Category: 3209-71-0

New learning discoveries about 3209-71-0

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

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.

To a solution of isoxazole-3-carboxylic acid; (119 mg, 1.05 mmol) in DCM (3 mL) was added (COd)2 (190 mg, 1.5 mmol). Then DMF (cat) was added in the mixture. The reaction was stirred at ft for 1 h. A solution of methyl 3-(1-ethyl-4-methyl-1H- benzo [di [1 ,2,3 jtriazol-5-yl)-3-( 1,2,3 ,4-tetrahydroisoquinolin-7-yl)propanoate (80 mg, 0.21 mmol) and TEA (530 mg, 5.25 mmol) in DCM (2 mL) was added to the mixture. The reaction was stirred at ft for another 2 h. The residue was concentrated to give methyl 3-(1- ethyl-4-methyl- 1H-benzo [di [1 ,2,3 jtriazol-5-yl)-3-(2-(isoxazole-3-carbonyl)- 1,2,3,4- tetrahydroisoquinolin-7-yl)propanoate (90 mg, yield: 90%) as white solid. ESI-MS (M+H) :474.2.

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

Reference£º
Patent; BIOGEN MA INC.; CAPACCI, Andrew, George; DECHANTSREITER, Michael; ENYEDY, Istvan; JONES, John, H.; LIN, Edward, Yin-Shiang; LUCAS, Brian, Stuart; MA, Bin; (273 pag.)WO2018/140876; (2018); A1;,
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Simple exploration of 3209-71-0

3209-71-0, 3209-71-0 Isoxazole-3-carboxylic Acid 11286453, aIsoxazoles compound, is more and more widely used in various fields.

3209-71-0, Isoxazole-3-carboxylic Acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 3 (24.0 g) and 16.17 g of isoxazole-3-carboxylic acid were suspended in 288 mL of acetone, 49.36 g of pyridine was added thereto and the suspension was cooled to -10C. 31.89 g of phosphorus oxychloride was poured into the suspension to react at 20 +/- 10C for about 30 minutes. The reaction mixture was cooled to 5C or below, 5.3 mL of water was added dropwise to the mixture at 20C, and 355 mL of water was poured therein. Then, 10% sodium hydroxide aqueous solution was added dropwise to the mixture until pH 4.5, and the mixture was stirred at 15 +/- 10C for about 2 hours to precipitate crystals. The crystallized slurry obtained was filtered, and the crystals were washed sequentially with 48 mL of 10% aqueous acetone, 192 mL of water, and 72 mL of 10% aqueous acetone, and dried in vacuo to afford Compound 4 (33.24 g, 91.4%).

3209-71-0, 3209-71-0 Isoxazole-3-carboxylic Acid 11286453, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; SHIONOGI & CO., LTD.; EP1408041; (2004); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Analyzing the synthesis route of 3209-71-0

3209-71-0, The synthetic route of 3209-71-0 has been constantly updated, and we look forward to future research findings.

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.

Exam le 5b; (2R,6S,13aS,14aR,16aS,Z)-ethyl 2-(3-(l,l-difluoroethyl)quinoxalin-2-yloxy)-6-(isoxazole-3- carboxamido)-5,16-dioxo-l,2,3,5,6,7,8,9,10,l l,13a,14,14a,15,16,16a- hexadecahydrocyclopropa[e]pyrrolo[l,2-a][l,4]diazacyclopentadecine-14a-carboxylate; To (2R,6S,13aS,14aR,16aS,Z)-ethyl 6-amino-2-(3-(l,l-difluoroethyl)quinoxalin-2-yloxy)- 5,16-dioxo-l,2,3,5,6,7,8,9,10,l l,13a,14,14a,15,16,16a- hexadecahydrocyclopropa[e]pyrrolo[l,2-a][l,4]diazacyclopentadecine-14a-carboxylate, hydrochloric acid (585.7 mg, 0.941 mmol) was added isoxazole-3-carboxylic acid (128 mg, 1.132 mmol) and DMF (9.4 ml). The reaction mixture was cooled to 0 C, and pyridine(0.761 ml, 9.41 mmol) then HATU (537.5 mg, 1.414 mmol) were added. The solution was stirred at rt 16 h, and LC/MS showed a small amount of SM remained. More isoxazole-3- carboxylic acid (52.3 mg) pyridine (0.2 ml) and HATU (179 mg) were added. The reaction mixture was stirred for an additional 16 h and LC/MS showed completion. The reaction mixture was concentrated under reduced pressure, and the oil was dissolved indichloromethane (100 ml) and washed with HC1 (1 N, 2 x 15 ml) and Na2C03 (1 N, 4 x 20 ml). The combined Na2C03 layer was back-extracted with dichloromethane (2 x 10 ml). The organic layers were combined, dried (MgS04) and concentrated, and purified bychromatography (SNAP50, acetonitrile/CHCl3 = 0-17%) to provide the title compound 5b (577 mg, 0.847 mmol, 90 % yield).

3209-71-0, The synthetic route of 3209-71-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBOTT LABORATORIES; ENANTA PHARMACEUTICALS, INC.; CHEN, Hui-ju; MCDANIEL, Keith, F.; GREEN, Brian, E.; SHANLEY, Jason, P.; KRUGER, Albert, W.; GANDARILLA, Jorge; WELCH, Dennie, S.; CINK, Russell, D.; GAI, Yonghua; WANG, Guoqiang; OR, Yat, Sun; WO2011/156337; (2011); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Analyzing the synthesis route of 3209-71-0

The synthetic route of 3209-71-0 has been constantly updated, and we look forward to future research findings.

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.

Under the protection of nitrogen gas, compound 56-a (230.00 mg, 2.03 mmol, 1.00 eq) was dissolved in dichloromethane (5 mL), and then HOBt (376.55 mg, 2.79 mmol, 1.37 eq), EDCI (534.22 mg, 2.79 mmol, 1.37 eq), NMM (617.26 mg, 6.10 mmol, 670.93 mL, 3.00 eq) were added thereto, and finally compound 7-a (415.72 mg, 2.64 mmol, 407.57 mL, 1.30 eq) as a substrate was added thereto. The reaction was stirred at 15C for 18 hours. The reaction system was added with 40 mL of ethyl acetate and 40 mL of water, and separated. The aqueous phase was further extracted once with ethyl acetate (30 mL). The combined organic phases were washed once with 50 mL of water and 50 mL of saturated brine. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was subjected to column chromatography (petroleum ether : ethyl acetate = 1:0?3:2) to give compound 56-b (243.00 mg, yield: 47%) as a brown liquid. LCMS m/z = 252.9 [M+H]+., 3209-71-0

The synthetic route of 3209-71-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; HE, Haiying; WU, Songliang; LUO, Zhi; MOU, Jianfeng; GUO, Fengying; WANG, Chuan; LI, Guoqing; ZENG, Minggao; CHEN, Shuhui; (199 pag.)EP3456711; (2019); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Brief introduction of 3209-71-0

3209-71-0, The synthetic route of 3209-71-0 has been constantly updated, and we look forward to future research findings.

3209-71-0, Isoxazole-3-carboxylic Acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

HOBt (4.5 g, 29.4 mmol) and EDCI (5.4 g, 28.2 mmol) were added to solution of isoxazole-3-carboxylic acid (2 1, 3 g, 26.5 mmol) and N,O-dimethylhydroxylamine (0205) hydrochloride (2.7 g, 27.7 mmol) in DMF (5 ml) and DCM (7ml). 4-methylmorpholine (3 ml, 27.3 mmol) was added, then the mixture was stirred overnight. It was extracted with ether (300 ml) and brine (100 ml), the organic layer was separated, it was washed with brine, dried over Na2S04, then filtered and the solvent was evaporated. The residue was purified by (0206) chromatography (Redisep 40 g column) eluting with 1/1 EtOAc/Hexanes yielding N-methoxy- N-methylisoxazole-3-carboxamide (2_2). LCMS (ESI) calc?d for C6H8N203 [M+H]+: 157.1, found: 157.1

3209-71-0, The synthetic route of 3209-71-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; CLAUSEN, Dane James; YU, Wensheng; KELLY, Joseph, M.; KIM, Hyunjin, M.; KOZLOWSKI, Joseph, A.; (202 pag.)WO2020/28150; (2020); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

New learning discoveries about 3209-71-0

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

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.

a) Ethyl 5-(isoxazol-3-yl)-l,2,4-oxadiazole-3-carboxylate Ethyl aminohydroxyiminoacetate (3.78 mmol, 0.5 g), 3-isoxazolecarboxylic acid (3.78 mmol, 0.428 g) and 1,3-diisopropylcarbodiimide (4.16 mmol, 0.525 g) were dissolved in DCM (70 ml) under nitrogen atmosphere. The mixture was stirred at RT for a day. The solvent was evaporated to dryness and the residue was dissolved in pyridine and refluxed for 6 h and overnight at RT. Pyridine was evaporated and the residue was diluted with DCM and water. The aqueous phase was extracted four times with DCM. The combined organics were washed with aqueous HC1 solution, saturated NaHC03, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.396 g of the title compound was obtained. Rotamers were obtained in 1 H-NMR and analysis was repeated at elevated temperature. 1 H-NMR (400 MHz, DMSO-c?, +60C): 5 1.38 (t, 3H), 4.49 (q, 2H), 7.21 (d, 1H), 9.05 (d, 1H).

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

Reference£º
Patent; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Downstream synthetic route of 3209-71-0

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

3209-71-0, Isoxazole-3-carboxylic Acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[00226] Isooxazole-3 -carboxylic acid ((8′), 92 wt % assay based on 1H-NMR, 3.86 kg, 34.1 mol, 1.0 equiv), toluene (19.3 L) and DMF (0.131 L, 1.69 mol, 0.05 equiv) were mixed in a 30 L jacketed reaction vessel equipped with a nitrogen inlet-outlet, overhead stirrer, a thermocouple and an addition funnel. The resulting slurry was heated to 45 to 55 C. Oxalyl chloride (4.80 kg, 37.8 mol, 1.11 equiv) was charged via the addition funnel over the course of 4 hours 30 minutes, while maintaining the reaction temperature between 45 to 55 C. Vigorous gas evolution was observed. A brown mixture was obtained after the addition. The brown mixture was held at 45 to 55 C for 30 minutes, then heated to 85 to 95 C and stirred at 85 to 95 C for 1 hour. During heating, the brown mixture turned into a black mixture. The black mixture was cooled to 20 to 25 C, over 4 hours and held at 20 to 25 C for a minimum of 16 hours. The reaction was monitored by quenching a portion of the reaction mixture into piperidine and monitoring the formation of the piperidine amide by HPLC ((8′) : piperidine amide area:area % was < 1.9). After the reaction was complete by HPLC the dark mixture was in-line filtered via gas a dispersion tube (coarse frit) into a 20 L rotavapor flask. Toluene (3.9 L) was used to rinse the reactor and the rinse was in-line filtered into the 20 L rotavapor flask. The filtered reaction mixture was concentrated under reduced pressure until no more distillate was seen coming off. As the paragraph descriping shows that 3209-71-0 is playing an increasingly important role. Reference£º
Patent; CYCLERION THERAPEUTICS, INC.; WALLACE, Debra Jane; ZHOU, Fenger; WANG, Yuguang; NAKAI, Takashi; KARNATI, Vishnu Vardhan Reddy; SCHAIRER, Wayne C.; KISSEL, Willaim; XUE, Song; HASHASH, Ahmad; (263 pag.)WO2019/140095; (2019); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

New learning discoveries about 3209-71-0

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

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.

A solution of isoxazole-3-carboxylic acid (10 mg, 0.084 mmol), HATU (32 mg, 0.084 mmol), triethylamine (30 ul, 0.212 mmol), 3-methyl-4-(7-methylbenzo[d]oxazol-2-yl)aniline (20 mg, 0.084) and catalytic amount of DMAP in THF (1 mL) was stirred at 65 C for 48 h. The reaction mixture was diluted with DCM, washed with saturated solution of NaHCO3 and brine. The organic solution was, dried over Na2SO4, decanted and evaporated under reduced pressure. The crude was purified by column chromatography on silica gel using 1:4 EtOAc:Hexane as mobile phase and the obtained product was triturated in hexane, filtered and dried to give N-(3-methyl-4-(7- methylbenzo[d]oxazol-2-yl)phenyl)isoxazole-3-carboxamide (3 mg, 10%). UPLC-MS (Acidic Method, 4 min): rt 2.12 min, m/z 334.1 [M+H]+ 1H NMR (400 MHz, METHANOL-d4) d ppm 7.32 (d, J=1.6 Hz, 1H), 6.63 (d, J=8.5 Hz, 1H), 6.26-6.32 (m, 2H), 6.02 (d, J=7.9 Hz, 1H), 5.71-5.77 (m, 1H), 5.65-5.69 (m, 1H), 5.40 (d, J=1.6 Hz, 1H), 1.27 (s, 3H), 1.06 (s, 3H).

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

Reference£º
Patent; JAGUAHR THERAPEUTICS PTE LTD; METE, Antonio; HITCHIN, James, R.; GRAHAM, Mark; (46 pag.)WO2020/43880; (2020); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Some tips on 3209-71-0

3209-71-0 Isoxazole-3-carboxylic Acid 11286453, aIsoxazoles compound, is more and more widely used in various.

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.

A solution of 3-isoxazolecarboxylic acid (500 mg, 4.42 mmol, commercially available from e.g. Manchester Organics, Bio-Farma or APAC) in dry dichloromethane (DCM) (14.700 ml) was stirred at room temeprature under an atmosphere of argon. EDC (1017 mg, 5.31 mmol) and HOBt (339 mg, 2.21 1 mmol) were added to the stirred soltuion and the resulting solution was stirred for 3/4 hour. After this time, 1 ,1- dimethylethyl hydrazinecarboxylate (701 mg, 5.31 mmol) was added to the stirred solution and strring continued for a further 18 hours at room temperature (overnight). The reaction mixture was partitioned between DCM (~ 20 ml) and saturated sodium bicarbonate solution (~ 20 ml). The aqueous phase was extracted with DCM (2 x 20 ml) and the combined organic extracts washed with saturated brine (~ 50 ml), dried over sodium sulphate, evaporated in vacuo and dried (vacuum oven, 40 0C, 72 hr) to afford the crude product as a brown oil. This was purified via Biotage SP4 (2-20 % MeOH/DCM; 100g SNAP Biotage column; 12 CV) to afford the required product as an orange oil in 510.6 mg, which was used without further purification in the next step. LCMS: [M-Boc+H]+ m/z = 128.0; RT. = 0.62-0.63 min.

3209-71-0 Isoxazole-3-carboxylic Acid 11286453, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (2010); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Brief introduction of 3209-71-0

The synthetic route of 3209-71-0 has been constantly updated, and we look forward to future research findings.

3209-71-0, Isoxazole-3-carboxylic Acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(Cis)-4-phenyldecahydroquinolin-4-ol (enantiomer A, 100 mg, 0.432 mmol), isoxazole-3- carboxylic acid (63.5 mg, 0.562 mmol), EDC (108 mg, 0.562 mmol), HOAt (1.124 ml, 0.5 M in DMF, 0.562 mmol), and TEA (0.078 ml, 0.562 mmol) were combined in DMF (2 ml) at RT. After 16 hr the mixture was filtered using a 0.45 mum PTFE syringe filter and concentrated. The residue was purified by preparative reversed-phase HPLC on a Waters Sunfire column (20×150 mm, 5mum) with gradient elution using 5-70% CH3CN/water containing 0.1% TFA over 20 minutes. Fractions containing the product were pooled and concentrated to give the title compound as an off-white solid (72 mg, 51%).

The synthetic route of 3209-71-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; WO2008/88744; (2008); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem