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CAS No. : | 55321-99-8 | MDL No. : | MFCD00233977 |
Formula : | C5H5N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SZPBAPFUXAADQV-UHFFFAOYSA-N |
M.W : | 139.11 | Pubchem ID : | 294642 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 32.15 |
TPSA : | 89.1 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.49 cm/s |
Log Po/w (iLOGP) : | 0.4 |
Log Po/w (XLOGP3) : | -0.48 |
Log Po/w (WLOGP) : | -0.72 |
Log Po/w (MLOGP) : | -1.82 |
Log Po/w (SILICOS-IT) : | -0.39 |
Consensus Log Po/w : | -0.6 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.78 |
Solubility : | 23.2 mg/ml ; 0.167 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.92 |
Solubility : | 16.6 mg/ml ; 0.119 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.64 |
Solubility : | 31.9 mg/ml ; 0.23 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.77 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
79% | With N-ethyl-N,N-diisopropylamine; trichlorophosphate In chlorobenzene at 0 - 90℃; | At 0 , a solution of 3-hydroxy-2-carboxamide (5g, 37mmol) in chlorobenzene (20 mL) was added dropwise phosphorus oxychloride (2mL, 40mmol) and diisopropylethylamine (3.5mL, 80mmol), dropwise addition, the reaction mixture was stirred overnight at 90 placed.After the reaction, the reaction solution was concentrated under reduced pressure the reaction solution, the residue was diluted with 20mL water, (20mL x 3) and extracted with EtOAc, the combined organic phases were dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, the residue was purified by silica gel column chromatography ( eluant: PE / EtOAc (V / V) = 10/1) to give the title compound as a white solid (4.5g, 79percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With N-ethyl-N,N-diisopropylamine; trichlorophosphate In chlorobenzene at 0 - 90℃; | At 0 , a solution of 3-hydroxy-2-carboxamide (5g, 37mmol) in chlorobenzene (20 mL) was added phosphorus oxychloride (2mL, 40mmol)And diisopropylethylamine (3.5mL, 80mmol), dropwise addition, the reaction mixture was stirred overnight at 90 placed. After the reaction, the reaction solution under reduced pressureConcentrated, then diluted with 20mL of water was added, the resulting mixture was extracted with EtOAc (20mL x 3), the combined organic phases were dried over anhydrous sodium sulfate,Then filtered and concentrated under reduced pressure, and finally the residue was purified by silica gel column chromatography (eluent: PE / EtOAc (V / V) = 10/1) to give a white solidThe title compound (4.5g, 79percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: at 90℃; for 3 h; Stage #2: With ammonia; dihydrogen peroxide In water at 0 - 20℃; |
Diethylaminomalonate Aminomalondiamide 2-Carbamido-3-hydroxypynazine To an aqueous solution of diethylaminomalonate (hydrochloride form) was added sodium hydrogenocarbonate (pH> 7). After extraction, the organic phase was evaporated under reduced pressure and treated with an ammoniacal solution of methanol at 80°C overnight to give aminomalondiamide quantitatively. This compound was used for next step without purification and dissolved in water. To that solution was added glyoxal sodium bisulfite hemihydrate, this reaction mixture was stirred at 90°C for 3h, and then made basic with 58percent NH4OH. Then, 30percent H2O2 was added dropwise with rapid stirring to the cold solution (0°C) [J. Med. Chem. 1983, 26, 283-86, J. Heterocyclic Chem. 1979, 16, 193]. The reaction mixture was <n="131"/>allowed to warm at room temperature and the desired 2-hydroxy-3- carboxamidopyrazine precipitated. The solid was collected (63percent yield) and part of it recrystallized. |
118 g | With phosphoric acid; sodium hydroxide In water at 20 - 30℃; for 1.5 h; | 13.7 g of sodium hydroxide, 19.7 g of 85percent phosphoric acid and 600 mL of water were mixed to obtain a phosphate buffer solution. 100 g of aminomalonamide was added to this phosphate buffer solution and a solution of 34.2 g of sodium hydroxide in 105 mL of water and 130 g of 40percent glyoxal aqueous solution were simultaneously added dropwise at 20 to 30 ° C. over 1 hour and stirred at the same temperature for 30 minutes . Concentrated hydrochloric acid (25 mL) was added to the reaction mixture, heated to 85 ° C., concentrated hydrochloric acid (60 mL) was added, and the mixture was cooled to 15 ° C. The solid was collected by filtration to obtain 118 g of 3-hydroxy-2-pyrazinecarboxamide as a brown solid. |
118 mg | With phosphoric acid; sodium hydroxide In aq. phosphate buffer; water at 20 - 30℃; for 1.5 h; | The Example was performed according to the method in Example 1 of JP 2010-24 1806 A. To obtain a phosphate buffer, 13.7 g of sodium hydroxide, 19.7 g of 85percent phosphoric acid and 600 mL of water were mixed. To the phosphate buffer was added 100 g of aminomalonamide, and a solution of 34.2 g of sodium hydroxide in 105 mL of water and 130 g of a 40percent aqueous glyoxal solution were simultaneously added at 20 to 30° C. over 1 hour, and the reaction mixture was stirred at that temperature for 30 minutes. To the reaction mixture was added 25 mL of concentrated hydrochloric acid, and the reaction mixture was heated to 85° C., and then 60 mL of concentrated hydrochloric acid was added, and the reaction mixture was cooled to 15° C. A solid was collected by filtration to obtain 118 g of 3-hydroxy-2-pyrazinecarboxam- ide (compound C) as a brown solid. The resulting compound C was a hydrate. Water content: 8.5percent ‘H-NMR (DMSO-d5) ö: 7.88-8.10 (3H, m), 8.69 (1H, s). The infrared absorption spectrum is illustrated inFIG. 9. The powder X-ray diffraction pattern is illustrated in FIG. 10 and the results are shown in Table 4. |
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