Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.32326-25-3,5-Methoxyisoxazol-3-amine,as a common compound, the synthetic route is as follows.

Example 1 A suspension of methyl chloroformate (167 mul; 2.16 mmol) and potassium thiocyanate (227 mg; 2.34 mmol) in acetonitrile (1.80 ml) was stirred at 70 C. for 30 minutes, and then 3-amino-5-methoxyisoxazole (205 mg; 1.80 mmol) was added to the suspension under stirring and ice-cooling. After stirring for 10 minutes at the same temparature and then for 15 minutes at room temperature, the reaction mixture was poured into ice-water (18ml). The precipitates formed were filtered off, washed with water, then with ether and dried under reduced pressure to give methyl 2-(5-methoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate (334 mg, yield 80.6%). m.p. 167-169 C. (MeOH) NMR delta (CDCl3): 3.73 (3H. s. COOCH3) 3.95 (3H. s. NHCOOCH3) 3.97 (2H. s. CH2) 10.50 (1H. bs. NH) IR (CHCL3)cm-1: 3406, 1736, 1549. Anal, Calcd, for C7 H9 N3 O4 S: C,36.36; H, 3.92; N,18.17(%). Found: C,36.40; H,3.94; N,18.11(%).

32326-25-3, As the paragraph descriping shows that 32326-25-3 is playing an increasingly important role.

Reference£º
Patent; Katayama Seiyakusyo Co. Ltd.; US5585494; (1996); A;,
Isoxazole – Wikipedia
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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

Epsilon Nu (5.6 mL, 42 mmol) and HATU (4.84 g, 13 mmol) were added to a mixture of ethyl fras-3-aminocyclobutane-l-carboxylate hydrochloride (1.89 g, 10 mmol) and 5- phenylisoxazole-3-carboxylic acid (2 g, 10 mmol) in THF (200 mL) at room temperature and the reaction mixture was stirred for 6 h at room temperature. Volatiles were removed under reduced pressure to get the crude compound. The reaction mixture was diluted with water (100 mL) and extracted using ethyl acetate (2 x 75 mL). Combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SC>4 and concentrated under reduced pressure. The mixture was purified by flash column chromatography using 30% EtOAc in hexane as eluent to give the product (2.65 g, 80 %) as white solid. Ti NMR (400 MHz, CDC13) : delta 7.80-7.77 (m, 2H), 7.49-7.46 (m, 3H), 7.00 (d, J = 7.2 Hz, 1H), 6.94 (s, 1H), 4.79-4.73 (m, 1H), 4.17 (q, J = 7.1 Hz, 2H), 3.10-3.09 (m, 1H), 2.78-2.72 (m, 2H), 2.40-2.32 (m, 2H), 1.30-1.26 (t, J= 7.2 Hz, 3H). LC-MS: [M+H] + 315.2

14441-90-8, As the paragraph descriping shows that 14441-90-8 is playing an increasingly important role.

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (178 pag.)WO2016/115090; (2016); A1;,
Isoxazole – Wikipedia
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1202769-66-1, 2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2-Synthesis of 4-(3-(2-aminopyrimidin-4-yl)-2-(2-hydroxyethoxy)-3H-benzo[d]imidazol-5-yl)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol A solution of 2-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]ethan-1-ol (80 mg, 0.19 mmol), 2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol (80 mg, 0.53 mmol), bis(triphenylphosphine)palladium(II) dichloride (20 mg, 0.03 mmol) and triethylamine (0.7 mL) in dimethylsulfoxide (3 mL) under nitrogen in a 10-mL sealed tube was irradiated with microwave radiation for 30 min at 70 C. The reaction mixture was concentrated and the crude product (80 mg) was purified by Flash-Preparative HPLC to give 24 mg (28%) of 4-[1-(2-aminopyrimidin-4-yl)-2-(2-hydroxyethoxy)-1H-1,3-benzodiazol-6-yl]-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 8.39 (d, J=5.6 Hz, 1H), 8.19 (s, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 7.06 (s, 3H), 6.43 (s, 1H), 6.37 (s, 1H), 5.03 (t, J=5.2 Hz, 1H), 4.62 (s, 2H), 3.82 (d, J=4.0 Hz, 2H), 2.41 (s, 3H), 1.81 (s, 3H); LC-MS: m/z=+455 (M+H)+., 1202769-66-1

As the paragraph descriping shows that 1202769-66-1 is playing an increasingly important role.

Reference£º
Patent; Genentech, Inc.; US2012/214762; (2012); 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.1136-45-4,5-Methyl-3-phenylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 13 N,N-Diethyl-5-methyl-3-phenylisoxazole-4-carboxamide To 3-phenyl-5-methylisoxazol-4-carboxylic acid (25 mg, 0.10 mmol) was added thionyl chloride (1 mL) and the neat solution allowed to stir 60 C. After 30 min, excess thionyl chloride was evaporated and neat diethylamine was added and allowed to stir overnight at ambient temperature. The residue was purified using reversed phase HPLC to afford the title compound (20 mg). HRMS (ESI, pos. ion) m/z calcd for C15H18N2O2: 258.1368, found 258.1378.; Example 14 N,N-Diisopropyl-5-methyl-3-phenylisoxazole-4-carboxamide To 3-phenyl-5-methylisoxazol-4-carboxylic acid (25 mg, 0.10 mmol) was added thionyl chloride (1 mL) and the neat solution allowed to stir 60 C. After 30 min, excess thionyl chloride was evaporated and neat diisopropylamine was added and allowed to stir overnight at ambient temperature. The residue was purified using reversed phase HPLC to afford the title compound (15 mg). HRMS (ESI, pos. ion) m/z calcd for C17H22N2O2: 286.1681, found 286.1678.; Example 15 4-(Azetidin-1-ylcarbonyl)-5-methyl-3-phenylisoxazole To 3-phenyl-5-methylisoxazol-4-carboxylic acid (25 mg, 0.10 mmol) was added thionyl chloride (1 mL) and the neat solution allowed to stir 60 C. After 30 min, excess thionyl chloride was evaporated and neat trimethylene imine was added and allowed to stir overnight at ambient temperature. The residue was purified using reversed phase HPLC to afford the title compound (18 mg). HRMS (ESI, pos. ion) m/z calcd for C14H14N2O2: 242.1055, found 242.1063.

1136-45-4, As the paragraph descriping shows that 1136-45-4 is playing an increasingly important role.

Reference£º
Patent; Amgen Inc.; Biovitrum AB; US2008/21022; (2008); 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.2510-36-3,3,5-Dimethylisoxasole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

A vial was charged with 3-fluoro-4- [[(3S)-3-methyl- 1,1 -dioxo-6-phenyl-thiazinan-2- ylimethyllaniline hydrochloride (75 mg, 0.19 mmol), 3,5-dimethylisoxazole-4-carboxylic acid (41 mg, 0.29 mmol), triethylamine (0.14 mL, 0.97 mmol) and N,N-dimethylformamide (1 mL), followed by O-(7-azabenzotriazol- 1 -yl)-N,N,N?,N?-tetramethyluronium hexafluorophosphate (92 mg, 0.23 mmol) and the reaction was stirred at room temperature for 2 hours. The reaction was then partitioned between dichloromethane and saturated sodium bicarbonate in water. The organic layer was separated, concentrated and purified by preparative HPLC to give N-[3-fluoro- 4- [[(3S)-3-methyl- 1,1 -dioxo-6-phenyl-thiazinan-2-yllmethyllphenyll -3,5 -dimethyl-isoxazole-4- carboxamide Stereoisomer A (23.6 mg, 0.050 mmol, 26% yield). ?H NMR (400 MHz, DMSO)o 10.22 – 10.18 (s, 1H), 7.67 – 7.60 (m, 1H), 7.51 – 7.44 (m, 3H), 7.44 – 7.34 (m, 4H), 4.54 – 4.46 (m, 2H), 4.39 – 4.33 (m, 1H), 4.17 – 4.07 (m, 1H), 2.57 – 2.52 (s, 3H), 2.47 – 2.39 (m, 1H),2.34- 2.29 (s, 3H), 2.16 -2.06 (m, 1H), 1.90- 1.75 (m, 1H), 1.71 – 1.61 (m, 1H), 1.13 – 1.07 (d, J = 6.8 Hz, 3H); LCMS [M+1j = 472.2.

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; RENE, Olivier; WO2014/202741; (2014); 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.123770-62-7,Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

Reference Production Example 43 (0685) 60% Sodium hydride (2.45 g, 61.40 mmol) was added to dry N,N-dimethylformamide (40 ml) cooled to 0C, under a nitrogen atmosphere, and a dry N,N-dimethylformamide (30 ml) solution of ethyl 5-hydroxymethylisoxazole-3-carboxylate (7 g, 40.89 mmol) was added dropwise thereto over 15 minutes, and then the mixture was further stirred for 30 minutes. 2-Chlorobenzyl bromide (8.4 g, 40. 93 mmol) was added thereto, and the reaction mixture was heated to room temperature, and the mixture was stirred for 16 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with water and saturated saline water, and then dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and then the residue was applied to a silica gel column chromatography to obtain 3.9 g of ethyl 5-(2-chlorobenzyloxymethyl)isoxazole-3-carboxylate represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 7.48 (d, 1H), 7.38(d, 1H), 7.31-7.23 (m, 2H), 6.73 (s, 1H), 4.75 (s, 2H), 4.71(s, 2H), 4.45(q, 2H), 1. 42 (t, 3H)

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
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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

A mixture of isoxazole-5-carboxylic acid (2.5 g 22.1 mmol), sodium bicarbonate (5.57 g, 66.32 mmol) and iodomethane (8.26 mL, 132.65 mmol) in DMF (30 mL) was stirred at 25 C. over 19 h. The mixture was diluted in H2O (30 mL) and extracted with ether (2¡Á50 mL). The ether layer washed with brine, dried over MgSO4, filtered, concentrated in vacuo to obtain a crude oil. The crude was further purified by Biotage chromatography (cartridge 40m), eluent EtOAc-Hexanes (1:2), then 100% EtOAc to obtain isoxazole-5-carboxylic acid methyl ester as an amorphous solid (1.2 g, 42.7%). Mass Spectrum (+ESI): 128 (M+H)+., 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; Wyeth; US2007/219186; (2007); 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

To a solution of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (50.0 mg, 0.29 mmol) in DCM (2 mL) was added diethylaminosulfur trifluoride (70.6 mg, 0.06 ml, 0.44 mmol). The mixture was stirred at 40 C for 1 hour. Water (3 mL) was added and the mixture was extracted with ethyl acetate (5 mLchi3). The combined organic layers were washed with brine (5 mL), dried over Na2S04and concentrated. The crude mixture was purified by flash chromatography with heptane:ethyl acetate = 1 :0 to 0:1 to give ethyl 5- (fluoromethyl)isoxazole-3-carboxylate (41 .0 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; (270 pag.)WO2018/7249; (2018); 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.108511-97-3,Isoxazol-4-amine,as a common compound, the synthetic route is as follows.

1-Chloro-4-iodo-2-trifluoromethylbenzene (10 mmol) obtained in Reaction 1.2 was dissolved in 20 ml of toluene.Isoxazole-4-amine (12 mmol) was added sequentially to the system.Palladium acetate (0.5 mmol),2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (12 mmol),3 ml of triethylamine,After stirring for 10 minutes,Add 10 ml of aqueous solution of cesium carbonate (10 mmol),Heat to 50 C for 4 hours.After the reaction was completed, 20 ml of water was added to the system, and the mixture was stirred for 20 minutes, and the organic phase was dried over anhydrous sodium sulfate, concentrated, and purified by flash column chromatography.2.2 g of yellow N-(4-chloro-3-trifluoromethylphenyl)-isoxazole-4-amine powder was obtained in a yield of 84%.

108511-97-3, The synthetic route of 108511-97-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Zhang Ruwei; Ge Baoyin; Jing Fan; (7 pag.)CN108440437; (2018); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

1228690-37-6, (R)-1-Phenylethyl (5-(4-bromophenyl)-3-methylisoxazol-4-yl)carbamate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Argon was bubbled through the mixture of compound CIII-7 (200 mg, 0.6 mmol), compound CIII-8 (242 mg, 0.6 mmol) and Na2C03 (127 mg, 1.20 mmol) in a mixed solvent of DME/H20 (6 mL, v/v = 3/1). Then the catalyst Pd(dppf)Cl2 (22 mg, 0.03 mmol) was added. The mixture was heated to 80 C and stirred for 2 hours. The mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by column chromatography over silica gel (PE/EA = 5/1) to yield compound CIII-9 (290 mg, yield 91 >). MS (ESI) m/z (M+H)+ 526.3., 1228690-37-6

The synthetic route of 1228690-37-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; INTERMUNE, INC.; BUCKMAN, Brad, O.; NICHOLAS, John, B.; EMAYAN, Kumaraswamy; SEIWERT, Scott, D.; WO2013/25733; (2013); A1;,
Isoxazole – Wikipedia
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