Structure of 26286-55-5
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 26286-55-5 |
Formula : | C10H11N3 |
M.W : | 173.21 |
SMILES Code : | NC1=CC=CC=C1N2C=CN=C2C |
MDL No. : | MFCD08699292 |
InChI Key : | LLSZMUSXQITSSJ-UHFFFAOYSA-N |
Pubchem ID : | 13656108 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H312-H315-H319-H332-H335 |
Precautionary Statements: | P304+P340-P305+P351+P338-P280-P261 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 11 |
Fraction Csp3 | 0.1 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 52.93 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.84 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.68 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.39 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.77 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.02 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.25 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.42 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.35 |
Solubility | 0.774 mg/ml ; 0.00447 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.91 |
Solubility | 2.11 mg/ml ; 0.0122 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.95 |
Solubility | 0.194 mg/ml ; 0.00112 mol/l |
Class? Solubility class: Log S scale |
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 |
-6.37 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 |
1.0 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) |
1.91 |
* 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 |
---|---|---|
98% | With palladium 10% on activated carbon; hydrazine hydrate; In ethanol; for 1.0h;Reflux; | Palladium-carbon 10% was added portion-wise during 10 min toa hot solution of 4 (4.52 g, 22.2 mmol) in dry ethanol (40 mL)containing hydrazine monohydrate (5.4 mL, 111 mmol). Themixture was heated under reflux for 1 h. The hot solution wasfiltered on a celite pad and the filtrate was evaporated under vacuum.The compound is obtained as yellow oil (98% yield). C10H11N3.MW: 173.21 g/mol. Mp 132-133 C. 1H NMR δ (ppm, 300 MHz,DMSO-d6) 2.09 (s, 3H, CH3), 4.88 (s, 2H, NH2), 6.62 (td, 1H, CH-C,J6 Hz), 6.87 (dd, 1H, CH-C-NH2, J9 Hz), 6.92 (d, 1H, CH-N,J3 Hz), 6.98 (dd, 1H, CH-C-N, J6 Hz), 7.04 (d, 1H, CH-N), 7.14(td, 1H, CH-C, J6 Hz). 13C NMR δ (ppm, 75 MHz, DMSO-d6) 13.17,116.20, 116.61, 121.17, 121.90, 127.85, 128.30, 129.96, 144.74, 144.92.MS (ESI+ , QTof, m/z): 173.8 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In 1,2-dichloro-benzene;Reflux; Inert atmosphere; | Compound 5 (0.5 g, 2.8 mmol) and carbonyldiimidazole (0.54 g,3.36 mmol) were dissolved in 30 mL of 1,2-dichlorobenzene andheated to reflux overnight under nitrogen. After cooling to roomtemperature, the solid was filtered and washed with diethylether.The compound is obtained as a yellow solid (93% yield). C11H9N3O.MW: 199 g/mol. Mp > 300 C. 1H NMR δ (ppm, 300 MHz, DMSO-d6)2.85 (s, 3H, CH3), 7.19 to 7.35 (m, 3H), 7.71 (s, 1H, CH 3), 8.03 (d, 1H,CH 6, J=6 Hz). 13C NMR d (ppm, 75 MHz, DMSO-d6) 18.00, 117.29,121.09, 122.46, 123.10, 124.00, 127.03, 129.90, 135.23,144.65, 154.96.MS (ESI+ , QTof, m/z): 200.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 13 1-(2-Amino)phenyl-2-methylimidazole (20) Following the procedure detailed in example 2, 2-iodoaniline (3, 4.38 g, 20 mmol) and 2-methylimidazole (5, 1.97 g, 24 mmol, 1.2 equiv) were coupled under the ligand-accelerated Cu(I)-catalyzed condition to generate 1-(2-amino)phenyl-2-methylimidazole (20, 2.35 g, 3.46 g theoretical, 68%) as white crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; triethylamine; In chloroform; water; | EXAMPLE 7 Synthesis of 1-[2-(N,N-dimethylsulfonylamino)phenyl]-2-methylimidazole A mixture of 1.1 g of triethylamine and 1.2 g of methanesulfonyl chloride was added to a solution of 1.5 g of 1-(2-aminophenyl)-2-methylimidazole in 30 ml of chloroform, and the mixture was refluxed with stirring for 5 hours. Then, 0.6 g of methanesulfonyl chloride was added to the reaction mixture and the mixture was refluxed with stirring for 3 hours. After completion of the reaction, the reaction mixture was naturally cooled and the solvent was removed by distillation under reduced pressure. Water was added to the residue and the resulting liquid was made alkaline by addition of an aqueous solution of sodium carbonate. The precipitated crystal was recovered by filtration, and washed with water, recrystallized from ethanol to obtain 0.9 g of the intended compound. The obtained compound was converted to a hydrochloride having a melting point of 215 to 220 C. according to customary procedures. Elementary analysis values as C12 H15 N3 S2 O4.HCl were as follows. Calculated: C=39.40%, H=4.42%, N=11.49%. Found: C=39.21%, H=4.33%, N=11.23%. |