Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.89102-73-8,Isoxazol-3-ylmethanol,as a common compound, the synthetic route is as follows.,89102-73-8

A mixture of 10.0 g (100.9 mmol) isoxazol-3-ylmethanol and THF is cooled to 0C and 4.0 g (100.9 mmol) 60% NaH are added in small portions. The reaction mixture is stirred for 45 min, and then 16.4 g (84.6 mmol) 2-chloro-5-bromo-pyrimidine in DMF is added. The reaction mixture is stirred for 45 min at RT, then cooled to 0C and diluted with water. The precipitate is filtered off, washed with water and dried yielding 20.1 g 3-[(5-bromopyrimidin-2-yl)oxymethyl]isoxazole .

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BLUM, Andreas; GODBOUT, Cedrickx; HEHN, Joerg, P.; PETERS, Stefan; (74 pag.)WO2017/194453; (2017); A1;,
Isoxazole – Wikipedia
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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

Example 41c 3,5-Dimethyl-4-((4-nitro-1H-pyrazol-1-yl)methyl)isoxazole 1H-Pyrazole (10 g, 147 mmol) was added in small portions to concentrated H2SO4 (100 mL), cooled to 0 C. via an ice/water bath, maintaining the internal reaction temperature below 40 C. Concentrated HNO3 (10 mL) was carefully added, dropwise, to the reaction mixture maintaining the internal reaction temperature below 55 C. The reaction was then heated to 55 C. and stirred for 5 hours. The mixture was cooled to 0 C. and carefully made basic (pH-8) with aqueous NaOH solution (110 g NaOH in 150 mL H2O) until a white precipitate formed, carefully ensuring the internal temperature of the solution remain below 40 C. The white solid was collected by filtration and washed with ethyl acetate/hexanes (1/3) then dried en vacuo to afford 4-nitro-1H-pyrazole (7 g, 42%, isolated yield). 13C NMR (DMSO-d6, 100 MHz) delta 137.0, 126.4. To 4-nitro-1H-pyrazole (9 g, 80 mmol) in DMF (100 mL) was added cesium carbonate (26 g, 80 mmol) followed by the addition of 4-(chloromethyl)-3,5-dimethylisoxazole (12.3 g, 85 mmol). The reaction mixture was stirred in DMF (100 mL) at 80 C. for 30 minutes, then cooled, diluted with H2O (150 mL) and extracted with ethyl acetate (3*, 75 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was taken up in ethyl acetate (200 mL) and washed with H2O (2*, 100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The solid product was triturated with ethyl acetate/hexanes (1/9) and collected by filtration. The product was dried under high vacuum to afford 3,5-dimethyl-4-((4-nitro-1H-pyrazol-1-yl)methyl)isoxazole (12 g, 67%) as a light yellow solid. 1H NMR (CDCl3, 400 MHz): delta 2.23 (s, 3H), 2.46 (s, 3H), 5.08 (s, 2H), 8.02 (s, 1H), 8.08 (s, 1H).

19788-37-5, The synthetic route of 19788-37-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SENOMYX, INC.; PATRON, Andrew; TACHDJIAN, Catherine; SERVANT, Guy; DITSCHUN, Tanya; (257 pag.)US2016/376263; (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.21169-71-1,Isoxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of the above compound (35 mg, 1.0 mmol) in DMF (1 mL), isoxazole-5-carboxylic acid (23 mg, 0.20 mmol), 1-ethyl-(3-dimethylaminopropyl)carbodimide hydrochloride (38 mg 0.20 mmol), 1-hydroxy-7-azabenzotriazole (13.6 mg, 0.10 mmol), and N,N-diisopropylethylamine were added until pH=9.5. The resulting solution was stirred at room temperature for 3 hours and then 0.3 mL of water was added. Purification was achieved by preparative HPLC on a delta-pack C18 column, 300 , pore size 15 muM with 0.05% HCl acid -aqueous acetonitrile solvent systems using various linear gradients to afford the HCl salt of the title compound as a white solid that gave a proton NMR spectrum consistent with theory and a mass ion (ES+) of 442.2 for M+H+: 1H NMR (500 MHz, DMSO-d6) delta 1.61 (d, J=6.7 Hz, 3H), 2.21 (s, 3H), 5.47 (d, 1H), 6.86 (br s, 1 H), 7.36 (d, J=1.9 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.55 (t, J=8.6 Hz, 1H), 7.83 (d, J=6.4 Hz, 1H), 7.85 (t, J=7.57 Hz, 1H), 8.86 (d, J=1.9 Hz, 1H), 10.54 (br s, 1H),, 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; Kuduk, Scott D.; Bock, Mark G.; Feng, Dong-Mei; Wai, Jenny Miu-Chun; US2004/29920; (2004); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

1072-67-9, 5-Methylisoxazol-3-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: 5-Methyl-3-aminoisoxazole (2 mmol) and aromatic aldehyde (2 mmol) were added to absolute ethanol (4~6 mL) with electromagnetic stirring for about 1 h, followed by adding p-nitroacetophenone (2 mmol) and concentrated HCl (0.1~0.2 mL) with continuous stirring. TLC monitored the reaction progress. Upon completion, the suspension was cooled overnight in a refrigerator (4C). The resulting solid was subsequently collected by filtration. The filter cake was washed successively with water (2×3 mL) and absolute ethanol (2×3 mL), dried to afford the corresponding crude product. The crude product was recrystallized in toluene or a mixed solvent of ethyl acetate and cyclohexane, dried in vacuum to give the pure product with 57.1% ~ 94.9% yields. All compounds were identified by 1H NMR, 13C NMR, ESI-MS and HR MS.

1072-67-9, The synthetic route of 1072-67-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Liu, Jinyu; Zhou, Zuwen; Liu, Jian; Yan, Jufang; Fan, Li; Tang, Xuemei; Liu, Jie; Chen, Feifei; Yang, Dacheng; Letters in drug design and discovery; vol. 16; 8; (2019); p. 835 – 845;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13999-39-8,3-Amino-4,5-dimethylisoxazole,as a common compound, the synthetic route is as follows.

[18]; 2-(6-Chlorobenzotriazol-l-yl)-l5l5353-tetramethyluronium tetrafluoroborate was used in place of 2-(7-azabenzotriazol-l-yl)-l5l53,3-tetramethyluronium hexafluorophosphate(V) as the coupling agent. The product gave the following characterising data :- 1H NMR Spectrum: (DMSOd6) 1.8 (s, 3H), 2.3 (s, 3H), 3.72 (s, 2H), 3.78 (s, 3H), 6.79 (d, IH)5 6.92 (m, IH)5 7.08 (d, IH)5 7.4 (d, IH)5 8.08 (s, IH)5 8.92 (d, IH)5 9.58 (s, IH)3 10.27 (br s, IH); Mass Spectrum: M+H+ 439 and 441.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Isoxazole – Wikipedia
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91252-54-9, Ethyl 5-(tert-butyl)isoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

91252-54-9, The title compound is prepared from S-tert-butyl-isoxazole-S-carboxylic acid ethyl ester by those skilled in the art by adaptation of a literature procedure (Kaluza et al, Tetrahedron, 2003, 59, 31,5893-5903).To a solution of S-tert-butyl-isoxazole-S-carboxylic acid ethyl ester (0.5 g, 2.54 mmol) in anhydrous tetrahydrofuran (10 mL) is added under nitrogen dibromomethane (356 muL, 0.88 g, 5.07 mmol). The mixture is cooled to -78 0C and 1.6M methyl lithium in diethyl ether (3.2 mL, 5.07 mmol) is added dropwise. The solution is stirred at -78 0C for 40 min and then quenched with acetic acid (582 muL, 610 mg, 10.16 mmol). The mixture is warmed to 0 0C and poured onto ice/water (40 mL) and extracted with tert-butyl methyl ether (3 x 40 mL). The organic layers are combined, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue is purified by chromatography on silica eluting with a heptane/dichloromethane gradient (1/0 to 1/1) to provide the title compound as a yellow oil (351 mg, 62%), m/z 246 [M+H+]. 1U NMR (400 MHz, CHLOROFORM-d) delta ppm 1.39 (9 H, s), 4.58 (2 H, s), 6.41 (1 H, s).

As the paragraph descriping shows that 91252-54-9 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/140089; (2009); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.946426-89-7,5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazole-4-methanol,as a common compound, the synthetic route is as follows.

10d) Methyl 7-[4-({[5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylate To a solution of [5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methanol (51 mg, 0.18 mmol), methyl 7-(4-hydroxyphenyl)-3-isoquinolinecarboxylate (50 mg, 0.18 mmol) and triphenylphosphine (52 mg, 0.20 mmol) in dichloromethane (1.5 mL) was added diisopropyl azodicarboxylate (0.035 mL, 0.20 mmol). The solution was heated in a microwave reactor at 90 C. for 10 minutes and then allowed to stand overnight. The mixture was adsorbed onto silica gel and purified by chromatography (silica gel, 0-1.25% methanol in dichloromethane) to afford methyl 7-[4-({[5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylate (54 mg, 55%). 1H-NMR (400 MHz, DMSO-d6) delta 9.39 (s, 1H), 8.63 (s, 1H), 8.44 (s, 1H), 8.29-8.14 (m, 2H), 7.75 (d, J=9 Hz, 2H), 7.61-7.50 (m, 3H), 6.96 (d, J=9 Hz, 2H), 4.94 (s, 2H), 3.91 (s, 3H), 2.50-2.46 (m, 1H), 1.21-1.14 (m, 4H).

