Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3209-70-9,Ethyl isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

A solution of ethyl nitroacetate (133 g, 1.0 mol) in dry dioxane (3 L) was treated with phenylisocyanate (130 g, 1.1 mol). Acetylene was bubbled through a solution, and triethylamine (111 g, 1.1 mol) was added dropwise for 5 h. The mixture was filtered, and the precipitate was washed with dioxane. The filtrate was evaporated, and the residue was distilled, providing the fraction with a boiling point of 110-112 C at 12 mmHg as the product isoxazole ester (89 g, 63%). This material was diluted into toluene (1 L), and this solution then added dropwise to a solution of diisobutyl aluminum hydride (630 mL, 0.63 mol, 1M toluene) at-75 C with stirring. The reaction mixture was stirred for 30 min, and 10% aqueous ammonium chloride (excess) was added. The organic partition was separated, washed with water (100 mL) and evaporated. The residue was distilled to provide the fraction with a boiling point of 85-90 C at 12 MMHG as the title compound (42 g, 43%).

3209-70-9, As the paragraph descriping shows that 3209-70-9 is playing an increasingly important role.

Reference£º
Patent; MERCK & CO., INC.; WO2004/58702; (2004); A2;,
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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.

General procedure: N-protected amino acid was dissolved in dichloromethane (DCM). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl, 1.3 eq.) and hydroxybenzotriazole (HOBt ¡¤xH2O, 1.3 eq.) were added at 0 C and the mixture was stirred for 50 min, after which thecorresponding amine (1.3 eq.) and N,N-Diisopropylethylamine (DIPEA, 1.3 eq.) were added at 0C. After stirring overnight, the mixture was washed with a 5% potassium sulfate solution(KHSO4), a 5% sodium bicarbonate solution (NaHCO3) and with water. After drying over sodiumsulfate (Na2SO4) and evaporation of the solvent, the residue was purified via columnchromatography., 108511-97-3

108511-97-3 Isoxazol-4-amine 13804278, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Article; Silva, Daniel G.; Ribeiro, Jean F.R.; De Vita, Daniela; Cianni, Lorenzo; Franco, Caio Haddad; Freitas-Junior, Lucio H.; Moraes, Carolina Borsoi; Rocha, Josmar R.; Burtoloso, Antonio C.B.; Kenny, Peter W.; Leitao, Andrei; Montanari, Carlos A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5031 – 5035;,
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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.14678-05-8,Isoxazol-5-amine,as a common compound, the synthetic route is as follows.

Example 26-Methyl-4-(3-methyl-lH-indazol-5-yl)-4,7-dihydroisoxazolo[5,4-b]pyridine-5-carbonitrileA mixture of 50 mg (0.22 mmol) (2?)-2-[(3-methyl-lH-indazol-5-yl)methylidene]-3-oxobutane- nitrile (Example 2A) and 19 mg (0.22 mmol) 1 ,2-oxazol-5-amine in propan-2-ol (1.0 ml) was stirred at reflux temperature overnight. The reaction mixture was then concentrated under reduced pressure, and the residue was purified by preparative RP-EtaPLC (acetonitrile/water + 0.1% TFA gradient) to yield 45 mg (69% of th.) of the racemic title compound.LC-MS (method 2): R, = 0.85 min; MS (ESIpos): m/z = 292 (M+Eta)+ 1H-NMR (400 MHz, DMSOd6): delta = 12.63 (br. s, IH), 10.91 (s, IH), 8.14 (s, IH), 7.55 (s, IH), 7.43 (d, IH), 7.19 (d, IH), 5.02 (s, IH), 2.48 (s, 3H), 2.16 (s, 3H) ppm., 14678-05-8

The synthetic route of 14678-05-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; MICHELS, Martin; FOLLMANN, Markus; VAKALOPOULOS, Alexandros; ZIMMERMANN, Katja; TEUSCH, Nicole; LOBELL, Mario; WO2011/3604; (2011); A1;,
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57684-71-6, 3-(Chloromethyl)isoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,57684-71-6

STR64 A compound of 3-(chloromethyl)-isoxazole (1.2 g) was added dropwise at a temperature of 20 to 30 C. under stirring to a mixture of 7-fluoro-6-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2H-1,4-benzoxazin-3(4H)-one (3.16 g), acetonitrile (50 ml) and potassium carbonate (1.5 g). The reaction mixture was heated under refluxing for 3 hours, cooled to room temperature, and filtered. The filtrate was concentrated under a reduced pressure to dryness. The resultant residue was mixed with toluene (150 ml) to form a suspension, which was then filtered to remove the undissolved materials therefrom. The filtrate was concentrated under a reduced pressure so as to obtain a viscous material, which was thereafter dissolved in a minimum amount of ethanol. The ethanol solution was cooled to precipitate a crystalline product. This product was separated by filtration and dried, so that the aimed compound, i.e. 7-fluoro-4-(isoxazol-3-ylmethyl)-6-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2H-1,4-benzoxazin-3(4H)-one (3.3 g) was obtained. m.p. 206-210 C.

57684-71-6 3-(Chloromethyl)isoxazole 4913025, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Nihon Tokushu Noyaku Seizo K.K.; US4902335; (1990); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.206055-91-6,(3-(4-Bromophenyl)isoxazol-5-yl)methanol,as a common compound, the synthetic route is as follows.

3-(4-bromophenyl)isoxazol-5-yl)methanol (5.0 g, 19.7 mmol) synthesized in Step 1 of Preparation Example 7, and 60% sodium hydride (1 g) were added to N,N-dimethylformamide (50 mL) and the mixture was stirred for 15 min. After methyl iodide was added thereto and completion of the reaction was confirmed by TLC, extraction was carried out with water (20 mL) and ethyl acetate (100 mL). The organic layer was washed with water (50 mL¡Á2) and brine (20 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered under reduced pressure to remove ethyl acetate. The residue was purified by silica gel column chromatography using ethyl acetate and hexane as a developing solvent, thus affording the title compound 3-(4-bromophenyl)-5-(methoxymethyl)isoxazole (11f). Yield: 95%.1H NMR (CDCl3, 400 MHz): 7.67 (d, 2H, J=7.2 Hz), 7.58 (d, 2H, J=7.6 Hz), 6.53 (s, 1H), 4.57 (s, 2H), and 3.45 (s, 3H).

206055-91-6, As the paragraph descriping shows that 206055-91-6 is playing an increasingly important role.

Reference£º
Patent; Moon, Ho-Sang; Yoo, Moo-Hi; Kim, Soon-Hoe; Lim, Joong-In; Son, Moon-Ho; Kim, Mi-Kyung; Shin, Chang-Yell; Kim, Jin-Kwan; Park, Sang-Kuk; Chae, Yu-Na; Shim, Hyun-Joo; Jeon, Sun-Ho; Kim, Hae-Sun; Wie, Gil-Tae; Kim, Dong-Hwan; Lee, Byung-Kyu; Park, Chan-Sun; Ahn, Byung-Nak; Kim, Eunkyung; Bae, Myung-Ho; Shin, Young-Ah; Hur, Youn; Lee, Chun-Ho; Choi, Hyun-Ho; Kim, Bongtae; Chong, Wonee; US2010/63041; (2010); A1;,
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123770-62-7, Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

INTERMEDIATE 5 – PREPARATION OF 5-(Hydroxymethyl)isoxazole-3-carboxylic acid. ; The mixture of Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (1.5 g; 8.76 mmol) and 1 M sodium hydroxide (18 ml 18 mmol) was stirred at room temperature for 3.5 h. Brine (40 mL) was added and the pH of the solution was adjusted to 2 by addition of 6N hydrochloric acid. The acidic solution was extracted with 8X60 mL of ethyl acetate. Organic extracts were dried over magnesium sulfate. Evaporation of the solvent produced 1.20 g (95%) of 5-(hydroxymethyl)isoxazole-3-carboxylic acid as a white solid which was used without further purification., 123770-62-7

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

Reference£º
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U. LEUVEN R&;D; reMYND; GRIFFIOEN, Gerard; VAN DOOREN, Tom; ROJAS DE LA PARRA, Veronica; MARCHAND, Arnaud; ALLASIA, Sara; KILONDA, Amuri; CHALTIN, Patrick; WO2010/142801; (2010); A1;,
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2510-36-3, 3,5-Dimethylisoxasole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 3,5-dimethylisoxazole-4-carboxylic acid (58 mg, 2.5 equiv.) in DMF (3 mL) was added D/PEA (202 uL, 7 equiv.), followed by TBTU (160 mg, 3 equiv.). The reaction mixture was stirred at RT for one hour, and then 4-[[4-(lH-pyrrolo[2,3-?]pyridin- 3-yl)-l-piperidyl]sulfonyl]aniline (59 mg, 1 equiv.) was added. The reaction mixture was stirred at RT for 30 min, and at 100 C for 2 h. The reaction mixture was cooled to RT, and the solvent was removed in vacuo. The residue was partitioned betweed EtOAc and water, organic phase was washed with brine, dried over Na2S04, filtered, and the solvent was removed in vacuo to yield the crude product. The crude product was purified by column chromatography, followed by preparative HPLC-MS to yield the expected product (11.5 mg). LCMS: MW (calc’d): 479.5; MS (ES+, m/z): 480.7 [M+H]+., 2510-36-3

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

Reference£º
Patent; E-THERAPEUTICS PLC; JURKOVIC, Mihaela; LANDEK, Ivana Ozimec; POLJAK, Tanja; RO?CIC, Maja; STUBBERFIELD, Colin; VADLAMUDI, Srinivasamurthy; (228 pag.)WO2019/43372; (2019); A1;,
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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

a solution of 5-phenyl-l,2-oxazole-3-carboxylic acid (850.5 mg, 4.50 mmol, 1.51 eq.) and 2-(3- aminocyclobutyl)ethan-l-ol hydrochloride (452 mg, 2.98 mmol, 1.00 eq.) in dichloromethane (25 mL)was placed in a 100-mL round-bottom flask. HATU (1.368 g, 3.60 mmol, 1.21 eq.) and DIEA (1.161 g, 8.98 mmol, 3.01 eq.) were added to the solution and stirred for 1 hour at room temperature. The resulting solution was diluted with 50 mL of water, extracted with chloromethane (3×30 mL) and the organic layers combined. The resulting mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash-Prep-HPLC with the following conditions (CombiFlash-1): Column, C18 silica gel; mobile phase, MeCN/H20=55:45 increasing to MeCN/H2O=60:40 within 2 min; Detector, UV 254 nm to give 110 mg (13%) of N-[3-(2-hydroxyethyl)cyclobutyl]-5-phenyl- l,2-oxazole-3-carboxamide as a off-white solid. The isomers were separated by Chiral-Prep- HPLC using the following conditions (Prep-HPLC-009): Column, Repaired IA, 21.2* 150mm, 5um; mobile phase, Hexane and ethanol (hold 20.0% ethanol in 20 min); Detector, UV 254/220 nm. This resulted in 23.8 mg (60%) of 5-phenyl-N-[ ram,-3-(2-hydroxyethyl)cyclobutyl]-l,2- oxazole-3-carboxamide as a white solid and 35.7 mg (70%) of 5-phenyl-N-[cw-3-(2- hydroxyethyl)cyclobutyl]-l,2-oxazole-3-carboxamide as a white solid. iV-iras-3-(2-hydroxyethyl)cyclobutyl)-5-phenylisoxazole-3-carboxamide: [0439] LC-MS: (M+H)+ = 287 [0440] Analytical data: XH NMR (CDC13, 400MHz): delta 7.83-7.81 (m, 2H), 7.54-7.49 (m, 3H), 7.05-7.02 (m, 1H), 6.97 (s, 1H), 4.72-4.67 (m, 1H), 3.73-3.68 (t, J = 10.0Hz, 2H), 2.49- 2.41 (m, 1H), 2.26-2.21 (m, 4H), 1.87-1.81 (m, 2H). [0441] HPLC purity: 99.4% at 254 nm. iV-cis-3-(2-hydroxyethyl)cyclobutyl)-5-phenylisoxazole-3-carboxamide: [0442] LC-MS: (M+H)+ = 287 [0443] Analytical data: XH NMR (CDC13, 400MHz): 7.83-7.80 (m, 2H), 7.54-7.49 (m, 3H), 7.02-6.93 (m, 3H), 4.50-4.44 (m, 1H), 3.67-3.63 (t, J= 8.0Hz, 2H), 2.68-2.62 (m, 2H), 2.22- 2.13 (m, 1H), 1.76-1.66 (m, 4H). [0444] HPLC purity: 99.0% at 254 nm., 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; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (178 pag.)WO2016/115090; (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.1136-45-4,5-Methyl-3-phenylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

1136-45-4, A solution of 3-phenyl-5-methyl-4-isoxazole formic acid (0.2 g, 1 mmol) in DMF (5 mL) was stirred. EDCI (1-(3-dimethylamino propyl)-3-2 ethyl carbon imine hydrochloride) (0.22 g, 1.2 mmol) and HOBt (N-hydroxybenzotrizole) (0.16 g, 1.2 mmol) were added sequentially and activated for approximately 1 h. Glucosamine hydrochloride (0.43 g, 2 mmol) and triethylamine (0.4 g, 4 mmol) were then added, and the solution was stirred for an additional 24 h at room temperature. The reaction was monitored by TLC. The mixture was extracted with ethyl acetate (EA) after the end of the reaction. The organic layer was separated, washed with a saturated sodium chloride solution, dried over MgSO4, and concentrated in vacuo. The residue was washed with ethanol/dichloromethane (v/v = 2:5), and the title compound A1 was obtained as a white solid (70% yield). 1H NMR (400 MHz, DMSO) delta 8.27 (m, 2H), 7.65 (m, 3H), 6.60 (s, 1H, NH-CO), 5.04 (d, 1H), 3.58 (m, 2H), 3.30 (d, J = 25.2 Hz, 2H), 3.05 (q, J = 7.3 Hz, 1H), 2.53 (d, J = 3.6 Hz, 3H, CH3), 1.18 (s, 4H, OH). 13C NMR (100 MHz, DMSO-d6) delta 169.75, 161.44, 159.95, 128.71, 127.83, 112.85, 90.29, 72.10, 71.12, 70.12, 61.01, 54.80, 45.26, 10.93, 8.37. HRMS (ESI) calcd for C17H20N2O7 [M+Na]+: 387.1179, found 387.1166.

The synthetic route of 1136-45-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Cao, Tingting; Li, Yong; Jiang, Lijuan; Yuan, Li; Dong, Lin; Li, Ying; Yin, Shufan; Carbohydrate Research; vol. 433; (2016); p. 73 – 79;,
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35166-33-7, 3-Hydroxymethyl-5-methylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) 3-(tert-Butyldimethylsilyloxymethyl)-5-methylisoxazole To a chilled (5 C.) solution of 3-hydroxymethyl-5-methylisoxazole (16.8 g, 148 mmol) and tert-butyldimethylsilyl chloride (24.6 g, 163 mmol) in dry methylene chloride (100 mL) was added over 15 minutes a solution of triethylamine (22.7 mL, 163 mmol) in methylene chloride (25 mL). 4-Dimethylaminopyridine (1.81 g, 14.8 mmol) was added and the thick reaction mixture was stirred at room temperature for 48 hours. Water (100 mL) was added and the aqueous layer extracted with methylene chloride (3*). The combined organic phases were washed with brine, dried (MgSO4), filtered through a pad composed of a layer of Florisil and a layer of Silica Gel 60, and concentrated in vacuo. The yellow oil obtained (36.6 g) was purified by chromatography (Silica Gel 60, 2% ethyl acetate in hexanes) to give 27.7 g (81.9%) of pure title compound as a pale yellow oil.

35166-33-7, The synthetic route of 35166-33-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sterling Winthrop Inc.; US5349068; (1994); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem