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CAS No. : | 108511-97-3 | MDL No. : | MFCD08234629 |
Formula : | C3H4N2O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | CVCYZCBJCQXUCN-UHFFFAOYSA-N |
M.W : | 84.08 | Pubchem ID : | 13804278 |
Synonyms : |
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Chemical Name : | Isoxazol-4-amine |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium chloride; zinc; In water; at 0 - 5℃; for 2h; | 4- Nitroisoxazole (may be prepared as described in Description 94; 850 mg, 7.45 mmol) was added to a solution of ammonium chloride (9169 mg, 171 mmol) in water (60 ml). The resultant suspension was cooled to 0°C, and zinc (4142 mg, 63.3 mmol) was added in portions whilst keeping the temperature below 5°C. After the addition, the mixture was stirred at 0-5°C for 2 hours. The reaction mixture was then filtered, and the filtrate was extracted with ethyl acetate (100 ml x 4). The organic phase was washed by water (100 ml x 2), dried over anhydrous MgS04, and concentrated to yield the title compound as a brown oil, 535 mg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With pyridine; In tetrahydrofuran; at 0 - 20℃; | To a solution of <strong>[108511-97-3]4-aminoisoxazole</strong> (2.00 g, 23.79 mmol; CASNo. 108511-97-3) in THF (50 mL) at 0 0C was added pyridine (1.92 mL, 23.79 mmol,) followed by phenyl chloroformate (3.28 mL, 26.17 mmol,). After stirring at 0 0C for 2.5 h, the reaction was warmed to room temp overnight. The reaction was diluted with ethyl acetate and washed with 2M HCI, water, saturated sodium bicarbonate, and brine. The organic layer was dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography (dichloromethane/hexane) to give the title compound as a white solid (2.07 g, 10.15 mmol, 50percent). |
50% | With pyridine; In tetrahydrofuran; at 0 - 20℃; | To a solution of <strong>[108511-97-3]4-aminoisoxazole</strong> (2.00 g, 23.79 mmol; CASNo. 108511-97-3) in THF (50 mL) at 0 0C was added pyridine (1.92 mL, 23.79 mmol,) followed by phenyl chloroformate (3.28 mL, 26.17 mmol,). After stirring at 0 0C for 2.5 h, the reaction was warmed to room temp overnight. The reaction was diluted with ethyl acetate and washed with 2M HCI1 water, saturated sodium bicarbonate, and brine. The organic layer was dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography40 (dichloromethane/hexane) to give the title compound as a white solid (2.07 g, 10.15 mmol, 50percent). |
50% | With pyridine; In tetrahydrofuran; at 0 - 20℃; | To a solution of <strong>[108511-97-3]4-aminoisoxazole</strong> (2.00 g, 23.79 mmol; CASNo. 108511-97-3) in THF (50 mL) at 0 0C was added pyridine (1.92 mL, 23.79 mmol,) followed by phenyl chloroformate (3.28 mL, 26.17 mmol,). After stirring at 0 0C for 2.5 h, the reaction was warmed to room temp overnight. The reaction was diluted with ethyl acetate and washed with 2M HCI, water, saturated sodium bicarbonate, and brine. The organic layer was dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography (dichloromethane/hexane) to give the title compound as a white solid (2.07 g, 10.15 mmol, 50percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 50℃; for 16h;Inert atmosphere; | To a suspension of 65 mg of 6-(pyridin-2-yl)imidazo[1,2-a]pyridine-2-carboxylic acid (intermediate 2) and 104 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 2 mL of anhydrous pyridine, placed under argon, are added 68 mg of <strong>[108511-97-3]isoxazol-4-ylamine</strong>. The reaction mixture is stirred for 16 hours at 50° C. and then concentrated under reduced pressure. The residue is taken up in dichloromethane and washed with water. The organic phase is dried over magnesium sulfate and concentrated to dryness under reduced pressure to give 49 mg of N-(isoxazol-4-yl)-6-(pyridin-2-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a beige-coloured solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 50℃; for 16h; | To a suspension of 200 mg of 6-iodoimidazo[1,2-a]pyridine-2-carboxylic acid and 266 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 1 mL of anhydrous pyridine are added 175 mg of <strong>[108511-97-3]isoxazol-4-ylamine</strong>. The reaction mixture is stirred for 16 hours at 50° C. and then concentrated under reduced pressure. The residue is taken up in 10 mL of a mixture of chloroform and water (1/1). The solid is triturated with 3 mL of water, filtered off by suction and washed with 3 mL of water and then with 3 mL of ethyl ether, and dried to give 280 mg of 6-iodo-N-(isoxazol-4-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a beige-coloured solid. 1H NMR spectrum (DMSO-d6, delta in ppm): 10.93 (broad s, 1H), 9.24 (broad s, 1H), 9.02 (broad s, 1H), 8.81 (broad s, 1H), 8.43 (broad s, 1H), 7.60-7.48 (m, 2H). Mass spectrum (APCI): m/z=258 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 100 mg, 0.30 mmol), EDC (172 mg, 0.90 mmol) and HOBT (137 mg, 0.90 mmol) in dimethylformamide (3 ml) was stirred in air at room temperature for 1 h, then <strong>[108511-97-3]4-isoxazolamine</strong> (may be prepared as described in Description 95; 100 mg, 1.189 mmol) was added in one charge. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with water (30 mi). The solid was filtered and dried in vacuo to obtain crude product, which was purified with Prep- HPLC (Waters, X-Bridge, 5Mm;30x100mm; A=0.05percentNH3.H2O/water, B:MeCN;v=30ml/min;0-7min, 42percent-54percent; 7-12min, 95percent; t=8.0min.) to yield the title compound as a white solid. 34 mg.'HNMR (400 MHz, DMSO-d6): 10.60 (s, 1 H), 9.27 (s, 1 H), 8.65 (s, 1 H), 8.62 (d, 2H, J=5.6), 8.08 {d, 1 H, J=2.0), 7.98 (dd, 1 H, J=2.0, 8.4), 7.74 (d, 2H, J=5.6), 7.52 (d, 2H, J=7.6), 7.42-7.33 (m, 4H), 5.36 (s, 2H).MS (electrospray); m/z [M+H]+ = 372.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h; | A mixture of 2-[(4-fluorophenyl)methyl]oxy}-5-(1-methyl-1H-pyrazol-4-yl)benzoic acid (may be prepared as described in Description 121 ; 100 mg, 0.31 mmol), isoxazol-4- amine (38.6 mg, 0.46 mmol), HOBT (70.4 mg, 0.46 mmol) and EDC (88 mg, 0.46 mmol) in N,N-dimethyIformamide (5 ml) was stirred at room temperature for 16 hours. Water (50 ml) was added. The mixture was extracted with ethyl acetate (50 ml x 3). The combined organic layers were washed with brine (50 ml), dried over Na2S04, and concentrated to give the crude product. The crude product was purified by a prep-HPLC (Instrument : Gilson GX-281 ; Column: Shimadzu PRC-ODS, 15.0 um, 19 mm * 250 mm; Mobile Phase: A:0.05percent NH3H20/H2O;B:CH3CN; Gradient 0-8min 42-54percentB;8-12min 95percent; Flow ate(ml/min) 30.00; Detective Wavelength (nm) 214; Retention Time(min) 7.5) to yield the title compound as a white solid. 17 mg.1HNMR (400 MHz, DMSO-cf6): 3.85 (3H, s), 5.25 (2H, s), 7.20-7.26 (3H, m), 7.53-7.55 (2H, q), 7.67-7.70 ( H, dd, J - 2.4 Hz, J = 8.8 Hz), 7.79 (1 H, d, J = 2.4 Hz), 7.85 (1 H, s), 8.13 (1 H, s), 8.63 (1H, s), 9.24 (1 H, s), 10.49 (1H, s)MS (electrospray): m/z [M+H]+ =393.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium hydrogencarbonate; sodium carbonate; In dichloromethane; at 0 - 20℃; for 1h;Inert atmosphere; | To a stirred solution of <strong>[108511-97-3]<strong>[108511-97-3]isoxazol-4-amin</strong>e</strong> (200 mg, 1.66 mmol) in CH2C12 (5 mL) under inert atmosphere were added 2 N Na2CO3 solution (2.6 mL), saturated NaHCO3 solution (5.6 mL), and bromo acetyl bromide (669 mg, 3.33 mmol) at 0 °C. The reaction mixture was warmed to RT and stirred for 1 h. The reaction progress was monitored by TLC; after reaction completion, the reaction mixture was diluted with water (15 mL) and extracted with CH2C12 (2 x 25 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude material. The crude material was purified through silica gel flash column chromatography using 25percent EtOAc/ hexanes to afford compound 1 (300 mg, 88percent) as an off-white solid. 1HNMR (400 MHz, CDC13): oe 8.99 (s, 1H), 8.43 (s, 1H), 8.10 (br s, 1H), 4.04 (s, 2H). LC-MS:98.0percent; (M+2) Found=203.5; (column: X Select C-18, 50 x 3.0 mm, 3.5 jim); RT 1.80 mm. 5 mM NH4OAc: ACN; 0.8 mL/min). |
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