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CAS No. : | 1137606-74-6 | MDL No. : | MFCD21362982 |
Formula : | C17H25FN4O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 320.41 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | N/A | |
Precautionary Statements: | UN#: | N/A | |
Hazard Statements: | Packing Group: | N/A |
* 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 |
---|---|---|
Stage #1: 3,6-difluoropyrazine-2-carbonitrile With acetic acid; triethylamine In N,N-dimethyl-formamide at 5 - 15℃; Stage #2: With ammonia In water Stage #3: N-cyclohexyl-cyclohexanamine In water; acetone; toluene | 1.2 4.11 ml of acetic acid was added at 5 to 15°C to a 17.5 ml N,N-dimethylformamide solution of 5.0 g of 3,6-difluoro-2-pyrazinecarbonitrile. Then 7.27 g of triethylamine was added dropwise and the solution was stirred for 2 hours. 3.8 ml of water and 0.38 ml of ammonia water were added to the reaction mixture, and then 15 ml of water and 0.38 g of active carbon were added. The insolubles were filtered off and the filter cake was washed with 11 ml of water. The filtrate and the washing were joined, the pH of the joined solution was adjusted to 9.2 with ammonia water, and 15 ml of acetone and 7.5 ml of toluene were added to the solution, followed by dropwise addition of 7.71 g of dicyclohexylamine. Then 15 ml of water was added dropwise, the solution was cooled to 5°C, and the precipitate was filtered and collected to give 9.68 g of dicyclohexylamine salt of 6-fluoro-3-hydroxy-2-pyrazinecarbonitrile as a slightly yellowish white solid product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | 10.0 mL of toluene and a sodium hydroxide aqueous solution (prepared by dissolving 0.656 g of sodium hydroxide in 20.0 mL of water) were added to 5.00 g (15.6 mmol) of dicyclohexylamine salt of T-705A, and the obtained mixture was then stirred at room temperature for 30 minutes. The reaction solution was left at rest for 10 minutes, and an upper layer was then removed. 10.0 mL of toluene was added to a lower layer, and it was then stirred and left at rest for 10 minutes. Thereafter, an upper layer was removed. A sodium hydroxide aqueous solution (prepared by dissolving 0.593 g of sodium hydroxide in 5.00 mL of water) was added to a lower layer. Subsequently, while keeping the internal temperature at 15 to 20 C., 2.68 mL (31.5 mmol) of 40.0% v/w hydrogen peroxide was added dropwise to the mixture. The obtained mixture was stirred at 25 C. for 30 minutes, and the pH of the solution was adjusted to pH 6.5 to 8.0 by hydrochloric acid. Thereafter, the mixture was heated to 40 C., so that the solid was completely dissolved in the solution. Thereafter, 0.250 g of activated carbon (SHIRASAGI A) was added to the reaction solution, and the obtained mixture was then stirred at 40 C. for 30 minutes, followed by filtration. A solid on a Nutsche was washed with 5.00 mL of water, and hydrochloric acid was then added to a mixed solution of a filtrate and a washing solution at an internal temperature of 35 to 45 C., so that the pH thereof was adjusted to pH 3 to 4. The mixed solution was cooled to 0 to 5 C., and it was then stirred for 1 hour. Thereafter, the precipitated solid was filtrated, and it was then washed with 5.00 mL of water and 5.00 mL of isopropyl alcohol, so as to obtain 2.06 g of a white solid (T-705). Yield: 84.0% | |
300 ml of toluene was added to a 600 ml water solution of 37.5 g of sodium hydroxide. Then 150 g of dicyclohexylamine salt of 6-fluoro-3-hydroxy-2-pyrazinecarbonitrile was added at 15 to 25C and the solution was stirred at the same temperature for 30 minutes. The water layer was separated and washed with toluene, and then 150 ml of water was added, followed by dropwise addition of 106 g of a 30% hydrogen peroxide solution at 15 to 30C and one-hour stirring at 20 to 30C. Then 39 ml of hydrochloric acid was added, the seed crystals were added at 40 to 50C, and 39 ml of hydrochloric acid was further added dropwise at the same temperature. The solution was cooled to 10C the precipitate was filtered and collected to give 65.6 g of 6-fluoro-3-hydroxy-2-pyrazinecarboxamide as a slightly yellowish white solid. 1H-NMR (DMSO-d6) delta values: 8.50 (1H, s), 8.51 (1H, d, J=7.8 Hz), 8.75 (1H, s), 13.41 (1H, s) |
A187524[ 356783-31-8 ]
6-Fluoro-3-oxo-3,4-dihydropyrazine-2-carbonitrile
Reason: Free-salt