Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57351-99-2,5-Methylisoxazole-3-carbonitrile,as a common compound, the synthetic route is as follows.,57351-99-2

Step 1 : To a solution of compound 197 (800 mg, 7.40 mmol) in DCE (30 ml.) was added NBS (2.79 g, 15.5 mmol) and AIBN (60.8 mg, 0.375 mmol). The reaction stirred at 85 C for overnight. Concentrate to give the cream solid. Water (20 ml.) was added, and extracted with EtOAc (30 mL x 2). The combined organic layers were washed with brine (20 ml_), dried over Na2S04 and concentrated to give compound 198(1 .44 g, 2.90 mmol) as an off-white semi-solid, which was taken into the next step without further purification.

57351-99-2 5-Methylisoxazole-3-carbonitrile 24229456, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

87988-94-1, 5-Methylisoxazol-4-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

87988-94-1, To a stirred slurry of 4-methyl-3-[6-(4-methylpiperazm-l-yl)-4-oxoquinazolin-3(4H)-yl]benzoic acid (0.38 g) in DMF (50 ml) was added 4-amino-5-methylisoxazole hydrochloride (0.27 g), EtaATU (0.68 g) and triethylamine (0.55 ml) and the reaction mixture stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extarcted with ethyl acetate. The ethyl aceate layer was washed with IN NaOH and dried (magnesium sulphate). The residue was purified by column chromatography on a silica column using initially ethyl acetate and then a 4: 1 mixture of ethyl acetate and methanol as eluent. There was thus obtained the title compound (150 mg); NMR Spectrum: (DMSOd6) 2.15 (s, 3Eta), 2.40 (s, 3H), 2.83 (m, 4H), 3.15 (s, 3H), 3.40 (m, 4H), 7.50 (d, IH), 7.60 (d, IH), 7.64 (m, 2H), 7.98 (s, IH), 8.04 (d, IH), 8.13 (s, IH), 8.70 (s, IH), 10.10 (s, IH); Mass Spectrum: M+H+ 459.The 4-amino-5-methylisoxazole hydrochloride used as starting material was prepared using the procedures detailed in J. Org. Chem 1987, 2714-2716.

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

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/90143; (2006); 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.98019-60-4,Isoxazol-5-ylmethanol,as a common compound, the synthetic route is as follows.

98019-60-4, Step 2Isoxazole-5-carbaldehydeIn a round-bottomed flask, isoxazol-5-yl-methanol (511 mg, 5.16 mmol) was dissolved in dichloromethane (30 ml). Dess-Martin periodinane (2.3 g, 5.41 mmol) was added and the reaction mixture was stirred at room temperature for 1.5 h. The reaction was quenched with 50 ml of a 1 :1 solution of 10%> aqueous Na2S203 and saturated aqueous NaHCC>3 and then extracted with dichloromethane (2x). The organic layers were washed with saturated aqueous NaHCC>3, water and brine. The aqueous layers were back extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue was chromato graphed over silica gel with EtOAc/hexanes (gradient 0-40% EtOAc) to afford 226 mg (45%) of isoxazole-5-carbaldehyde as a colorless oil. 1H NMR (CDC13, 300 MHz): ? (ppm)10.05 (s, 1H), 8.44 (d, J=1.9 Hz, 1H), 7.02 (d, J=1.9 Hz, 1H).

As the paragraph descriping shows that 98019-60-4 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O’YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu; WO2013/30138; (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.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

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.

To a solution of 7-amino-4-(4-chlorobenzyl)-6-methoxy-2H-benzo [b] [1 ,4]oxazin-3 (4H)- one (0.10 g, 0.31 mmol) in DCM (5 mL) were added 3,5-dimethylisoxazole-4-carboxylic acid (0.05 g, 0.33 mmol), HOBt (0.02, 0.15 mmol), EDC.HC1 (0.12 g, 0.63 mmol), Triethylamine (0.11 ml, 0.77 mmol) and stirred at RT for 16 h. After completion of reaction, the reactionmixture was diluted with DCM (100 mL), washed with water (50 mL), brine (50 mL), dried over sodium sulphate and concentrated. The residue was purified by preparative TLC to afford title product as a yellow solid (0.03 g 22%). 1H NMR (400 MHz, DMSO-d6): oe 9.08 (bs, 1H), 7.63 (s, 1H), 7.40 (d, J=8.3 Hz, 2H), 7.35 (d, J=8.3 Hz, 2H), 6.80 (s, 1H), 5.22 (s, 2H), 4.73 (s, 2H), 3.70 (s, 3H), 3.56 (s, 3H), 2.34 (s, 3H); LC-MS: m/z 442.1 (M+1).

2510-36-3, 2510-36-3 3,5-Dimethylisoxasole-4-carboxylic acid 75636, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; SASMAL, Sanjita; HOSAHALLI, Subramanya; WO2015/104653; (2015); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

54593-26-9,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.54593-26-9,3,5-Dimethyl-4-isoxazolecarbaldehyde,as a common compound, the synthetic route is as follows.

[000298] 4-Piperidinone (0.92 gr, 6 mmol) was placed in a 25 ml round bottom flask and cooled to 0 C. Boron trifluoride (10 mL) was added dropwise followed by the aldehyde (1.5 gr, 12 mmol) in one portion. The reaction mixture was stirred overnight at room temperature under nitrogen atmosphere. The reaction was carefully quenched with a saturated solution of NaHCC . The solid precipitated out from the solution was filtered under reduced pressure, washed with water and EtOH to give the intermediate El-1 (Scheme 7) as a yellow solid (1.2 gr, 3.8 mmol, 63%).

As the paragraph descriping shows that 54593-26-9 is playing an increasingly important role.

Reference£º
Patent; PI THERAPEUTICS LTD.; KALID, Ori; GOTLIV, Irina; LEVY-APTER, Einat; FINKELSHTEIN BEKER, Danit; JAGTAP, Prakash; (0 pag.)WO2019/171379; (2019); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

14441-90-8, 5-Phenylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

DIEA (943 mg, 7.30 mmol, 3.00 eq.) was added dropwise to a cold solution of 5-phenylisoxazole-3-carboxylic acid (550 mg, 2.91 mmol, 1.20 eq.), trans-3 -[5- [(1 R)- 1 -methoxyethyl] -1,3 ,4-oxadiazol-2-yl]cyclobutan- 1-amine (480 mg, 2.43mmol, 1.00 eq.) and HATU (1.387 g, 3.65 mmol, 1.50 eq.) in dichloromethane (50 mL) at 0 C. The resulting solution was stirred for 1 hour at room temperature and then diluted with 50 mL of dichloromethane. The resulting mixture was washed with water (2×50 mL) and brine (1×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to give 628 mg (70%)of 5 -phenyl-N- [trans-3 -[5- [(1 R)- 1 -methoxyethyl]- 1,3 ,4-oxadiazol-2-yl]cyclobutyl] isoxazole-3 – carboxamide as an off-white solid.[0535] Analytical data:[0536] HPLC purity: 98.9% at 254 nm[0537] LC-MS (ES, m/z): [M+1] = 369[0538] ?H NMR (400MHz, DM50-cl6): 9.33-9.31 (d, J= 7.6 Hz, 1H), 7.96-7.94 (t, J= 5.6Hz, 2H), 7.59-7.56 (m, 3H), 7.38 (s, 1H), 4.74-4.67 (m, 2H), 3.76-3.70 (m, 1H),3.29 (s, 3H), 2.74-2.61 (m, 4H), 1.5 1-1.49 (d, J= 6.8 Hz, 3H)., 14441-90-8

As the paragraph descriping shows that 14441-90-8 is playing an increasingly important role.

Reference£º
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
Isoxazole – Wikipedia
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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, a) Methyl 4-(4-isoxazol-5-yl(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (872 mg, 2.51 mmol) was allowed to react with 2-bromo-1-isoxazol-5-ylethan-1-one (737 mg, prepared from from isoxazole-5-carbonyl chloride [Maybridge Chemicals, Cornwall, UK] as described in Example 177, step (a) as described in Example 154, step (a) to give 704 mg (83% yield) of methyl 4-(4-isoxazol-5-yl(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate. 1H NMR (DMSO-d6, 300 MHz) delta 2.75 (s, 3H), 3.85 (s, 3H), 6.93 (d, 1H, J=1.8 Hz), 8.22 (s, 1H), 8.38 (s, 1H), 8.70 (d, 1H, J=1.8 Hz).

62348-13-4 Isoxazole-5-carbonyl chloride 2736707, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; 3-Dimensional Pharmaceuticals, Inc.; US6291514; (2001); B1;,
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, A mixture of 2-{[(4-f.uorop enyl)methyl]oxy}-5-(1-methyl-1 H-pyrazol-4-yl)benzoic acid (may be prepared as described in Description 121 ; 80 mg, 0.25 mmol), 3- methylisoxazol-4-amine (49.5 mg, 0.37 mmol), HOBT (56.3 mg, 0.37 mmol) and EDC (70.5 mg, 0.37 mmol) in N,N-dimethylformamide (2 ml) was stirred at room temperature for 16 hours. Water (50 ml) was added. A white precipitate was filtered, washed with ethyl acetate, and dried in vacuo to yield the title compound as a white solid. 54 mg, 1HNMR (400 MHz, DMSO-c 6): 1 .99 (3H, s), 3.86 (3 H, s), 5.25 (2 H, s), 7.25 (2H, t, J= 8.8 Hz), 7.32 (2H, d, J = 8.4 HZ), 7.59-7.62 ( H, q, J = 2.8, J = 8.8), 7.73-7.75 ( H, dd, J = 2.4 Hz, J = 8.4 Hz), 7.88 (1 H, s), 7.92 (1 H, d, J = 2.4), 8.16 (1 H, s), 9.17 (1 H, s), 9.88 (1 H, s)MS (electrospray): m/z [M+H]+ =407.1

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

Reference£º
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (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.42831-50-5,5-Methylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

Thionyl chloride (4.3 ml, 39.5 mmol) was added dropwise to 5-methylisoxazole-4-carboxylic acid (0.44 g, 3.4 mmol) at 26C. The mixture was heated at 89C for 1 hr and allowed to cool. Excess thionyl chloride was evaporated under reduced pressure to give an acid chloride as a brown oil, which was used in the next reaction.

42831-50-5, As the paragraph descriping shows that 42831-50-5 is playing an increasingly important role.

Reference£º
Patent; The New Industry Research Organization; EP1627873; (2006); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem