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CAS No. : | 32587-10-3 | MDL No. : | MFCD03407446 |
Formula : | C5H6N4O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SFSMATGDLFHTHE-UHFFFAOYSA-N |
M.W : | 138.13 | Pubchem ID : | 280292 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 34.53 |
TPSA : | 94.89 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) : | -7.99 cm/s |
Log Po/w (iLOGP) : | 0.58 |
Log Po/w (XLOGP3) : | -1.2 |
Log Po/w (WLOGP) : | -0.83 |
Log Po/w (MLOGP) : | -1.82 |
Log Po/w (SILICOS-IT) : | -0.63 |
Consensus Log Po/w : | -0.78 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.32 |
Solubility : | 66.4 mg/ml ; 0.48 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.3 |
Solubility : | 69.4 mg/ml ; 0.503 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.85 |
Solubility : | 19.3 mg/ml ; 0.14 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.74 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
56% | Stage #1: With trichlorophosphate In N,N-dimethyl-formamide at 20 - 80℃; for 0.25 h; Stage #2: With sodium hydroxide; water In N,N-dimethyl-formamide Stage #3: at 70℃; for 0.5 h; |
EXAMPLE 3 Synthesis of 3-Aminopyrazine-2-carbonitrile (Intermediate 2) To a solution of intermediate 1 (3.5 g, 25 mmol) in DMF (40 mL) at RT was added POCl3 (4.5 mL, 49 mmol) slowly. The resulting mixture was heated at 80° C. for 15 min and then cooled to RT. The mixture was poured into ice water and the mixture neutralized with 10percent NaOH solution. The resulting solid was filtered and redissolved in 5percent HCl. The solution was heated at 70° C. for 30 min and the resulting solid filtered. After thoroughly washed with water, the title compound was obtained as a brown solid (1.7 g, 56percent). 1H NMR (500 MHz, DMSO-d6): δ 8.28 (d, J=2.4 Hz, 1H), 7.90 (d, J=2.4 Hz, 1H), 7.32 (br s, 2H). MS (ES+): m/z 121 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.6% | at 20℃; for 10 h; | In fitted with magnetic stirring and reflux condensation tube (with drying tail pipe) 250 ml three-necked bottle are respectively added with a 3 - amino pyrazine -2 - carboxylic acid methyl ester 15.4g (about 0.1 µM), 120 ml of concentrated ammonia water, stirring at room temperature under the condition of 10h, filtering, washing, 60 °C drying, be 12.5g yellow solid that 3 - amino pyrazine -2 - formamide. Yield: 90.6 |
82% | With ammonia In water at 60℃; for 3 h; | EXAMPLE 2 Synthesis of 3-Aminopyrazine-2-carboxamide (Intermediate 1) A solution of 3-amino-pyrazine-2-carboxylic acid methyl ester (5.0 g, 33 mmol) in concentrated ammonium hydroxide solution (30 mL) was heated at 60° C. for 3 h. The mixture was cooled to RT and the resulting solid filtered. After thoroughly washed with water followed by ether, the title compound was obtained as a brown solid (3.7 g, 82percent). 1H NMR (500 MHz, DMSO-d6): δ 8.19 (d, J=2.4 Hz, 1H), 8.07 (br s, 2H), 7.80 (d, J=2.4 Hz, 1H), 7.59 (br s, 2H). MS (ES+): m/z 139 (M+H)+. |
12 g | at 20℃; for 22 h; | Added 17 g of 3-aminopyrazine-2-carboxylic acid methyl ester to 300 ml of ammonia water and stir at room temperature for 22 hours. Add ethyl acetate to extract and separate the organic phase. Collect the organic phase, dry, and concentrate to obtain 12 g of 3-aminopyrazine-2-one. Formamide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10 g | for 3 h; Reflux | 12 g of 3-aminopyrazine-2-carboxamide was added to 150 ml of acetic acid, 19 g of bromoform was slowly added, and the mixture was heated under reflux and stirred for 3 hours. The mixture was concentrated, water and ethyl acetate were added for extraction, concentrated, and the residue was applied to a silica gel column. 10 g of 3-amino-6-bromopyrazine-2-carboxamide was isolated. |
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