 mg, 0.579 mmol), BINAP (25 mg, 0.040 mmol) and Pd(OAc)2 (10 mg, 0.044 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 20 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give 5-((1R,2R)-2-amino-3,3-difluorocyclohexylamino)-3-(4-(isoxazol-5-yl)phenylamino)pyrazine-2-carbonitrile (4 mg).

As the paragraph descriping shows that 832740-73-5 is playing an increasingly important role.

Reference£º
Patent; Portola Pharmaceuticals, Inc.; Song, Yonghong; Xu, Qing; Jia, Zhaozhong J.; Kane, Brian; Bauer, Shawn M.; Pandey, Anjali; US2013/131040; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2510-36-3,3,5-Dimethylisoxasole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 2; N-[(3,5-dimethylisoxazol-4-yl)carbonyl]-3-{5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]thiophen-2-yl}-L-alanine; O-benzotriazol-1-yl-N,N,N’,N’-tetramethyluronium tetrafluoroborate (268 mg, 0.83 mmol), 4-methylmorpholine (0.084 ml, 0.76 mmol) and 3,5-dimethylisoxazole-4-carboxylic acid (98 mg, 0.70 mmol) were added under an argon atmosphere to a stirred solution of methyl 3-{5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]thiophen-2-yl}-L-alaninate (250 mg, 0.70 mmol) dissolved in DMF (2.5 mL). The resulting solution was stirred at 25 C. for 2 hours. Then NaOH 6N (0.464 ml, 2.78 mmol) was added to the stirred mixture. The resulting solution was stirred at 25 C. for 1 hour. The reaction mixture was purified by C18 reverse phase chromatography (basic conditions). The fractions containing the desired compound were evaporated to dryness to afford the title compound as a beige solid (157 mg, 48.2%); Mass spectrum [M+H]+=467; 1H NMR Spectrum (DMSOd6) 1.70-1.78 (m, 2H), 1.81-1.90 (m, 2H), 2.18 (s, 3H), 2.39 (s, 3H), 2.45 (t, 2H), 2.60 (t, 2H), 2.70 (t, 2H), 3.15 (dd, 1H), 3.20-3.26 (m, 2H), 3.32 (dd partially hidden by H2O, 1H), 4.49 (ddd, 1H), 6.23 (d, 1H), 6.42 (bs, 1H), 6.64 (d, 1H), 6.71 (d, 1H), 7.03 (d, 1H), 8.27 (d, 1H).

2510-36-3, As the paragraph descriping shows that 2510-36-3 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; US2008/255183; (2008); 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.21169-71-1,Isoxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 3 (Compound 3) N-[2-[ l-[4-chloro-3-(trifluoromethyl)phenyl]pyrazole-4-carbonyl]-4-(l- piperidyl) phenyl] isoxazole-5-carboxamide A solution of (2-amino-5-(l-pipendyl)phenyl)(l-(4-chloro-3-(tnfluoromethyl)-phenyl)- lH-pyrazol-4-yl)methanone (Intermediate 1.5) (50 umol), l,2-oxazole-5-carboxylic acid (60 umol), DIEA (150 umol) and HATU (60 umol) in DMSO (300 uL) was stirred at room temperature overnight. The residue was purified by preparative HPLC/MS_method A2 to afford the title compound. 1H NMR (DMSO-d6, 600 MHz) delta = 10.88 (s, 1H), 9.25 (s, 1H), 8.75 (d, 1H), 8.37 (d, 1H), 8.28 (dd, 1H), 8.19 (s, 1H), 7.92 (d, 1H), 7.66 (d, 1H), 7.24 (dd, 1H), 7.18 (d, 1H), 7.09 (d, 1H), 3.21 (t, 4H), 2.54 (s, OH), 1.66 – 1.59 (m, 4H), 1.58 – 1.51 (m, 2H).

21169-71-1, The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LEO PHARMA A/S; SOERENSEN, Morten Dahl; LARSEN, Jens Christian Hoejland; NOERREMARK, Bjarne; LIANG, Xifu; HUANG, Guoxiang; CHEN, Jinzhong; WO2013/82756; (2013); A1;,
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3209-70-9, Ethyl isoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3209-70-9, (a) 3-Hydroxymethyl isoxazole A solution of ethyl isoxazole-3-carboxylate (9.92 g, 70 mmol) in anhydrous ether (10 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (2.67 g, 70 mmol) in ether (100 ml). The mixture was then refluxed until tlc indicated the reaction was complete (ca. 30 min) then the reaction was cautiously quenched with 2% sulphuric acid. The ether layer was separated, dried (MgSO4) and the solvent removed under reduced pressure to yield the 3-hydroxymethylisoxazole (4.23 g, 42.7 mmol, 61%); deltaH (CDCl3) 4.00 (1H, bs, OH), 4.70 (2H, s, CH2 –OH), 6.40 (1H, d, J 2 Hz, CH-4), 8.30 (1H, d, J 2 Hz, CH-5).

3209-70-9 Ethyl isoxazole-3-carboxylate 10034712, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Beecham Group p.l.c.; US4812470; (1989); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7063-99-2,Ethyl 5-phenylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

7063-99-2, Preparation of Int-II-B: Ethyl 4-iodo-5-phenylisoxazole-3-carboxylate[00177] A mixture of ethyl S-phenylisoxazole-S-carboxylate (406 mg, 1.87 mmol) and N-iodosuccinimide (505 mg, 2.24 mmol) in trifluoroacetic acid (10 mL) was stirred at room temperature for 1.5 h. The volatiles were removed under reduced pressure, and the residue was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with a IN aqueous solution of sodium hydroxide (50 mL), washed with a 2.5% aqueous solution of sodium bisulfite (50 mL), washed with brine (50 mL), and dried over anhydrous magnesium sulfate. Concentration under reduced pressure afforded ethyl 4-iodo-5-phenylisoxazole-3-carboxylate (641 mg, 1.87 mmol, 100% yield) as a light yellow oil. The compound had an HPLC retention time = 3.36 minutes (YMC- Combi 4.6 x 50 mm S-5 ODS column) eluting with 10-90% aqueous methanol + 0.2% phosphoric acid over a 4 minute gradient. MS:(M+H) = 343.97. 1H NMR (400 MHz, CDCl3) delta ppm 1.47 (t, J=IA Hz, 3H), 4.50 (q, J=7.0Hz, 2H), 7.52-7.56 (m, 3H), and 8.05 (m, 2H).

7063-99-2 Ethyl 5-phenylisoxazole-3-carboxylate 571142, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILMORE, John L.; SHEPPECK, James E.; WO2011/17578; (2011); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7063-99-2,Ethyl 5-phenylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.,7063-99-2

Step 3: ethyl 4-fluoro-5-phenyl-1,2-oxazole-3-carboxylate: selectfluor (1.71 g, 4.83 mmol, 1.05 equiv) was added to a solution of ethyl 5-phenyl-1,2-oxazole-3-carboxylate (1 g, 4.60 mmol, 1.00 equiv) in sulfone (5 mL). The resulting solution was stirred for 16 hours at 105 C. and then diluted with 100 mL of ethyl acetate. The resulting mixture was washed with brine (2¡Á100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20) to give 0.15 g (14%) of ethyl 4-fluoro-5-phenyl-1,2-oxazole-3-carboxylate as a yellow solid. LC-MS: [M+H]+=236.

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

Reference£º
Patent; PROTEOSTASIS TEHRAPEUTICS, INC.; Bastos, Cecilia M.; Munoz, Benito; Tait, Bradley; (48 pag.)US2017/1993; (2017); A1;,
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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

To a solution of 5-cyclopropylisoxazole-3-carboxylic acid (300 mg, 1.9 mmol) in DMF (3 ml), was added HATU (1.1 17 g, 2.9 mmol). The reaction mixture was stirred for 20 min at room temperature. After being cooled to 0 C 1 ,4-dimethylpyrrolidin-3 -amine (250 mg, 2.1 mmol) and DIPEA (380 mg, 2.9 mmol) were added to the reaction mixture. It was stirred at room temperature for 2 hrs. Completion of the reaction was confirmed by TLC. After completion, water (30 mL) was added and the product was extracted with ethyl acetate (2 x 30 mL). The combined organic layer was washed with brine, dried over sodium sulfate and concentrated under vacuum to get the crude product which was purified by column chromatography using 1% MeOH in DCM. Distillation of the pure fractions afforded 392 mg of a mixture of diastereomers and enantiomers. The cis and trans isomers were separated by chiral prep. HPLC using 0.1% diethyamine in n- Heptane: IPA as the mobile phase. Evaporation of pure fractions afforded pure diastereomers. Yields of the isomers were 28 mg, 5.73 %) and (54 mg, 11.06 %). The NMR spectra and LC/MS of the isomers were 1H NMR (400 MHz, MeOD): delta 6.39 (s, 1H), 4.71-4.65 (m, 1H), 3.12 (dd, J = 7.2, 10.4 Hz, 1H), 2.98-2.94 (dd, J = 7.6, 9.2 Hz, 1H), 2.60-2.51 (m, 1H), 2.41 (s, 3H), 2.28 (t, J = 9.2 Hz, 1H), 2.21-2.14 (m, 1H), 1.18- 1.13 (m, 2H), 1.00-0.98 (m, 5H): LCMS: m/z = 249.9 [M+H]+, and 1H NMR (400 MHz, MeOD): delta 6.38 (s, 1H), 4.16-4.12 (m, 1H), 3.02 (dd, J = 7.6, 8.8 Hz, 1H), 2.88 (dd, J = 7.6,10.4 Hz, 1H), 2.70 (dd, J = 5.2, 10 Hz, 1H), 2.39 (s, 3H), 2.28-2.15 (m, 3H), 1.18- 1.12 (m, 5H), 1.00-0.97 (m, 2H); LCMS: m/z = 250.40 [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.; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; HARVEY, Darren Martin; (151 pag.)WO2016/40504; (2016); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57684-71-6,3-(Chloromethyl)isoxazole,as a common compound, the synthetic route is as follows.

57684-71-6, (c) 3-Diethylphosphonomethyl isoxazole 3-Chloromethyl isoxazole (1.41 g, 12 mmol) and triethylphosphite (3.13 ml, 18 mmol) were heated at 140 C. for 1 h. Distillation (short path) yielded the phosphonate (390 mg, 1.78 mmol, 15%); bp 110-120 C. at 0.7 mm Hg; deltaH (CDCl3) 1.30 (6H, t, J 7 Hz, OCH2 CH3), 3.30 (2H, d, JP-H 22 Hz, CH2 –P), 4.10 (4H, m, OCH2 CH3), 6.40 (1H, s, CH-4), 8.35 (1H, s, CH-5).

57684-71-6 3-(Chloromethyl)isoxazole 4913025, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Beecham Group p.l.c.; US4812470; (1989); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.28883-91-2,5-Amino-3-(4-methylphenyl)isoxazole,as a common compound, the synthetic route is as follows.

General procedure: To a stirred solution of ynamide 4a (57.0 mg, 0.2 mmol) in DCE (2.0 mL, 0.1 M) was added isoxazol-5-amine 8a (21.6 mg, 0.22 mmol, 1.1 equiv), followed by AgNTf2 (3.9 mg, 5 mol %). The resulting mixture was placed into an oil bath of 80 C with stirring for 2 h generally, monitoredby TLC. After completion, the reaction mixture was cooled and the desired product was precipitated. The solid was filtered and washed with DCM twice, then dried in a vacuum drying oven at 50 C for 24 h to give the pure pyrrole product 10aa, 75.8 mg, 99% yield. For products 10ab-ae, 10ka-la, the purification method was as follows: evaporation of volatiles under reduced pressure to give the residue, which was suffered from column chromatographyon silica gel (petrol ether/ethyl acetate 1:1-1:2, v/v) to afford the pure pyrrole., 28883-91-2

The synthetic route of 28883-91-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Cao, Ziping; Zhu, Jiekun; Liu, Li; Pang, Yuanling; Tian, Laijin; Sun, Xuejun; Meng, Xin; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 2623 – 2630;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

10557-85-4, 3,5-Dimethyl-4-iodoisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Raw material 4-iodo-3,5-dimethylisoxazole25 (0.28 g, 1.3 mmol) in anhydrous THF was added dropwise to a 2.93 mol/L n-BuLi hexane solution (0.47 mL, 1.4 mmol) at -78 C under an argon atmosphere. Stirring was continued for 30 min and 8a (0.52 g, 1.3 mmol) was slowly added to the reaction mixture at -78 C and stirred for 1 h at this temperature. The reaction was quenched with 20 mL water. The mixture was warmed to room temperature and extracted with ether. The organic layer was dried over MgSO4, filtrated, and evaporated. The crude product was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (v/v=6/1) as the eluent resulting in 0.23 g of 1o being obtained in 38% yield as a pale yellow solid.

10557-85-4, The synthetic route of 10557-85-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Pu, Shouzhi; Li, Hui; Liu, Gang; Liu, Weijun; Cui, Shiqiang; Fan, Congbin; Tetrahedron; vol. 67; 7; (2011); p. 1438 – 1447;,
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