Category: 13999-39-8

Some tips on 13999-39-8

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13999-39-8,3-Amino-4,5-dimethylisoxazole,as a common compound, the synthetic route is as follows.

[18]; 2-(6-Chlorobenzotriazol-l-yl)-l5l5353-tetramethyluronium tetrafluoroborate was used in place of 2-(7-azabenzotriazol-l-yl)-l5l53,3-tetramethyluronium hexafluorophosphate(V) as the coupling agent. The product gave the following characterising data :- 1H NMR Spectrum: (DMSOd6) 1.8 (s, 3H), 2.3 (s, 3H), 3.72 (s, 2H), 3.78 (s, 3H), 6.79 (d, IH)5 6.92 (m, IH)5 7.08 (d, IH)5 7.4 (d, IH)5 8.08 (s, IH)5 8.92 (d, IH)5 9.58 (s, IH)3 10.27 (br s, IH); Mass Spectrum: M+H+ 439 and 441.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Simple exploration of 13999-39-8

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

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

Downstream synthetic route of 13999-39-8

As the paragraph descriping shows that 13999-39-8 is playing an increasingly important role.

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

13999-39-8, Example 7; N-(3,4-Dimethyl-5-isoxazolyl)-2-(4-(2-butyl-4-oxo-l,3-diazospiro[4.4]non-l-en- 3yl)methyl-2-ethoxymethylphenyl)phenylsulfonamide (Compound 1); [0062] To a solution of 5-amino-3,4-dimethylisoxazole (60 mg, 0.54 mmol) in THF at -60 C was added dropwise potassium tert-butoxide (1 mL of 1 M solution) followed by a solution of crude 2-(4-((2-butyl-4-oxo-l,3-diazaspiro[4.4]non-l-en-3- yl)methyl)-2-ethoxymethylphenyl)benzenesulfonyl chloride (Compound 16) (0.28 g, 0.54 mmol) in THF (4 mL). The resulting mixture was stirred at about -60 C for 1 hour, allowed to warm to room temperature overnight, and then quenched with IN HCl solution to about pH 4. Standard workup of extraction with ethyl acetate, washing with water, drying, and concentration provided the final compounds as a white solid. 1H NMR (400 MHz, CDCl3) 8.03 (dd, J = 8.0 and 1.2, IH), 7.60 (td, J = 7.5 and 1.5, IH), 7.50 (td, J = 7.7 and 1.5, IH), 7.36 (s, IH), 7.28 (d, J= 2.1, 1 H), 7.25 (dd, J = 7.5 and 1.2, IH), 7.09 (dd, J= 7.9 and 1.6, IH), 6.61 (bs, IH), 4.77 (AB quartet, J= 15.5 and 8.1, 2H), 4.18 (AB quartet, J= 12.0 and 35, 2H), 3.45-3.32 (m, 2H), 2.39 (t, J= 7.5, 2H), 2.26 (s, 3H), 2.02- 1.84 (m, 8H), 1.82 (s, 3H), 1.63 (quint, J = 7.5, 2H), 1.37 (sextet, J = 7.3, 2H), 1.07 (t, J = 7.0, 3H), and 0.90 (t J= 7.3, 3H).

As the paragraph descriping shows that 13999-39-8 is playing an increasingly important role.

Reference£º
Patent; PHARMACOPEIA, LLC; ZHI, Lin; PICKENS, Jason; VAN OEVEREN, Cornelius, A.; HENDERSON, Ian; WO2010/135350; (2010); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Downstream synthetic route of 13999-39-8

13999-39-8, As the paragraph descriping shows that 13999-39-8 is playing an increasingly important role.

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

The iV-(4,5-dimethylisoxazol-3-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide used as starting material was prepared as follows :-Using a similar procedure to that described in the portion of Example 17 that is concerned with the preparation of starting materials, 2-(4-benzyloxy-2-methoxyphenyl)acetic acid (0.1 g) was reacted with oxalyl chloride (0.093 ml) and DMF (3 drops) in methylene chloride (5 ml). The reaction mixture was stirred at ambient temperature for 1 hour. The mixture was evaporated to give 2-(4-benzyloxy-2-methoxyphenyl)acetyl chloride. A mixture of the material so obtained, 3-amino-4,5-dimethylisoxazole (0.062 g), diisopropylethylamine (0.065 ml), 4-dimethylaminopyridine (0.005 g) and methylene chloride (5 ml) was stirred at ambient temperature for 14 hours. The resultant mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and ethyl acetate as eluent. There was thus obtained iV-(4,5-dimethylisoxazol-3-yl)- 2-(4-benzyloxy-2-methoxyphenyl)acetamide; 1H NMR: (DMSOd6) 1.77 (s, 3H), 2.28 (s, 3H), 3.55 (s, 2H)5 3.74 (s, 3H)5 5.09 (s, 2H)5 6.54 (m, IH)5 6.63 (d, IH)5 7.09 (d, IH)5 7.33 (m, IH)5 7.39 (m, 2H)5 7.45 (m, 2H), 10.15 (br s, IH); Mass Spectrum: M+H+ 367.

13999-39-8, As the paragraph descriping shows that 13999-39-8 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/99326; (2007); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Downstream synthetic route of 13999-39-8

As the paragraph descriping shows that 13999-39-8 is playing an increasingly important role.

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

[19]; 2-(6-Chlorobenzotriazol-l-yl)-l,l,3,3-tetramethyluronium tetrafluoroborate was used in place of 2-(7-azabenzotriazol-l-yl)-l,l,3,3-tetramethyluronium hexafluorophosphate(V) as the coupling agent. The reaction product was purified using column chromatography on silica and a solvent gradient from methylene chloride to a 19:1 mixture of methylene chloride and methanol as eluent. The product gave the following characterising data :- 1H NMR Spectrum: (DMSOd6) 1.8 (s, 3H), 2.3 (s, 3H), 3.71 (s, 2H)5 3.78 (s, 3H)5 4.02 (s, 3H)5 6.53 (d, IH)5 6.89 (m, IH), 7.04 (d, IH), 7.23 (s, IH), 7.38 (d, IH), 8.77 (d, IH)5 9.43 (s, IH), 10.27 (br s, IH); Mass Spectrum: M+H+ 435., 13999-39-8

As the paragraph descriping shows that 13999-39-8 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

New learning discoveries about 13999-39-8

As the paragraph descriping shows that 13999-39-8 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.13999-39-8,3-Amino-4,5-dimethylisoxazole,as a common compound, the synthetic route is as follows.

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 20 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-d6) delta ppm 10.67 (br. s., 1 H), 7.40 (t, J=8.0 Hz, 2 H), 7.17 – 7.27 (m, 3 H)1 2.12 (s, 3 H), 1.82 (s, 3 H)., 13999-39-8

As the paragraph descriping shows that 13999-39-8 is playing an increasingly important role.

Reference£º
Patent; PFIZER INC.; WO2009/127944; (2009); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Brief introduction of 13999-39-8

13999-39-8, The synthetic route of 13999-39-8 has been constantly updated, and we look forward to future research findings.

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

STEP07: Synthesis of 5-methyl-thiophene-2-sulphonic acid (4, 5-dimethyl-isoxazol-3yl) amide.; The solution of 5-Methyl thiophene-2-sulphonyl chloride (10.5 gm, 0.053 mol) in (15ml) methylene chloride was added to the solution of 3-amino-4, 5-dimethylisoxazole (4 gm, 0.035 mol) and dimethylaminopyridine (500 mg) in pyridine (20 ml) at 0 C. After the completion of the addition the temperature of the reaction mixture was slowly raised to room temperature and stirred for 6 hours. The reaction mixture was then concentrated under vacuum, the residue thus obtained was acidified using IN hydrochloric acid followed by extraction with methylene chloride (100 ml x2). The combined extracts were washed with water and brine solution. Organic layer was then dried over sodium sulphate and concentrated to give 4.0 gm of 5-methyl-thiophene-2-sulphonic acid (4, 5-dimethyl- isoxazol-3yl) amide as brown colored solid.; STEP09: Synthesis of 5-methyl-thiophene-2-sulphonic acid (4, 5-dimethyl-isoxazol-3yl) amide.; The solution of 5-Methyl thiophene-2-sulphonyl chloride (10.5 gm, 0.053 mol) in (15ml) methylene chloride was added to the solution of 3-amino-4, 5-dimethylisoxazole (4 gm, 0.035 mol) and dimethylaminopyridine (500 mg) in pyridine (20 ml) at 0 C. After the completion of the addition the temperature of the reaction mixture was slowly raised to s room temperature and stirred for 6 hours. The reaction mixture was then concentrated under vacuum, the residue thus obtained was acidified using IN hydrochloric acid followed by extraction with methylene chloride (100 ml x2). The combined extracts were washed with water and brine solution. Organic layer was then dried over sodium sulphate and concentrated to give 4.0 gm of 5-methyl-thiophene-2-sulphonic acid (4, 5-dimethyl- o isoxazol-3yl) amide as brown colored solid.; STEP05: Synthesis of 5-methyl-thiophene-2-sulphonic acid (4, 5-dimethyl-isoxazol-3yl) amide.; The solution of 5-Methyl thiophene-2-sulphonyl chloride (10.5 gm, 0.053 mol) in (15ml) methylene chloride was added to the solution of 3-amino-4, 5-dimethylisoxazole (4 gm, 0.035 mol) and dimethylaminopyridine (500 mg) in pyridine (20 ml) at 0 C. After the completion of the addition the temperature of the reaction mixture was slowly raised to room temperature and stirred for 6 hours. The reaction mixture was then concentrated under vacuum, the residue thus obtained was acidified using IN hydrochloric acid followed by extraction with methylene chloride (100 ml x2). The combined extracts were washed with water and brine solution. Organic layer was then dried over sodium sulphate and concentrated to give 4.0 gm of 5-methyl-thiophene-2-sulphonic acid (4, 5-dimethyl- isoxazol-3yl) amide as brown colored solid.; STEPIl: Synthesis of 5-methyl-thiophene-2-sulphonic acid (4, 5-dimethyl-isoxazol-3yl) amide.; The solution of 5-Methyl thiophene-2-sulphonyl chloride (l.Ogm, 0.081mol) in (25ml) methylene chloride was added to the solution of 3-amino-4, 5-dimethylisoxazole (6.2gm, 0.055mol ) and dimethylaminopyridine (500 mg) in pyridine (40 ml) at 0 C. After the completion of the addition the temperature of the reaction mixture was slowly raised to room temperature and stirred it for 6 hours. The reaction mixture was then concentrated under vacuum, the residue thus obtained was acidified using IN hydrochloric acid followed by extraction with methylene chloride (100 ml x2). The combined extracts were washed with water and brine solution. Organic layer was then dried over sodium sulphate and concentrated to give 18 gm of 5-methyl-thiophene-2-sulphonic acid (4, 5-dimethyl- isoxazol-3yl) amide as brown colored solid.; STEP05: Synthesis of 5-methyl-thiophene-2-sulphonic acid (4, 5-dimethyl-isoxazol-3yl) amide.; The solution of 5-Methyl thiophene-2-sulphonyl chloride (16.0gm, 0.08 lmol) in (25ml) methylene chloride was added to the solution of 3-amino-4, 5-dimethylisoxazole (6.2gm, 0.055mol ) and dimethylaminopyridine (500 mg) in pyridine (40 ml) at 0 C. After the completion of the addition the temperature of the reaction mixture was slowly raised to room temperature and stirred it for 6 hours. The reaction mixture was then concentrated under vacuum, the residue thus obtained was acidified using IN hydrochloric acid followed by extraction with methylene chloride (100 ml x2). The combined extracts were washed with water and brine solution. Organic layer was then dried over sodium sulphate and concentrated to give 18 gm of 5-methyl-thiophene-2-sulphonic acid (4, 5-dimethyl- isoxazol-3yl) amide as brown colored solid.; STEP05: Synthesis of 5-methyl-thiophene-2-sulphonic acid (4, 5-dimethgammal-isoxazol-3yl) amide.; The solution of 5-Methyl thiophene-2-sulphonyl chloride (l.Ogm, 0.08 lmol) in (25ml) methylene chloride was added to the solution of 3-amino-4, 5-dimethylisoxazole (6.2gm, 0.055mol ) and dimethylaminopyridine (500 mg) in pyridine (40 ml) at 0 C. After the completion of the addition the temperature of the reaction mi…

