Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.36958-61-9,5-(Bromomethyl)-3-methylisoxazole,as a common compound, the synthetic route is as follows.

Sodium hydride (60% w/w) (34.1 mg, 0.85 mmol) was added to a stirring solution of 7-benzylsulfanyl-4-(cyclopropanecarbonyl)-2H-isoquinolin-1 -one (220. mg, 0.66 mmol) in DMF (8 mL). After 15 min 5-(bromomethyl)-3-methyl-1 ,2-oxazole (0.15 mL, 0.85 mmol) was added and the reaction mixture stirred at ambient temperature for 1 h. DCM (25 mL) and saturated aq. NaHC03 (25 mL) were added and the mixture stirred for 5 min. The DCM layer was isolated by passing through a hydrophobic frit and the aqueous layer washed with DCM. The combined DCM extracts were concentrated under reduced pressure and purified by automated column chromatography, SiO2, eluent 0-100% EtOAc in iso- Hexane to yield 7-benzylsulfanyl-4-(cyclopropanecarbonyl)-2-[(3-methylisoxazol-5- yl)methyl]isoquinolin-1 -one (263 mg, 0.61 mmol, 93%). Used directly in the synthesis of Intermediate S10-C1, 36958-61-9

As the paragraph descriping shows that 36958-61-9 is playing an increasingly important role.

Reference£º
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan; WASZKOWYCZ, Bohdan; HUTTON, Colin; WADDELL, Ian; HITCHIN, James R.; SMITH, Kate Mary; HAMILTON, Niall M.; (497 pag.)WO2016/92326; (2016); A1;,
Isoxazole – Wikipedia
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59669-59-9,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.59669-59-9,3-(tert-Butyl)isoxazol-5-amine,as a common compound, the synthetic route is as follows.

To a cold slurry of (S)-1-(4-Chloro-phenyl)-4-oxo-azetidine-2-carboxylic acid (0.2g; 1.037mmol) and 5-amino-3-tert-butylisoxazole (0.145g; 1.037mmol) in pyridine (1.258mL; 15.555mmol) is added phosphorous oxychloride (O.l lbetamL; 1.244mmol). The mixture is stirred at O¡ãC for 30 minutes and then diluted with water and extracted with ethyl acetate several times. The organics are combined and washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by preparative HPLC affords title compound, m/z 348 [M+H+]

The synthetic route of 59669-59-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HICKEY, Eugene, Richard; RIETHER, Doris; THOMSON, David, Smith; WU, Lifen; ZINDELL, Renee, M.; WO2010/147791; (2010); A1;,
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21169-71-1, Isoxazole-5-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

21169-71-1, General procedure: To a solution of the benzoxazole core (1.0 eq) in DCM (2 mL) was added the carboxylic acid (1.2 eq), EDCI (1.2 eq) and DMAP (0.1 eq). The solution was stirred under nitrogen at 45 C overnight. Work-up 1 (W1): The solution was extended with DCM, a saturated solution of sodium bicarbonate was added and the mixture was extracted three times with DCM. The combined organic layers were then washed with brine, dried with sodium sulphate and the solvent was removed in vacuo. Purification by column chromatography on silica gel, eluting ethyl acetate/cyclohexane 50:50 led to the desired carboxamide.

The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ferrins, Lori; Rahmani, Raphael; Sykes, Melissa L.; Jones, Amy J.; Avery, Vicky M.; Teston, Eliott; Almohaywi, Basmah; Yin, JieXiang; Smith, Jason; Hyland, Chris; White, Karen L.; Ryan, Eileen; Campbell, Michael; Charman, Susan A.; Kaiser, Marcel; Baell, Jonathan B.; European Journal of Medicinal Chemistry; vol. 66; (2013); p. 450 – 465;,
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, As the paragraph descriping shows that 288-14-2 is playing an increasingly important role.

Reference£º
Patent; AGOURON PHARMACEUTICALS, INC.; US2006/46991; (2006); A1;,
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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

Example 111N-((ls,4s)-4-(2-(4′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)biphenyl-3-yloxy)-5- fluoronicotinamido)cyclohexyl)-5-methylisoxazole-3-carboxamide HATU (0.104 g, 0.27 mmol) was added to a solution of 5-methylisoxazole-3-carboxylic acid (0.035 g, 0.27 mmol), N-((ls,4s)-4-aminocyclohexyl)-2-(4′-(((3S,5R)-3,5-dimethylpiperazin- l-yl)methyl)biphenyl-3-yloxy)-5-fluoronicotinamide (0.15 g, 0.25 mmol) and DIPEA (0.173 mL, 0.99 mmol) in DMF (5 mL) and the solution stirred at RT for 20 h. The mixture was purified by reverse phase HPLC with aqTFA/MeCN as eluant to the title compound as a white solid. Yield: 47 mg1U NMR (400 MHz, CD3OD) delta 8.45 (d, J = 7.9 Hz, IH), 8.11 (d, J = 3.4 Hz, IH), 8.07 (m, IH), 7.61 (d, J = 8.2 Hz, 2H), 7.49 (d, J = 5.3 Hz, 2H), 7.42 (m, 3H), 7.16 (m, IH), 6.38 (s, IH), 4.13 (m, IH), 3.94 (m, IH), 3.79 (s, 2H), 3.43 (m, 2H), 3.17 (m, 2H), 2.44 (s, 3H), 2.25 (m, 4H), 1.92 – 1.66 (m, 8H), 1.28 (d, J = 6.9 Hz, 6H). MS: APCI (+ve):641 (M+l)., 3405-77-4

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

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Isoxazole – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1083224-23-0,5-(2,4-Difluorophenyl)isoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.,1083224-23-0

[0301] To a solution of 5 -(2, 4-difluorophenyl)isoxazole-3 -carboxylic acid (100 mg, 0.44 mmol, 1 equiv) in DMF (1 mL), were added HATU (185 mg, 0.48 mmol, 1.1 equiv). The mixture was treated drop wise with DIPEA (183 mg, 1.42 mmol, 3.2 equiv). After stirring at RT for 15 minutes, the mixture was treated drop wise with a solution of the l-(2,4- bis(trifluoromethyl)benzyl)-lH-pyrazol-4-amine (137 mg, 0.44 mmol, 1 equiv) in DMF (1 mL). The reaction mixture was kept under stirring for 24 hrs at RT. Product formation was confirmed with TLC & LCMS and reaction mixture was diluted EtOAc (50 mL) & washed with water (50 mL X 2). Organic layer dried over Na2S04 & concentrated under reduced pressure to obtain crude which was further purified by flash column chromatography to obtain pure product N-(l-(2,4-bis(trifluoromethyl)benzyl)-lH-pyrazol-4-yl)-5-(2,4- difluorophenyl)isoxazole-3-carboxamide. (36 mg, 15.7% as off white solid) ‘fl NMR (400 MHz, DMSO-c 6) d 11.16 (s, 1H), 8.33 (s, 1H), 8.10 (q, J= 8.3 Hz, 3H), 7.78 (s, 1H), 7.6l(t, J= 10.9 Hz, 1H), 7.35 (dd, J= 10.1, 7.7 Hz, 1H), 7.26 (d, J= 2.9 Hz, 1H), 7.06 (d, J= 8.1Hz, lH),5.67 (s, 2H).

The synthetic route of 1083224-23-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PRAXIS BIOTECH LLC; ALFARO, Jennifer; BELMAR, Sebastian; NUNEZ VASQUEZ, Gonzalo Esteban; PUJALA, Brahmam; SATHE, Balaji Dashrath; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; THAKRAL, Pooja; PATIDAR, Rajesh Kumar; (344 pag.)WO2019/195810; (2019); A2;,
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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, To a -78 C solution of l-(isoxazol-3-yl)ethanone (2.18 g, 19.62 mmol) in tetrahydrofuran (58 mL) was added lithium hexamethyldisilazide (1 M in toluene, 18 mL, 18 mmol) dropwise over the course of 20 minutes. The solution was warmed to 0 C and stirred for 30 minutes, at which point diethyl oxalate (2.9 mL, 21.6 mmol) was added over the course of 5 minutes. The solution was warmed to room temperature and stirred for 45 minutes. Ethanol (58 mL), hydrazine hydrate (0.88 mL, 18 mmol), and acetic acid (5.8 mL) were sequentially added. The heterogeneous solution was heated to 70 C. After stirring for 2.25 hours at this temperature, the solvent was removed under vacuum. Water (300 mL) and dichloromethane (300 mL) were added, the layers were separated, and the aqueous layer was extracted with dichloromethane (5 x 150 mL). The organics were combined, dried over magnesium sulfate, filtered, and the solvent was removed under vacuum. Purification by silica gel chromatography (0-15% methanol in dichloromethane) and re-purification (ethyl acetate in dichloromethane) gave impure product. The resulting solid was triturated with diethyl ether to give Interraediate-3 (2.21 g, 59%) as a white solid.

As the paragraph descriping shows that 88511-37-9 is playing an increasingly important role.

Reference£º
Patent; IRONWOOD PHARMACEUTICALS, INC.; KIM, Charles; NAKAI, Takashi; MOORE, Joel; PERL, Nicholas, Robert; IM, G-yoon, Jamie; BARDEN, Timothy, Claude; IYENGAR, Rajesh, R.; ZIMMER, Daniel, P.; FRETZEN, Angelika; RENHOWE, Paul, Allan; WO2013/101830; (2013); 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.42831-50-5,5-Methylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

A round bottomed flask equipped with a mechanical stiner, condenser, thermometer pocket and a stopper were added 5-Methylisoxazole-4-carboxylic acid (3.00 g, 0.02 mol) and Thionyl chloride (14.66 g, 0.12 mol) and the reaction mixture was gradually heated to 45¡À5C and stined at same temperature for 2 to 3 h. The progress of the reaction was monitored by TLC (Acid chloride was analyzed as corresponding methyl ester by quenching the samplein methanol). After the completion of reaction, the reaction mixture was concentrated under reduced pressure at 45¡À5C to afford 5-Methylisoxazole-4-carbonyl chloride as a liquid (0.59 mol).

42831-50-5, 42831-50-5 5-Methylisoxazole-4-carboxylic acid 1425240, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; BIOCON LIMITED; PALLE, Venkata, Raghavendracharyulu; BHAT, Ramakrishna, Parameshwar; KALIAPPAN, Mariappan; BABU, Jithendra, R.; SHANMUGHASAMY, Rajmahendra; (39 pag.)WO2016/203410; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

110256-15-0, 5-Cyclopropylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0267] To a stirred solution of 5-cyclopropylisoxazole-3-carboxylic acid (0.750 g, 4.90 mmol) in DCM (5 ml) was added oxalyl chloride (1.68 ml, 19.60 mmol) and 2 drops of DMF. The reaction was stirred at RT 2 hr. After complete consumption of starting material, the solvent was removed under reduced pressure to obtain 5-cyclopropylisoxazole-3-carbonyl chloride as a residue (0.6 g, crude). The material was used without further purification., 110256-15-0

110256-15-0 5-Cyclopropylisoxazole-3-carboxylic acid 1092113, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; EPIZYME, INC.; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MILLS, James Edward John; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; HARVEY, Darren Martin; (208 pag.)WO2016/40498; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

21169-71-1, Isoxazole-5-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 85-a (200.00 mg, 1.77 mmol, 1.00 eq) was dissolved in dichloromethane (15.00 mL), and compound 7-a (305.88 mg, 1.95 mmol, 299.88 mL, 1.10 eq), EDCI (464.54 mg, 2.42 mmol, 1.37 eq), HOBt (327.43 mg, 2.42 mmol, 1.37 eq) and NMM (536.75 mg, 5.31 mmol, 583.42 mL, 3.00 eq) were added thereto. The reaction solution was stirred at 10C for 15 hours. After the reaction was completed, the reaction solution was added with water (100 mL), and extracted with dichloromethane (100 mL 3 3). The organic phases were combined, 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?2:1) to give the product of compound 85-b (380.00 mg, yield: 85%) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) delta=8.31 (d, J=1.51 Hz, 1H), 6.75 (d, J=1.51 Hz, 1H), 4.44 (d, J=13.05 Hz, 1H), 4.14-4.22 (m, 2H), 4.08 (d, J=12.55 Hz, 1H), 3.30 (t, J=11.29 Hz, 1H), 3.10 (t, J=11.04 Hz, 1H), 2.57-2.68 (m, 1H), 1.99 (br. s., 2H), 1.77-1.87 (m, 2H), 1.26-1.29 (m, 3H).

21169-71-1, The synthetic route of 21169-71-1 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
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