Month: October 2020

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

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.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

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.51677-09-9,Methyl 5-phenylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.,51677-09-9

General procedure: To a stirred solution of substrate 1 (1.0 equiv) in THF (0.1 M) was added Grignardreagent (10 equiv) at -78 C and stirred at the same temperature under Ar. After the substrate 1 wasconsumed or the reaction did not proceed any more (judged by TLC), sat. NH4Cl aq. at -78 C was added tothe reaction mixtures and the resulting solution was extracted with AcOEt. The combined organic layerwas dried over Na2SO4 and concentrated in vacuo. The ratio of substrate 1, ketone 2, and tertiaryalcohol 3 was determined by 1H NMR spectrum of crude reaction mixtures.Tertiary alcohol 3ab-3db was prepared by the reaction of substrate 1 and Grignard reagent at rt.

51677-09-9 Methyl 5-phenylisoxazole-3-carboxylate 905953, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Article; Murai, Kenichi; Miyazaki, Shuji; Fujioka, Hiromichi; Tetrahedron Letters; vol. 53; 29; (2012); p. 3746 – 3749;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

354795-62-3, 3-Methylisoxazol-4-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 435-Chloro-4-[(3,3-difluoro-1-pyrrolidinyl)carbonyl]- V-(3-methyl-4-isoxazolyl)-2- [(phenylmethyl)oxy]benzamide (E43)To a solution of 5-chloro-4-[(3,3-difluoro-1-pyrrolidinyl)carbonyl]-2- [(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 65; 90 mg, 0.23 mmol) in N,N-dimethylformamide (3 ml) was added diisopropylethylamine (0.08 ml, 0.46 mmol), HATU (156 mg, 0.41 mmol) and 3-methyl-4-isoxazolamine (26.8 mg, 0.27 mmol). The solution was stirred for 18 hours. The solvent removed in vacuo and purified by MDAP to give the title compound as a white solid. 65 mg.MS (electrospray): m/z [M+H]+ 4761 H NMR (DMSO-d6): 1.94 (3 H, d, J=3.26 Hz), 2.40 – 2.60 (2 H, m), 3.40 (1 H, t, J=7.28 Hz), 3.54 – 3.68 (1 H, m), 3.75 (1 H, t, J=7.53 Hz), 3.93 (1 H, t, J=13.18 Hz), 5.28 (2 H, s), 7.32 – 7.45 (4 H, m), 7.51 (2 H, d, J=6.78 Hz), 7.81 (1 H, s), 9.16 (1 H, s), 9.97 (1 H, br. s.).

354795-62-3, The synthetic route of 354795-62-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; ANDREOTTI, Daniele; DAI, Xuedong; EATHERTON, Andrew John; JANDU, Karamjit Singh; LIU, Qian; PHILPS, Oliver James; WO2012/28629; (2012); 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;,
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

1228690-37-6, (R)-1-Phenylethyl (5-(4-bromophenyl)-3-methylisoxazol-4-yl)carbamate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1228690-37-6

Step 3: {4′-[3-Methyl-4-((R)-l-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-4-yl}- acetic acid ethyl ester[00484] [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)- 1 -phenyl-ethyl ester (39g, 97.2mmol), [4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (31g, 107mmol), and sodium bicarbonate (32.6g, 389mmol) were combined in 3: 1 DME:H20 (500mL), and the mixture was purged with N2 for 15 minutes. (l,l’-Bis(diphenylphosphino)ferrocene)- dichloropalladium(II) (2.13g, 2.91mmol) was added, and the reaction was purged with N2 for an additional 10 minutes and then stirred at 90C overnight. The mixture was partitioned between EtOAc and H20, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with H20, dried over MgS04, filtered, and concentrated, and the residue was purified by silica gel chromatography (EtOAc/hexane gradient) to give the title compound.

As the paragraph descriping shows that 1228690-37-6 is playing an increasingly important role.

Reference£º
Patent; AMIDRA PHARMACEUTICALS, INC.; BRITTAIN, Jason, Edward; SEIDERS, Thomas, Jon; KING, Christopher, David; WO2011/159550; (2011); 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.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