Heterocyclic Building Blocks-isoxazole

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.

Example Llsoxazole-5-carboxylic acid [2-(2-o-tolyl-chroman-6-yloxy)-thiazol-5-ylmethyl]-amideTo a solution of [2-(2-o-tolyl-chroman-6-yloxy)-thiazol-5-ylmethyl]amine (150 mg, 0.43 mmol) in DMF (2 ml), 1 -(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (1 14 mg, 0.60 mmol, 1 .4 eq), 1 -hydroxy-benzotriazole (81 mg, 0.60 mmol, 1 .4 eq) and N-methylmorpholine (107 mg, 1 .07 mmol, 2.5 eq) and isoxazole-5- carboxylic acid (72 mg, 0.64 mmol, 1 .5 eq) were added. The mixture was stirred for 16 h, then diluted with water, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with a diluted aqueous solution of sodium carbonate and brine, dried over sodium sulfate and filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, ethyl acetate/methanol gradient), lsoxazole-5-carboxylic acid [2-(2-o-tolyl-chroman-6-yloxy)-thiazol-5-ylmethyl]-amide (1 12 mg, 59%) was obtained as a white solid.

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; SANOFI; CZECHTIZKY, Werngard; WESTON, John; RACKELMANN, Nils; PODESCHWA, Michael; ARNDT, Petra; WIRTH, Klaus; GOEGELEIN, Heinz; RITZELER, Olaf; KRAFT, Volker; BELLEVERGUE, Patrice; McCort, Gary; WO2013/37724; (2013); 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.51677-09-9,Methyl 5-phenylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

51677-09-9, 9-B. Methyl 4-bromo-5-phenylisoxazole-3-carboxylate; [00180] A solution of methyl 5-phenylisoxazole-3-carboxylate (100 mg, 0.492 mmol) and N-bromosuccinimide (119 mg, 0.669 mmol) in 5% fuming nitric acid in acetic acid (2 mL) was heated to 150 0C for 10 minutes via microwave. The reaction mixture was concentrated and purified by silica gel chromatography with hexanes/ethyl acetate (10/1) to afford methyl 4-bromo-5-phenylisoxazole-3- carboxylate (108 mg). The compound had an HPLC ret. time = 3.21 min. – Column: YMC S5 COMBISCREEN 4.6X50 mm; Gradient time: 4 min; Flow rate = 4 ml/min; Solvent A = 10% MeOH – 90% Water – 0.2% H3PO4; Solvent B = 90% MeOH – 10% water – 0.2% H3PO4; Start % B = O; Final % B = 100. LC-MS: M+1 = 284+.

The synthetic route of 51677-09-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott, Hunter; DYCKMAN, Alaric, J.; PITTS, William, J.; SPERGEL, Steven, H.; WO2010/85581; (2010); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

62348-13-4, Isoxazole-5-carbonyl chloride is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

62348-13-4, General procedure: Sequentially, acid chloride (1.5 equiv) including furan-2-carbonylchloride, m-fluorobenzoylchloride, p-fluorobenzoylchloride, isoxazole-5-carbonyl chloride, adamantane-1-carbonylchloride, or naphthalene-1-sulfonylchloride (1.5 equiv) and quinoline-8-sulfonyl chloride (1.5 equiv), was added to the resulting solutionin the presence of NEt3 (3.0 equiv) and stirredat reflux for 4 h. When the sequentialone-pot multicomponent synthesis reaction was completed, the reactionmixture was added to saturate sodium bicarbonate (15 mL) and extracted withdichloromethane (15 mL ¡Á 2). Thecombined organic layer was washed saturated aqueous NaHCO3 (15 mL),dried over MgSO4, filtered, and concentrated under reduced pressure.The residue solution was purified by column chromatography on silica gel togive the corresponding N,O-disubstitutedglycolamides 5a-f, 7-11, 12a-e, and 13a-b in 66-84 % yields.

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

Reference£º
Article; Lu, Shi-Han; Yen, Wan-Ping; Tsai, Henry J.; Chen, Chien-Shu; Wong, Fung Fuh; Tetrahedron; vol. 71; 38; (2015); p. 6749 – 6758;,
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.

21169-71-1, Example 88. The title compound was prepared by using the same procedure as described in example 83. MS (ESI): m/z 753.15 (M+H).

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

Reference£º
Patent; ENANTA PHARMACEUTICALS, INC.; WO2009/76173; (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.110256-15-0,5-Cyclopropylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

In a 100-mL round-bottom flask 5 -cyclopropylisoxazole-3 -carboxylic acid (100 mg, 0.65 mmol, 1.00 equiv), tert-butyl N-[(lr,4r)-4-aminocyclohexyl]carbamate (154 mg, 0.72 mmol, 1.10 equiv) and TEA (198 mg, 1.96 mmol, 3.00 equiv) were dissolved in 10 ml dichloromethane, then HATU (496 mg, 1.31 mmol, 2.00 equiv) was added to the solution. The resulting solution was stirred overnight at room temperature. The mixture was then concentrated under vacuum. The residue was purified on a silica gel column with ethyl acetate/petroleum ether (4: 1). This resulted in 210 mg (92%) tert-butyl (lr,4r)- 4-(5 -cyclopropylisoxazole-3 -carboxamido)cyclohexylcarbamate as a white solid. LCMS (method A, ESI): RT=1.48 min, m/z =294.0 [M-56]+.

110256-15-0, The synthetic route of 110256-15-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EPIZYME, INC.; CHESWORTH, Richard; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MITCHELL, Lorna Helen; PETTER, Russell C.; SCHWARTZ, Carl Eric; (62 pag.)WO2016/40511; (2016); 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.108511-97-3,Isoxazol-4-amine,as a common compound, the synthetic route is as follows.

Will be equipped with a stir bar,A 250 mL round bottom flask of the Dean-Stark trap and reflux condenser was removed from the oven.Cooling under vacuum,And backfill with argon.Under argon flow,Toluene (100 mL),(Structural formula is as follows) Compound 6 synthesized(11.91g, 19.82mmol),4-aminoisoxazole (1.665 g, 19.82 mmol) and p-toluenesulfonic acid monohydrate (1-2 mol%) were introduced into the reaction flask.Then reflux under stirring,A certain amount (about 0.36 g) of water was collected up to the bottom of the Dean-Stark trap.The reaction mixture was then filtered through celite.And evaporate volatile organic compounds,It is then distilled by Kugelrohr (boiling point is 105 C pressure of about 1 mTorr)Yielded 9.68 g of product(E)-6-(tert-butyl)-2-(1-(3-(isoxazol-4-yl)imino)butyl)-2,5-diisopropyl-4-phenyl- Synthesis of 1H-pyrrole-3-carboxamido)benzo[b]thiophene-3-carboxylic acid ethyl ester (Compound 7),Is a yellow crystal,The yield was 73.2%., 108511-97-3

The synthetic route of 108511-97-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Li Huaxu; (8 pag.)CN108191845; (2018); A;,
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Isoxazole | C3H3NO – PubChem

1202769-66-1, 2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: A mixture of 66 (200 mg, 0.49 mmol, 1.00 equiv, 95%), 2-(5-methyl-l,2-oxazol-3-yl)but-3-yn-2- ol (200 mg, 1.32 mmol, 2.70 equiv), (PPh3)2Pd(II)Cl2 (350 mg, 0.50 mmol, 1.02 equiv) and TEA (2 mL) in DMSO (3 mL) was stirred under nitrogen at 70 C for 2 h. The reaction mixture was cooled to RT and loaded onto a C18 column. The column was eluted with acetonitrile/water (5:95 ~ 80:20) to afford 88 mg (38%) of ( 1 -(2-aminopyrimidin-4-yl)-6-(3-hydroxy-3-(5-methylisoxazol-3-yl)but- 1 -yn- 1 -yl)-lH- benzo[d]imidazol-2-yl)(pyrrolidin-l -yl)methanone as a light yellow solid. FontWeight=”Bold” FontSize=”10″ H NMR (300 MHz, DMSO- d6) delta 8.42 (d, 7 = 5.1Hz, 1H), 7.86 (s, 1H), 7.79 (d, 7 = 8.4Hz, 1H), 7.41 (d, 7 = 8.7Hz, 1H), 7.03 (s, 2H), 6.74 (d, 7 = 5.1Hz, 1H), 6.50 (s, 1H), 6.36 (s, 1H), 3.61 (d, 7 = 6.6Hz, 2H), 3.48 (d, 7 = 6.6Hz, 2H), 2.40 (s, 3H), 1.92 (s, 4H), 1.80 (s, 3H); LC-MS: m z= 458 (M+H)+., 1202769-66-1

As the paragraph descriping shows that 1202769-66-1 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; HOEFLICH, Klaus P.; LYLE, Karen S.; STABEN, Steven; WO2014/170421; (2014); 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.87988-94-1,5-Methylisoxazol-4-amine,as a common compound, the synthetic route is as follows.

87988-94-1, Example 15(a)2,2,2-Trifluoro-N-isopropyl-N-(5-methyl-isoxazol-4-yl)-acetamide 5-Methyl-4-amino-isoxazole (Reiter, L. A., J. Org. Chem. 1987, 52, 2714-2726) (0.68 g, 5.1 mmol) and acetic acid (0.61 g, 10.2 mmol) were dissolved in MeOH (20 mL). Acetone (0.56 ml, 7.6 mmol) was added and the mixture was cooled to 0-(-5) C. and stirred for 1 h. Sodium cyanoborohydride (0.32 g, 5.1 mmol) was added to the reaction mixture at -5 C., causing weak exothermic and gas evolution. The cooling bath was removed and the mixture was stirred at r.t. for 1 h, followed by the addition of a second portion of sodium cyanoborohydride (0.1 g, 1.6 mmol). After stirring for 2 h at r.t., the mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in toluene and re-concentrated. The residue was dissolved in THF (10 mL) and trifluoro acetic anhydride (3.2 g, 15.3 mmol) was added. The resulting mixture was stirred overnight at r.t. then for 1 h at +50 C. The volatiles were removed in vacuo and the residue was dissolved in toluene and concentrated in vacuo to give the title compound (0.84 g, 77%) as a solid.1H NMR (400 MHz, CDCl3) delta ppm 8.11 (s, 1H) 4.82-5.03 (m, 1H) 2.39 (s, 3H) 1.16 (d, J=6.82 Hz, 3H) 1.08 (d, J=6.82 Hz, 3H); MS (CI) m/z 236 (M+).

As the paragraph descriping shows that 87988-94-1 is playing an increasingly important role.

Reference£º
Patent; AstraZeneca AB; US2008/214560; (2008); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

21169-71-1, Isoxazole-5-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

21169-71-1, 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%).

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

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108511-97-3,Isoxazol-4-amine,as a common compound, the synthetic route is as follows.

To a solution of 4-aminoisoxazole (2.00 g, 23.79 mmol; CASNo. 108511-97-3) in THF (50 mL) at 0 0C was added pyridine (1.92 mL, 23.79 mmol,) followed by phenyl chloroformate (3.28 mL, 26.17 mmol,). After stirring at 0 0C for 2.5 h, the reaction was warmed to room temp overnight. The reaction was diluted with ethyl acetate and washed with 2M HCI, water, saturated sodium bicarbonate, and brine. The organic layer was dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography (dichloromethane/hexane) to give the title compound as a white solid (2.07 g, 10.15 mmol, 50%)., 108511-97-3

As the paragraph descriping shows that 108511-97-3 is playing an increasingly important role.

Reference£º
Patent; PFIZER INC.; WO2009/127943; (2009); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem