Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Et3N (5.6 mL, 42 mmol) and HATU (4.84 g, 13 mmol) were added to a mixture of ethyl trans-3-aminocyclobutane-1-carboxylate hydrochloride (1.89 g, 10 mmcl) and 5-phenyliscxazcle-3-carbcxylic acid (2 g, 10 mmcl) in THF (200 mL) at room temperature and the reaction mixture was stirred for 6 h at room temperature. Volatiles were removed under reduced pressure to get the crude compound. The reaction mixture was diluted with water (100 mL) and extracted using ethyl acetate (2 x 75 mL). Combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. Themixture was purified by flash column chromatography using 30% EtOAc in hexane as eluent to give the product (2.65 g, 80 %) as white solid. ?H NMR (400 MHz, CDC13) : oe 7.80-7.77 (m, 2H), 7.49-7.46 (m, 3H), 7.00 (d, J= 7.2 Hz, 1H), 6.94 (s, 1H), 4.79-4.73 (m, 1H), 4.17 (q, J=7.1 Hz, 2H), 3.10-3.09 (m, 1H), 2.78-2.72 (m, 2H), 2.40-2.32 (m, 2H), 1.30-1.26 (t, J 7.2 Hz, 3H). LC-MS: [M+H] + 315.2

14441-90-8, The synthetic route of 14441-90-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
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.

110256-15-0, To a solution of 5-cyclopropylisoxazole-3-carboxylic acid (650 mg, 4.24 mmol) in DMF (2 mL) were added N,O-dimethylhydroxylamine hydrochloride (497 mg, 5.09 mmol), DIPEA (2.22 mL, 12.73 mmol) and 1-propanephosphonic anhydride (3.75 mL, 6.37 mmol) at room temperature. The reaction mixture was stirred at the same temperature for 16 h. The reaction mixture was diluted with water and extracted twice with ethyl acetate (20 mL). The combined organic layer was dried over Na2SO4 and evaporated under reduced pressure to dryness. The crude product was purified by flash column chromatography (Column: 24g silica; Solvent run: 0-50% EtOAc in pet ether). The product was eluted at 30% EtOAc in pet ether to yield 5-cyclopropyl-N-methoxy-N- methylisoxazole-3-carboxamide (450 mg, 2.16 mmol, 50.8 % yield). LCMS: m/z, 197.1 (M+H); rt 1.07 min; Column: Waters Acquity UPLC BEH C18 (2.1 x 50 mm) 1.7 mm, Mobile phase A: 10 mM ammonium acetate:acetonitrile (95:5); Mobile phase B: 10 mM ammonium acetate:acetonitrile (5:95), Gradient = 20-90 % B over 1.1 minute, then a 0.6 minute hold at 90 % B; Temperature: 50 C; Flow rate: 0.7 mL/min; Detection: UV at 220 nm

As the paragraph descriping shows that 110256-15-0 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; CHUPAK, Louis S.; DARNE, Chetan Padmakar; DING, Min; GENTLES, Robert G.; HUANG, Yazhong; KAMBLE, Manjunatha Narayana Rao; MARTIN, Scott W.; MANNOORI, Raju; MCDONALD, Ivar M.; OLSON, Richard E.; RAHAMAN, Hasibur; JALAGAM, Prasada Rao; ROY, Saumya; TONUKUNURU, Gopikishan; VELAIAH, Sivasudar; WARRIER, Jayakumar Sankara; ZHENG, Xiaofan; TOKARSKI, John S.; DASGUPTA, Bireshwar; REDDY, Kotha Rathnakar; RAJA, Thiruvenkadam; (0 pag.)WO2020/6018; (2020); 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

To a solution of CH3ONHCH3.HC1 (780 mg) and acid chloride (1 g) in CH2C12 at 0 C. was added dry pyridine (1.35 ml) to afford a heterogenous mixture The solution was warmed to room temperature and stirred overnight. 1 M HC1 was added to the reaction and the organic layer was separated, washed with brine, dried with Na2SO4, filtered, and concentrated in vacuo to give 1 g of product (85%).

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

Reference£º
Patent; Schering Corporation and Pharmacopeia, Inc.; US2004/147559; (2004); A1;,
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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;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

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
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;,
Isoxazole – Wikipedia
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;,
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.

A suspension of 5-cyclopropylisoxazole-3-carboxylic acid (5.00 g, 32.7 mmol) in DCM (30 mL) was treated sequentially with oxalyl chloride (7.15 mL, 81.6 mmol) and DMF (30 muL, 32.7 mmol). The reaction mixture was stirred for 1.5 h at RT, and then concentrated. The resulting residue was suspended in THF (65.3 mL), cooled to 0 C, and then treated with malononitrile (2.59 g, 39.2 mmol) and DIPEA (14.3 mL, 81.6 mmol). After stirring the reaction mixture for 48 h at 0 C, and 2 h at RT, dimethyl sulfate (9.36 mL, 98.0 mmol) was added. The resulting reaction mixture was stirred at 70 C until LCMS indicated complete consumption of starting materials. The mixture then was cooled to RT, and diluted with water (50 mL). The aqueous mixture was extracted with EtOAc. The combined organic extracts were concentrated. The resulting residue was purified by silica chromatography (0-20% EtOAc in hexanes) to afford the title compound (2.27 g, 32%)., 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; ARRAY BIOPHARMA INC.; BLAKE, James F.; DAI, Donghua; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI,, Gabrielle R.; METCALF, Andrew T.; MORENO, David A.; PRIGARO, Brett; REN, Li; (330 pag.)WO2019/143991; (2019); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

3356-89-6, 5-Chloro-3-phenylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a stirred suspension of NaH (60% in mineral oil, 440 mg, 11 mmol, prewashed with hexane) in anhydrous THF (20 mL) was added the appropriate alcohol (15 mmol) at r.t. and the reaction mixture was stirred for 0.5 h. Next, 5-chloro-3-phenylisoxazole (2) (1.0 g, 5.6mmol) was introduced as a solid and the mixture was refluxed for 1 h. After cooling to r.t., the mixture was quenched with H2O (20 mL). For 4a and 4b, the resulting precipitate was collected, washed with H2O and recrystallized from hexane-Et2O mixture. For 3a, the reaction mixture was extracted with CH2Cl2 (3 ¡Á 20 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give isoxazole 3a. 5-tert-Butoxy-3-phenylisoxazole (4c) was synthesized analogously using commercially available potassium tert-butoxide.

3356-89-6, The synthetic route of 3356-89-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Rostovskii, Nikolai V.; Agafonova, Anastasiya V.; Smetanin, Ilia A.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; Ruvinskaya, Julia O.; Starova, Galina L.; Synthesis; vol. 49; 19; (2017); p. 4478 – 4488;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

3405-77-4, 5-Methylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,3405-77-4

(R)-Methyl 3-(5-methyl isoxazole-3-carboxamido)-2,3-dihydro-1H-indene-5-carboxylate (B-25)HATU (4.4 g, 11.7 mmol, 1.5 eq) and DIPEA (3.0 ml, 15.6 mmol, 2 eq) were added to an ice-cooled solution of 5-methylisoxazole-3-carboxylic acid (990 mg, 7.8 mmol, 1 eq) in dichloromethane (80 ml), and stirring was carried out for 30 min. (R)-Methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate (A-07) (7.8 mmol, 1 eq) was dissolved in dichloromethane (20 ml) and added dropwise to the reaction solution, and stirring was carried out for 16 h at RT.The reaction solution was diluted with dichloromethane (250 ml), washed with sat. sodium hydrogen carbonate solution (50 ml), sat. ammonium chloride solution (50 ml), water (50 ml) and sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure.After purification by column chromatography (silica gel, 2percent MeOH in dichloro-methane), the desired product was obtained in the form of a yellowish solid. Yield: 68percent (1.6 g, 5.3 mmol).

3405-77-4 5-Methylisoxazole-3-carboxylic acid 76947, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; GRUENENTHAL GmbH; US2012/71461; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem