Structure of 3034-31-9
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CAS No. : | 3034-31-9 |
Formula : | C12H10N2O |
M.W : | 198.22 |
SMILES Code : | O=C(NC1=CC=CC=C1)C2=CC=NC=C2 |
MDL No. : | MFCD00459246 |
InChI Key : | FCTZHFATVFONMW-UHFFFAOYSA-N |
Pubchem ID : | 220840 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 58.45 |
TPSA ? Topological Polar Surface Area: Calculated from |
41.99 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.66 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.55 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.14 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.47 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.07 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.78 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.44 |
Solubility | 0.721 mg/ml ; 0.00364 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.04 |
Solubility | 1.8 mg/ml ; 0.00909 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.55 |
Solubility | 0.00564 mg/ml ; 0.0000284 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.41 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.3 |
* 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 |
---|---|---|
99% | A solution of isonicotinic acid (14, 5.0 g, 40.6 mmol) in thionyl chloride (40 mL) was heated at reflux for 2 h. After completion of the reaction, thionyl chloride was removed under reduced pressure. THF (50 mL), K2CO3 (16.8 g, 121.9 mmol) and aniline (3.78 g, 40.6 mmol) were added to the residue and the reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layer was concentrated and the residue was recrystallized from EtOAc-hexanes (60:40) to afford the product 15 (8.0 g, 99%) as a light yellow solid: mp 166-168 C. IR (KBr) 1344, 1653, 1465, 665 cm 1; *H NMR (DMSO-ifc, 300 MHz) δ 10.49 (s, 1 H), 8.78 (m, 2 H), 7.86 (m, 2 H), 7.78 (m, 2 H), 7.39 (t, = 8.0 Hz, 2 H), 7.15 (t, = 6.5 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | A 2.5 M n-BuLi solution in hexanes (17.8 mL, 44.4 mmol) was added to a solution of 15 (4.0 g, 20 mmol) in dry THF (120 mL) at -78 C. The solution was held at -78 C for 0.5 h and then allowed to rise to 0 C and kept at 0 C for 6 min. The mixture was cooled to -78 C and DMF (2.94 mL, 40.4 mmol) was added. After 1 h at -78 C, the reaction mixture was warmed to 0 C and kept at 0 C for 1 h. H20 (40 mL) was added, the organic layer was separated, and the water layer was extracted with CHCI3 (2 x 40 mL). The combined organic layer was dried over Na2S04, concentrated, and purified by silica gel flash column chromatography (60:40 EtOAc- hexanes) to afford compound 16 (3.0 g, 67%) as an off-white solid: mp 209-211 C. IR (KBr) 3356, 1721, 776 cm ; lH NMR (DMSC fc, 300 MHz) δ 8.97 (s, 1 H), 8.86 (d, = 4.9 Hz, 1 H), 7.77 (m, 3 H), 7.48 (t, = 6.1 Hz, 2 H), 7.28 (t, = 7.5 Hz, 1 H), 7.10 (br s, 1 H), 6.69 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; acetic acid; | PREPARATION A Preparation of 4-(N-phenylcarbamoyl)piperidine 4-(N-phenylcarbamoyl)pyridine [75.0 g, prepared as in Chem. Abs., 2013h (1958)] was hydrogenated in acetic acid (800 ml) using a platinum oxide catalyst at 50 p.s.i./30. The catalyst was then removed by filtration, the solution evaporated, the residue basified to about pH 12 with sodium hydroxide, extracted with chloroform, and the organic extract discarded. The aqueous phase was evaporated to dryness, the residue boiled with chloroform, filtered and evaporated to leave 4-(N-phenylcarbamoyl)piperidine (17.0 g), m.p. 121-127. The hydrochloride salt, m.p. 231-233, was prepared in isopropanol from the free base and hydrogen chloride, and was recrystallized from isopropanol/ethyl acetate. Analysis %: Found: C, 60.1; H, 7.2; N, 11.7. Calculated for C12 H16 N2 O.HCl: C, 59.9; H, 7.1; N, 11.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium borohydrid; In ethanol; N,N-dimethyl-formamide; | Step 1: 1-Benzyl-1,2,3,6-tetrahydropyridinyl-4-carboxylic acid phenylamide A mixture of <strong>[3034-31-9]pyridine-4-carboxylic acid phenylamide</strong> (3.96 g, 20 mmol), benzyl bromide (3.76 g, 22 mmol) and DMF (10 ml) was stirred at 105 C. for 15 h and the resulting solid mass, on cooling, suspended in ethanol (40 ml). Sodium borohydride (0.95 g, 25 mmol) was added in portions and the suspension stirred for 3 h, after which it was filtered, the filtrate evaporated, and the residue partitioned between water (100 ml) and ethyl acetate (2*75 ml). The organic layers were extracted with HCl (1M: 3*50 ml), the combined extracts basified with aqueous sodium hydroxide, and the suspension re-extracted with dichloromethane (2*50 ml). After drying (MgSO4), the dichloromethane layers were evaporated to leave the product as a yellow gum (4.58 g). δH (CDCl3) 2.52 (2H, br s, tetrahydropyridinyl CH2), 2.68 (2H, t, J 5.7 Hz, tetrahydropyridinyl CH2), 3.17 (2H, dd, J 6.0, 2.7 Hz, tetrahydropyridinyl CH2), 3.64 (2H, s, PhCH2 N), 6.62 (1H, dd, J 3.3, 1.8 Hz, CR=CH), 7.10 (1H, t, J 7.3 Hz, ArH), 7.26-7.48 (7H, m, ArH) and 7.53 (2H, d, J 7.6 Hz, ArH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With n-butyllithium; In tetrahydrofuran; 1,4-dioxane; methanol; | Step 1 3-(2-Hydroxyethyl)-<strong>[3034-31-9]N-phenylisonicotinamide</strong> To a solution of <strong>[3034-31-9]N-phenylisonicotinamide</strong> (1.98 g, 10 mmol) in tetrahydrofuran (40 ml) at -78 C. was added a solution of n-butyllithium (1.6M in hexanes; 13.5 ml, 21.6 mmol) and the resulting red solution stirrred for 40 minutes before addition of a solution of ethylene oxide in dioxane (3.56M; 3.0 ml, 11 mmol). After allowing the mixture to warm to room temperature over 21/2 hours, the reaction was quenched by addition of methanol (8 ml). The solvent was evaporated and the residue partitioned between ethyl acetate (70 ml) and water (25 ml). The organic layer was washed with saturated brine (25 ml), dried (MgSO4) and evaporated. The residue was chromatographed on silica eluding with 10% methanol/dichloromethane to afford the title compound as a solid (1.05 g, 43%); δH (CDCl3) 3.07 (2H, t, J 5.6 Hz, ArCH2 CH2 OH), 3.70 (1H, br s, OH), 4.10 (2H, t, J 5.6 Hz, ArCH2 CH2 OH), 7.15-7.19 (1H, m, ArH), 7.35-7.39 (2H, m, ArH), 7.49 (1H, d, J 5.2 Hz, ArH), 7.69-7.71 (2H, m, ArH), 8.44-8.48 (2H, m, ArH), 9.77 (1H, s, NH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Reference Example 4-28 Production of 1'-benzyl-1H-spiro[furo[3,4-c]pyridine-3,4'-piperidin]-1-one At -78C, a hexane solution (500 mL) of 2.71 M n-butyllithium was dropwise added to a THF solution (4.00 L) of<strong>[3034-31-9]N-phenyl-4-pyridinecarboxamide</strong> (131 g). After stirred for 2.5 hours, a THF solution (650 mL) of 1-benzyl-4-piperidone (125 g) was dropwise added to it at -78C, and stirred for 1 hour. After warmed up to -20C, aqueous 1 N sodium hydroxide solution (1.00 L) was added to it, and concentrated under reduced pressure. After extracted with ethyl acetate, the aqueous layer was made acidic (pH ~1) by adding concentrated hydrochloric acid. After stirred for 1 hour, this was neutralized (pH ~8) with aqueous 12 % potassium carbonate solution. The precipitated solid was collected through filtration, washed with water, and dissolved in chloroform. This was washed with aqueous saturated sodium hydrogencarbonate solution, and dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to obtain the entitled compound (152 g) as a white solid. ESI-MS Found: m/z 295[M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The ISONICOTINAMIDE 1-1 (100 g, 0.50 mol, Kingchem), THF (0.5 L) and a 1 M LiBr solution (prepared by dissolving 1.50 mol of LiBr in 1.5 L of THF) were mixed in a flask. The resulting solution was degassed with nitrogen and cooled TO-65 C. n-BuLi (1.56 M in hexane; 666 ML, 1.04 mol) was then added while maintaining the batch temperature BELOW-55 C. The resulting solution was then aged at a temperature less THAN-55 C for a period between 1 to 7 hours to give a metalated anilide mixture. A solution of ethyl 4-oxocyclohexanecarboxylate 1-2 (100 mL, 0.63 mol, EMS Dottikon AG) in THF (1 L) was cooled in a separate flask to a temperature BELOW-60 C. To the solution was added the above metalated anilide mixture, while maintaining the batch temperature below-55 C. The resulting solution was aged at a temperature BELOW-55 C for 1 hour and then carefully quenched into H20 (1 L). The resulting mixture was warmed to 40 C and aged at 40 C for a period between 1 to 4 hours. After cooling to room temperature, the organic layer was removed and the aqueous layer (1.3 L; pH - 11) was washed with THF (1 L) to give an aqueous solution of the diacid 1-3. |
Tags: 3034-31-9 synthesis path| 3034-31-9 SDS| 3034-31-9 COA| 3034-31-9 purity| 3034-31-9 application| 3034-31-9 NMR| 3034-31-9 COA| 3034-31-9 structure
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H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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