Heterocyclic Building Blocks-isoxazole

88511-37-9, 1-(Isoxazol-3-yl)ethanone is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,88511-37-9

Step 2:Pyrazole formation: Dione enolate B was diluted with ethanol and consecutively charged with HCI (e.g., 3 equiv, 1.25 M solution in ethanol) and arylhydrazine hydrate (e.g., 1.15 equiv). The reaction mixture was heated to 70 C and stirred at this temperature until cyclization was deemed complete (e.g., by LC/MS analysis, typically 30 minutes). Once complete, the reaction mixture was treated carefully with solid sodium bicarbonate (e.g., 4 equiv) and diluted with dichloromethane and water. Layers were separated, and aqueous layer was futher diluted with water before extraction with dichloromethane (3x). The combined organics were washed with brine, dried over MgS04, filtered, and concentrated in vacuo. The resulting pyrazole C was then purified by S1O2 chromatography using an appropriate gradient of EtOAc in hexanes.

The synthetic route of 88511-37-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IRONWOOD PHARMACEUTICALS, INC.; RENNIE, Glen Robert; PERL, Nicholas; LEE, Thomas Wai-Ho; RENHOWE, Paul Allan; NAKAI, Takashi; MERMERIAN, Ara; IM, G-Yoon Jamie; (235 pag.)WO2016/44445; (2016); 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.21169-71-1,Isoxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: Compounds were synthesized in solution phase using Boc-protected amino acids on 100-200mg scale. Firstly, the amino acid (1.2-1.5equiv) was activated with HBTU (1.5equiv) and DIPEA (1.5equiv) as 0.2-0.5M solution in DMF for 10min. Then the solution was added to an amino group bearing C-terminal moiety (R1R2NH) and the mixture was stirred for a minimum of 1h at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (2¡Á). The organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude product was then treated with 20% TFA in DCM and stirred for 1-2h to remove the Boc group. TFA was removed by evaporating the reaction mixture under a stream of N2. The residue was dissolved in DCM and washed with saturated NaHCO3 (2¡Á). DCM phase was dried with MgSO4, filtered and evaporated in vacuo. Subsequent N-Boc-amino acids and amines were sequentially coupled under the same conditions. Each coupling reaction was monitored by ESMS, with most reactions going to completion overnight. All final compounds were purified on rpHPLC (97% by analytical HPLC) and fully characterized by NMR and HRMS (yields between 30% and 40%).

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

Reference£º
Article; Yau, Mei-Kwan; Liu, Ligong; Lim, Junxian; Lohman, Rink-Jan; Cotterell, Adam J.; Suen, Jacky Y.; Vesey, David A.; Reid, Robert C.; Fairlie, David P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 986 – 991;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

108655-63-6, 3-(Trifluoromethyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution OF 3- (TRIFLUOROMETHYL) isoxazol-5-amine (0.08 g, 0.55 mmol) in DMF (10 ML) is added NaH 60% dispersion in mineral oil (0.02 g, 0.55 MMOL). After stirring the mixture at RT for 15 min phenyl 4-METHOXY-2- (1, 3-OXAZOL-2- yl) phenylcarbamate (0.17 g, 055 mmol) is added and the reaction mixture is heated at 50oC for 30 min. The mixture is neutralized with 0. 1M HCl, extracted with EtOAc, and the combined organic layers are dried (MGS04), filtered, and concentrated under vacuum. The residue is triturated with CH2CL2/N-HEXANES to afford Example 16 as a white solid 0.131 g (65%). HRMS (ESI) calcd for C15HLLN404F3+H 369. 0811, found 369.0803.

108655-63-6, The synthetic route of 108655-63-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/85433; (2004); 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.1136-45-4,5-Methyl-3-phenylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

5-Methyl-3-phenylisooxazole-4-carboxylic acid (40 mg, 0.197 mmol), piperazine acetic acid pyrrolidid (42.4 mg, 0.215 mmol), O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (86.2 mg, 0.268 mmol) and diisopropylethylamine (25.4 mg, 0.197 mmol) were mixed in dimethylformamide (1.5 mL) and stirred at room temperature. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The combined fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C21H26N4O3: 382.2005, found 382.2016., 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; Amgen Inc.; Biovitrum AB; US2008/21022; (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.1083224-23-0,5-(2,4-Difluorophenyl)isoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: To a solution of rac-(3R*,4R*)-4-amino-1-benzyl-piperidine-3-carboxylic acid methyl ester (10.00 g, 33.4 mmol) in DMF (200 mL) is added 5-(2,4-difluorophenyl)isoxazole-3-carboxylic acid (7.74 g, 33.4 mmol). DIPEA (24.5 mL, 140 mmol) is then added followed by HATU (13.32 g, 35 mmol). The reaction mixture is stirred for 1 h. The reaction mixture is concentrated, diluted with DCM (750 mL) and treated with aq. sat. NaHC03 (600 mL). The organic layer is dried over MgS04 and evaporated. The crude residue is purified by prep. LC- MS in basic conditions to give the title compound; LC-MS method D tR = 1.14 min; [M+H]+ = 456.18.

1083224-23-0, The synthetic route of 1083224-23-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IDORSIA PHARMACEUTICALS LTD; AISSAOUI, Hamed; GUERRY, Philippe; LEHEMBRE, Francois; POTHIER, Julien; POUZOL, Laetitia; RICHARD-BILDSTEIN, Sylvia; YUAN, Shuguang; (273 pag.)WO2018/19929; (2018); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

36958-61-9, 5-(Bromomethyl)-3-methylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Potassium hydroxide (1.588 g) was added to a solution of 6-bromo-2-methyl-1H-imidazo[4,5-b]pyridine (2 g), 5-(bromomethyl)-3-methylisoxazole (1.8 g) and TBAI (3.48 g) in THF at 60C. The mixture was stirred under a nitrogen atmosphere at 60C for 2 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was sequentially washed with water and a saturated brine, then dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (0.89 g). 1H NMR (300 MHz, DMSO-d6) delta 2.18 (3H, s), 2.63 (3H, s), 5.71 (2H, s), 6.38 (1H, s), 8.40-8.42 (1H, m), 8.42-8.46 (1H, m)., 36958-61-9

36958-61-9 5-(Bromomethyl)-3-methylisoxazole 10607354, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; KAWAKITA Youichi; KOJIMA Takuto; NII Noriyuki; ITO Yoshiteru; SAKAUCHI Nobuki; BANNO Hiroshi; LIU Xin; ONO Koji; IMAMURA Keisuke; IMAMURA Shinichi; (165 pag.)EP3450436; (2019); 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.21169-71-1,Isoxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

Boc protected amine Ba (35 mg, 0.044 mmol) is charged in a vial, then a 4 M solution of HCI in dioxane (1 mL, 4 mmol) is added. The solution is stirred at RT for 2 h, after which a precipitate forms. The solution is evaporated to dryness. Acid R2o (6.5 mg, 0.057 mmol, 1 .30 equiv) is dissolved in DMF (0.5 mL), then TEA (30 mu, 0.22 mmol, 5.0 equiv) is added followed by TBTU (17 mg, 0.53 mmol, 1 .2 equiv). The solution is stirred for 15 mins, after which the amine hydrochloride Da is added in DMF (0.5 mL). This solution is stirred at RT for 16 h. Water (2 mL) is added and the organic layer is extracted with EtOAc (3 x 5 mL). The solvent is evaporated and the residue is purified on prep HPLC (MeCN:H20, 0.1 % TFA). The pure fractions are combined, concentrated, frozen and lyophilized to provide compound 1032. FIA M.S.(electrospray) : 793.4 (M+H)+ Retention time (min) = 5.6 min1H NMR (400 MHz,DMSO-d6): delta 11.03 (s, 1H), 9.13 (d, 1H, J = 6.6 Hz), 8.80 (s, 1H), 8.72 (d, 1H, J = 2.1 Hz), 7.86 (d, 1H, J = 9.1 Hz), 7.11 (d, 1H J = 2 Hz), 7.10 (d, 1H, J = 9.2 Hz), 6.36 (s, 1H), 5.67-5.59 (m, 1H), 5.55-5.44 (m, 2H), 5.14 (dd, 1H, J = 10.1, 8.7 Hz), 4.60-4.51 (m, 2H), 4.36 (dd, 1H, J = 9.9, 7.0 Hz), 4.01 (dd, 1H, J = 11.7, 3.5 Hz), 3.89 (s, 3H), 2.94-2.87 (m, 1H), 2.69-2.56 (m, 2H) , 2.44 (s, 3H), 2.41- 2.31 (m, 2H), 2.07-1.95 (m, 1H), 1.83-1.71 (m, 1H), 1.60-1.35 (m, 13H), 1.33-1.19 (m, 2H), 1.12-0.99 (m, 4H).

