Downstream synthetic route of 59669-59-9

As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.

59669-59-9, 3-(tert-Butyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,59669-59-9

A mixture of 4-Methoxy-benzenethiol (0.20g, 1 eq) and potassium carbonate (0.47g, 2.5eq) in dry THF was allowed to stir at room temperature under argon for an hour. Then the stirred suspension was cooled to0 C and to it was added drop wise a solution of phosgene (0.17g1. 2eq). The reaction stirred at0 C for half an hour. Then 3-tert-Butyl-isoxazol-5- ylamine (0.20g, leq) in THF was added dropwise. The reaction was allowed to warm to room temperature and stirred overnight. The solvent was removed and extracted with ethyl acetate and water. The organic layer was dried over magnesium sulfate and solvent removed. It was purified by HPLC. Yield: 157mg (36percent)

As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.

Reference£º
Patent; AMBIT BIOSCIENCES CORPORATION; WO2005/48948; (2005); A2;,
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Isoxazole | C3H3NO – PubChem

Simple exploration of 59669-59-9

59669-59-9 3-(tert-Butyl)isoxazol-5-amine 2095694, aIsoxazoles compound, is more and more widely used in various fields.

59669-59-9, 3-(tert-Butyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

59669-59-9, (a) 5-Amino-4-bromo-3-tert-butylisoxazole 5-Amino-4-bromo-3-tert-butylisoxazole was prepared from 5-amino-3-tert-butylisoxazole and N-bromosuccinimide in 64percent yield as described in Example 1a.

59669-59-9 3-(tert-Butyl)isoxazol-5-amine 2095694, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; Immunopharmaceutics, Inc.; US5514691; (1996); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Downstream synthetic route of 59669-59-9

As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.

59669-59-9, 3-(tert-Butyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

59669-59-9, Step 2: Synthesis of (S)-l-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid (3-tert- butyl-isoxazol-5-yl)-amideTo a cold slurry of (S)-l-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid (0.2g; 0.788mmol) and 5-amino-3-tert-butylisoxazole (0.11Og; 0.788mmol) in pyridine (0.956mL; 11.820mmol) is added phosphorous oxychloride (O.O88mL; 0.946mmol). The mixture is stirred at O0C 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 (Na2SO4), filtered and concentrated in vacuo. Purification by preparative HPLC affords title compound, m/z 376 [M+H+].

As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BERRY, Angela; CIRILLO, Pier Francesco; HICKEY, Eugene Richard; RIETHER, Doris; WU, Lifen; ZINDELL, Renee M.; WO2010/96371; (2010); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Analyzing the synthesis route of 59669-59-9

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

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.

59669-59-9, General procedure: A solution of compounds 10a?d or compounds 17a?d (1.0 mmol) in dichloromethane (10 mL) was slowly added to a stirred solution of triphosgene (109 mg, 0.36 mmol) in dichloromethane (50 mL) over a period of 30 min using a syringe. After stirring for a further 30 min, a solution of compound 25a?r (0.6 mmol) and triethylamine (0.4 mL, 2.77 mmol) in dichloromethane (10 mL) was added in one portion. The reaction mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction was poured into water (50 mL) and extracted three times with dichloromethane. The organic layer was washed with water (5 mL), sat. NaCl solution (5 mL), anddried over Na2SO4. After evaporation of solvent under vacuum, the residue was purified by silica gel chromatography to give the desired chromanylurea or 2H-chromenyl urea compounds.

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

Reference£º
Article; Li, Xingzhou; Zhou, Xinming; Zhang, Jing; Wang, Lili; Long, Long; Zheng, Zhibing; Li, Song; Zhong, Wu; Molecules; vol. 19; 2; (2014); p. 2004 – 2028;,
Isoxazole – Wikipedia
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Simple exploration of 59669-59-9

59669-59-9 3-(tert-Butyl)isoxazol-5-amine 2095694, aIsoxazoles compound, is more and more widely used in various fields.

59669-59-9,59669-59-9, 3-(tert-Butyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

100 mg of 5-(2-fluoropyridin-4-yl)-2-(tetrahydropyran-4-yloxy)benzonitrile are suspended in 6 ml of dioxane in a 50 ml three-necked flask under N2, 52 mg of 3-tert-butylisoxazol-5-ylamine and 79 mg of KOtBu are added The yellow solution is stirred at 80¡ã C. for 2.5 h. For work-up, the reaction mixture is evaporated in a rotary evaporator, the residue is taken up in ethyl acetate and water and extracted. The collected organic phases are dried, filtered and evaporated. The crude product is purified by preparative HPLC, giving the desired product in 46percent yield; HPLC-MS Rt. [min] 2.556; HPLC-MS [M+H] 419; [0327] 1H NMR (500 MHz, DMSO-d6) delta [ppm] 8.36 (d, J=5.7, 1H), 8.19 (d, J=2.4, 1H), 8.04 (dd, J=8.9, 2.4, 1H), 7.53 (d, J=9.1, 1H), 7.42 (dd, J=5.8, 1.6, 1H), 7.38 (s, 1H), 5.00-4.88 (m, 1H), 3.96-3.85 (m, 2H), 3.64-3.50 (m, 2H), 2.12-2.00 (m, 2H), 1.79-1.66 (m, 2H), 1.38-1.24 (s, 9H).

59669-59-9 3-(tert-Butyl)isoxazol-5-amine 2095694, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK PATENT GMBH; Hoelzemann, Guenter; Dorsch, Dieter; Eggenweiler, Hans-Michael; US2014/228340; (2014); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

New learning discoveries about 59669-59-9

As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.

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.

59669-59-9, Step 6: Synthesis of compound B-7Activation of 55.9 g (22.3 mmol) of compound B-6 is achieved by treatment with thionyl chloride (600 mL) at 60 ¡ãC for 3 h. The reaction mixture is cooled to room temperature and excess thionyl chloride is removed under reduced pressure.The crude acid chloride is dissolved in DCM (400 mL) and added to a solution of 31.3 g (22.3 mmol) of 3-tert-Butyl-isoxazol-5-ylamine and N,N-diisopropylethylamine (194 mL) in DCM (250mL). The reaction is stirred at room temperature for 16 h. The reaction mixture is diluted with DCM (1350 mL) and washed with saturated aqueous NaHCC>3 solution (1000 mL). The organic layer is dried over Na2S04, filtered and the filtrate is concentrated under reduced pressure. The crude product is purified by dry-flash column chromatography (2 kg silica, eluent: DCM, 0-20percent ethyl acetate). The resulting solid is recrystallised from isopropanol/heptanes (1/1. 2 L), then dried under reduced pressure to afford 80 g of compound B-7 as an off-white powder. Yield 96percent; ES-MS: m/z 373 [M+H]; XH NMR (360 MHz, CHLOROFORM-d) delta ppm 1.35 (9 H, s), 1.41 – 1.55 (2 H, m), 1.74 (6 H, s), 1.82 – 1.91 (2 H, m), 2.29 – 2.52 (1 H, m), 2.92 (2 H, d, 7=6.58 Hz), 3.34 – 3.49 (2 H, m), 3.88 – 4.00 (2 H, m), 6.30 (1 H, s), 9.38 (1 H, s).

As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HICKEY, Eugene Richard; RIETHER, Doris; ERMANN, Monika; WO2012/12307; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

New learning discoveries about 59669-59-9

As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.

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 solution of phosgene (20percent in toluene, 1.13 mL, 2.18 mmol) in CH2Cl2 (20 mL) at 0 ¡ãC was added anh. pyridine (0.176 mL, 2.18 mmol), followed by 5-amino-3-tert-butylisoxazole (0.305 g, 2.18 mmol). The resulting solution was allowed to warm to room temp. over 1 h, and then was concentrated under reduced pressure. The solid residue dried in vacuo for 0.5 h.

As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.

Reference£º
Patent; Bayer Pharmaceuticals Corp.; EP1047418; (2005); B1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Some tips on 59669-59-9

59669-59-9 3-(tert-Butyl)isoxazol-5-amine 2095694, aIsoxazoles compound, is more and more widely used in various.

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.,59669-59-9

To a solution of the starting pyrazole amine (1 eq) in EtOAc were added 2,2,2-trichloroethylchloroformate (1.1 eq) and saturated NaHCO3 (2-3 eq) at 0¡ã C. After stirring for 3 h at RT, the layers were separated and the aqueous layer extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under vacuum to yield the crude TROC carbamate of the pyrazole amine.Example 2To a solution of 2,2,2-trichloroethyl 3-tert-butylisoxazol-5-ylcarbamate (0.080 g, 0.25 mmol), formed via General method B from Example B1, in dioxane (3 mL) was added Example A2 (70 mg, 0.25 mmol) and 1-methylpyrrolidine (22 mg, 0.25 mmol). The reaction mixture was heated overnight at 65¡ã C. The reaction mixture cooled to RT, concentrated in vacuo, DCM (2 mL) was added and the slurry was stirred for 1 hour. The solid was filtered and air dried to obtain 1-(4-(2-(1H-1,2,4-triazol-1-yl)pyridin-4-yloxy)-2-fluorophenyl)-3-(3-tert-butylisoxazol-5-yl)urea. 1H NMR (400 MHz, DMSO-d6): delta 10.3 (s, 1H), 9.56 (s, 1H), 8.70 (s, 1H), 8.34 (s, 1H), 8.29 (d, J=6.0 Hz, 1H), 8.03 (t, J=9.2 Hz, 1H), 7.68 (dd, J=2.0, and 5.6 Hz, 1H), 7.57 (d, J=1.2 Hz, 1H), 7.26 (dd, J=2.8, and 12.0 Hz, 1H), 7.03 (m, 1H), 6.05 (s, 1H), 1.24 (s, 9H); MS (ESI) m/z: 438.1 (M+H+).

59669-59-9 3-(tert-Butyl)isoxazol-5-amine 2095694, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; Deciphera Pharmaceuticals, LLC; US2008/261961; (2008); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Brief introduction of 59669-59-9

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

59669-59-9, 3-(tert-Butyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,59669-59-9

Step 7: Synthesis of compound D-8Activation of 60 g (0.25 mol) of compound D-7as the corresponding acid chloride is achieved by treatment with thionyl chloride (0.9 L, 12.39 mol) at 60 ¡ãC for 1.5 h. The reaction is cooled to room temperature and acid chloride mixture was evaporated to dryness. The acid chloride mixture is dissolved in DCM (200 mL).This acid chloride solution is added dropwise over 20 mins to a stirred suspension of 36 g (0.25 mol) of 3-tert-butyl-isoxazol-5-ylamine and 0.6 L (0.50 mol) of N,N- diisopropylethylamine in DCM (400 mL) at 35 ¡ãC. After complete addition the reaction is stirred at room temprature for 17 h. The solvent is removed under reduced pressure. The residue is purified by dry-flash column chromatography (silica, eluent heptanes, 20percent ethyl acetate) to yield 50 g of light brown solid. Solid is re-crystallized from (50percent IPA in heptane) to afford 34 g of compound D-8 Yield: 43percent; ES-MS: m/z 359 [M+H];’H-NMR (400 MHz, CHLOROFORM-d) delta ppm 1.33 (9 H, s), 1.76 (6 H, s), 1.83 – 1.91 (2H, m), 1.92 – 2.05 (2 H, m), 3.34 – 3.51 (3 H, m), 4.07 (2 H, ddd, 7=11.86, 2.20, 2.08 Hz), 6.27 (1 H, s), 9.60 (1 H, s)

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; ERMANN, Monika; WO2012/12307; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Downstream synthetic route of 59669-59-9

As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.

59669-59-9, 3-(tert-Butyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N-(3-tert-Butyl-5-isoxazolyl)-N’-(4-phenoxyphenyl)urea: To a solution of 5-amino-3-tert-butylisoxazole (8.93 g, 63.7 mmol, 1 eq.) in CH2Cl2 (60 mL) was added 4-phenyloxyphenyl isocyanate (15.47 g, 73.3 mmol, 1.15 eq.) dropwise. The mixture was heated at the reflux temp. for 2 days, eventually adding additional CH2Cl2 (80 mL). The resulting mixture was poured into water (500 mL) and extracted with Et2O (3.x.200 mL). The organic layer was dried (MgSO4) then concentrated under reduced pressure. The residue was recrystallized (EtOAc) to give the desired product (15.7 g, 70percent): mp 182-184¡ã C.; TLC (5percent acetone/95percent acetone) Rf 0.27; 1H-NMR (DMSO-d6) delta 1.23 (s, 9H), 6.02 (s, 1H), 6.97 (dd, J=0.2, 8.8 Hz, 2H), 6.93 (d, J=8.8 Hz, 2H), 7.08 (t, J=7.4 Hz, 1H), 7.34 (m, 2H), 7.45 (dd, J=2.2, 6.6 Hz, 2H), 8.80 (s, 1H), 10.04 (s, 1H); FAB-MS m/z (rel abundance) 352 ((M+H)+, 70percent).

As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.

Reference£º
Patent; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Paulsen, Holger; Riedl, Bernd; Scott, William J.; Smith, Roger A.; Wood, Jill; Hatoum-Mokdad, Holia; Lee, Wendy; Redman, Aniko; Johnson, Jeffrey; Sibley, Robert; US2012/46290; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem