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CAS No. : | 915394-28-4 | MDL No. : | MFCD11036617 |
Formula : | C10H10N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FYRQAESAYXPEBZ-UHFFFAOYSA-N |
M.W : | 190.20 | Pubchem ID : | 15541324 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 54.28 |
TPSA : | 69.61 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.81 cm/s |
Log Po/w (iLOGP) : | 1.53 |
Log Po/w (XLOGP3) : | 2.32 |
Log Po/w (WLOGP) : | 2.4 |
Log Po/w (MLOGP) : | 1.21 |
Log Po/w (SILICOS-IT) : | 0.35 |
Consensus Log Po/w : | 1.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.67 |
Solubility : | 0.41 mg/ml ; 0.00216 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.42 |
Solubility : | 0.0722 mg/ml ; 0.00038 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.69 |
Solubility : | 0.388 mg/ml ; 0.00204 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.84 |
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 |
---|---|---|
43% | With sodium hydride In tetrahydrofuran at 0℃; | To an ice-cold slurry of 50percent sodium hydride (2.17g, 90.4mmol) in anhydrous THF (15ml), was slowly added a solution of (3-nitro-phenyl)-acetonitrile (2.2g, 13.58mmol) in anhydrous THF (5ml). After 30 min, methyl iodide (6.67ml, 107mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred overnight. It was then quenched with ice- water. The compound was then extracted with ethyl acetate, the organic layer separated and washed with water, dried over anhydrous sodium sulphate, filtered and concentrated to oil. Column chromatography over silica gel by eluting with ethyl acetate/pet ether (5:95) gave 2-methyl-2-(3-nitrophenyl)- propionitrile (1. Ig, 43percent) as a solid. |
30% | With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 16 h; Inert atmosphere | To a solution of 3 (400.0 mg, 2.47 mmol) in anhydrous THF (5 mL) was slowly added a suspension of 60percent sodium hydride in mineral oil (641.4 mg, 16.03 mmol) in anhydrous THF (4.2 mL) under argon at 0 °C. Methyl iodide (1.23 mL, 19.74 mmol) was added to the mixture. The temperature was allowed to rise to room temperature and stirred for 16 h. After being quenched by the addition of water, the aqueous layer was extracted with EtOAc (2 × 15 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 5:95 to 10:90) to afford 4 (141.3 mg, 30percent) as a brown solid; 1H NMR (CDCl3, 400 MHz) 8.31 (1 H, t, J = 2.3 Hz), 8.21–8.19 (1 H, m), 7.90–7.87 (1 H, m), 7.61 (1 H, t, J = 7.8 Hz), 1.79 (6 H, s); 13C NMR (CDCl3, 100 MHz) 148.5, 143.5, 131.6, 130.1, 123.3, 123.0, 120.1, 37.1, 28.9. |
23% | Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.5 h; Stage #2: at 20℃; for 12 h; |
NaH (4.34 g, 90.4 mmol) was stirred in a solvent of tetrahydrofuran (20 mL) at 0°C. The reaction solution was slowly added with 2-(3-nitrophenyl)acetonitrile (2.2 g, 13.6 mmol), and stirred for about 30 minutes at 0°C. The reaction solution was added with MeI (6.67 mL, 107 mmol), followed by stirring for about 12 hours at room temperature. The reaction mixture was added with an ice water. The organic layer was separated out and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography (EA:HEX = 1:9) to obtain the title compound (0.6 g, 23 percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 8.33 (s, 1H), 8.22 (d, 1H), 7.91 (d, 1H), 7.65 (t, 1H), 1.81 (s, 6H). MS (ESI+, m/z): 191 [M+H]+ |
23% | Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.5 h; Stage #2: at 20℃; for 12 h; |
NaH (4.34 g, 90.4 mmol) was stirred in a solvent of tetrahydrofuran (20 mL) at 0° C. The reaction solution was slowly added with 2-(3-nitrophenyl)acetonitrile (2.2 g, 13.6 mmol), and stirred for about 30 minutes at 0° C. The reaction solution was added with MeI (6.67 mL, 107 mmol), followed by stirring for about 12 hours at room temperature. The reaction mixture was added with an ice water. The organic layer was separated out and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography (EA:HEX=1:9) to obtain the title compound (0.6 g, 23percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 8.33 (s, 1H), 8.22 (d, 1H), 7.91 (d, 1H), 7.65 (t, 1H), 1.81 (s, 6H). MS (ESI+, m/z): 191 [M+H]+ |
2.1 g | Stage #1: With sodium hydride In tetrahydrofuran for 0.5 h; Cooling with ice Stage #2: at 20℃; |
To an ice-cold slurry of 50 percent NaH (6.84 g, 171 mmol) in anhydrous THF (30.0 ml) was slowly added a solution of 2-(3-nitrophenyl) acetonitrile (4.2 g, 25.9 mmol) in anhydrous THF (30 ml). After 30 min, methyl iodide ( 12.63 ml, 202 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred overnight. It was then quenched with ice-water. The reaction mixture was then extracted with ethyl acetate, the organic layer was separated and washed with water, dried over anhydrous sodium sulphate; filtered and concentrated to get crude oil. The crude oil was purified by column chromatography over silica gel by eluting with ethyl acetate/ hexane (5:95) gave 2-methyl-2-(3-nitro phenyl) propanenitrile (2.1 g). iHNMR (400 MHz, CDC13), 8 8.33-8.32 (m, IH), 8.24-8.21 (m, IH), 7.92-7.89 (m, IH), 7.63 (t, J= 8.00 Hz, IH), 1.82(s, 6H).GCMS: 190.11 [M+] |
2.1 g | Stage #1: With sodium hydride In tetrahydrofuran; mineral oil for 0.5 h; Cooling with ice Stage #2: at 22 - 26℃; Cooling with ice |
Step a: Synthesis of 2-methyl-2-(3-nitrophenyl)propanenitrile To an ice-cold slurry of 50percent NaH (6.84 g, 171 mmol) in anhydrous THF (30.0 ml) was slowly added a solution of 2-(3-nitrophenyl)acetonitrile (4.2 g, 25.9 mmol) in anhydrous THF (30 ml). After 30 min, methyl iodide (12.63 ml, 202 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred overnight. It was then quenched with ice-water. The reaction mixture was then extracted with ethyl acetate, the organic layer was separated and washed with water, dried over anhydrous sodium sulphate; filtered and concentrated to get crude oil. The crude oil was purified by column chromatography over silica gel by eluting with ethyl acetate/hexane (5:95) gave 2-methyl-2-(3-nitrophenyl) propanenitrile (2.1 g). 1HNMR (400 MHz, CDCl3), δ 8.33-8.32 (m, 1H), 8.24-8.21 (m, 1H), 7.92-7.89 (m, 1H), 7.63 (t, J=8.00 Hz, 1H), 1.82 (s, 6H). GCMS:190.11[M+] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With palladium on activated charcoal; hydrogen In methanol at 20℃; for 2 h; | 2-Methyl-2-(3-nitrophenyl)propanenitrile (0.6 g, 3.15 mmol) obtained in Step (1) above was stirred in a solvent of methanol. The reaction solution was mixed with Pd/C (0.06 g, 0.56 mmol), followed by stirring under hydrogen conditions for about 2 hours at room temperature. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with methanol. The filtrate was concentrated under reduced pressure to obtain the title compound (0.48 g, 95 percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 7.06 (t, 1H), 6.71 (s, 1H), 6.61 (d, 1H), 6.52 (d, 1H), 5.21 (s, 2H), 1.61 (s, 6H). MS (ESI+, m/z): 161 [M+H]+ |
95% | With palladium on activated charcoal; hydrogen In methanol at 20℃; for 2 h; | 2-Methyl-2-(3-nitrophenyl)propanenitrile (0.6 g, 3.15 mmol) obtained in Step (1) above was stirred in a solvent of methanol. The reaction solution was mixed with Pd/C (0.06 g, 0.56 mmol), followed by stirring under hydrogen conditions for about 2 hours at room temperature. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with methanol. The filtrate was concentrated under reduced pressure to obtain the title compound (0.48 g, 95percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 7.06 (t, 1H), 6.71 (s, 1H), 6.61 (d, 1H), 6.52 (d, 1H), 5.21 (s, 2H), 1.61 (s, 6H). MS (ESI+, m/z): 161 [M+H]+ |
83% | With hydrogen In methanol | 2-Methyl-2-(3-nitrophenyl)-propionitrile (0.5g) was hydrogenated over 10percent Pd-C in methanol (10ml) at atmospheric pressure until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to oil. Column chromatography over silica gel by eluting with ethyl acetate/pet ether (1:9) gave 2-(3- amino-phenyl)-2-methyl-propionitrile (0.35g, 83percent) as an oil. |
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