Day: November 5, 2020

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.

To a solution of 5-cyclopropylisoxazole-3-carboxylic acid (lOOmg, 0.653mmol) in DMF (2ml) was added HATU (370 mg, 0.980 mmol). The reaction stirred at room temperature for 30 minutes and then was cooled to 0C. l-Cyclopropyl-4- methylpyrrolidin-3 -amine (109 mg, 0.781 mmol) was added followed by DIPEA (252 mg, 1.960 mmol). The reaction stirred at ambient temperature for 2 hours. After completion of the reaction the reaction mixture was poured into 50 ml of water. The aqueous phase was extracted with ethyl acetate (3 x 25ml). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated under vacuum. The material was purified using column chromatography. The product was eluted at 2% MeOH in DCM. Appropriate fractions were combined and concentrated under vacuum to get 150 mg (83.79 %) of 5-cyclopropyl-N-(l-cyclopropyl-4- methylpyrrolidin-3-yl)isoxazole-3-carboxamide as a mixture of enantiomers and diastereomers. Cis and trans isomers were seperated out by chiral preparative HPLC using 0.1% TFA in hexanes/isopropanol as mobile phase to afford 35 mg of (¡À)-cis-5- cyclopropyl-N-(l-cyclopropyl-4-methylpyrrolidin-3-yl)isoxazole-3-carboxamide (Fraction- 1) and 49 mg of (¡À)-tra/?5-5-cyclopropyl-N-(l-cyclopropyl-4-methylpyrrolidin- 3 -yl)isoxazole-3 -carboxamide (Fraction-2) . [0196] (¡À)-cz5-5-cyclopropyl-N-(l-cyclopropyl-4-methylpyrrolidin-3-yl)isoxazole-3- carboxamide: 1H NMR (400 MHz, MeOD): delta 6.41 (s, 1H), 4.33 (bs, 1H), 3.94-3.66 (m, 3H), 3.15-3.00 (m, 2H), 2.56-2.53 (m, 1H), 2.22-2.15 (m, 1H), 1.37-1.33 (d, J = 18.4 Hz, 3H), 1.23 (d, J = 6.8 Hz, 2H), 1.00-0.99 (m, 5H); LCMS: m/z = 277.23 [M+H]+. [0197] (¡À)-tra/?5-5-cyclopropyl-N-(l-cyclopropyl-4-methylpyrrolidin-3-yl)isoxazole-3- carboxamide: 1H NMR (400 MHz, MeOD): delta 6.42 (s, 1H), 4.15 (bs, 1H), 3.77-3.66 (m, 3H), 3.52-3.37 (m, 2H), 3.04 (bs, 2H), 2.62 (bS, 1H), 2.22-2.26 (m, 1H), 1.19-1.12 (m, 2H), 1.09 (d, J = 7.2 Hz, 3H), 1.01-0.98 (m, 5H), 0.97-0.90 (m, 2H); LCMS: m/z = 276.18 [M+H]+.

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

Reference£º
Patent; EPIZYME, INC.; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; HARVEY, Darren Martin; (151 pag.)WO2016/40504; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

19788-37-5, 4-(Chloromethyl)-3,5-dimethylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-Chloromethyl-3,5-dimethyl-isoxazole (1.5 eq. ) was directly added to a solution of 2-furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (0.14 mmol; see Example 1 (a) above) and Et3N (0.3 mmol) in 3 mL of CH3CN. The resulting reaction mixture was stirred at room temp for 18 hours. It was then concentrated and purified by preparative HPLC using a mixture of aqueous CH3CN that has been buffered with 0.1 % TFA. 1H NMR (DMSO-d6) delta 7.60 (d, J = 1.0 Hz, 1 H), 7.28 (br s, 2 H), 7.22 (d, J = 3.6 Hz, 1 H), 6.68 (dd, J = 3.6 Hz, 1.0 Hz, 1 H), 3.8 (br s, 2 H), 2.2-3.2 (m, 8H), 1.6 (br s, 6H). MS: m/z: 396 [M + H] +., 19788-37-5

19788-37-5 4-(Chloromethyl)-3,5-dimethylisoxazole 88246, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; BIOGEN IDEC MA INC.; WO2004/92170; (2004); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

62348-13-4,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.

