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CAS No. : | 769-28-8 | MDL No. : | MFCD00006269 |
Formula : | C8H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OCYMJCILWYHKAU-UHFFFAOYSA-N |
M.W : | 148.16 | Pubchem ID : | 69856 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 41.71 |
TPSA : | 56.65 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) : | -6.91 cm/s |
Log Po/w (iLOGP) : | 1.51 |
Log Po/w (XLOGP3) : | 0.42 |
Log Po/w (WLOGP) : | 0.86 |
Log Po/w (MLOGP) : | 0.31 |
Log Po/w (SILICOS-IT) : | 2.35 |
Consensus Log Po/w : | 1.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.43 |
Solubility : | 5.54 mg/ml ; 0.0374 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.18 |
Solubility : | 9.86 mg/ml ; 0.0666 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.77 |
Solubility : | 0.25 mg/ml ; 0.00169 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.83 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-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 |
---|---|---|
94% | Stage #1: at 120℃; Stage #2: at 0℃; for 0.5 h; Stage #3: With sodium hydrogencarbonate In water |
Example 6 3-(5-_ELhLI-2,4-dimgLhyl-6-oxo-1,6-dihydroMidin-3-yl)benzonitrile Step 1: 2-Chloro-3-cyano-4,6-dimethylpyridine: A stirred mixture of 3-cyano-4,6-dimethyl- 2-hydroxypyridine (4.35 g, 29.39 mmol) and phosphorous pentachloride (6.92 g, 33.21 mmol) is heated to 120°C. The reaction mixture becomes clear and is stirred for an additional 1 hr. It is then poured onto ice/water (250 mL) and allowed to stand for 30 min. The solution is neutralized with sodium bicarbonate (pH 6) and extracted with dichloromethane (400 mL). The separated organic layer is dried, filtered and concentrated to yield 2-chloro-3-cyano-4,6- dimethylpyridine (4.60 g, 94percent yield) as a tan solid containing ca 15percent impurity. LC/MS: MS m/e = 167/169 (M + H) ; RT 2.98 min; NMR (CDCl3, 8 ppm) 7.08 (1H, s), 2.57 (3H, s), 2.55 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | for 2 h; Heating / reflux | 2-Chloro-4, 6-dimethylnicotinonitrile4,6-Dimethyl-2-oxo-l,2-dihydropyridine-3-carbonitrile (5g, 34mmol) was added to phosphorus oxychloride (20ml). The reaction was stirred at reflux for 2 h, after which it was seen complete. Volatiles were removed and the residue triturated with petrol.The resultant solid was filtered off and washed with hexane,and dried to give a pure white solid (5.1g, 90percent). δH (250 MHz, CDCl3) 2.55 (3 H, s, CH3), 2.57 (3 H, s, CH3),7.09 (1 H, s, ArH); δc ( 250 MHz, CDCl3) 162.64 (C), 154.39 (C), 152.26 (C), 123.22 (CH), 114.28 (C), 108.31 (C), 24.5 (CH3), 20.54 (CH3).; m/z 189 (M + Na) |
90% | for 2 h; Heating / reflux | 4,6-Dimethyl-2-oxo-l,2-dihydropyridine-3-carbonitrile '(5g, 34mmol) was added to phosphorus oxychloride (20ml). The reaction was stirred at reflux for 2 h, after which it was seen complete. Volatiles were removed and the residue triturated with petrol. The resultant solid was filtered off and washed with hexane,and dried to give a pure white solid (5.1g, 90percent). δH (250 MHz, CDCl3) 2.55 (3 H, s, CH3), 2.57 (3 H, s, CH3), 7.09 (1 H, s, ArH); δc ( 250 MHz5 CDCl3) 162.64 (C), 154.39 (C), 152.26 (C), 123.22 (CH), 114.28 (C), 108.31 (C), 24.5 (CH3), 20.54 (CH3).; m/z 189 (M + Na) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With bromine In acetic acid at 20℃; for 0.5 h; | To a solution of 4,6-dimethyl-2-oxo-l,2-dihydropyridine-3-carbonitrile (35 g, 236 mmol) in Acetic Acid (200ml) was added bromine (41.5 g, 260 mmol). The reaction mixture stirred for about 30 min at ambient temperature. The reaction mixture was then concentrated to dryness under reduced pressure. The resulting resin precipitated from aqueous EtOH to obtain 5-bromo-4,6-dimethyl-2-oxo-l ,2- dihydropyridine-3-carbonitrile (70 g, 95percent). LCMS (Table 1, Method c) RT= 1.63 min.; MS m/z = 226, 228 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: With platinum(IV) oxide; palladium 10% on activated carbon; hydrogen; sodium acetate In acetic acid for 48 h; Stage #2: With hydrogenchloride In ethanol; water at 0℃; for 2 h; Inert atmosphere |
