Structure of 7089-68-1
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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. : | 7089-68-1 |
Formula : | C12H7ClN2 |
M.W : | 214.65 |
SMILES Code : | ClC1=CC=C2C=CC3=CC=CN=C3C2=N1 |
MDL No. : | MFCD00185678 |
InChI Key : | JHRMQHFRVPVGHL-UHFFFAOYSA-N |
Pubchem ID : | 355193 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 14 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 62.05 |
TPSA ? Topological Polar Surface Area: Calculated from |
25.78 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.98 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.74 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.44 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.4 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.58 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.83 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.59 |
Solubility | 0.0555 mg/ml ; 0.000258 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.94 |
Solubility | 0.249 mg/ml ; 0.00116 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.63 |
Solubility | 0.000507 mg/ml ; 0.00000236 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) |
Yes |
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) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.66 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 |
2.0 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) |
1.77 |
* 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 |
---|---|---|
75% | Reference Example 32-Chloro-1,10-phenanthroline (3) [0113] [Chem. 20] [0114] Under a stream of argon, to compound (2) (8 g; 38 mmol), phosphorus oxychloride (72 mL) and phosphorus pentachloride (9.8 g; 47.6 mmol) were added in an ice bath. The resulting reaction mixture was stirred and refluxed for 8 hours, and excess phosphorus oxychloride was removed under reduced pressure. To the resulting reaction concentrate, ice water and concentrated aqueous ammonia were added and the resulting mixture was made alkaline to precipitate crude crystals. The crude crystals were separated by filtration and washed with water, and then dried under reduced pressure to give 6.1 g (yield: 75percent) of the title compound (3). [0115] 1H NMR (DMSO-d6) d: 7.80-7.88 (m, 2 H), 8.07 (s, 2 H), 8.54 (d, J = 8.5 Hz, 1 H), 8.60 (d, J = 8.5 Hz, 1 H), 9.14 (d, J = 7 Hz, 1 H) | |
75% | Production Example 32-Chloro-1,10-phenanthroline (3)[0149] [Chem. 26] [0150] Under a stream of argon, to compound (2) (8 g; 38 mmol), phosphorus oxychloride (72 mL) and phosphorus pentachloride (9.8 g; 47.6 mmol) were added in an ice bath. The resulting reaction mixture was stirred and refluxed for 8 hours, and excess phosphorus oxychloride was removed under reduced pressure. To the resulting reaction concentrate, ice water and concentrated aqueous ammonia were added and the resulting mixture was made alkaline to precipitate crude crystals. The crude crystals were separated by filtration and washed with water, and then dried under reduced pressure to give 6.1 g (yield: 75percent) of the title compound (3).[0151] 1H NMR (DMSO-d6)d: 7.80-7.88 (m, 2H), 8.07 (s, 2H), 8.54 (d, J=8.5 Hz, 1H), 8.60 (d, J=8.5 Hz, 1H), 9.14 (d, J=7 Hz, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With acetamide; potassium carbonate; at 200℃; for 5h; | <strong>[7089-68-1]2-Chloro-1,10-phenanthroline</strong> (100 mg, 0.5 mmol) and potassiumcarbonate (451 mg, 3.3 mmol) and acetamide (688 mg,11.7 mmol) were stirred at 200 C for 5 h. The reaction mixturewas cooled to room temperature, and poured into water. The aqueouslayer was extracted with chloroform (40 mL) twice. The combinedorganic layers were washed with brine and dried overmagnesium sulfate. The crude product was purified by silica gelchromatography eluted with chloroform/methanol = 100:1 to give2 (85 mg, 94%) as white solids. |
52.5% | With acetamide; potassium carbonate; at 200℃; for 1h; | <strong>[7089-68-1]2-chloro-1,10-phenanthroline</strong> (859 mg, 4 mmol), acetamide (4.73 g, 80 mmol), potassium carbonate (3.87 g, 28 mmol), and heated to 200 C, stirred for 1 hour, dropped to room temperature, add water (30 mL) to the reaction and extract with dichloromethane. The organic phase was collected, dried over anhydrous sodium sulfate and filtered. The organic phase was removed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography to afford 2-amino-1,10-phenanthroline 409 mg (2.1 mmol, 52.5%). |