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CAS No. : | 1023813-21-9 | MDL No. : | MFCD09881212 |
Formula : | C5H3Cl2N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZEJGTWZTXZLSLR-UHFFFAOYSA-N |
M.W : | 192.00 | Pubchem ID : | 33726600 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 40.15 |
TPSA : | 68.87 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) : | -6.83 cm/s |
Log Po/w (iLOGP) : | 0.82 |
Log Po/w (XLOGP3) : | 0.91 |
Log Po/w (WLOGP) : | 0.88 |
Log Po/w (MLOGP) : | -0.39 |
Log Po/w (SILICOS-IT) : | 1.4 |
Consensus Log Po/w : | 0.73 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.94 |
Solubility : | 2.2 mg/ml ; 0.0114 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.94 |
Solubility : | 2.2 mg/ml ; 0.0114 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.48 |
Solubility : | 0.64 mg/ml ; 0.00333 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.99 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H317-H319 | 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 |
---|---|---|
Stage #1: 2-hydroxy-5-bromopyrazine With trichlorophosphate at 60℃; for 2h; Stage #2: formamide With dipotassium peroxodisulfate; iron In water at 80 - 85℃; | 2.1; 2.2 (1) Preparation of mixture of 2,5-dichloropyrazine and 2-chloro-5-bromopyrazine Add 50 grams of 2-hydroxypyrazine to 250 milliliters of N,N-dimethyl sulfoxide, reduce the temperature to 10-12°C, add 74 grams of dibromohydantoin in batches, and after holding for 1 hour, add 500 milliliters of water to precipitate a large amount The yellow solid was filtered and dried to obtain 80.1 g of 2-hydroxy-5-bromopyrazine. Add 2-hydroxy-5-bromopyrazine to 341 grams of phosphorus oxychloride and heat up to 60°C for 2 hours, pour it into 800 grams of ice-water mixture, filter, 350 ml of isopropyl acetate, extract and concentrate to obtain 72 Grams of dark brown oil is a mixture of 2,5-dichloropyrazine and 2-chloro-5-bromopyrazine. The total yield of the two steps is about 79%. (2) Preparation of mixture of 3,6-dichloro-2-amidopyrazine and 6-bromo-3-chloro-2-amidopyrazine 350 grams of a mixture of 2,5-dichloropyrazine and 2-chloro-5-bromopyrazine (the mass ratio is about 4:3), add 1.5 liters of water, and add 950 grams of potassium persulfate in batches at room temperature. 2 grams of iron, slowly increase the temperature to 80°C, add 52 grams of formamide dropwise, add dropwise for about 15 minutes, the temperature does not exceed 85°C, keep for about 1.5 hours, cool down to 25°C and keep for 1 hour, filter with suction, 300 ml of water , 300 ml of methanol to wash the filter cake, vacuum drying to obtain 323 g of yellow powder, which is a mixture of 3,6-dichloro-2-amidopyrazine and 6-bromo-3-chloro-2-amidopyrazine (yield 72-76%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium peroxodisulfate at 80℃; for 12h; | 4 Embodiment 4: the preparation method of 3,6-dichloropyrazine-2-carboxamide Take 2,5-dichloropyrazine (1.48g, 1.0equiv.),Formamide (5mL, 12.6equiv.) in the reaction flask,Then add potassium persulfate (5.4g, 2.0equiv.),Stir at 80°C for 12 hours,Saturated sodium bicarbonate solution was added to quench, extracted with ethyl acetate, dried over anhydrous sodium sulfate,Filter, concentrate the aqueous phase under reduced pressure to remove all the solvent, pass through the column,The solid product compound 4 was obtained (1.44 g, 75%). |
72% | With iron(II) sulfide; potassium peroxodisulfate In lithium hydroxide monohydrate at 80 - 85℃; | 1.1 (1) Preparation of 3,6-dichloro-2-amide pyrazine Add 3 grams of 2,5-dichloropyrazine to 20 ml of water, add 10.4 grams of potassium persulfate and 0.2 grams of ferrous sulfide in batches at room temperature, slowly increase the temperature to 80°C, and add 5 grams of formamide dropwise at 80-85°C. After the addition, keep it warm for 1 hour, cool to 30°C, stir for half an hour, and filter with suction. The filter cake is washed with 10 ml of water, 5 ml of methanol, and dried under vacuum to obtain 2.8 g of light yellow product (yield 72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 75 °C 2: potassium fluoride / dimethyl sulfoxide / 60 - 90 °C / Large scale |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 75 °C 2: potassium fluoride / dimethyl sulfoxide / 60 - 90 °C / Large scale 3: sodium acetate; water / dimethyl sulfoxide / 4 h / 5 - 45 °C / Large scale |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: 3,6-dichloropyrazine-2-carboxamide With caesium fluoride In <i>tert</i>-butyl alcohol at 90℃; Stage #2: With Sodium hydrogenocarbonate In lithium hydroxide monohydrate; <i>tert</i>-butyl alcohol at 60℃; | 10 Example 10: One-pot preparation of favipiravir Take 3,6-dichloropyrazine-2-carboxamide (1.92 g, 1.0 equiv.),Cesium fluoride (9.0g, 6equiv.) was placed in a 50mL Teflon reaction flask,Add tert-butanol (15mL)Heat and stir at 90°C.TLC spot plate to monitor the reaction, after the reaction is complete,Add sodium bicarbonate (4.2 g, 5.0 equiv.) and water (15.0 mL) to the reaction flask and heat to 60°C.The reaction was monitored by TLC dot plate. After the reaction was complete, 2M HCl was added dropwise to adjust the pH to 3-4, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to remove all the solvent, and recrystallized.The product favipiravir (1.04 g, 66%) was obtained. |
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 75 °C 2: potassium fluoride / (methylsulfinyl)methane / 60 - 90 °C / Large scale 3: anhydrous Sodium acetate; lithium hydroxide monohydrate / (methylsulfinyl)methane / 4 h / 5 - 45 °C / Large scale 4: sodium hydroxide / lithium hydroxide monohydrate / 5.5 h / 5 - 45 °C / Large scale |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With N-ethyl-N,N-diisopropylamine; trichlorophosphate at 75℃; for 1h; | 1.2 (2) Preparation of compound 3 Add 1.9 g of the product 3,6-dichloro-2-amide pyrazine obtained in step 1 to 9.4 ml of phosphorus oxychloride, and add 3.9 g of diisopropylethylamine dropwise to the temperature to 75°C, keep it for 1 hour, HPLC shows The reaction of the raw materials is complete, the temperature is lowered and poured into 50 ml of ice water, filtered, and 10 ml of ethanol is recrystallized to obtain 1.5 g of a pale yellow powder product, which is compound 3 (yield 82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With caesium fluoride In <i>tert</i>-butyl alcohol at 90℃; | 6-8 Example 6: Preparation of 3,6-difluoropyrazine-2-carboxamide using cesium fluoride Take 3,6-dichloropyrazine-2-carboxamide (192 mg, 1.0 equiv.) andCesium Fluoride (900mg, 6equiv.)was added to tert-butanol (3.0 mL),Heat and stir at 90°C.The reaction was monitored by TLC dot plate. After the reaction was completed, water was added to quench, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to remove all solvent, and passed through column to obtain solid product compound 3 (105 mg, 66%). |
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