Structure of 1207-69-8
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 1207-69-8 |
Formula : | C13H8ClN |
M.W : | 213.66 |
SMILES Code : | ClC1=C2C=CC=CC2=NC2=CC=CC=C12 |
MDL No. : | MFCD00022266 |
InChI Key : | BPXINCHFOLVVSG-UHFFFAOYSA-N |
Pubchem ID : | 71013 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | 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 | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 64.26 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.89 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.57 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.05 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.04 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.6 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.13 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.68 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.41 |
Solubility | 0.00837 mg/ml ; 0.0000392 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.02 |
Solubility | 0.0202 mg/ml ; 0.0000945 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.0 |
Solubility | 0.000214 mg/ml ; 0.000001 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) |
Yes |
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 |
-4.73 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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.34 |
* 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 |
---|---|---|
6% | Following the procedure outlined in Step 2 of Example 1, but substituting 4-piperidin-1-yl-1-nitrobenzene for 1-methyl-4-(4-nitrophenyl)piperazine, afforded 4-piperidin-1-ylaniline, which was reacted with 9-chloroacridine (according to Step 4 in the procedure of Example 1) to obtain the title compound with 6% overall yield. 1H NMR (CDCl3, 500 MHz): 8.05 (2H, m), 8.00 (2H, m), 7.48 (2H, m), 7.09 (4H, m), 6.86 (2H, m), 3.13 (4H, m), 1.71 (4H, m), 1.58 (2H, m); MS (ESI+TOF): 354 (M+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tert-butyl alcohol; at 20 - 80℃; for 14h;Inert atmosphere; | General procedure: A dry round bottom flask was cooled to rt under nitrogen, and was charged with Pd2(dba)3 (3.38mg, 0.0037mmol), cesium carbonate (361mg, 1.11mmol), and arenesulfonamide (69mg, 0.44mmol). Tertiary-butanol (2mL) was added, followed by ligand, xantphos (6.4mg, 0.011mmol) and 9-chloroacridine (80mg, 0.37mmol). The resulting suspension was stirred at rt for 5min, then heated to 80C for 12-17h. The reaction mixture was then cooled to rt and filtered through suction filtration. The organic fraction was evaporated, and the resulting residue was purified by silica gel chromatography with a hexane/Et-OAc as eluent (60:40). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.3% | With [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride; sodium carbonate; In water; toluene; at 60℃; for 5h; | In a 250 mL three-necked flask, 21.4 g (0.1 mol) of 9-chloroacridine, 18.0 g (0.11 mol) of <strong>[216019-28-2]3-isopropylphenylboronic acid</strong>, 0.11 g of PdCl2 (dppb) catalyst, 100 g of toluene, and 2 g of sodium carbonate were sequentially added. 18 g of deionized water, heated to 60 C., reacted for 5 hours, cooled to 25 C., removed the solvent by rotary evaporation, washed with 100 g of methanol and dispersed, and filtered to obtain a crude product. The crude product was refined with 80 g of toluene and dried to obtain 28.9 g of the product in a yield 97.3%, HPLC content 99.57%. |
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