13999-39-8, The synthetic route of 13999-39-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TORRENT PHARMACEUTICALS LTD; WO2007/100295; (2007); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Simple exploration of 13999-39-8

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

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 10-mL RBF was charged with (P)-perfluorophenyl perfluorophenyl 1-(4-bromo-5-fluoro-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (58 mg, 0.098 mmol) and 4,5-dimethylisoxazol-3-amine (16.4 mg, 0.146 mmol) then purged with nitrogen. Tetrahydrofuran (732 muL) and dimethyl sulfoxide (244 muL) were introduced, and the resultant brown solution cooled to 0 C. A solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1.0 M, 215 muL, 0.215 mmol) was added dropwise via syringe to the stirred reaction mixture over 3 min. After 15 min, 1.0 N HCl (5 mL) was introduced and the resultant reaction mixture was allowed to warm to ambient temperature. The mixture was diluted with and EtOAc (10 mL) and the layers were separated, and the aqueous layer was further extracted with EtOAc (3*10 mL). The combined organic layers were then washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to furnish a yellow oil, which was dissolved in DMSO (2 mL) filtered through a 0.2 micron filter and purified by reverse-phase HPLC (Waters XBridge Prep Shield RP18 10 mum OBD 19*100 mm) gradient, 20 to 75% MeCN in water (containing 0.1% trifluoroacetic acid as an additive), flow rate 40 mL/min to afford (P)-1-(4-bromo-5-fluoro-2-methoxyphenyl)-N-(4,5-dimethyl-3-isoxazolyl)-2-oxo-1,2-dihydro-6-quinolinesulfonamide (29.0 mg, 0.056 mmol, 56.9% yield) as a white amorphous solid. 1 H NMR (500 MHz, DMSO-d6) delta ppm 10.79 (br. s., 1 H) 8.32 (d, J=2.01 Hz, 1 H) 8.23 (d, J=9.67 Hz, 1 H) 7.85 (dd, J=8.99, 2.04 Hz, 1 H) 7.67 (d, J=6.23 Hz, 1 H) 7.62 (d, J=8.56 Hz, 1 H) 6.86 (d, J=8.95 Hz, 1 H) 6.79 (d, J=9.67 Hz, 1 H) 3.70 (s, 3 H) 2.21 (s, 3 H) 1.80 (s, 3 H). m/z (ESI) 522.0 (M+H)+., 13999-39-8

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

Reference£º
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Simple exploration of 13999-39-8

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

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. 2-Bromo-N-(4,5-dimethyl-3-isoxazolyl)benzenesulfonamide To 4,5-dimethyl-3-isoxazolamine (1.62 g, 13.00 mmol, prepared as described in T. Konoike et al., Tetrahedron Letters, 37, 3339 (1996)) and 4-dimethylaminopyridine (159 mg, 1.3 mmol) in 6.5 ml pyridine at 0 C., 2-bromobenzenesulphonyl chloride (3.65 g, 14.3 mmol) was added in portions over 10 minutes. After stirring at room temperature overnight, the mixture was added dropwise to 40 ml 6N HCl at 0 C. The mixture was extracted with 3*50 ml EtOAc. The combined organic extracts were washed with 30 ml each of 1N HCl and brine and dried and concentrated. The residue was dissolved in 160 ml MeOH and 160 ml 3% aqueous NaHCO3 solution was added and the mixture was concentrated in vacuo to remove most of the MeOH. The solid was filtered off and the aqueous filtrate was acidified to pH 2 with solid NaHSO4, and extracted with 3*100 ml of EtOAc. The extracts were washed with brine, dried and concentrated to give the title compound of this step (3.0 g, 70%). Rf=0.57, silica gel, 1:1 hexane/EtOAc.

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

Reference£º
Patent; Bristol-Myers Squibb Company; US5780473; (1998); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem