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CAS No. : | 1721-23-9 | MDL No. : | MFCD06254420 |
Formula : | C7H6N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UBKKNWJGYLSDSJ-UHFFFAOYSA-N |
M.W : | 118.14 | Pubchem ID : | 4738308 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 33.92 |
TPSA : | 36.68 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.33 cm/s |
Log Po/w (iLOGP) : | 1.44 |
Log Po/w (XLOGP3) : | 0.97 |
Log Po/w (WLOGP) : | 1.26 |
Log Po/w (MLOGP) : | 0.13 |
Log Po/w (SILICOS-IT) : | 1.78 |
Consensus Log Po/w : | 1.12 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.68 |
Solubility : | 2.49 mg/ml ; 0.021 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.33 |
Solubility : | 5.55 mg/ml ; 0.047 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.45 |
Solubility : | 0.423 mg/ml ; 0.00358 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
81% | With 5%-palladium/activated carbon; ammonium formate In methanol at 23℃; for 12 h; | 2-Methylnicotinonitrile (133) 6-Chloro-2-methylnicotinonitrile (132, 10 g, 66 mmol) and ammonium formate (41 g, 0.65 mol) were dissolved in methanol (250 mL), and palladium (5percent on activated carbon, 3.5 g, 2.5 mol percent) was added. The mixture was stirred at room temperature for 12 h, filtered through Celite, and washed with methanol (3*50 mL). The combined filtrates were evaporated, and the yellow oily residue was subjected to flash column chromatography on silica gel, eluting with chloroform to provide 133 as an off-white solid (6.3 g, 81percent): mp 55° C. (lit. (J. Med. Chem. 2000, 43, 3168-3185) mp 56-58° C.). 1H NMR (300 MHz, CDCl3) δ 7.80 (dd, J=4.9, 1.6 Hz, 1H), 7.02 (dd, J=7.8, 1.7 Hz, 1H), 6.37 (dd, J=7.8, 5.0 Hz, 1H), 1.88 (s, 3H); positive ion ESIMS m/z (rel intensity): 119 (MH+, 100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With isocyanuric acid In N,N-dimethyl-formamide at 0℃; for 2.5 h; | 30) 2-methyl-nicotinonitrileCyanuric acid (418 mg, 2.2 mmol) was added in one portion to a suspension of 2-methylnicotinamide (intermediate 29) (613 mg, 4.5 mmol) in 2.5 ml of DMF cooled in ice. The 0 reaction was stirred for 2.5 hours then poured into ice. The reaction was extracted with ethyl acetate until the organic layer no longer contained product. The combined organic layers, were dried over Na2SO4, filtered and concentrated. Purified on normal phase chromatography with ethyl acetate/heptane 0 to 50 gradient then 50/50 EA/heptane. Yield (216 mg, 41 percent). IH NMR (400 MHz, CHLOROFORM-D) δ ppm 2.78 (s, 3 H), 7.25 (dd, s J=7.71, 4.98 Hz, 1 H), 7.89 (dd, J=7.81, 1.56 Hz5 1 H), 8.68 (s, 1 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 175℃; for 2 h; Microwave irradiation; Inert atmosphere | 3-Bromo-2-methylpyridine (344 mg, 2 mmol), Zn(CN)2 (235 mg, 2 mmol) and Pd(PPh3)4 (75 mg, 0.06 mmol) were dissolved in DMF (5 mL). The mixture was vacuumed for N2 three times, The reaction solution was reacted in the microwave (175° C.) for 2 h under N 2 protection. After cooling, it was diluted with EtOAc (60 mL). After washing with saturated saline, dry over anhydrous sodium sulfate. Concentration by filtration and column chromatography of the residue provided the title compound as a white solid (212 mg, yield 90percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With trifluoroacetic anhydride In dichloromethane; water; triethylamine | Step 2 Preparation of 3-cyano-2-methylpyridine: To a suspension of 2-methylnicotinamide from step 1 (11.1 g, 0.081 mol) in triethylamine (24.8 g, 0.243 mol) and 400 mL of methylene chloride was added trifluoroacetic anhydride (21.0 g, 0.100 mol) rapidly at 0° C. The reaction was complete after a few minutes at this temperature. Water was added and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with water, brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1) to give 7.2 g of 3-cyano-2methylpyridine as a pale yellow solid (75percent): mp(DSC) 56°-58° C. |
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