946426-89-7, The synthetic route of 946426-89-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SmithKline Beecham Corporation; US2008/96921; (2008); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3209-71-0,Isoxazole-3-carboxylic Acid,as a common compound, the synthetic route is as follows.

3209-71-0, Amine 34-4 (119 mg, 0.298 mmol) was added to anhydrous dimethylformamide (3.0 mL). Isoxazole-3-carboxylic acid (33.7 mg, 0.298 mmol), EDC (57.2 mg, 0.298 mmol), EtaOmicronBetaTau (45.7 mg, 0.298 mmol) and triethylamine (83 mu, 0.596 mmol) were added sequentially and the resulting reaction mixture was allowed to stir at room temperature for 18 h. Following this duration, the contents were filtered and the resulting filtrate was purified via reverse-phase HPLC (5-95%, 0.1% TFA in H20: acetonitrile) to give 34-5 as a white solid. MS m z (M+H): calculated = 493.2170; observed = 493.2172.

The synthetic route of 3209-71-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; LAYTON, Mark, E.; PERO, Joseph, E.; RODZINAK, Kevin, J.; ROSSI, Michael, A.; WO2011/34741; (2011); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

1188032-12-3, 5-(3-Fluorophenyl)isoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 130 Synthesis of 5-(3-Fluoro-phenyl)-isoxazole-3-carboxylic acid {2-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide DIPEA (253 mg, 1.96 mmol) was added to a stirred solution 5-(3-fluoro-phenyl)-isoxazole-3-carboxylic acid (81 mg, 0.39 mmol) (prepared by the method used for the synthesis of Intermediate 25, starting from 3′-fluoroacetophenone) in DMF (2 mL) followed by HOBt (56 mg, 0.41 mmol) and EDCI.HCl (79 mg, 0.41 mmol). After 2 minutes 2-amino-1-[4-(5-Chloro-pyridin-3-yloxy)-piperidin-1-yl]-ethanone hydrochloride (120 mg, 0.38 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added to the reaction mixture and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water, extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. Purification by recrystallisation from 1% methanol in ethyl acetate to afford 35 mg (19.5% Yield) of 5-(3-fluoro-phenyl)-isoxazole-3-carboxylic acid {2-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 459, 100%. 1H NMR (300 MHz, DMSO-d6): delta 8.7 (t, 1H), 8.32 (d, 1H), 8.22 (s, 1H), 7.78 (t, 2H), 7.72 (s, 1H), 7.58 (m, 1H), 7.5 (s, 1H), 7.36 (m, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 3.9 (m, 1H), 3.7 (m, 2H), 3.4 (m, 1H), 3.2 (m, 1H), 2.0 (m, 2H), 1.6 (m, 2H).

1188032-12-3, As the paragraph descriping shows that 1188032-12-3 is playing an increasingly important role.

Reference£º
Patent; Forest Laboratories Holdings Limited; US2009/239810; (2009); A1;,
Isoxazole – Wikipedia
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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

EXAMPLE 6 6,7-Dimethoxy-3-(5-methyl-3-phenylisoxazol-4-yl)-2,4-dihydroindeno[1,2-c]pyrazole 5,6-Dimethoxy-1-indanone (1.92 g, 10 mmol) in tetrahydrofuran (10 ml) was added dropwise to a solution of lithium diisopropylamide (10 mmol) in tetrahydrofuran (10 ml) at -78 C. and stirred for 0.5 h. 5-Methyl-3-phenylisoxazole-4-carboxylic acid (1.02 g, 5 mmol) was stirred with N,N’-carbonyldiimidazole (810 mg, 5 mmol) in tetrahydrofuran (5 ml) for 1 h and then added to the dimethoxyindanone solution with 4-dimethylaminopyridine (610 mg, 5 mmol).This was stirred at -78 C. for 1.5 h and warmed to RT over 2 h then diluted with EtOAc, washed with citric acid solution, brine, dried (MgSO4) and evaporated.The resulting yellow oil was dissolved in ethanol (5 ml), saturated copper acetate solution (10 ml) was added and the precipitate formed was filtered off and washed with H2O, methanol, diethyl ether, dried (MgSO4) and evaporated.The residue was dissolved in ethanol, hydrazine hydrochloride (500 mg) and sodium acetate (1 g) and H2O were added and heated to reflux for 24 h.The solvent was evaporated, the residue dissolved in EtOAc, washed with brine, dried (MgSO4) and evaporated.Purified by prep HPLC to give the title compound (7 mg).1H NMR (360 MHz, CDCl3) delta7.52 (d, J=6.8 Hz, 2H), 7.43-7.33 (m, 5H), 3.94 (s, 3H), 3.91 (s, 3H), 3.28 (s, 2H), 2.57 (s, 3H), m/z (ES+) 374 (M+H)+.

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

Reference£º
Patent; Ladduwahetty, Tamara; MacLeod, Angus Murray; Merchant, Kevin John; Sternfeld, Francine; US2004/6226; (2004); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem