Heterocyclic Building Blocks-isoxazole

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

3-(4-Chlorophenyl)-N-isopropyl-N,4-dimethyl-1 -[(3-methyl-isoxazol-5-yl)-methyl]-5- (trifluoromethyl)-1 H-pyrrole-2-carboxylic acid amide (example 067)To the stirred solution of 3-(4-chlorophenyl)-N-isopropyl-N,4-dimethyl-5-(trifluoromethyl)-1 H-pyrrole-2- carboxamide (200mg, 0.581 mmol) in MeCN was added Cs2C03at 0C under N2atmosphere. The reaction mixture was stirred for 30 min at 0C then charged 5-(bromomethyl)-3-methylisoxazole (11 1 mg, 0.639mmol). The mixture was warmed to RT and refluxed for 12 h. It was then quenched into ice water (100ml_) and extracted with EtOAc (3x100mL). The combined organic layer was washed successively with water, brine, dried (Na2S04) and concentrated to dryness in vacuo. The residue was purified by flash column chromatography (silica gel; 60-120mesh) and the compound eluted with 20% EtOAc in petroleum ether to give 82mg (39%) of example 67 as pale yellow liquid. [TLC system: 30% EtOAc -petroleum ether; Rf= 0.31]

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; GRUeNENTHAL GMBH; REICH, Melanie; SCHUNK, Stefan; JAKOB, Florian; STEINHAGEN, Henning; DAMANN, Nils; HAURAND, Michael; HAMLYN, Richard; ROGERS, Marc; SUTTON, Kathy; WO2015/90599; (2015); A1;,
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42831-50-5,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.

Preparation 4 N-(6-Amino-5-chloropyrazin-2-yl)-5-methylisoxazole-4-carboxamide Oxalyl chloride (0.8 ml, 10.3 mmol) was added to a solution of 5-Methyl-isoxazole-4-carboxylic acid (1 g, 6.9 mmol) in dichloromethane (30 ml) followed by 1 drop of dimethylformamide. The mixture was stirred at room temperature for 5 hours before concentrating in vacuo and azeotroping with dichloromethane. The residue was taken up in pyridine (3 ml) and added to a solution of 3-chloro-pyrazine-2,6-diamine (Preparation 1) (0.65 g, 4.6 mmol) in anhydrous pyridine (30 ml) and the mixture heated at 50 C. for 3 hours before cooling to room temperature and concentrating in vacuo. The residue was purified by silica gel column chromatography, eluding with ethyl acetate:heptane 1:1, to afford the product as a white solid (360 mg). 1H-NMR (d6-DMSO): 2.51 (s, 3H), 6.71 (br, s, 2H), 8.35 (s, 1H), 9.12 (s, 1H), 10.63 (br, s, 1H). MS m/z 254 [MH]+

42831-50-5 5-Methylisoxazole-4-carboxylic acid 1425240, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Pfizer Limited; US2007/105872; (2007); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1018297-63-6,(3-(4-Fluorophenyl)-5-methylisoxazol-4-yl)methanol,as a common compound, the synthetic route is as follows.

Step e: 6- r3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxyl -nicotinic acid methyl ester: To a suspension of sodium hydride (55% dispersion in mineral oil, 852 mg, 20 mmol) in THF (27 mL) was added a solution of [3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol (103 mg, 0.55 mmol) (3.68 g, 18 mmol) in THF (54 mL) at 0 C and the reaction mixture warmed to room temperature over 30 min. Then a solution of methyl 6-chloronicotinate (3.35 g, 20 mmol) in THF (1.5 mL) was added dropwise at 0 C and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then poured into aqueous sodium chloride (saturated) and the mixture was extracted with ethyl acetate. The combined organic layers were then washed with water and brine and then dried over sodium sulfate, filtered and evaporated. Purification by chromatography (Si02, heptane:ethyl acetate = 7:3) afforded the title compound (81 mg, 47%) which was obtained as a light yellow solid. MS: m/e = 343.3 [M+H]+., 1018297-63-6

As the paragraph descriping shows that 1018297-63-6 is playing an increasingly important role.

Reference£º
Patent; IP Gesellschaft fuer Management mbH; Trinius, Frank; EP2792360; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.36958-61-9,5-(Bromomethyl)-3-methylisoxazole,as a common compound, the synthetic route is as follows.

lodomethylcyclopropane (0.03 mL, 0.20 mmol) was added to a stirring mixture of N-(1 -cyanocyclopropyl)-N-[[3-[(2-methylthiazol-5-yl)methyl]-2,4-dioxo- 1H- quinazolin-6-yl]sulfonyl]acetamide (76 mg, 0.170 mmol) and potassium carbonate (92 mg, 0.66 mmol) in DMF (3 mL) and left to stir at room temperature for 16 h. Concentrated ammonia (100 muL) was added and the mixture heated to 40 C for 10 min. The mixture was allowed to cool and DCM (8 mL) and saturated aqueous ammonium chloride solution (8 mL) was added and the mixture stirred for 5 min. The DCM layer was isolated by passing through a hydrophobic frit and the aqueous layer washed with DCM (10 mL). The combined DCM extracts were concentrated under reduced pressure and purified by prep HPLC (low pH) yielding the desired product (8 mg, 0.017 mmol, 10%) as a white powder.This compound was prepared from 5-(bromomethyl)-3-methyl-1 ,2-oxazole (0.02 mL, 0.20 mmol) and N-(1 -cyanocyclopropyl)-N-[[3-[(2-methylthiazol-5-yl)methyl]-2,4- dioxo- 7H-quinazolin-6-yl]sulfonyl]acetamide (76 mg, 0.170 mmol) according to the method described in Example 399. This gave the desired product (10 mg, 0.020 mmol, 12%) as a white powder

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; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan; WASZKOWYCZ, Bohdan; HUTTON, Colin; WADDELL, Ian; HITCHIN, James R.; SMITH, Kate Mary; HAMILTON, Niall M.; (497 pag.)WO2016/92326; (2016); A1;,
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Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3209-71-0,Isoxazole-3-carboxylic Acid,as a common compound, the synthetic route is as follows.,3209-71-0

To a 0 C. solution of (081) (160 mg, 0.43 mmol) and isoxazole-3-carboxylic acid (082) (60 mg, 0.5 mmol), HOBT (65 mg, 0.5 mmol) and HBTU (175 mg, 0.5 mmol) in tetrahydrofuran (50 mL) was added a solution of N,N-diisopropylethylamine (0.5 mL) in tetrahydrofuran (2 mL) and the mixture was stirred at room temperature for another 5 hours. It was then diluted with ethyl acetate (200 mL) and washed with saturated aqueous sodium bicarbonate (2¡Á10 mL) and brine (10 mL). The organic layers were dried over sodium sulfate and filtered through Celite-545. The solvents were removed under reduced pressure and the residue was purified by HPLC (aqueous ammonium acetate and acetonitrile) to provide (083) (74 mg) which was characterized by LC/MS (LCRS (MH) m/z: 469.22); >80% proteasome CT-L inhibition at 20 mg/kg PO.

As the paragraph descriping shows that 3209-71-0 is playing an increasingly important role.

Reference£º
Patent; Proteolix, Inc.; US2007/105786; (2007); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.62348-13-4,Isoxazole-5-carbonyl chloride,as a common compound, the synthetic route is as follows.,62348-13-4

General procedure: Acyl chloride (1.1 equiv) was added to a suspension of 5(1.0 equiv) and potassium carbonate (10 equiv) in THF at roomtemperature under nitrogen. After 2 h, the reaction was quenchedby the addition of H2O and the resulting mixture was extractedwith EtOAc. The organic layer was dried over MgSO4, filtered,and concentrated under reduced pressure. The residue was purifiedby column chromatography to provide the desired products6a-6q.

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

Reference£º
Article; Chu, Kuang-Feng; Yao, Chun-Hsu; Song, Jen-Shin; Chen, Chiung-Tong; Yeh, Teng-Kuang; Hsieh, Tsung-Chih; Huang, Chung-Yu; Wang, Min-Hsien; Wu, Szu-Huei; Chang, Wei-En; Chao, Yu-Sheng; Lee, Jinq-Chyi; Bioorganic and Medicinal Chemistry; vol. 24; 10; (2016); p. 2242 – 2250;,
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Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3405-77-4,5-Methylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Step 5. A solution of 5-methylisoxazole-3-carboxylic acid (8.6 mg, 68 mumol), diisopropylethylamine (12 muL, 68 mumol), and 2-chloro-5-(1-((R)-1-(3-chlorophenyl)ethylamino)ethyl)benzenamine 109 (21 mg, 68 mumol) in DMF was stirred under N2 and chilled to 0¡ã C. HATU (26 mg, 68 mumol) was then added to the solution. The reaction was allowed to warm to room temperature and stirred for 3 h. Afterwards, the reaction was diluted with water and EtOAc. The organic solution was extracted with saturated NaHCO3, water, and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography using a 5percent to 60percent gradient of EtOAc in hexanes as the eluent. The desired fractions were combined and concentrated to give N-(2-chloro-5-(1-((R)-1-(3-chlorophenyl)ethylamino)ethyl)phenyl)-5-methylisoxazole-3-carboxamide 110 (20 mg, 70percent yield) as a colorless oil and as a mixture of diastereomers. 1H NMR (400 MHz, MeOH) delta ppm 1.60-1.66 (m, 6H) 2.53 (s, 3H) 4.19 (m, 2H) 6.61 (s, 1H) 7.19 (dd, J=8.31, 2.05 Hz, 1H) 7.30 (m, 1H) 7.40 (s, 1H) 7.48 (d, J=4.89 Hz, 2H) 7.63 (d, J=8.41 Hz, 1H) 8.09 (s, 1H). Mass spectrum: calculated for C21H21Cl2N3O2 418.3; found 418.4 (M++1)., 3405-77-4

The synthetic route of 3405-77-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Amgen Inc.; US2008/221101; (2008); A1;,
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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

14441-90-8, a solution of [5-[(3-aminocyclobutyl)methyl]-l,3,4-thiadiazol-2-yl]methanol hydrochloride (500 mg, 2.12 mmol, 1.00 eq., 99%), 5-phenyl-l,2-oxazole-3-carboxylic acid (481 mg, 2.54 mmol, 1.20 eq.), HCTU (1.061 g, 2.55 mmol, 1.20 eq.) and DIEA (1.09 g, 8.43 mmol, 1.20 eq.) in dichloromethane (30 mL) was stirred for 2 hours at room temperature. The resulting mixture was concentrated under vacuum. The crude product was purified by Prep- Flash with acetonitrile and water (0-46% within 40 min). The isomers were separated by Prep- SFC with the following conditions (prep SFC 350-2): Column, Phenomenex Lux 5mu Cellulose- 4, 250*50mm; mobile phase, C02 (50%), MeOH (0.2%DEA) (50%); Detector, UV 220nm. 5-phenyl-iV- [(ci’s-3- [ [5-(hydroxymethyl)-l,3,4-thiadiazol-2-yl] methyl] cyclobutyl] – 1,2- oxazole-3-carboxamide: [0198] Yield: 37% [0199] Appearance: off-white solid [0200] Analytical data: XH NMR (400MHz, OMSO-d6, ppm): delta: 9.06 (d, J= 8.0Hz, 1H), 7.94-7.92 (m, 2H), 7.58-7.54 (m, 3H), 7.35 (s, 1H), 6.14-6.11 (m, 1H), 4.80 (d, J = 6.0Hz, 2H), 4.35-4.33 (m, 1H), 3.19-3.17 (m, 2H), 2.43-2.33 (m, 3H), 1.99-1.93 (m, 2H). [0201] LC-MS: 371.1 [M+H]+ 5-phenyl-iV- [(trans-3- [ [5-(hydroxymethyl)-l,3,4-thiadiazol-2-yl] methyl] cyclobutyl] – 1,2- oxazole-3-carboxamide: [0202] Yield: 37% [0203] Appearance: light yellow solid [0204] Analytical data: NMR (400MHz, OMSO-d6, ppm): delta: 9.14 (d, J= 7.2Hz, 1H), 7.94-7.92 (m, 2H), 7.56-7.54 (m, 3H), 7.36 (s, 1H), 6.14-6.11 (m, 1H), 4.80 (d, J= 6.0Hz, 2H), 4.63-4.55 (m, 1H), 3.33-3.28 (m, 2H), 2.51-2.49 (m, 1H), 2.33-2.31 (m, 2H) , 2.14-2.13 (m, 2H).

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

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (178 pag.)WO2016/115090; (2016); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.123770-62-7,Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

Reference Production Example 105 (0747) 60% Sodium hydride (1.04 g, 26.0 mmol) was added to dehydrated N,N-dimethylformamide (10 ml) cooled to 0C, under a nitrogen atmosphere, and a dehydrated N,N-dimethylformamide (10 ml) solution of ethyl 5-hydroxymethylisoxazole-3-carboxylate (3.0 g, 17.54 mmol) was added dropwise thereto, and then the mixture was further stirred for 30 minutes. A dehydrated N,N-dimethylformamide (5 ml) solution of 1-bromo-3-phenylpropane (3.5 g, 17.54 mmol) was added thereto, and the mixture was heated to room temperature and stirred for 16 hours. Then, the mixture was added to a saturated aqueous ammonium chloride solution, and extracted twice with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 1.9 g of ethyl 5-(3-phenylpropoxymethyl)isoxazole-3-carboxylate represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 7.30-7.25 (m, 2H), 7.20-7.15 (m, 3H), 6.65 (s, 1H), 4.61 (s, 2H), 4.40 (q, 2H), 3.53(t, 2H), 2.70 (t, 2H), 1.98-1.88(m, 2H), 1.42 (t, 3H), 123770-62-7

As the paragraph descriping shows that 123770-62-7 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); A1;,
Isoxazole – Wikipedia
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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, General procedure: Dione enolate formation: To a solution of ketone A in THF cooled to -78 C, LiHMDS (e.g., 0.9 equiv, 1.0 M in toluene) was added dropwise via syringe. The reaction was allowed to warm to 0 C, then charged with diethyl oxalate (1.2 equiv). At this time, the reaction was warmed to room temperature and stirred at that temperature until judged complete (e.g., using either TLC or LC/MS analysis). Once the reaction was complete (reaction time was typically 45 minutes), the product dione enolate B was used ?as-is? in Step 2, i.e., the cyclization step, without any further purification. The above compound was prepared following general procedure A, using 1-(isoxazol-3-yl)ethanone in step 1 and 2,3-difluorobenzylhydrazine in step 2.

88511-37-9 1-(Isoxazol-3-yl)ethanone 21349800, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; NAKAI, Takashi; MOORE, Joel; PERL, Nicholas Robert; IYENGAR, Rajesh R.; MERMERIAN, Ara; IM, G-Yoon Jamie; LEE, Thomas Wai-Ho; HUDSON, Colleen; RENNIE, Glen Robert; JIA, James; RENHOWE, Paul Allen; BARDEN, Timothy Claude; YU, Xiang Y; SHEPPECK, James Edward; IYER, Karthik; JUNG, Joon; WO2014/144100; (2014); A2;,
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Isoxazole | C3H3NO – PubChem