Heterocyclic Building Blocks-isoxazole

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.

To a solution of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (50 mg, 0.29 mmol) in MeCN (2 mL) was added triphenylphosphine (153 mg, 0.58 mmol), 2,6-lutidine (31.3 mg, 0.034 mL, 0.29 mmol) and CBr4 (194 mg, 0.58 mmol). The reaction mixture was stirred at room temperature for 1.5 hours. The mixture is concentrated and purified directly by flash chromatography with heptane:ethyl acetate = 1:0 to 0:1 to give ethyl 5-(bromomethyl)isoxazole-3-carboxylate (68 mg)., 123770-62-7

The synthetic route of 123770-62-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (278 pag.)WO2019/115567; (2019); 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.,21169-71-1

General procedure: Compounds were synthesized in solution phase using Boc-protected amino acids on 100-200mg scale. Firstly, the amino acid (1.2-1.5equiv) was activated with HBTU (1.5equiv) and DIPEA (1.5equiv) as 0.2-0.5M solution in DMF for 10min. Then the solution was added to an amino group bearing C-terminal moiety (R1R2NH) and the mixture was stirred for a minimum of 1h at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (2¡Á). The organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude product was then treated with 20% TFA in DCM and stirred for 1-2h to remove the Boc group. TFA was removed by evaporating the reaction mixture under a stream of N2. The residue was dissolved in DCM and washed with saturated NaHCO3 (2¡Á). DCM phase was dried with MgSO4, filtered and evaporated in vacuo. Subsequent N-Boc-amino acids and amines were sequentially coupled under the same conditions. Each coupling reaction was monitored by ESMS, with most reactions going to completion overnight. All final compounds were purified on rpHPLC (97% by analytical HPLC) and fully characterized by NMR and HRMS (yields between 30% and 40%).

As the paragraph descriping shows that 21169-71-1 is playing an increasingly important role.

Reference£º
Article; Yau, Mei-Kwan; Liu, Ligong; Lim, Junxian; Lohman, Rink-Jan; Cotterell, Adam J.; Suen, Jacky Y.; Vesey, David A.; Reid, Robert C.; Fairlie, David P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 986 – 991;,
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

To a stirred solution of 5-cyclopropylisoxazole-3-carboxylic acid (1.0 g, 6.5 mmol) in DMF (3 mL) was added HATU (3.72 g, 9.8 mmol) and diisopropylethylamine (3.5 ml, 19.6 mmol). The solution was stirred for 10 min at 0 C. tert-Butyl 4-(l- aminoethyl)piperidine-l-carboxylate (1.45 g, 6.5 mmol) was added and the reaction stirred at RT for 2 h. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction was quenched with water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain a crude residue which was purified by column chromatography to afford compound tert-butyl 4-(l-(5- cyclopropylisoxazole-3-carboxamido)ethyl)piperidine-l-carboxylate (2.1 g, 84%). 1H NMR (400 MHz, OMSO-d6) delta 8.44 (d, J = 8.9 Hz, 1H), 6.46 (s, 1H), 3.98-3.90 (m, 2H), 3.79 (p, J = 7.3 Hz, 1H), 2.53-2.47 (m, 2H), 2.19-2.16 (m, 1H), 1.6-1.58 (m, 3H), 1.38 (s, 9H), 1.18-0.86 (m, 9H); LCMS: m/z = 386.25 (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; MILLS, James Edward John; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; HARVEY, Darren Martin; (208 pag.)WO2016/40498; (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.1018297-63-6,(3-(4-Fluorophenyl)-5-methylisoxazol-4-yl)methanol,as a common compound, the synthetic route is as follows.

4.98 g (24.0 mmol) of [3-(4-fluorophenyl)-5-methyl-1 ,2-oxazol-4-yl]methanol (WO 2013/057123 A1 , Hoffmann-La Roche) was dissolved in 80 ml_ of anhydrous dichloromethane, and 9.76 g (3.39 ml_, 36.1 mmol) of phosphorus tribromide was added dropwise to the stirred solution. The reaction mixture was stirred for 1 hour at room temeprature, and poured into 50 ml_ of saturated sodium bicarbonate solution. The mixture was stirred for another 10 minutes, and the phases were separated. The organic phase was washed with water, dried over anhydrous sodium sulfate, and evaporated to afford 5.89 g (97%) of the title compound as a yellow-brownish solid. MS (ESI) m/z: 269.9 [M+H]+., 1018297-63-6

1018297-63-6 (3-(4-Fluorophenyl)-5-methylisoxazol-4-yl)methanol 28473136, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; RICHTER GEDEON NYRT.; SZABO, Gyoergy; TUROS, Gyoergy Istvan; ELIAS, Oliver; KAROLYI, Benedek Imre; ERDELYI, Peter; KAPUS, Gabor Laszlo; (75 pag.)WO2020/65597; (2020); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

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

3,5-Dimethyl-isoxazole-4-carboxylic acid (CAS 2510-36-3, 42.3 mg, 0.30 mmol), followed by HATU (91.5 mg, 0.24 mmcl) were added to a mixture of 2-amino-1-(4-chlorophenyl)-3- methylbutan-1-one hydrochloride (Example 20a, 49.0 mg, 0.20 mmol) and DIPEA (64.0 mg,0.30 mmol) in DCM (2 mL). The resulting mixture was stirred at 30C for 16 h and evaporatedto dryness. The residue was then purified by preparative HPLC to give amide N-(1-(4- chlorophenyl)-3-methyl-1-oxobuta n-2-yl)-3,5-dimethyl-isoxazole-4-ca rboxa mide (26.3 mg, 39%).1H NMR (500 MHz, CDCI3) 5 ppm 0.81 (d, 3 H) 1.11 (d, 3 H) 2.26 (td, 1 H) 2.53 (s, 3 H) 2.68 (s,3 H) 5.72 (dd, 1 H) 6.56 (d, 1 H) 7.45 – 7.57 (m, 2 H) 7.90 – 8.02 (m, 2 H).MS (ESI) m/z 335.1 [M+H]

2510-36-3, 2510-36-3 3,5-Dimethylisoxasole-4-carboxylic acid 75636, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; ACTURUM LIFE SCIENCE AB; LINDE, Christian Erik; PAULSEN, Kim; SOHN, Daniel; SVENSSON, Mats A; VALLIN, Karl S A; WEIGELT, Dirk; MINIDIS, Alexander; WO2014/184235; (2014); 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, Example 9; 1 -(4-(5-(4-( 1 , 1 -Difluoroethyl)-5-phenylisoxazol-3 -yl)- 1 ,2,4-oxadiazol-3 – yl)benzyl)azetidine-3-carboxylic acid, 2,2,2-trifluoroacetic acid salt; 9-A. Methyl S-phenylisoxazole-S-carboxylate; [00179] A solution of S-phenylisoxazole-S-carboxylic acid (0.86 g, 4.55 mmol) in toluene (15.0 mL) and methanol (3 mL) was added a 2M solution of TMS- diazomethane in hexanes (3.1 mL, 6.14 mmol) dropwise at room temperature. The reaction mixture was stirred for 30 minutes and concentrated. The residue was dispersed in methanol (3 mL), stirred for 5 minutes, and filtered to give methyl 5- phenylisoxazole-3-carboxylate (897 mg). The compound had an HPLC ret. time = 2.67 min. : YMC S5 COMBISCREEN 4.6X50 mm; Gradient time: 4 min; Flow rate = 4 ml/min; Solvent A = 10% MeOH – 90% Water – 0.2% H3PO4; Solvent B = 90% MeOH – 10% water – 0.2% H3PO4; Start % B = O; Final % B = 100. LC-MS: M+1 = 204+.

14441-90-8 5-Phenylisoxazole-3-carboxylic acid 151916, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott, Hunter; DYCKMAN, Alaric, J.; PITTS, William, J.; SPERGEL, Steven, H.; WO2010/85581; (2010); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

3356-94-3, Ethyl 5-chloro-3-methylisoxazole-4-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0863] to a mixture of compound 139b (400 mg, 2.1 mmol) and 2h-indazole (299 mg, 2.5 mmol) in DMF(3 ml) was added K2CO3 (1.2 g, 8.4 mmol) in one portion. The mixture was stirred at 80 C for 12 hours. Then H2O (9ml) was added into the mixture, and the aqueous phase was extracted with EtOAc (15 ml x 3), and the combined organic layer was concentrated to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether: ethyl acetate = 300: 1 to 40: 1) to give compound 139c (340 mg, yield: 59.4%) as a pale yellow solid. 1H NMR (400mhz, CDCl3) s 8.33 (s, 1h), 7.82 (d, = 7.9 hz, 1h), 7.68 (d, = 8.8 hz, 1h), 7.57 – 7.51 (m, 1h), 7.35 (t, j = 7.7 hz, 1h), 4.24 (q, j = 7.0 hz, 2h), 2.56 (s, 3h), 1.13 (t, = 7.2 hz, 3h).

3356-94-3, As the paragraph descriping shows that 3356-94-3 is playing an increasingly important role.

Reference£º
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

35166-33-7, 3-Hydroxymethyl-5-methylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(c) 3-Chloromethyl-5-methylisoxazole A solution of 3-hydroxymethyl-5-methyl isoxazole (6.50 g, 57.5 mmol) and triphenylphosphine (15.1 g, 57.5 mmol) in carbon tetrachloride (120 ml) were heated at reflux in 18 h. Solvent was removed from the cooled mixture under reduced pressure then the residue taken up in ether and filtered. The filtrate was concentrated under reduced pressure then flash chromatographed through silica using 1:1 ether: 40-60 C. petroleum ether fraction as eluant to give 3-chloromethyl-5-methylisoxazole (5.43 g, 41.3 mmol, 72%); numax (film) 3130, 2960, 2920, 1610, 1475, 1400, 1270, 1250, 1160, 1130, 1010, 920, 890, 800, 750 cm-1; deltaH (CDCl3) 2.40 (3H, s, CH3 -5), 4.55 (2H, s, CH2 –Cl), 6.10 (1H, s, CH-4).

35166-33-7, 35166-33-7 3-Hydroxymethyl-5-methylisoxazole 2736567, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Beecham Group p.l.c.; US4812470; (1989); A;,
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.

To a solution of the product of Example 1B (120 mg, 0.40 mmol) in tetrahydrofuran (3 mL) at 0 C. was added NaH (95 weight %, 31 mg, 1.22 mmol). The mixture was allowed to warm to ambient temperature and 4-(chloromethyl)-3,5-dimethylisoxazole (88 mg, 0.61 mmol) was added. The resulting mixture was stirred at ambient temperature for 18 hours. The reaction was quenched with water (0.5 mL) and concentrated in vacuo. The residue was dissolved in a solvent mixture of dimethyl sulfoxide (3 mL), methanol (2 mL) and water (0.5 mL), filtered through a glass microfiber frit and purified by preparative HPLC [Waters XBridge C18 5 mum column, 50*100 mm, flow rate 90 mL/minute, 5-95% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the titled compound (155 mg, 0.38 mmol, 94% yield). 1H NMR (400 MHz, methanol-d4) delta ppm 8.38 (s, 1H), 7.61 (td, J=7.7, 1.6 Hz, 1H), 7.58-7.51 (m, 1H), 7.49-7.34 (m, 3H), 7.13 (dd, J=8.5, 2.9 Hz, 1H), 7.10 (d, J=7.5 Hz, 1H), 4.36 (s, 2H), 4.12-3.94 (m, 2H), 3.58-3.43 (m, 2H), 2.46 (s, 3H), 2.31 (s, 3H); MS (ESI+) m/z 406 [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; AbbVie Inc.; Daanen, Jerome F.; DeGoey, David A.; Frost, Jennifer M.; Koenig, John R.; Latshaw, Steve; Matulenko, Mark; Scanio, Marc; Shi, Lei; Bunnelle, William H.; (128 pag.)US2016/75692; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

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

Reference Production Example 208 (0851) Ethyl 5-hydroxymethylisoxazole-3-carboxylate (1.71 g, 10.0 mmol) was dissolved in tetrahydrofuran (50 mL), and 3,5-difluorobenzyl bromide (2.48 g, 12.0 mmol) and 18-crown-6 (0.26 g, 1.0 mmol) were added thereto. Sodium hydride (60% oil-based) (0.80 g, 20.0 mmol) was slowly added thereto at room temperature, and the mixture was stirred at room temperature overnight. Then, dilute hydrochloric acid was added thereto, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was dissolved in ethanol (20 mL), and an aqueous solution obtained by dissolving potassium hydroxide (2.81 g, 50 mmol) in water (10 mL) was added thereto at room temperature, and then the mixture was stirred at 80C for 3 hours. Water was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Tert-butyl methyl ether was added to the concentrate, and the aqueous layer was fractionated. Dilute hydrochloric acid was added to the resulting aqueous layer, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 1.38 g of 5-(3,5-difluorobenzyloxymethyl)isoxazole-3-carboxylic acid represented by the following formula. The product was subjected to a next reaction without purification., 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