Structure of 2875-79-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 2875-79-8 |
Formula : | C16H13N3O |
M.W : | 263.29 |
SMILES Code : | O=C(N1C=CN=C1)N(C2=CC=CC=C2)C3=CC=CC=C3 |
MDL No. : | MFCD02585208 |
InChI Key : | FYSIBSOBMCDYHZ-UHFFFAOYSA-N |
Pubchem ID : | 661299 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 20 |
Num. arom. heavy atoms | 17 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 78.04 |
TPSA ? Topological Polar Surface Area: Calculated from |
38.13 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.53 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.02 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.69 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.55 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.55 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.67 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.74 |
Solubility | 0.0479 mg/ml ; 0.000182 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.49 |
Solubility | 0.086 mg/ml ; 0.000327 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.73 |
Solubility | 0.00489 mg/ml ; 0.0000186 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) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
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 |
-5.76 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 |
0.0 |
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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.43 |
* 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 |
---|---|---|
The following compounds were found to give greater than 70 percent control of mildew in both tests. ... 1-(N-2-chlorobenzyl-N-2-phenethylcarbamoyl)imidazole 1-(N-2,4-dichlorobenzyl-N-2-chlorophenylcarbamoyl)imidazole 1-(N,N-bis-phenylcarbamoyl)imidazole |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Example 1 - Preparation of Amide-Method A(R) The following procedures can be operated on either the racemic or the enantiopure starting butyn-2-ol. To a stirred solution of sulfuric acid (cone, 40//L) in THF (24OmL) were sequentially added (R)-3 butyn-2-ol (40g, 0.57 mol) and then hexamethyldisilazane (49.6g, 0.31 mol) at room temperature. The solution was refluxed for 3-4 hours and then slowly cooled to -4O0C. The resulting mixture was slowly charged in hexyllithium (2.5M in hexane, 249 mL, 0.62 mol) while maintaining the temperature at -40 0C. This solution and a solution of <strong>[2875-79-8]diphenylcarbamylimidazole</strong> (180 g, 0,68 mol) in a mixed solvent of THF (1088mL) and toluene (435 mL) were mixed using pumps through a chilled static mixer and directly quenched into 5N sulfuric acid (56OmL, -50C). The quenched solution was warmed to 250C and stirred for 1 hour. The organic layer was separated, washed with 5N sulfuric acid (80 mL) and then twice with 10% brine (20OmL each EPO <DP n="29"/>time). The pH of the final brine wash was adjusted to 5-7 with a 5% NaHCO3 solution. The organic layer was then distilled and replaced with toluene (440 ml_). The toluene solution was added to heptane (40OmL) at 850C, cooled slowly to 2O0C and filtered. The filtered cake was washed with a mixed solution of toluene (8OmL) and heptane (SOmL). Ths cake was then dried in a vacuum oven at 50GC to afford the title compound in 84% molar yield (120.6g, purity 99%). Mp 1050C.1H NMR (400MHz, DMSO-d6) δ 1.04 (d, J=6.4Hz, 3H), δ 4.27 (dq, J=5.6 Hz, 6.4Hz, 1H), δ 5.49 (d, J = 5.6 Hz, 1H), δ 7.2-7.5 (m, 10H); 13C NMR (DMSO-d6) δ 23.7, 56.3, 76.9, 96.4, 126.8, 127.0, 128.5, 129.2, 129.4, 129.6, 141.5, 142.2, 152.9. | |
The following procedures can be operated on either the racemic or the enantiopure starting butyn-2-ol. To a stirred solution of sulfuric acid (cone, 40 μL) in THF (240 mL) were sequentially added (R) -3 butyn-2-ol (40 g, 0.57 mol) and then hexylmethyldisilazane (49.6g, 0.31 mol) at room temperature. The solution was refluxed for 3-4 hours and then slowly cooled to -400C. The resulting mixture was slowly charged in hexyllithium (2.5M in hexane, 249 mL, 0.62 mol) while maintaining the temperature at -40 0C. This solution and a solution of <strong>[2875-79-8]diphenylcarbamylimidazole</strong> (180 g, 0,68 mol) in a mixed solvent of THF (1088 mL) and toluene (435 mL) were mixed using pumps through a chilled static mixer and directly quenched into 5N sulfuric acid (560 mL, -50C). The quenched solution was warmed to 250C and stirred for 1 hour. The organic layer was separated, washed with 5N sulfuric acid (80 mL) and then twice with 10% brine (200 mL each time). The pH of the final brine wash was adjusted to 5-7 with a 5% NaHCU3 solution. The organic layer was then distilled and replaced with toluene (440 mL) . The toluene solution was added to heptane (40OmL) at 850C, cooled slowly to 200C and filtered. The filtered cake was washed with a mixed solution of EPO <DP n="40"/>toluene (80 mL) and heptane (80 mL). The cake was then dried in vacuum oven at 500C to afford the title compound in 84% molar yield (120.6 g, purity 99%). Mp 1050C. 1H NMR (400MHz, DMSOd6) δ 1.04 (d, J=6.4Hz, 3H), δ 4.27 (dq, J=5.6 Hz, 6.4 Hz, IH), δ 5.49 (d, J = 5.6 Hz, IH), δ 7.2-7.5 (m, 10H); 13C NMR (DMSO-d6) δ 23.7, 56.3, 76.9, 96.4, 126.8, 127.0, 128.5, 129.2, 129.4, 129.6, 141.5, 142.2, 152.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium tetrahydroborate; In tetrahydrofuran; water; at 20℃; | General procedure: To a solution of compound a 1.0mmol in THF (8mL) at room temperature, NaBH4 (3.0mmol for N-aliphatic substituted carbonylimidazolides and 1.0mmol for N-aromatic substituted carbonylimidazolides) in 1mL H2O was added with vigorous stirring. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled with ice water, 1 M HCl was added carefully till pH=2-3. The solution was extracted with dichloromethane (3×20mL) and the organic layers were combined. The organic extract was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crudes were purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 20 - 66℃; for 6h; | 500 mg (1.9 mmol) of <strong>[2875-79-8]N,N-diphenyl-1-imidazolecarboxamide</strong> was added to a 50 mL round bottom flask, and dissolved in 20 mL of THF.359 mg (9.5 mmol) of sodium borohydride and 482 mg (1.9 mmol) of iodine were added thereto under stirring at room temperature, and the mixture was transferred to an oil bath at 66 C to reflux.The reaction progress was detected by TLC, and the reaction liquid was completely obtained after the reaction for 6 hours.Then, the obtained reaction liquid was washed with 5% hydrochloric acid, water, 5% sodium hydroxide and water in an ice bath, and after washing, it was extracted twice with 50 mL of dichloromethane, and the organic layer was washed with saturated brine. Dry with anhydrous sodium sulfate. The dried solution is then steamed to remove the solution.And the crude product is separated and purified by column chromatography.The target product N-methyldiphenylamine 271 mg was obtained in a yield of 78%. |
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