Month: September 2020

123770-62-7, Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of ethyl chlorooximidoacetate (15 g, 0.1 mol) in CH2Cl2 is added dropwise over 4 h to propargyl alcohol (29 mL, 0.5 mol) and Et3N (14 mL, 0.1 mmol) in 200 mL CH2Cl2. When the addition is complete, the reaction mixture is concentrated and triturated with Et2O. The solid is filtered and the organics are concentrated again. The remaining oil is chromatographed over silica gel (EtOAc/Hex:20/80) to give ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate an oil. The remaining propargyl alcohol is removed by azeotroping from n-heptane to yield 11.7 g (69% yield). 1H NMR (400 MHz, CDCl3) delta 6.69, 4.84, 4.44, 1.42. To a solution of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (4.0 g, 23 mmol) and TBSCl (3.7 g, 25 mmol) in DMF is added Et3N (3.4 mL, 24 mmol) dropwise over 20 minutes. The reaction is allowed to stir for 30 minutes after which it is diluted with EtOAc (300 mL), washed with 1 M HCl (3¡Á100 mL), 5% CuSO4 (2¡Á50 mL) and concentrated in vacuo to yield 6.91 g (>100% yield) of oily material with visible TBS impurities by NMR. 1H NMR (400 MHz, CDCl3) delta 6.49, 4.69, 4.31, 1.30, 0.80, 0.02. A mixture of ethyl-5-({[tert-butyl(dimethylsilyl)]oxy}methyl)isoxazole-3-carboxylate (1.68 g, 5.9 mmol) and hydrazine hydrate (044 g, 8.8 mmol) in ethanol (30 mL) is heated to 60 C. for 4 h. The mixture is cooled to RT and the solvents are removed in vacuo to yield 1.40 g (87% yield) of orange crystals. 1H NMR (400 MHz, DMSO-d6) delta 9.95, 6.61, 4.74, 4.51, 0.79. A mixture of 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)isoxazole-3-carbohydrazide (1.32 g, 4.9 mmol) in concentrated hydrochloric acid (40 mL) is cooled to 0 C., followed by a dropwise addition of aqueous NaNO2 (0.42 g, 6.1 mL), maintaining the temperature below 5 C. After 1 h, the yellow mixture is diluted with water (100 mL) and extracted with EtOAc (3¡Á50 mL). Organics are dried (MgSO4) and concentrated in vacuo to yield 0.93 g (>100% yield) of 5-(hydroxymethyl)isoxazole-3-carbonylazide as tan crystals. 1H NMR (400 MHz, DMSO-d6) delta 6.82, 4.64. Example 611 is obtained according to Method F. Yield 20%. MS (ESI) for C13H14BrN3O5 m/z 372 (M-H)-.

123770-62-7, The synthetic route of 123770-62-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Piotrowski, David W.; Rogers, Bruce N.; McWhorter JR., William W.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Groppi JR., Vincent E.; Rudmann, Daniel G.; US2003/236287; (2003); 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.53983-15-6,Ethyl 5-amino-4-phenylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.,53983-15-6

5-amino-obtained Example 2 The 4-phenyl-isoxazole-3-carboxylic acid ethyl ester A1 (0.464g, 2mol), benzaldehyde(0.212g, 2mol) and 10mL absolute ethanol, was added one drop of concentrated sulfuric acid as a catalyst, was heated to reflux, TLC monitoring of the reaction,After completion of the reaction, cooled to room temperature, suction filtered, washed with water and purified by column chromatography to give a white powdery solid 0.45g. Yield 71.77%.

As the paragraph descriping shows that 53983-15-6 is playing an increasingly important role.

Reference£º
Patent; Shenyang Pharmaceutical University; Xu, Wei; Chen, Yu; Zhang, Rui; (15 pag.)CN105777661; (2016); A;,
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.

To a solution of 1.5 g of 5-methyl-3-phenyl-4-isoxazolecarboxylic acid in 50 ml of anhydrous tetrahydrofuran stirred at -78C under N2 atmosphere, 5.9 ml of a 2.5M solution of n-butyl lithium in n-hexane was added and the solution was stirred at -78C for 2 hours. Afterwards, 0.89 ml of benzyl bromide was added at -78C and the solution stirred at room temperature for 2 hours. After overnight resting, the solution was poured into water (300 ml), acidified with 1N hydrochloric acid and extracted with ethyl acetate (2 ? 200 ml). The combined organic layers were washed with water, dried (sodium sulphate) and the solvents were evaporated to dryness. The solid residue was washed with petroleum ether to give 1.82 g (84%) of the title compound as an amorphous solid.1H-NMR (200MHz, CDCl3, delta): 9.20-11.80, br, 1H, COOH; 7.10-7.90, m, 10H, phenyl CHs; 3.45, t, 2H, CH2CH2Ph; 3.10, t, 2H, CH2CH2Ph., 1136-45-4

As the paragraph descriping shows that 1136-45-4 is playing an increasingly important role.

Reference£º
Patent; Leonardi, Amedeo; EP1226131; (2003); B1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

354795-62-3, 3-Methylisoxazol-4-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of 3-methylisoxazol-4-ylamine (140 mg, 1.04 mmol) in DCM (5 mL) and pyridine (0.252 uL, 3.12 mmol) was added 4-fluoro-3-cyanobenzene sulfonylchloride (275 mg, 1.25 mmol) and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was washed with water, the organic layer collected, dried over MgSO4 and concentrated in vacuo. The residue was re-dissolved in DCM, washed with 2N HCl (aq), the organic layer collected, dried over MgSO4 and concentrated in vacuo to afford the title compound as a yellow solid (196 mg, 67%), which was used without further purification The following Preparations were prepared according to the procedure described in Preparation 33 using the appropriate arylsulfonylchloride and aminoheterocycle as described below:, 354795-62-3

354795-62-3 3-Methylisoxazol-4-amine 13804284, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER LIMITED; Owen, Robert McKenzie; Storer, Robert Ian; US2014/315933; (2014); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

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