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CAS No. : | 100367-55-3 | MDL No. : | MFCD07368184 |
Formula : | C6H3N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YZDHDHMJKCKESU-UHFFFAOYSA-N |
M.W : | 149.11 | Pubchem ID : | 10261236 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 37.77 |
TPSA : | 82.5 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) : | -6.46 cm/s |
Log Po/w (iLOGP) : | 0.73 |
Log Po/w (XLOGP3) : | 1.05 |
Log Po/w (WLOGP) : | 0.86 |
Log Po/w (MLOGP) : | -1.32 |
Log Po/w (SILICOS-IT) : | -0.82 |
Consensus Log Po/w : | 0.1 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.76 |
Solubility : | 2.57 mg/ml ; 0.0172 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.37 |
Solubility : | 0.631 mg/ml ; 0.00423 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.47 |
Solubility : | 5.02 mg/ml ; 0.0337 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.11 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
90.8% | for 16 h; Reflux | A mixture of 2-bromo-5-nitropyridine (12.0 g, 59.1 mmol, CAS No.: 4487-59-6) and copper (I) cyanide (7.94 g, 88.7 mmol) in N,N-dimethylformamide (50 mL) was heated under reflux for 16 hours. After being cooled down to room temperature, the reaction mixture was poured into water and then extracted with ethyl acetate (100 mL x 3). The combined organiclayer was washed with brine, and then dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford 8.0 g of 5-nitropyridine-2-carbonitrile (yield was 90.8percent). |
40% | at 100℃; for 2 h; | Step A: 5-Nitropicolinonitrile (20) [00383] A mixture of 2-bromo-5-nitropyridine (19) (10 g, 50 mmol) and CuCN (8.9 g, 100 mmol) in DMF (25 mL) was stirred at 100°C for 2 h. The reaction mixture was then cooled to room temperature and diluted with DCM (200 mL). Solid was filtered; the filtrated was then concentrated and purified by silica gel column chromatography with petroleum ether/ ethyl acetate (3 : 1) to give the product (3 g, 40percent) as a yellow solid. LC-MS: (M + H)+ 150.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | at 100 - 150℃; for 2.08333 h; | Synthesis of compound E; Copper cyanide (I) (662 mg, 7.34 mmol) and sodium cyanide (I) (242 mg, 4.93 mmol) were dissolved in N,N-dimethylformamide (7.5 ml), and the solution was stirred at 150°C for 25 minutes. A solution of 2-bromo-5-nitropyridine (113 mg, 0.700 mmol) completely dissolved in N,N-dimethylformamide (2.5 ml) at 100°C was added to the solution, and the mixture was stirred with heating at 150°C for 100 minutes. The completion of the reaction was confirmed using a TLC plate (ethyl acetate:hexane = 1:3), and the reaction was terminated with 10 ml of an aqueous solution of 1 M monopotassium phosphate, followed by extraction with ethyl acetate (50 ml .x. 3). The ethyl acetate layer was washed with water (100 ml) and with saturated saline (100 ml). The resultant was dried over magnesium sulfate and filtered, followed by removal of a solvent by distillation under reduced pressure. The product was separated via flash column chromatography (ethyl acetate:hexane = 1:7 --> 1:3) to obtain a yellow, oil-like target compound E (624 mg, 4.19 mmol). Yield: 85percent 1H-NMR (300 MHz, CDCl3) δ: 9.54 (dd, 1H, J = 2.5, 0.7 Hz, Py-H), 8.68 (dd, 1H, J = 8.4, 2.5 Hz, Py-H), 7.98 (dd, 1H, J = 8.4, 0.7 Hz, Py-H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1935 g | at 80 - 160℃; for 5.5 h; | 1) first equipped with a mechanical stirrer 30L glass reactor was added 7616mL dimethylformamide and612.8gNaCN and 1680gCuCN configured as a cyanide solution,The oil bath was then heated to 142 ° C,Continue to cyanide solution was added at a temperature of 80 ° C,A solution of 2-bromo-5-nitropyridine in dimethylformamide,Among them, 2-bromo-5-nitropyridine and dimethylformamide were 2538.6g and 5077mL respectively,And add within 5min,After adding at 160 reaction temperature, the reaction was 5.5h.2) After the reaction is completed, the temperature is lowered to 125 DEG C, 5757.5g of KH2PO4 buffer consisting of KH2PO4 and 42.2L of water are added,Keep the temperature of the mixture at 80 ~ 85 ° C for 1 h and cool to room temperature.3) The reaction mixture in step 2) was filtered, and the filtrate and filter cake were separated: the filtrate was extracted with 10 L of ethyl acrylate 3Times; the same filter cake was filtered after beating with ethyl acrylate, the two combined organic phase, and concentrated to 20L with KH2PO4 slowThe solution was washed sequentially with 14 L of water; the washed buffer and the aqueous layer were extracted twice more with 5 L of ethyl acrylate, and the combined organic phases were concentratedThe yield was 1935 g of 2-cyano-5-nitropyridine as an orange solid with a purity of 97percent and a yield of 103.8percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.3% | With carbamic Acid; palladium 10% on activated carbon In methanol for 16 h; Reflux | To a solution of 5-nitropyridine-2-carbonitrile (7.0 g, 46.9 mmol) in methanol (150 mL) was added 10percent palladium on carbon (2.0 g) and carbamic acid (7.0 g, 115 mmol). After being heated under reflux for 16 hours, the resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in water (150 mL) and the resulting mixture was extracted with ethyl acetate (150 mL x 3). The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 5.1 g of 5-aminopyridine-2-carbonitrile (yield was 9 1.3percent). |
85.3% | With iron; acetic acid In ethyl acetate at 81 - 89℃; for 5.16667 h; | 4) 1864.7 g of reduced Fe powder was added to 16780 g of ethyl acetate and 1864.7 g of 2-cyano-5-nitropyridine,Oil bath heated to 81 began to drop 8299g of acetic acid, acetic acid was added dropwise to maintain a steady reflux, with the dropping of reflux temperature byGradually rise to 89 , and the need to be added within 310min was completed; after completion of the dropwise addition at 81 reaction temperature incubated for 5h.5) The reaction solution obtained in step 4) was filtered while hot at 65 ° C, the filtrate, the filter cake separately treated, wherein the filtrate withNaOH temperature was controlled at 5 ~ 10 , pH adjusted to 8.5, with ethyl acrylate back to the aqueous phase; to the filter cake was added the amount of propyleneEthyl acetate and NaHSO3 aqueous solution, warmed to 60 ° C, stirred for 15min and filtered, again with ethyl acrylate back to the aqueous phase; mergeThe organic phase obtained above was washed with saturated NaCl solution and then concentrated. Finally, 1270 g of tan solid B, 2-cyano-5-Aminopyridine, yield 85.3percent, purity 97percent. |
42% | With ammonium chloride; zinc In ethanol at 20℃; for 2 h; | Step B: 5-Aminopicolinonitrile (21) [00384] A mixture of 5-nitropicolinonitrile (20, step A) (3 g, 20 mmol), Zn (6.5 g, 100 mmol) and H4C1 (10 g, 185 mmol) in EtOH (40 mL) was stirred for at room temperature for 2 h. The reaction was diluted with DCM (150 mL) and filtered; filtrate was concentrated and purified by silica gel column chromatography with petroleum ether/ ethyl acetate (3 : 1) to give the product (1 g, 42percent) as a yellow solid. LC-MS: (M + H)+ 120.0 |
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