Palladium on carbon (10percent) (324mg) and platinum oxide (21.8mg) were added to a mixture of 4,6-dimethyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (3g, 20.3 mmol), sodium acetate (3.1g, 37.5 mmol) and acetic acid (100 mL), and the whole mixture was stirred under an atmosphere of H2 for 2 days. After the reaction mixture was filtered off via a celite pad, filtrate was concentrated to dryness, and the residue was treated with conc. HCl (3 mL) and EtOH (15 mL). The mixture was cooled to 0°C, and stirred at 0°C for 2h, resulting in a suspension. The precipitate was collected by suction filtration, and then washed with cold EtOH and ether, and vacuum-dried to give a white solid (3.5 g, 92percent yield); m.p. 253-258°C. 1H NMR (400 MHz, DMSO-d6): δ 2.16 (s, 3H), 2.22(s, 3H), 3.72-3.80 (m, 2H), 5.93-6.01 (m, 1H), 8.13 (s, 3H), 11.85 (s, 1H); 13C NMR (100 MHz, DMSO-d6): δ 17.9, 18.7, 35.6, 111.2, 115.6, 145.9, 155.0, 163.7; HRMS (ESI): m/z calcd. for C8H13N2O [M+H]+ 153.1022, found 153.1018. |
60% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2 h; | 3-(aminomethyl)-4,6-dimethylpyridin-2(lH)-one. To a solution of 4,6-dimethyl-2-oxo-l,2- dihydropyridine-3-carbonitrile (500 mg, 3.4 mmol) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (258 mg, 6.8 mmol) at 0°C. The mixture was stirred at 20°C for 2 hours. Then water (1 mL) was added and the product 3-(aminomethyl)-4,6-dimethylpyridin- 2(lH)-one was obtained as a white solid (300 mg, 60percent). 1H NMR (300 MHz, /-DMSO): δ 11.84 (s, 1H), 7.95 (s, 2H), 5.97 (s, 1H), 3.77 (s, 2H), 2.19 (s, 3H), 2.15 (s, 3H). |
60% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2 h; | To a solution of 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (500 mg, 3.4 mmol) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (258 mg, 6.8 mmol) at 0° C. The mixture was stirred at 20° C. for 2 hours. Then water (1 mL) was added and the product 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one was obtained as a white solid (300 mg, 60percent). 1H NMR (300 MHz, d6-DMSO): δ 11.84 (s, 1H), 7.95 (s, 2H), 5.97 (s, 1H), 3.77 (s, 2H), 2.19 (s, 3H), 2.15 (s, 3H). |
2.0 g | With ammonium hydroxide; hydrogen In methanol for 24 h; | Compound g 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (3 g, 1.0 eq) and an appropriate amount of Raney nickelAdd to methanol (50 ml), add saturated aqueous ammonia (25 ml), react under hydrogen for 24 hours, filter, and concentrate.Crystallization gave 2.0 g of product h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogenchloride; hydrogen; palladium(II) hydroxide In methanol; water at 20℃; for 26 h; Inert atmosphere | To a solution of 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (10.0 g, 67.5 mmol) in MeOH (1.50 L) and conc. HCl (30 mL) was added 10percent Pd(OH)2 (19 g) under N2 atmosphere. The N2 gas was displaced by H2 gas and the mixture was stirred for 26 hours at RT under hydrogen atmosphere. The H2 gas was displaced by N2 gas. The mixture was filtered through Celite, washed with MeOH and concentrated. The residue was triturated with EtOH, collected with Buchner funnel, and dried under vacuum pressure to give the titled compound as a white solid (11.5 g, 90percent). 1H NMR (400 MHz, DMSO-d6): δ ppm 11.86 (brs, 1H), 5.98 (s, 1H), 3.78 (m, 2H), 2.20 (s, 3H), 2.16 (s, 3H). |
51 g | Stage #1: for 48 h; Stage #2: With hydrogenchloride In water |
Intermediate 83-(Aminomethyl)-4,6-dim pyridinone hydrochloridePalladium on carbon (10percent) (3.24 g) was charged into a 2L dry Parr bottle and a small amount of acetic acid was added. Next added 4,6-dimethyl-2-oxo-l,2-dihydro- pyridine- 3-carbonitrile (30 g , 202.7 mmol), sodium acetate (30.75 g, 375.0 mmol), platinum oxide (0.218 g), and acetic acid (1 L).. The bottle was capped, placed on Parr apparatus, and shaken under an atmosphere of H2 (100 psi) for 2 days. The reaction mixture was filtered.The solvent was removed to give a residue, which was treated with 150 mL of cone. HCl, and the formed solids were filtered. The yellow filtrate was concentrated . To the crude compound was added 30 mL of cone. HCl and 150 mL EtOH, the contents cooled to 0 °C, and stirred at 0 °C for 2h. The formed solids were filtered, washed with cold EtOH, ether, and dried. The product was collected as 36 g. This batch was combined with other batches prepared on smaller scales and triturated with ether to give 51 g of pure compound.. 1H NMR (400 MHz, DMSO- 6) ? ppm 11.85 (br s,l H) 8.13 (br s, 3 H) 5.93 - 6.01 (m, 1 H) 3.72 - 3.80 (m, 2 H) 2.22 (s, 3 H) 2.16 (s, 3 H). |
36g | With platinum(IV) oxide; palladium 10% on activated carbon; hydrogen; sodium acetate In acetic acid for 48 h; | Palladium on carbon (10percent) (3.24 g) was charged into a 2 L dry Parr bottle and asmall amount of acetic acid was added. Next added 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (30 g, 202.7 mmol), sodium acetate (30.75 g, 375.0 mmol),platinum oxide (0.218 g), and acetic acid (1 L) .. The bottle was capped, placed on Parrapparatus, and shaken under an atmosphere ofH2 (100 psi) for 2 days. The reaction mixture was filtered. The solvent was removed to give a residue, which was treated with150 mL of cone. HCl, and the formed solids were filtered. The yellow filtrate wasconcentrated. To the crude compound was added 30 mL of cone. HCl and 150 mL EtOH,the contents cooled to 0 °C, and stirred at 0 oc for 2h. The formed solids were filtered,washed with cold EtOH, ether, and dried. The product was collected as 36 g. This batchwas combined with other batches prepared on smaller scales and triturated with ether togive 51 g of pure compound. IH NMR (400 MHz, DMSO-d6) 8 ppm 11.85 (br s,l H) 8.13(br s, 3 H) 5.93-6.01 (m, 1 H) 3.72-3.80 (m, 2 H) 2.22 (s, 3 H) 2.16 (s, 3 H). |
51 g | Stage #1: for 48 h; Inert atmosphere Stage #2: With hydrogenchloride In ethanol; water at 0℃; for 2 h; Inert atmosphere |
Palladium on carbon (10percent) (3.24 g) was charged into a 2L dry Parr bottle and a small amount of acetic acid was added. Next added 4,6-dimethyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (30 g, 202.7 mmol), sodium acetate (30.75 g, 375.0 mmol), platinum oxide (0.218 g), and acetic acid (1 L). The bottle was capped, placed on Parr apparatus, and shaken under an atmosphere of H2 (100 psi) for 2 days. The reaction mixture was filtered. The solvent was removed to give a residue, which was treated with 150 mL of conc. HCl, and the formed solids were filtered. The yellow filtrate was concentrated. To the crude compound was added 30 mL of conc. HCl and 150 mL EtOH, the contents cooled to 0° C., and stirred at 0° C. for 2 h. The formed solids were filtered, washed with cold EtOH, ether, and dried. The product was collected as 36 g. This batch was combined with other batches prepared on smaller scales and triturated with ether to give 51 g of pure compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.85 (br s, 1H) 8.13 (br s, 3H) 5.93-6.01 (m, 1H) 3.72-3.80 (m, 2H) 2.22 (s, 3H) 2.16 (s, 3H). |
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