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET , Montse; BORDELEAU, Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63502; (2011); 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.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

To a stirred suspension of LAH in THF (10 mL, 1M solution in THF) at 0 C. was added a solution of 5-phenylisoxazole-3-carboxylic acid (0.9 g in 5 mL of THF) and after completion of addition the reaction was slowly warmed to room temperature (30 min). The reaction mixture was cooled to 0 C. and ethyl acetate was added (30 mL), followed by slow addition of saturated sodium sulfate solution. The solid was rinsed with ether several times and the solvent decanted. The combined organic layer was dried over MgSO4, filtered and concentrated in vacuo to get (5-phenylisoxazol-3-yl)methanol (0.8 g, 96% yield)., 14441-90-8

14441-90-8 5-Phenylisoxazole-3-carboxylic acid 151916, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; VICURON PHARMACEUTICALS INC.; US2006/211603; (2006); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

7063-99-2, Ethyl 5-phenylisoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7063-99-2, A solution of phenyl-substituted isoxazole ethyl ester (53) (1.89 g, 8.70 mmol) in ethanol (30 mL) was stirred at room temperature. To this solution was added a 2 M NaOH solution (6.5 mL, 13.1 mmol). After 5 min, TLC showed that the reaction was complete. To the reaction mixture was added 0.5 M HCl to adjust the pH to 34, before extracting with ethyl acetate (2¡Á75 mL). The organic extracts were combined, washed with brine, dried over sodium sulfate, and concentrated to afford 5-phenyl-isoxazole-3-carboxylic acid (57) obtained as a white solid (1.54 g, 94%). 57: 1H NMR (500 MHz, CDCl3): delta 9.4 (broad, 1H), 7.83 (d, 2H), 7.51 (m, 3H), 6.99 (s, 1H)

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

Reference£º
Patent; Chapal, Nicolas; McNicol, Patricia; Jette, Lucie; US2006/223884; (2006); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

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

(Step 1) Production of ethyl 3-(5-methyl-isoxazol-3-yl)-3-oxo-propionate To a suspension of 5-methyl-isoxazole-3-carboxylic acid (2.78 g) in tetrahydrofuran (20 mL) was gradually added CDI (3.60 g). After stirring at room temperature for 30 minutes, the reaction mixture was heated on an oil bath to 60¡ã C. After 1 hour, the reaction mixture was cooled to room temperature, magnesium chloride (2.30 g) was added followed by addition of ethyl potassium malonate (4.50 g). After stirring at room temperature for 3 hours, water (15 mL) was added to the reaction mixture followed by addition of 6 N hydrochloric acid (5.0 mL). The reaction mixture was concentrated, and the produced solid was collected by filtration, washed with water, and dried to obtain the title compound (3.99 g) as a white solid., 3405-77-4

3405-77-4 5-Methylisoxazole-3-carboxylic acid 76947, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; JAPAN TOBACCO, INC.; US2009/36450; (2009); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem