Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3209-70-9,Ethyl isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.,3209-70-9

(i) The preparation of 3-aminomethylisoxazole is described below: Di-isobutylaluminium hydride (1.5M in toluene, 29 ml) was added to a solution of ethyl isoxazole-3-carboxylate (6.1 g; Can. J. Chem., 1970, 48, 475) in toluene (20 ml) which was cooled in an ice-bath. The mixture was stirred at laboratory temperature for 16 hours. The analysis indicated that the reduction was incomplete. A second portion of di-isobutylaluminium hydride (28.8 ml) was added and the mixture was stirred for 16 hours. The bulk of the toluene was evaporated and the mixture was poured into a saturated aqueous ammonium chloride solution. The precipitate was filtered off and dried. There was thus obtained 3-hydroxymethylisoxazole (2.1 g).

The synthetic route of 3209-70-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Imperial Chemical Industries PLC; National Research Development Corporation; US5089499; (1992); A;,
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59669-59-9, 3-(tert-Butyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,59669-59-9

Step 7: Synthesis of compound D-8Activation of 60 g (0.25 mol) of compound D-7as the corresponding acid chloride is achieved by treatment with thionyl chloride (0.9 L, 12.39 mol) at 60 ¡ãC for 1.5 h. The reaction is cooled to room temperature and acid chloride mixture was evaporated to dryness. The acid chloride mixture is dissolved in DCM (200 mL).This acid chloride solution is added dropwise over 20 mins to a stirred suspension of 36 g (0.25 mol) of 3-tert-butyl-isoxazol-5-ylamine and 0.6 L (0.50 mol) of N,N- diisopropylethylamine in DCM (400 mL) at 35 ¡ãC. After complete addition the reaction is stirred at room temprature for 17 h. The solvent is removed under reduced pressure. The residue is purified by dry-flash column chromatography (silica, eluent heptanes, 20percent ethyl acetate) to yield 50 g of light brown solid. Solid is re-crystallized from (50percent IPA in heptane) to afford 34 g of compound D-8 Yield: 43percent; ES-MS: m/z 359 [M+H];’H-NMR (400 MHz, CHLOROFORM-d) delta ppm 1.33 (9 H, s), 1.76 (6 H, s), 1.83 – 1.91 (2H, m), 1.92 – 2.05 (2 H, m), 3.34 – 3.51 (3 H, m), 4.07 (2 H, ddd, 7=11.86, 2.20, 2.08 Hz), 6.27 (1 H, s), 9.60 (1 H, s)

The synthetic route of 59669-59-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HICKEY, Eugene Richard; RIETHER, Doris; ERMANN, Monika; WO2012/12307; (2012); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.87988-94-1,5-Methylisoxazol-4-amine,as a common compound, the synthetic route is as follows.,87988-94-1

EXAMPLE 2 4-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (3-methylisoxazole-4-yl)-amide Starting from 4-difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (150 mg) and 5-methylisoxazol-4-ylamine (60 mg). Purification by column chromatography on silica eluding with 50% ethyl acetate in heptane afforded the title compound as a white solid (110 mg). TLC Rf 0.32 (ethyl acetate). M.p. 103-104.5 C.

The synthetic route of 87988-94-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Darwin Discovery, Ltd.; US6403791; (2002); B1;,
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89102-73-8, Isoxazol-3-ylmethanol is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,89102-73-8

(b) 3-Chloromethyl isoxazole A solution of 3-hydroxymethyl isoxazole (4.23 g, 43 mmol) and triphenylphosphine (11.3 g, 42 mmol) in carbon tetrachloride (100 ml) was heated at reflux for 18 h. Solvent was removed under reduced pressure then the residue taken up in ether and filtered. The filtrate was concentrated under reduced pressure and further purified by short path distillation (bp 60 C. at 10 mm) to give the desired chloride (1.41 g, 12 mmol, 28%); deltaH (CDCl3) 4.50 (2H, s, CH2 –Cl), 6.40 (1H, d, J 2 Hz, CH-4), 8.40 (1H, d, J 2 Hz, CH-5).

The synthetic route of 89102-73-8 has been constantly updated, and we look forward to future research findings.

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.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) r3-(4-Fluorophenyl)-5-methyl-isoxazol-4-yll -methanol Alternative 2) Preparation by reduction of the ethyl ester (i) with L1AIH4 as reducing agent: To a suspension of LiAlH4 (75.9 mg, 2.0 mmol) in THF (2 mL) was added at 0-10C within 15 minutes a solution of 3-(4-Fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (0.50 g, 2.0 mmol) in THF (3 mL) and the resulting solution was allowed to warm to room temperature and subsequently stirred at this temperature for at least one hour. Water (15 mL) was added dropwise and the resulting suspension was then filtered and the filter cake washed with ethyl acetate (15 mL). From the biphasic filtrate the layers were separated and the organic layer was washed with water (1×15 mL). Both combined aqueous layers were back extracted with ethyl acetate (2×15 mL). The combined organic layers were dried over Na2S04 and subsequently concentrated to dryness (45C/25 mbar) to afford 0.375 g (90%) of the title compound as a slightly yellow solid with a purity of 100% (by HPLC).

The synthetic route of 954230-39-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; DOTT, Pascal; HANLON, Steven Paul; HILDBRAND, Stefan; IDING, Hans; THOMAS, Andrew; WALDMEIER, Pius; WO2013/57123; (2013); A1;,
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954230-39-8, Ethyl 3-(4-fluorophenyl)-5-methylisoxazole-4-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,954230-39-8

o 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 mu) added followed by sodium hydroxide (15% solution, 518 mu) 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 (Si02, 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]+.

The synthetic route of 954230-39-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; DOTT, Pascal; GRASSMANN, Olaf; KAMMERER, Michael; MANNS, Joachim; SCHWITTER, Urs; THOMAS, Andrew; WYTTENBACH, Nicole; WO2013/57124; (2013); A1;,
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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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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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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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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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