Month: October 2020

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

832740-73-5, 4-(Isoxazol-5-yl)aniline is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

832740-73-5, Example 18 5-((1R,2R)-2-amino-3,3-difluorocyclohexylamino)-3-(4-(isoxazol-5-yl)phenylamino)pyrazine-2-carboxamide A mixture of 5-((1R,2R)-2-amino-3,3-difluorocyclohexylamino)-3-chloropyrazine-2-carbonitrile (74 mg, 0.257 mmol), 4-(isoxazol-5-yl)aniline (60 mg, 0.375 mmol), K2CO3 (80 mg, 0.579 mmol), BINAP (25 mg, 0.040 mmol) and Pd(OAc)2 (10 mg, 0.044 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 20 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give 5-((1R,2R)-2-amino-3,3-difluorocyclohexylamino)-3-(4-(isoxazol-5-yl)phenylamino)pyrazine-2-carbonitrile (4 mg).

As the paragraph descriping shows that 832740-73-5 is playing an increasingly important role.

Reference£º
Patent; Portola Pharmaceuticals, Inc.; Song, Yonghong; Xu, Qing; Jia, Zhaozhong J.; Kane, Brian; Bauer, Shawn M.; Pandey, Anjali; US2013/131040; (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.2510-36-3,3,5-Dimethylisoxasole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 2; N-[(3,5-dimethylisoxazol-4-yl)carbonyl]-3-{5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]thiophen-2-yl}-L-alanine; O-benzotriazol-1-yl-N,N,N’,N’-tetramethyluronium tetrafluoroborate (268 mg, 0.83 mmol), 4-methylmorpholine (0.084 ml, 0.76 mmol) and 3,5-dimethylisoxazole-4-carboxylic acid (98 mg, 0.70 mmol) were added under an argon atmosphere to a stirred solution of methyl 3-{5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]thiophen-2-yl}-L-alaninate (250 mg, 0.70 mmol) dissolved in DMF (2.5 mL). The resulting solution was stirred at 25 C. for 2 hours. Then NaOH 6N (0.464 ml, 2.78 mmol) was added to the stirred mixture. The resulting solution was stirred at 25 C. for 1 hour. The reaction mixture was purified by C18 reverse phase chromatography (basic conditions). The fractions containing the desired compound were evaporated to dryness to afford the title compound as a beige solid (157 mg, 48.2%); Mass spectrum [M+H]+=467; 1H NMR Spectrum (DMSOd6) 1.70-1.78 (m, 2H), 1.81-1.90 (m, 2H), 2.18 (s, 3H), 2.39 (s, 3H), 2.45 (t, 2H), 2.60 (t, 2H), 2.70 (t, 2H), 3.15 (dd, 1H), 3.20-3.26 (m, 2H), 3.32 (dd partially hidden by H2O, 1H), 4.49 (ddd, 1H), 6.23 (d, 1H), 6.42 (bs, 1H), 6.64 (d, 1H), 6.71 (d, 1H), 7.03 (d, 1H), 8.27 (d, 1H).

2510-36-3, As the paragraph descriping shows that 2510-36-3 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; US2008/255183; (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.21169-71-1,Isoxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 3 (Compound 3) N-[2-[ l-[4-chloro-3-(trifluoromethyl)phenyl]pyrazole-4-carbonyl]-4-(l- piperidyl) phenyl] isoxazole-5-carboxamide A solution of (2-amino-5-(l-pipendyl)phenyl)(l-(4-chloro-3-(tnfluoromethyl)-phenyl)- lH-pyrazol-4-yl)methanone (Intermediate 1.5) (50 umol), l,2-oxazole-5-carboxylic acid (60 umol), DIEA (150 umol) and HATU (60 umol) in DMSO (300 uL) was stirred at room temperature overnight. The residue was purified by preparative HPLC/MS_method A2 to afford the title compound. 1H NMR (DMSO-d6, 600 MHz) delta = 10.88 (s, 1H), 9.25 (s, 1H), 8.75 (d, 1H), 8.37 (d, 1H), 8.28 (dd, 1H), 8.19 (s, 1H), 7.92 (d, 1H), 7.66 (d, 1H), 7.24 (dd, 1H), 7.18 (d, 1H), 7.09 (d, 1H), 3.21 (t, 4H), 2.54 (s, OH), 1.66 – 1.59 (m, 4H), 1.58 – 1.51 (m, 2H).

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; LEO PHARMA A/S; SOERENSEN, Morten Dahl; LARSEN, Jens Christian Hoejland; NOERREMARK, Bjarne; LIANG, Xifu; HUANG, Guoxiang; CHEN, Jinzhong; WO2013/82756; (2013); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

3209-70-9, Ethyl isoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3209-70-9, (a) 3-Hydroxymethyl isoxazole A solution of ethyl isoxazole-3-carboxylate (9.92 g, 70 mmol) in anhydrous ether (10 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (2.67 g, 70 mmol) in ether (100 ml). The mixture was then refluxed until tlc indicated the reaction was complete (ca. 30 min) then the reaction was cautiously quenched with 2% sulphuric acid. The ether layer was separated, dried (MgSO4) and the solvent removed under reduced pressure to yield the 3-hydroxymethylisoxazole (4.23 g, 42.7 mmol, 61%); deltaH (CDCl3) 4.00 (1H, bs, OH), 4.70 (2H, s, CH2 –OH), 6.40 (1H, d, J 2 Hz, CH-4), 8.30 (1H, d, J 2 Hz, CH-5).

3209-70-9 Ethyl isoxazole-3-carboxylate 10034712, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Beecham Group p.l.c.; US4812470; (1989); 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.7063-99-2,Ethyl 5-phenylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

7063-99-2, Preparation of Int-II-B: Ethyl 4-iodo-5-phenylisoxazole-3-carboxylate[00177] A mixture of ethyl S-phenylisoxazole-S-carboxylate (406 mg, 1.87 mmol) and N-iodosuccinimide (505 mg, 2.24 mmol) in trifluoroacetic acid (10 mL) was stirred at room temperature for 1.5 h. The volatiles were removed under reduced pressure, and the residue was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with a IN aqueous solution of sodium hydroxide (50 mL), washed with a 2.5% aqueous solution of sodium bisulfite (50 mL), washed with brine (50 mL), and dried over anhydrous magnesium sulfate. Concentration under reduced pressure afforded ethyl 4-iodo-5-phenylisoxazole-3-carboxylate (641 mg, 1.87 mmol, 100% yield) as a light yellow oil. The compound had an HPLC retention time = 3.36 minutes (YMC- Combi 4.6 x 50 mm S-5 ODS column) eluting with 10-90% aqueous methanol + 0.2% phosphoric acid over a 4 minute gradient. MS:(M+H) = 343.97. 1H NMR (400 MHz, CDCl3) delta ppm 1.47 (t, J=IA Hz, 3H), 4.50 (q, J=7.0Hz, 2H), 7.52-7.56 (m, 3H), and 8.05 (m, 2H).

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILMORE, John L.; SHEPPECK, James E.; WO2011/17578; (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.7063-99-2,Ethyl 5-phenylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.,7063-99-2

Step 3: ethyl 4-fluoro-5-phenyl-1,2-oxazole-3-carboxylate: selectfluor (1.71 g, 4.83 mmol, 1.05 equiv) was added to a solution of ethyl 5-phenyl-1,2-oxazole-3-carboxylate (1 g, 4.60 mmol, 1.00 equiv) in sulfone (5 mL). The resulting solution was stirred for 16 hours at 105 C. and then diluted with 100 mL of ethyl acetate. The resulting mixture was washed with brine (2¡Á100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20) to give 0.15 g (14%) of ethyl 4-fluoro-5-phenyl-1,2-oxazole-3-carboxylate as a yellow solid. LC-MS: [M+H]+=236.

As the paragraph descriping shows that 7063-99-2 is playing an increasingly important role.

Reference£º
Patent; PROTEOSTASIS TEHRAPEUTICS, INC.; Bastos, Cecilia M.; Munoz, Benito; Tait, Bradley; (48 pag.)US2017/1993; (2017); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem