Category: 1136-45-4

1136-45-4, 5-Methyl-3-phenylisoxazole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 6 6,7-Dimethoxy-3-(5-methyl-3-phenylisoxazol-4-yl)-2,4-dihydroindeno[1,2-c]pyrazole 5,6-Dimethoxy-1-indanone (1.92 g, 10 mmol) in tetrahydrofuran (10 ml) was added dropwise to a solution of lithium diisopropylamide (10 mmol) in tetrahydrofuran (10 ml) at -78 C. and stirred for 0.5 h. 5-Methyl-3-phenylisoxazole-4-carboxylic acid (1.02 g, 5 mmol) was stirred with N,N’-carbonyldiimidazole (810 mg, 5 mmol) in tetrahydrofuran (5 ml) for 1 h and then added to the dimethoxyindanone solution with 4-dimethylaminopyridine (610 mg, 5 mmol).This was stirred at -78 C. for 1.5 h and warmed to RT over 2 h then diluted with EtOAc, washed with citric acid solution, brine, dried (MgSO4) and evaporated.The resulting yellow oil was dissolved in ethanol (5 ml), saturated copper acetate solution (10 ml) was added and the precipitate formed was filtered off and washed with H2O, methanol, diethyl ether, dried (MgSO4) and evaporated.The residue was dissolved in ethanol, hydrazine hydrochloride (500 mg) and sodium acetate (1 g) and H2O were added and heated to reflux for 24 h.The solvent was evaporated, the residue dissolved in EtOAc, washed with brine, dried (MgSO4) and evaporated.Purified by prep HPLC to give the title compound (7 mg).1H NMR (360 MHz, CDCl3) delta7.52 (d, J=6.8 Hz, 2H), 7.43-7.33 (m, 5H), 3.94 (s, 3H), 3.91 (s, 3H), 3.28 (s, 2H), 2.57 (s, 3H), m/z (ES+) 374 (M+H)+.

1136-45-4, The synthetic route of 1136-45-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ladduwahetty, Tamara; MacLeod, Angus Murray; Merchant, Kevin John; Sternfeld, Francine; US2004/6226; (2004); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

1136-45-4, 5-Methyl-3-phenylisoxazole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of YD-014 (320 mg, 1.58 mmol) in anhydrous dichloromethane (10 mL) was added in sequence diisopropylethylamine (DIEA, 305 mg, 2.36 mmol), YD-05 (380 mg, 1.58 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI, 1.2 g, 6.30 mmol). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane, and washed in sequence with aqueous sodium hydroxide (2 M), water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography eluting with petroleum ether in ethyl acetate (3:1) to give YD-01 (290 mg, 43% yield) as a light yellow solid.1H-NMR (400 MHz, DMSO-d6) delta 8.23 (d, 111, J=2.6 Hz, 1′-H), 8.15 (dd, 1H, J=9, 2.6 Hz, 2′-H), 7.63-7.60 (m, 2H, 1-H, 5-H), 7.55-7.52 (m, 3H, 2-H, 3-H, 4-H), 7.20 (d, 1H, J=9 Hz, 3′-H), 3.81 (br s, 2H, CH2), 3.39 (br s, 21-1, CH2), 3.20 (br s, 2H, CH2), 2.85 (br s, 2H, CH2), 2.50 (s, 3H, -CH3);13C-NMR (100 MHz, DMSO-d6) delta 168.8, 161.2, 159.6, 153.9, 141.9, 130.2, 129.1, 127.9, 127.3, 126.3, 125.9, 123.7, 120.6, 110.7, 50.1, 49.7, 46.3, 41.3, 11.4; LRMS (API-ES): 427 (M++H)., 1136-45-4

1136-45-4 5-Methyl-3-phenylisoxazole-4-carboxylic acid 14343, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; The University of Hong Kong; US2011/212975; (2011); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

1136-45-4, 5-Methyl-3-phenylisoxazole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 8 5-Methyl-3-phenyl-isoxazole-4-carbonyl Chloride. 5-Methyl-3-phenyl-isoxazole-4-carboxylic acid (0.54 g, 2.56 mmol) was treated with SOCl2 (2 mL) at 70 C. for 1 hr. Concentration in vacuum gave a yellow oil which was used without purification.

1136-45-4, 1136-45-4 5-Methyl-3-phenylisoxazole-4-carboxylic acid 14343, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Green, Jeremy; Bemis, Guy; Grillot, Anne-Laure; Ledeboer, Mark; Salituro, Francesco G.; Harrington, Edmund; Gao, Huai; Baker, Christopher; Cao, Jingrong; Hale, Michael; US2003/149051; (2003); 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.1136-45-4,5-Methyl-3-phenylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

Dissolve the free piperazino-piperidine of Example 11, step 6 (1.7 g, 3.3 mmol) in CHCl3 (30 ml;=Stock solution A). Add 250 ul of stock solution A (0.027 mmol) to a slurry of 0.15 g (0.14 mmol ) of resin bound cardodiimide (prepared by reacting Argopore-Cl resin with 1-(3-dimethyl-aminopropyl)3-ethyl carbodiimide in DMF at 100 C. in DMF (1.5 ml) in a polyethylene SPE cartridge. To this mixture add 75 ul of a 1 M solution of 5-methyl-3-phenylisoxazole-4-carboxylic acid in DMF (0.075 mmol), and HOBT (24 ul of a 1M solution in DMF). Shake this mixture for 14 h, filter and add 0.1 g of Amberlyst-15 resin (0.47 mmol) to the filtrate. Shake for 1 to 2 h, filter and wash the resin twice with each of the following solvents THF, CH2Cl2 and CH3OH, then wash with THF and CH2Cl2. Treat the resin with 2M NH3 in CH3OH (1 time for 30 min, and 1 time for 5 min). Combine and concentrate the filtrates under reduced pressure to afford the title compound. LCMS found MH+=599.1 (calculated MW 598); TLC Rf=0.74 (CH2Cl2/CH3OH/NH4OH (95/5/0.5)).

1136-45-4, The synthetic route of 1136-45-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Schering Corporation; US6391865; (2002); B1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

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.

5.0 g of commercially-available ArgoGel-MB-CHO ResinR (0.4 mmol/g) was suspended in DMF (20 ml) and AcOH (1.0 ml), and then methylamine hydrochloride (405 mg) and NaBH(OAc)3 (2.12 g) were added thereto in order, and stirred at room temperature for 12 hours. The reaction mixture was filtered, and the residual resin was washed with DMF, MeOH, THF and methylene chloride in that order twice each, and then dried. Dewatered methylene chloride (30 ml) was added to the thus-obtained resin to suspend it therein, and then N,N-diisopropylethylamine (5.2 ml), 5-methyl-3-phenylisoxazole-4-carboxylic acid (2.03 g) and DMC (1.70 g) were added thereto in that order, and stirred at room temperature for 1 hour. The reaction mixture was filtered, and the residual resin was washed with DMF, MeOH, THF and methylene chloride twice each, and then dried to obtain the resin of formula (II).

1136-45-4, 1136-45-4 5-Methyl-3-phenylisoxazole-4-carboxylic acid 14343, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1408042; (2004); 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.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.1136-45-4,5-Methyl-3-phenylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of 1.5 g of 5-methyl-3-phenyl-4-isoxazolecarboxylic acid in 50 ml of anhydrous tetrahydrofuran stirred at -78C under N2 atmosphere, 5.9 ml of a 2.5M solution of n-butyl lithium in n-hexane was added and the solution was stirred at -78C for 2 hours. Afterwards, 0.89 ml of benzyl bromide was added at -78C and the solution stirred at room temperature for 2 hours. After overnight resting, the solution was poured into water (300 ml), acidified with 1N hydrochloric acid and extracted with ethyl acetate (2 ? 200 ml). The combined organic layers were washed with water, dried (sodium sulphate) and the solvents were evaporated to dryness. The solid residue was washed with petroleum ether to give 1.82 g (84%) of the title compound as an amorphous solid.1H-NMR (200MHz, CDCl3, delta): 9.20-11.80, br, 1H, COOH; 7.10-7.90, m, 10H, phenyl CHs; 3.45, t, 2H, CH2CH2Ph; 3.10, t, 2H, CH2CH2Ph., 1136-45-4

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

Reference£º
Patent; Leonardi, Amedeo; EP1226131; (2003); B1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

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.

5-Methyl-3-phenylisooxazole-4-carboxylic acid (40 mg, 0.197 mmol), piperazine acetic acid pyrrolidid (42.4 mg, 0.215 mmol), O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (86.2 mg, 0.268 mmol) and diisopropylethylamine (25.4 mg, 0.197 mmol) were mixed in dimethylformamide (1.5 mL) and stirred at room temperature. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The combined fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C21H26N4O3: 382.2005, found 382.2016., 1136-45-4

The synthetic route of 1136-45-4 has been constantly updated, and we look forward to future research findings.

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.1136-45-4,5-Methyl-3-phenylisoxazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

1136-45-4, A solution of 3-phenyl-5-methyl-4-isoxazole formic acid (0.2 g, 1 mmol) in DMF (5 mL) was stirred. EDCI (1-(3-dimethylamino propyl)-3-2 ethyl carbon imine hydrochloride) (0.22 g, 1.2 mmol) and HOBt (N-hydroxybenzotrizole) (0.16 g, 1.2 mmol) were added sequentially and activated for approximately 1 h. Glucosamine hydrochloride (0.43 g, 2 mmol) and triethylamine (0.4 g, 4 mmol) were then added, and the solution was stirred for an additional 24 h at room temperature. The reaction was monitored by TLC. The mixture was extracted with ethyl acetate (EA) after the end of the reaction. The organic layer was separated, washed with a saturated sodium chloride solution, dried over MgSO4, and concentrated in vacuo. The residue was washed with ethanol/dichloromethane (v/v = 2:5), and the title compound A1 was obtained as a white solid (70% yield). 1H NMR (400 MHz, DMSO) delta 8.27 (m, 2H), 7.65 (m, 3H), 6.60 (s, 1H, NH-CO), 5.04 (d, 1H), 3.58 (m, 2H), 3.30 (d, J = 25.2 Hz, 2H), 3.05 (q, J = 7.3 Hz, 1H), 2.53 (d, J = 3.6 Hz, 3H, CH3), 1.18 (s, 4H, OH). 13C NMR (100 MHz, DMSO-d6) delta 169.75, 161.44, 159.95, 128.71, 127.83, 112.85, 90.29, 72.10, 71.12, 70.12, 61.01, 54.80, 45.26, 10.93, 8.37. HRMS (ESI) calcd for C17H20N2O7 [M+Na]+: 387.1179, found 387.1166.

The synthetic route of 1136-45-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Cao, Tingting; Li, Yong; Jiang, Lijuan; Yuan, Li; Dong, Lin; Li, Ying; Yin, Shufan; Carbohydrate Research; vol. 433; (2016); p. 73 – 79;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

1136-45-4, 5-Methyl-3-phenylisoxazole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 7 Synthesis of 5-(2-hydroxyphenyl)-N-(5-methyl-3-phenylisoxazol-4-yl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamide (I-323) To a solution of 5-methyl-3-phenylisoxazole-4-carboxylic acid (29.7 mg, 0.146 mmol) in DCE (1 mL) was added a solution of TEA (14.8 mg, 0.146 mmol) in DCE (0.5 mL) at rt followed by the addition of a solution of diphenylphosphonic azide (40.2 mg, 0.146 mmol) in DCE (0.5 mL). The reaction mixture was heated at 90 C. for 2 h and then the solution was allowed to cool to rt and further to below -30 C., whereupon a solution of 2-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (35.0 mg, 0.146 mmol) in DMF (0.5 mL) was added. The mixture was shaken at rt for 16 h. The residue was partitioned between water (4 mL) and DCM (3 mL). The aqueous solution was extracted with DCM. The organic solutions were combined, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by RP-HPLC to give 5-(2-hydroxyphenyl)-N-(5-methyl-3-phenylisoxazol-4-yl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazole-1-carboxamide (5.53 mg, 8.6%). LCMS: (AAC) ES+440.3. Compounds in the following table were prepared from the appropriate starting materials in a method analogous to that of Example 7:

1136-45-4, 1136-45-4 5-Methyl-3-phenylisoxazole-4-carboxylic acid 14343, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem