Category: Isoxazoles

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

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. Mp 73-74 C. Anal. Calcd for C22H17F6NO2S (%): calcd C, 55.81; H, 3.62; N, 2.96. Found C, 55.93; H, 3.69; N, 2.93; 1H NMR (400 MHz, CDCl3, TMS): delta 2.02 (d, 6H, J=8.0 Hz, -CH3), 2.23 (s, 3H, -CH3), 3.84 (s, 3H, -OCH3), 6.92 (d, 2H, J=8.0 Hz, benzene-H), 7.11 (s, 1H, thiophene-H), 7.45 (d, 2H, J=8.0 Hz, benzene-H); 13C NMR (100 MHz, CDCl3, TMS): delta 10.70, 12.09, 14.43, 55.40, 105.09, 114.28, 114.48, 120.92, 124.84, 125.85, 127.03, 128.38, 140.15, 142.97, 158.58, 159.76, 169.54; IR (nu, KBr, cm-1): 457, 503, 544, 744, 808, 823, 895, 985, 1036, 1063, 1105, 1136, 1182, 1248, 1277, 1340, 1400, 1512, 1550, 1608, 1658, 2169, 2854, 2930, 3439, 3526.

As the paragraph descriping shows that 10557-85-4 is playing an increasingly important role.

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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54593-26-9, 3,5-Dimethyl-4-isoxazolecarbaldehyde is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (2.0 g, 4.64 mmol, Intermediate 10: step d) was added THF (65 mL) at room temperature which resulted in a colorless homogeneous mixture. The solution was cooled to -70 C. which remained homogeneous and then n-BuLi (2.5 M in hexanes, 2.1 mL, 5.25 mmol) was added dropwise. The color of the solution became a dark opaque reddish-brown color. After 2 minutes, 3,5-dimethylisoxazole-4-carbaldehyde (705 mg, 5.63 mmol in 2 mL THF) was introduced. The reaction mixture immediately became a homogeneous yellow solution. After 25 minutes the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous layer was extracted with EtOAc (3*50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to afford a faint yellow oil. FCC on silica gel (100% DCM increasing to 20% CH3CN-DCM) afforded the title compound as an off white amorphous solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.17 (s, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.56-7.48 (m, 3H), 7.39 (d, J=8.1 Hz, 2H), 5.96 (d, J=3.2 Hz, 1H), 4.35 (s, 2H), 4.07 (s, 3H), 2.34 (s, 3H), 2.32 (br. s, 1H), 2.10 (s, 3H). MS (ESI): mass calcd. for C24H20ClF3N2O3, 476.1; m/z found, 476.9 [M+H]+.

54593-26-9 3,5-Dimethyl-4-isoxazolecarbaldehyde 289576, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; US2015/105372; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3405-77-4,5-Methylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

a 5-Methyl-3-isoxazolecarboxylic Acid 2-(Pyrido[3,4-d]pyridazin-4(3H)-one-1-yl)hydrazide 1-Hydrazinopyrido[3,4-d]pyridazin-3(4H)-one [prepared by the method of K. Kormendy, T. Kovacs, F. Ruff and I. Kovesdi, Acta Chim. Hung., 1983, 112(4), 487] (1.72 g, 9.7 mmol), triethylamine (1.36 ml, 9.7 mmol), 5-methylisoxazole-3-carboxylic acid (1.23 g, 9.7 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic acid (2.48 g, 9.7 mmol) in 1,2-dichloroethane (60 ml) were heated at reflux under nitrogen for 18 h. The mixture was allowed to cool and diluted with water (20 ml). The precipitate was filtered off and washed successively with water (2*50 ml) and diethyl ether (2*50 ml) to give the title compound (2.2 g, 79percent), 1H NMR (400 MHz, d6 DMSO) delta 2.50 (3H, s, Ar-CH3), 6.62 (1H, s, Ar-H), 8.04 (1H, d, J=5.5 Hz, Ar-H), 9.10 (1H, d, J=5.5 Hz, Ar-H), 9.11 (1H, s, Ar-H), 9.45 (1H, s, NH), 10.62 (1H, s, NH), 12.08 (1H, s, NH).

As the paragraph descriping shows that 3405-77-4 is playing an increasingly important role.

Reference£º
Patent; Merck Sharp & Dohme Ltd.; US6613766; (2003); B1;,
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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.

3,5-Dimethylisoxazole-4-carboxylic acid (0.53 g), dicyclohexylcarbodiimide (1.55 g), HOBT (0.675 g) were dissolved in 30 ml of THF, and stirred for 10 minutes, then 1 g of compound 9 was added. The reaction was carried out under nitrogen for 12 hours.After the completion of the reaction, the reaction mixture was evaporated to dryness crystals crystals crystalsSpin over the column to give a white solid 0.32 g.The yield was 80%.

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

Reference£º
Patent; China Pharmaceutical University; Xiang Hua; Qiu Rongmao; Huang Ali; Zheng Fan; Li Haolin; Yang Qizhen; Hu Weikang; Zhang Jin; Liu Man; Chen Mingqi; Chen Deying; You Qidong; (9 pag.)CN107987116; (2018); A;,
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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

The compound obtained in Example 1, performed in the 10ml flasks 2 Hydra possess -N, N- bis (2,2,2-trifluoro-ethyl) -4 (trifluoro Methyl) quinoline-6-amine 100mg (0.247mmol) into a 4-methyl-1,3-oxazole-5-carboxylic acid 31.4mg (0.247mmol) in dichloromethane And dissolved by stirring into a 2ml. 42ul of triethylamine (0.296mmol) and then the insert isoxazole-5-carbonyl chloride Put 24ul (0.247mmol) was stirred for 5 hours at room temperature. After the completion of the reaction by concentration under reduced pressure and column separation title compound 25mg (20%) was obtained

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

Reference£º
Patent; DONG-A ST CO., LTD.; CHOI, SUNG PIL; CHOI, SEUL MIN; SON, BYOUNG HWA; KIM, HYUN JUNG; KIM, JU MI; JANG, BYUNG JUN; SUNG, JI HYUN; LEE, JI HYE; KIM, EUN JIN; KANG, KYUNG KOO; KIM, SOON HOE; (56 pag.)KR2015/123006; (2015); A;,
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21169-71-1, Isoxazole-5-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 55.2-(6-Fluoro- 1 -methyl- 1 H-indazol-3 -yl)-5H-pyrrolo [2,3 -b]pyrazine-7-carboxylic acid (1 – isoxazol-5 – l-ethyl)-amideIn a round-bottomed flask, isoxazole-5-carboxylic acid (1.0 g, 8.84 mmol) was dissolved in THF (35 ml). The solution was cooled to 0C and triethylamine (1.4 ml, 10.0 mmol) was added followed by ethyl chloroformate (0.94 ml, 9.8 mmol). A thick precipitate was formed upon the addition of the latter. The suspension was stirred at 0C for 15 min then a solution of sodium borohydride (1.00 g, 26.5 mmol) in water (14 ml) was added portionwise via pipet. Vigorous gas evolution was observed. The reaction mixture was stirred at 0C for 1 h then diluted with water and saturated aqueous NH4C1 and extracted with dichloromethane (3x). The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue waschromato graphed over silica gel with EtOAc/hexanes (gradient 0-50% EtOAc) to afford 513 mg (59%) of isoxazol-5-yl-methanol as a colorless oil. 1H NMR (CDC13, 300 MHz): ? (ppm) 8.23 (d, J=1.9 Hz, 1H), 6.26 – 6.30 (m, 1H), 4.82 (s, 2H), 2.13 (br. s., 1H).

As the paragraph descriping shows that 21169-71-1 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O’YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu; WO2013/30138; (2013); A1;,
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4369-55-5, 5-Amino-3-phenylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a 100ml four-necked flask, 3-phenyl-5-aminoisoxazole and benzisothiazolin-3-one-2-yl acetic acid, Its molar ratio is 1:1.1, Dissolve with DMF (N,N-dimethylformamide), Adding HOBT (1-hydroxybenzotriazole) and EDCI [1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride], The molar ratio of HOBT, EDCI and 3-phenyl-5-aminoisoxazole was 1:1:1, and the reaction was completed at 25 ¡ã C for 26 h. The solution was poured into water and a large amount of solid was precipitated. Filtration, caustic washing, pickling, and washing. The crude product was obtained by column chromatography (ethyl acetate: petroleum ether = 1 : 1.1). Yield: 68.5percent. Melting point: 189 to 191 ¡ãC.

The synthetic route of 4369-55-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nanjing Tech University; Yu Peng; Liu Biming; Pan Jian; Li Xi; Xu Yanhua; (10 pag.)CN109535153; (2019); A;,
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3405-77-4, 5-Methylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[00261] Isobutyl chloroformate (0.281 g, 2.06 mmcl) was added dropwise to a solution of 5-methylisooxazole-3-carboxylic acid (0.25 g, 1 .7 mmol) in THE (2.5 mL), followed by addition of N-methylmorpholine (0.208 g, 2.06 mmol). The reaction mixture was stirred at rt for 30 mm and then filtered to remove solids. In a separate flask, a solution of LHMDS (1 .3 M in THE, 2.6 mL, 3.4 mmol) was added dropwise to a solution of tert-butyl (S)-2-methyl-4-oxopiperidine-1- carboxylate (0.37 g, 1 .7 mmol) in THE (2.5 mL) at 0 00 under a nitrogen atmosphere. The reaction was stirred at 0 00 for 1 0 mm and then cooled to -78 00. To this reaction mixture, the filtrate containing the mixed anhydride from the first flask was added dropwise at -78 00. After the addition was complete, the reaction mixture was stirred at rt for 2 h. The reaction mixture was then acidified with aqueous 1 N HCI. The mixture was extracted with EtOAc (twice). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give a mixture of crude tert-butyl (2S)-2-methyl-5-(5-methylisoxazole-3-carbonyl)-4-oxopiperidine- 1- carboxylate and tert-butyl (2S) -2-methyl-3-(5-methylisoxazole-3-carbonyl)-4-oxopiperidine- 1- carboxylate (0.43 g) which was used without further purification. MS m/z 323.5 (M+H).

As the paragraph descriping shows that 3405-77-4 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; FU, Jiping; LINDVALL, Mika; MANNING, James R.; MCENROE, Glenn; (103 pag.)WO2019/97479; (2019); 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

A solution of (S)-N- [2-OXO-3- (6-OXO-6, 7,8, 9-tetrahydro-5H- BENZOCYCLOHEPTEN-2-YL)-OXAZOLIDIN-5-YLMETHYL]-ACETAMIDE (500 mg, 1.58 mmol) in THF (15 mL) was cooled to 0 C and 1 M solution of LiHMDS in THF (3.32 mL, 3.32 mmol) was added. The mixture was stirred at 0 C for 30 minutes then ISOXAZOLE-5-CARBONYL chloride (257 mg, 1.90 mmol) was added dropwise as a solution in THF (10 ML) over 50 minutes After warming to room temperature overnight, the mixture was worked up with saturated ammonium chloride, extracted with dichloromethane, dried over sodium sulfate and concentrated in vacuo. The resulting oil was purified with column chromatography to result in the title compound. Isolated yield: 269 mg (41% Y). MS-APCI (m/z+): 412 (M+H).

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

Reference£º
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/69832; (2004); A2;,
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1136-45-4, 5-Methyl-3-phenylisoxazole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 5-methyl-3-phenylisoxazole-4-carboxylic acid (8.00 g, 39.4 mmol) and DMF (200 mL) was cooled to 0-10 C. N,N-Diethyl-p-phenylenediamine (6.47 g, 39.4 mmol) and O-ibenzotriazol- l-yl)-N,N,N’,N’ -tetramethyluronium tetrafluoroborate (TBTU, 15.17 g, 47.3 mmol, 1.2 equiv.) were added to the reaction mixture and the mixture was stirred at 0-10 C for 10 min. Nu,Nu-Diisopropylethylamine (DIPEA, 6.11 g, 47.3 mmol, 1.2 equiv.) was slowly added, and the mixture was stirred at 0-10C for 2.5 h. Ethyl acetate (400 mL) and a 5% aqueous NaHC03-solution (160 mL) were added to the reaction mixture and the mixture was stirred at ambient temperature for 15 min. The layers were separated and the organic phase was washed with water (3 x 200 mL) and brine (180 mL). The organic layer was dried with sodium sulphate, the drying agent was filtered off and the solution was evaporated to dryness to give 12.8 g of the crude product. The crude product was dissolved in warm ethyl acetate (300 mL) and activated carbon (0.5 g) was added to the solution. The mixture was stirred for 20 min and filtered through Celite. n-Heptane (120 mL) was added to the previous solution at 55 C and the mixture slowly cooled to 0-5 C. The precipitated product was filtered off, washed with n-heptane (2 x 50 mL) and dried in vacuo at 45 C overnight to give 8.52 g (62 %) off-white powder. M.p. 139.3-140.2 C. 1H NMR (200 MHz, DMSO-d6) delta 10.12 (s, 1H, NH), 7.71 (m, 2H, arom), 7.50-7.35 (m, 5H arom.), 6.63 (d, 2H, arom.), 3.30 (q, 4H, 2 x CH2), 2.55 (s, 3H, CH3), 1.05 (t, 6H, 2 x CH3) ppm. MS: m/z 350.2 (100%, M+l), 351.2 (25%).

The synthetic route of 1136-45-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITY OF HELSINKI; UNIVERSITY OF OULU; KINNUNEN, Sini; TOeLLI, Marja; VAeLIMAeKI, Mika; JUMPPANEN, Mikael; BOIJE AF GENNAeS, Gustav; YLI-KAUHALUOMA, Jari; RUSKOAHO, Heikki; (75 pag.)WO2018/55235; (2018); A1;,
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