Example 90 N-{[1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4- b]pyridin-5-yl]methyl}-5-isoxazolecarboxamideA solution of Intermediate 14 (20mg) in anhydrous acetonitrile (0.4ml) was treated with isoxazole-5-carbonyl chloride [e.g. available from Lancaster Synthesis Ltd.] (13mg) and DIPEA (0.016ml) and stirred at room temperature for 24 hours. The solution was blown to dryness and the residue was purified by mass directed autoprep HPLC to give Example 90 as a clear colourless gum (12mg). LCMS showed MH+ = 371; TREtau = 2.03min.

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

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/36733; (2007); 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.88511-37-9,1-(Isoxazol-3-yl)ethanone,as a common compound, the synthetic route is as follows.,88511-37-9

A solution of l -(isoxazol-3-yl)ethanone (4.0 g, 36.3 mmol) in THF (200 mL) was cooled in dry ice/acetone. Lithium bis(trimethylsilyl)amide (1M in toluene, 33.8 mL, 33.8 mmol) was added over 10 min followed by 30 min of stirring at -65 to -70C. The ester pyrimidine obtained above (4.5 g, 24.2 mmol) in THF (20 mL) was dripped into the enoate solution over 5 min and stirring was continued overnight at room temperature. The solvents were removed in vacuo, then the residue was broken up under ether (100 mL) and filtered. The filter cake was washed with ether (20 mL) and air dried to leave 8.2 g crude diketo isoxazole which was carried on directly to the next reaction without further purification. LCMS (m/e) 266 (M+H).

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

Reference£º
Patent; IRONWOOD PHARMACEUTICALS, INC.; BARDEN, Timothy Claude; SHEPPECK, James Edward; RENNIE, Glen Robert; RENHOWE, Paul Allan; PERL, Nicholas; NAKAI, Takashi; MERMERIAN, Ara; LEE, Thomas Wai-Ho; JUNG, Joon; JIA, James; IYER, Karthik; IYENGAR, Rajesh R.; IM, G-Yoon Jamie; (293 pag.)WO2016/44447; (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.19788-37-5,4-(Chloromethyl)-3,5-dimethylisoxazole,as a common compound, the synthetic route is as follows.

4-Chloromethyl-3,5-dimethyl-isoxazole (500 muL, 3.40 mmol) was added to a mixture of phthalimide (500 mg, 3.40 mmol) and K2CO3 (500 mg, 3.62 mmol) in DMF (5mL) and stirred at ambient temperature overnight. The reaction was then heated to 70 C for 5 hours and subsequently cooled and partitioned between ethyl acetate and water. The organic layer was washed several times with water and concentrated to give 1.0 g of the sub-title compound as a white solid. MS: ESI (positive): 257 (M+H)., 19788-37-5

19788-37-5 4-(Chloromethyl)-3,5-dimethylisoxazole 88246, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; ATHERSYS, INC.; WO2006/34419; (2006); 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.21080-81-9,Ethyl 5-cyclopropylisoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

Into a 10-L round-bottom flask was placed ethyl 5-cyclopropylisoxazole-3- carboxylate (280 g, 1.55 mol, 1.00 equiv) and a solution of sodium hydroxide (74.3 g, 1.20 equiv) in water (4 L). The resulting solution was stirred for 1 h at room temperature. The resulting mixture was washed with ether. The pH value of the aqueous solution was adjusted to 2-3 with hydrochloric acid (12N). The resulting solution was extracted with ethyl acetate and the organic layers combined and concentrated under vacuum. This resulted in 220 g (93%>) of 5-cyclopropylisoxazole-3-carboxylic acid as an off- white solid. LCMS (method A, ESI): RT = 1.99 min, m z = 153.9 [M+H]+. 1H-NMR (300 MHz CDCls): 8.42(brs, 1H), 6.37(s, 1H), 2.16-2.05(m, 1H), 1.29-1.12(m, 2H), 1.12-0.99(m, 2H) ppm., 21080-81-9

21080-81-9 Ethyl 5-cyclopropylisoxazole-3-carboxylate 55251041, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; EPIZYME, INC.; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; (124 pag.)WO2016/40502; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

24068-54-0, 1-(5-Methylisoxazol-3-yl)ethanone is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2-Synthesis of 2-(5-methylisoxazol-3-yl)but-3-yn-2-ol To a stirred solution of ethynylmagnesium bromide (0.5 M in THF, 50 mL, 25 mmol) maintained under nitrogen below 0 C. was added a solution of 1-(5-methyl-1,2-oxazol-3-yl)ethan-1-one (2.5 g, 19.98 mmol) in tetrahydrofuran (20 mL) dropwise over 5 min. The resulting solution was warmed to room temperature and then stirred for a further 3 hr. The reaction was quenched by the addition of saturated ammonium chloride solution (100 mL) then extracted with ethyl acetate (2*100 mL). The combined organic layers was washed with brine (200 mL), dried with anhydrous sodium sulphate and concentrated in vacuo. The residue was purified on a silica gel column, elution with ethyl acetate/petroleum ether (0:1-1:4) afforded the title compound (2.3 g, 75%) as a colorless oil: 1H NMR (300 MHz, CDCl3) delta 6.12 (s, 1H), 3.47 (s, 1H), 2.63 (s, 1H), 2.42 (s, 3H), 1.86 (s, 3H).

24068-54-0, 24068-54-0 1-(5-Methylisoxazol-3-yl)ethanone 11147714, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Genentech, Inc.; US2012/214762; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

288-14-2, Isoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General Procedure 49 Isoxazole (0.64 mL, 10 mmol) was added to a solution of N-iodosuccinimide (2.3 g, 10 mmol) in trifluoroacetic acid (20 mL). After stirring overnight, water (50 mL), hexanes (50 mL) and sodium bisulfite were added to the reaction. The phases were separated and the organic phase was dried over Na2SO4, filtered and concentrated by rotary evaporation to give 4-iodo-isoxazole (218 mg, 11%)., 288-14-2

288-14-2 Isoxazole 9254, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; AGOURON PHARMACEUTICALS, INC.; US2006/46991; (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.21169-71-1,Isoxazole-5-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of isoxazole-5-carboxylic acid (1.0 g, 8.8 mmol,) in THF (10 mL) was added borane-THF complex (26.4 mL,26.4 mmol) at 0 C. The reaction was stirred at room temperature until the substrate was consumed. The reaction was quenched with ethanol (5 mL) at 0 C. The reaction mixture was partitioned between ethyl acetate and water. The combined organic phase was dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether/ ethyl acetate (2: 1 to give isoxazol-5-ylmethanol (670 mg, 77.0% yield) as a light yellow oil. LCMS retention time 0.329 min; LCMS MH+ 100.

21169-71-1, 21169-71-1 Isoxazole-5-carboxylic acid 2060599, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; HYDRA BIOSCIENCES, INC.; CHENARD, Bertrand; GALLASCHUN, Randall; WO2014/143799; (2014); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

51677-09-9,51677-09-9, Methyl 5-phenylisoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a stirred solution of substrate 1 (1.0 equiv) in THF (0.2 M) was added Grignardreagent (5.0 equiv) or organolithium reagent (2.0 or 3.0 equiv) at -78 C and the resulting solution wasstirred at the same temperature under Ar. After the substrate 1 was consumed or the reaction did not proceedany more (judged by TLC), sat. NH4Cl aq. was added to the reaction mixture and the resultingsolution was warm to rt and extracted with AcOEt. The combined organic layer was dried overNa2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography onsilica gel.p-Fluorophenylmagnesium chloride was prepared form p-fluoroiodobenzene and iPrMgCl according to theliterature.4Organolithium reagents were prepared by adding n-butyl lithium (hexane solution, 1.0 equiv) to a solution ofalkyne (1.1 equiv) in THF (0.8M) at -78 C and stirring at rt for 1 h.

As the paragraph descriping shows that 51677-09-9 is playing an increasingly important role.

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