Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.51677-09-9,Methyl 5-phenylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.,51677-09-9

General procedure: To a stirred solution of substrate 1 (1.0 equiv) in THF (0.1 M) was added Grignardreagent (10 equiv) at -78 C and stirred at the same temperature under Ar. After the substrate 1 wasconsumed or the reaction did not proceed any more (judged by TLC), sat. NH4Cl aq. at -78 C was added tothe reaction mixtures and the resulting solution was extracted with AcOEt. The combined organic layerwas dried over Na2SO4 and concentrated in vacuo. The ratio of substrate 1, ketone 2, and tertiaryalcohol 3 was determined by 1H NMR spectrum of crude reaction mixtures.Tertiary alcohol 3ab-3db was prepared by the reaction of substrate 1 and Grignard reagent at rt.

51677-09-9 Methyl 5-phenylisoxazole-3-carboxylate 905953, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Article; Murai, Kenichi; Miyazaki, Shuji; Fujioka, Hiromichi; Tetrahedron Letters; vol. 53; 29; (2012); p. 3746 – 3749;,
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354795-62-3, 3-Methylisoxazol-4-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 435-Chloro-4-[(3,3-difluoro-1-pyrrolidinyl)carbonyl]- V-(3-methyl-4-isoxazolyl)-2- [(phenylmethyl)oxy]benzamide (E43)To a solution of 5-chloro-4-[(3,3-difluoro-1-pyrrolidinyl)carbonyl]-2- [(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 65; 90 mg, 0.23 mmol) in N,N-dimethylformamide (3 ml) was added diisopropylethylamine (0.08 ml, 0.46 mmol), HATU (156 mg, 0.41 mmol) and 3-methyl-4-isoxazolamine (26.8 mg, 0.27 mmol). The solution was stirred for 18 hours. The solvent removed in vacuo and purified by MDAP to give the title compound as a white solid. 65 mg.MS (electrospray): m/z [M+H]+ 4761 H NMR (DMSO-d6): 1.94 (3 H, d, J=3.26 Hz), 2.40 – 2.60 (2 H, m), 3.40 (1 H, t, J=7.28 Hz), 3.54 – 3.68 (1 H, m), 3.75 (1 H, t, J=7.53 Hz), 3.93 (1 H, t, J=13.18 Hz), 5.28 (2 H, s), 7.32 – 7.45 (4 H, m), 7.51 (2 H, d, J=6.78 Hz), 7.81 (1 H, s), 9.16 (1 H, s), 9.97 (1 H, br. s.).

354795-62-3, The synthetic route of 354795-62-3 has been constantly updated, and we look forward to future research findings.

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;,
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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

To a solution of CH3ONHCH3.HC1 (780 mg) and acid chloride (1 g) in CH2C12 at 0 C. was added dry pyridine (1.35 ml) to afford a heterogenous mixture The solution was warmed to room temperature and stirred overnight. 1 M HC1 was added to the reaction and the organic layer was separated, washed with brine, dried with Na2SO4, filtered, and concentrated in vacuo to give 1 g of product (85%).

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

Reference£º
Patent; Schering Corporation and Pharmacopeia, Inc.; US2004/147559; (2004); A1;,
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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.

110256-15-0, To a solution of 5-cyclopropylisoxazole-3-carboxylic acid (650 mg, 4.24 mmol) in DMF (2 mL) were added N,O-dimethylhydroxylamine hydrochloride (497 mg, 5.09 mmol), DIPEA (2.22 mL, 12.73 mmol) and 1-propanephosphonic anhydride (3.75 mL, 6.37 mmol) at room temperature. The reaction mixture was stirred at the same temperature for 16 h. The reaction mixture was diluted with water and extracted twice with ethyl acetate (20 mL). The combined organic layer was dried over Na2SO4 and evaporated under reduced pressure to dryness. The crude product was purified by flash column chromatography (Column: 24g silica; Solvent run: 0-50% EtOAc in pet ether). The product was eluted at 30% EtOAc in pet ether to yield 5-cyclopropyl-N-methoxy-N- methylisoxazole-3-carboxamide (450 mg, 2.16 mmol, 50.8 % yield). LCMS: m/z, 197.1 (M+H); rt 1.07 min; Column: Waters Acquity UPLC BEH C18 (2.1 x 50 mm) 1.7 mm, Mobile phase A: 10 mM ammonium acetate:acetonitrile (95:5); Mobile phase B: 10 mM ammonium acetate:acetonitrile (5:95), Gradient = 20-90 % B over 1.1 minute, then a 0.6 minute hold at 90 % B; Temperature: 50 C; Flow rate: 0.7 mL/min; Detection: UV at 220 nm

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; CHUPAK, Louis S.; DARNE, Chetan Padmakar; DING, Min; GENTLES, Robert G.; HUANG, Yazhong; KAMBLE, Manjunatha Narayana Rao; MARTIN, Scott W.; MANNOORI, Raju; MCDONALD, Ivar M.; OLSON, Richard E.; RAHAMAN, Hasibur; JALAGAM, Prasada Rao; ROY, Saumya; TONUKUNURU, Gopikishan; VELAIAH, Sivasudar; WARRIER, Jayakumar Sankara; ZHENG, Xiaofan; TOKARSKI, John S.; DASGUPTA, Bireshwar; REDDY, Kotha Rathnakar; RAJA, Thiruvenkadam; (0 pag.)WO2020/6018; (2020); A1;,
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1228690-37-6, (R)-1-Phenylethyl (5-(4-bromophenyl)-3-methylisoxazol-4-yl)carbamate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1228690-37-6

Step 3: {4′-[3-Methyl-4-((R)-l-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-4-yl}- acetic acid ethyl ester[00484] [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)- 1 -phenyl-ethyl ester (39g, 97.2mmol), [4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (31g, 107mmol), and sodium bicarbonate (32.6g, 389mmol) were combined in 3: 1 DME:H20 (500mL), and the mixture was purged with N2 for 15 minutes. (l,l’-Bis(diphenylphosphino)ferrocene)- dichloropalladium(II) (2.13g, 2.91mmol) was added, and the reaction was purged with N2 for an additional 10 minutes and then stirred at 90C overnight. The mixture was partitioned between EtOAc and H20, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with H20, dried over MgS04, filtered, and concentrated, and the residue was purified by silica gel chromatography (EtOAc/hexane gradient) to give the title compound.

As the paragraph descriping shows that 1228690-37-6 is playing an increasingly important role.

Reference£º
Patent; AMIDRA PHARMACEUTICALS, INC.; BRITTAIN, Jason, Edward; SEIDERS, Thomas, Jon; KING, Christopher, David; WO2011/159550; (2011); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Et3N (5.6 mL, 42 mmol) and HATU (4.84 g, 13 mmol) were added to a mixture of ethyl trans-3-aminocyclobutane-1-carboxylate hydrochloride (1.89 g, 10 mmcl) and 5-phenyliscxazcle-3-carbcxylic acid (2 g, 10 mmcl) in THF (200 mL) at room temperature and the reaction mixture was stirred for 6 h at room temperature. Volatiles were removed under reduced pressure to get the crude compound. The reaction mixture was diluted with water (100 mL) and extracted using ethyl acetate (2 x 75 mL). Combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. Themixture was purified by flash column chromatography using 30% EtOAc in hexane as eluent to give the product (2.65 g, 80 %) as white solid. ?H NMR (400 MHz, CDC13) : oe 7.80-7.77 (m, 2H), 7.49-7.46 (m, 3H), 7.00 (d, J= 7.2 Hz, 1H), 6.94 (s, 1H), 4.79-4.73 (m, 1H), 4.17 (q, J=7.1 Hz, 2H), 3.10-3.09 (m, 1H), 2.78-2.72 (m, 2H), 2.40-2.32 (m, 2H), 1.30-1.26 (t, J 7.2 Hz, 3H). LC-MS: [M+H] + 315.2

14441-90-8, The synthetic route of 14441-90-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
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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;,
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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;,
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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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