Month: November 2020

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

Into a 500-mL round-bottom flask was placed 5-cyclopropyl-1,2-oxazole-3- carboxylic acid (6.12 g, 39.96 mmol, 1.00 equiv), tert-butyl (2R)-4-amino-2- methylpiperidine-1-carboxylate (8.57 g, 39.99 mmol, 1.00 equiv), dichloromethane (300 g), TEA (12.12 g, 120.00 mmol, 3.00 equiv) and HATU (22.8 g, 60.00 mmol, 1.50 equiv). The resulting solution was stirred for 15 h at room temperature. The resulting mixture was then washed with 2x100mL of Na2CO3 (1M, aq.). Then the organic phase was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (C18 gel, CH3CN/H2O = 1:1) to give 10.8 g diastereomeric tert- butyl 4-(5-cyclopropylisoxazole-3-carboxamido)-2-methylpiperidine-1-carboxylate. Then the purified product was separated by Prep-SFC with the following conditions (prep SFC 350): Column, CHIRALPAK AD-H SFC, 5x25cm,5um; mobile phase, CO2(50%), methanol(50%); Detector, uv 220nm. This was resulted in 7.48 g (54%) of tert-butyl (2R,4R)-4-(5-cyclopropyl-1,2-oxazole-3-amido)-2-methylpiperidine-1-carboxylate as light yellow oil. 1H-NMR (300 MHz, CDCl3): 6.86 (d, J = 6.9 Hz, 1H), 6.33 (s, 1H), 4.30-4.15 (m, 2H), 3.93-3.80(m, 1H), 3.22-3.07(m, 1H), 2.20-1.90 (m, 3H), 1.79-1.65(m, 2H), 1.46(s, 9H), 1.26(d, J = 6.9 Hz, 3H), 1.17-1.06(m, 2H), 1.06-0.94(m, 2H) ppm. LCMS (method A, ESI): RT=1.46 min, m/z =372.2 [M+H]+. And 2.52 g (18%) of tert- butyl (2R,4S)-4-(5-cyclopropyl-1,2-oxazole-3-amido)-2-methylpiperidine-1-carboxylate as a light yellow solid. 1H-NMR (300 MHz, CDCl3): 6.55 (d, J = 8.1 Hz, 1H), 6.33 (s, 1H), 4.63-4.39 (m, 1H), 4.39-4.15(m, 1H), 4.15-3.95(m, 1H), 3.0-2.85 (m, 1H), 2.15- 1.98(m, 2H), 1.92-1.78(m, 1H), 1.65-1.50 (m, 1H), 1.46(s, 9H), 1.42-1.26 (m, 1H), 1.23(d, J = 6.9 Hz, 3H), 1.17-1.06(m, 2H), 1.06-0.94(m, 2H) ppm. LCMS (method A, ESI): RT=1.46 min, m/z =372.2 [M+H]+.

110256-15-0, The synthetic route of 110256-15-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EPIZYME, INC.; MITCHELL, Lorna Helen; BELL, Andrew Simon; CHESWORTH, Richard; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (375 pag.)WO2016/40515; (2016); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

19788-37-5, 4-(Chloromethyl)-3,5-dimethylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of the product of step 4 (0.15g, 0.255 mmol) in CH2Cl2 (4 mL), Huenig’s base (0.12 g, 0.9 mmol) and 4-chloromethyl-3,5-dimethyl-isoxazole (37 mg, 0.255 mmol) was stirred at RT for 3 days under N2. After completion, the reaction was diluted with CH2Cl2 (40 mL), washed with brine (30 mL, 3x), dried (Na2SO4), filtered and evaporated to give the product as a brown oil. Product was purified by flash silica gel chromatography, eluting with 5 % [(1:9)NH4OH-CH3OH] /95 % CH2Cl2 to give a yellow solid (1.4 g), m.p. 78-80 C; FABMS 35Cl[M+1] 624.2; HRMS 35Cl[M+1]+:cal’d for C33H40N5O3Cl3:624.2508; Found : 624.2506., 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; SCHERING CORPORATION; EP937069; (2006); B1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

31329-64-3, 3,5-Dimethylisoxazol-4-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

31329-64-3, EXAMPLE 1 7-Methoxy-2-(tetrahydrofuran-3-yl)-benzofuran-4-carboxylic acid (3,5-dimethylisoxazol-4-yl)-amide To a stirred solution of 3,5-dimethylisoxazol-4-ylamine (88 mg) in N,N-dimethylformamide (7 ml) under an atmosphere of dry nitrogen at room temperature was added sodium bis(trimethylsilyl)amide (0.78 ml, 1.0M solution in tetrahydrofuran). The reaction was stirred for 5 minutes. 7-Methoxy-2-(tetrahydro-furan-3-yl)-benzofuran-4-carboxylic acid 4-nitrophenyl ester (200 mg) was then added and stirring continued for 15 minutes. Water (1 ml) was added and the solvent was removed in vacuo. The resulting residue was purified by column chromatography on silica eluding with 50% ethyl acetate in heptane followed by trituration with diethyl ether affording the title compound as a cream solid (52 mg). TLC Rf 0.60 (50% ethyl acetate in heptane). Mp 183.5-185.2 C.

The synthetic route of 31329-64-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Dyke, Hazel Joan; Lowe, Christopher; Montana, John Gary; US2001/31777; (2001); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

13999-39-8, 3-Amino-4,5-dimethylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 4,5-dimethylisoxazol-3-amine (4.9 g, 44 mmol, 1.0 equiv; CASNo. 13999-39-8, Org. Proc. Res. Dev. 2007, 11, 275-277) and triethylamine (6.4 mL, 46 mmol, 1.05 equiv) in acetonitrile (25 mL) was added portionwise to a 0 0C solution of phenyl chloroformate (5.8 mL, 46 mmol, 1.05 equiv) in THF (100 mL). After stirring at 0 0C for 1 h, the reaction was warmed to room temp overnight. The reaction was concentrated to about one-half the volume and partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography (20 to 40% ethyl acetate/heptane) to give the title compound as a white solid (8.39 g, 83%). m/z 233 (MH+). 1H NMR (400 MHz, DMSO-Cf6) delta ppm 10.67 (br. s., 1 H), 7.40 (t, J=8.0 Hz, 2 H), 7.17 – 7.27 (m, 3 H), 2.12 (s, 3 H), 1.82 (s, 3 H)., 13999-39-8

13999-39-8 3-Amino-4,5-dimethylisoxazole 84148, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER INC.; WO2009/127943; (2009); 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.14678-02-5,5-Amino-3-methylisoxazole,as a common compound, the synthetic route is as follows.

Prepared by following a methodology reported by M. Ohkubo et al. in Chem Pharm Bull. 1995, 43 (9), 1497-1504.To a solution of 5-amino-3-methylisoxazole (0.165 g, 1.67 mmol) in anhydrous toluene (6.5 ml) and anhydrous pyridine (0.18 ml, 2.0 mmol) cooled in an ice/water bath (T=10 C.) was slowly added bromoacetyl bromide (0.402 g, 2.0 mmol). The reaction mixture was stirred for 1.5 h under argon, then poured into water (20 ml), and extracted with ethyl acetate (2¡Á40 ml). The combined organics were washed with water (30 ml), brine (30 ml), dried (Na2SO4), and concentrated in vacuo. The residue was triturated with diethyl ether, the precipitate was removed by filtration, and the filtrate was concentrated in vacuo to afford the title compound as a white solid (0.200 g, 55%); 1H-NMR (500 MHz, DMSO-d6) 2.18 (s, 3H, CH3), 4.08 (s, 2H, CH2Br), 6.15 (s, 1H, isoxazole C-H), 11.94 (s, 1H, CONH);LC (Method B)-MS (ESI, m/z): Rt=2.92 min-219, 221 [(M+H)+, Br isotopic pattern]., 14678-02-5

As the paragraph descriping shows that 14678-02-5 is playing an increasingly important role.

Reference£º
Patent; THE INSTITUTE OF CANCER RESEARCH; US2009/247507; (2009); 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.354795-62-3,3-Methylisoxazol-4-amine,as a common compound, the synthetic route is as follows.

Example 165-Bromo-2-{[(4-fluorophenyl)methyl]oxy}- V-(3-methyl-4-isoxazolyl)-4-(4- morpholinylmethyl)benzamide (E16)To a solution of 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acid (may be prepared as described in Description 20; 150 mg, 0.35 mmol) in N,N- dimethylformamide (4 ml) was added 3-methyl-4-isoxazolamine (41.6 mg, 0.42 mmol), diisopropylethylamine (0.12 ml, 0.71 mmol), 1 -hydroxy- 7-azabenzotriazole (57.7 mg, 0.42 mmol) and EDC (102 mg, 0.53 mmol). The mixture was stirred for 18 hours, then the solvent removed in vacuo to give a residue. The residue was purified by column chromatography (10% 7M NH3 in methanol/dichloromethane) to yield the title compound as a solid. 178 mg. MS (electrospray): m/z, [M+H]+ = 504/506

354795-62-3, 354795-62-3 3-Methylisoxazol-4-amine 13804284, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXO GROUP LIMITED; ANDREOTTI, Daniele; DAI, Xuedong; EATHERTON, Andrew John; JANDU, Karamjit Singh; LIU, Qian; PHILPS, Oliver James; WO2012/28629; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

108655-63-6, 3-(Trifluoromethyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Pyridine (5.4 mL, 0.067 mol) is added dropwise to 5-chloro-2,4-dimethoxyaniline (10.45 g, 0.056 mol) and phenyl chloroformate (8.4 mL, 0.067 mol) in CH2Cl2 (500 mL) at 0 C. The reaction is stirred for 1.5 h and diluted with 0.1M HCl (100 mL). The organics are separated, washed w/5% NaHCO3 (100 mL) and brine (150 mL), dried (MgSO4), and the solvent is removed. The resulting solid is recrystallized (EtOAc/hexanes) to give phenyl 5-chloro-2,4-dimethoxyphenylcarbamate (16.72 g, 97% yield) as a purple solid. Sodium hydride(1.82 g, 0.046 mol, 60% oil disp.) is added to 3-(trifluoromethyl)isoxazole-5-amine (6.93 g, 0.046 mol) in DMF (350 mL) at RT. After 0.5 h, a DMF solution (100 mL) of phenyl 5-chloro-2,4-dimethoxyphenylcarbamate (14.0 g, 0.046 mol) is added and the reaction warmed to RT. The reaction is heated at 50 C. for 1 h, cooled to RT and the solvent is removed. The residue is dissolved in EtOAc (150 mL), washed with 1M HCl (150 mL), H2O (150 mL), and brine (150 mL). The organics are separated, dried (MgSO4) and the solvent is removed under reduced pressure. The dark solid is dissolved in EtOH (500 mL) and stirred with Darco activated carbon (15) for 4 h. The mixture is filtered over Celite and the solvent is removed to give a solid, which is recrystallized (EtOAc/hexanes) to give Example 500 as a tan solid (10.47 g, 63% yield). HRMS (ESI) calcd for C13H11ClF3N3O4+H 366.0468 found 366.0475., 108655-63-6

108655-63-6 3-(Trifluoromethyl)isoxazol-5-amine 13913996, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Piotrowski, David W.; Rogers, Bruce N.; McWhorter JR., William W.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Groppi JR., Vincent E.; Rudmann, Daniel G.; US2003/236287; (2003); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

62348-13-4, Isoxazole-5-carbonyl chloride is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

62348-13-4, EXAMPLE 2 6.52 parts of 2-methylpyridine were added to a stirred mixture of 15.7 parts of 7-chloro-5-nitro-8-hydroxyquinoline in 190 parts of 1,2-dichloroethane at 25 C. in the course of 5 minutes, and the mixture was stirred for 5 minutes. 9.2 parts of isoxazole-5-carbonyl chloride were then added at from 20 to 25 C. in the course of 10 minutes, while stirring, and stirring was continued for 3 hours at 55 C. The reaction mixture was evaporated to dryness under reduced pressure, and the residue was stirred in 200 parts of 0.5N hydrochloric acid for 5 minutes. The precipitate was filtered off under suction, washed with water and stirred for 10 minutes in 200 parts of dilute sodium carbonate solution. Filtration under suction, washing with water at 60 C. and drying gave 17.5 parts of 7-chloro-5-nitro-8-(isoxazole-5′-carbonyl)-oxyquinoline of melting point 132-134 C.

As the paragraph descriping shows that 62348-13-4 is playing an increasingly important role.

Reference£º
Patent; BASF Aktiengesellschaft; US4829072; (1989); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

7063-99-2, Ethyl 5-phenylisoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7063-99-2

The ethyl 5-phenyl-isoxazole-3-carboxylate (1g, 4.6mmol) and hydrazine hydrate (0.69g, 13.8mmol) was dissolved in 20mL of ethanol and refluxed overnight.The solid was precipitated by cooling to room temperature, suction filtered, and dried to give a solid, about 0.63 g, yield: 69%.

As the paragraph descriping shows that 7063-99-2 is playing an increasingly important role.

Reference£º
Patent; China Pharmaceutical University; Wang Jinxin; Shang Yanguo; Song Meng; (13 pag.)CN110156708; (2019); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

1018297-63-6, (3-(4-Fluorophenyl)-5-methylisoxazol-4-yl)methanol is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) 2-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-isoindole-1,3-dione To a solution of [3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol (5.0 g, 24 mmol) in THF (290 mL) was added phthalimide (4.7 g, 32 mmol) and triphenylphosphine (8.4 g, 32 mmol) at ambient temperature under an argon atmosphere. Then a solution of diethyl azodicarboxylate (40% in toluene, 12.5 mL, 32 mmol) was added and the reaction mixture was stirred for 1 h at room temperature. Concentration and repeated trituration and then purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (6.0 g, 74%) as a white solid. MS: m/e=337.1 [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; Buettelmann, Bernd; Jakob-Roetne, Roland; Knust, Henner; Thomas, Andrew; US2009/143385; (2009); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem