Structure of 4897-50-1
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 4897-50-1 |
Formula : | C10H20N2 |
M.W : | 168.28 |
SMILES Code : | C2C(N1CCCCC1)CCNC2 |
MDL No. : | MFCD00006475 |
InChI Key : | QDVBKXJMLILLLB-UHFFFAOYSA-N |
Pubchem ID : | 78607 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 59.48 |
TPSA ? Topological Polar Surface Area: Calculated from |
15.27 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.35 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.23 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.46 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.52 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.81 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.47 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.59 |
Solubility | 4.3 mg/ml ; 0.0256 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.15 |
Solubility | 12.0 mg/ml ; 0.0711 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.81 |
Solubility | 2.62 mg/ml ; 0.0156 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
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) |
No |
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 |
-6.45 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) |
1.43 |
* 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 |
---|---|---|
100% | In tetrahydrofuran; at 0 - 20℃; for 0.25h; | (Step 1) <strong>[5147-80-8][Bis(methylthio)methylene]malononitrile</strong> (1.94 g, 11.3 mmol) was dissolved in THF (10 mL) and the solution was added with a solution of 4-piperidinopiperidine (2.30 g, 13.7 mmol) in THF (10 mL) under ice bath. After stirring at room temperature for 0.25 hour, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol (9:1)) to obtain [(methylthio)(4-piperidinopiperidino)methylene]malononitrile (3.31 g, 100 %) as a yellow crystal. 1H NMR (CDCl3, δppm): 1.39-1.50 (m, 2H), 1.52-1.74 (m, 6H), 1.94-2.05 (m, 2H), 2.44-2.56 (m, 5H), 2.58 (s, 3H), 3.32 (td, J =2.6, 12.7 Hz, 2H), 4.29 (d, J = 12.7 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.2% | EXAMPLE 2 4.00 g (10.2 mmol) 7-Ethyl-10-hydroxycamptothecin (purity 80percent) are dissolved in 60 ml CH2Cl2. 2.15 g (16.3 mmol) diisopropylethylamine, dissolved in 10 ml CH2Cl2, 0.16 g (1 mmol) DABCO and 1.1 g (36 mmol) bis(trichloromethyl)carbonate, dissolved in 10 ml CH2Cl2 are added at a temperature of 20° C. within 15 min. The solution is stirred for a further 20 min. Then 1.80 g (16 mmol) piperidinopiperidine, dissolved in 10 ml CH2Cl2, and 2.15 g (16.2 mmol) diisopropylethylamine, dissolved in 10 ml CH2Cl2, are added simultaneously within 15 min at 22° C. The resulting clear solution is stirred for 2-4 h at 25° C. The organic layer is extracted with 2.x.80 ml saturated NaHCO3 solution and 3.x.60 ml H2O. The aqueous layers are collected and extracted with 2.x.40 ml CH2Cl2. The combined organic layers are extracted again with 2.x.60 ml H2O, dried over 2 g Na2SO4, filtered and concentrated. The residue is recrystallized from 2-methoxyethanol and dried in vacuo. Yield: 5.1 g 85.2percent of theory Appearance: yellow powder |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | In tetrahydrofuran; at 50℃; | General procedure: To a stirred solution of 12b (4.6 g, 20 mmol) in THF (50 mL) was added N,N-dimethylamine (2M solution in THF, 1.8 g, 20 mL, 40 mmol) dropwise at rt. The resulting mixture was stirred at 50 C overnight and was then evaporated to dryness under reduced pressure. The residue was triturated with a saturated aqueous solution of NaHCO3, and the solid product was collected by filtration, washed with water followed by hexane, and dried to give 14a. Yield: 4.1 g (87%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl acetamide; at 150℃; for 0.166667h;Microwave irradiation; | A solution of <strong>[51323-43-4](3-(bromomethyl)phenyl)boronic acid</strong> (129.5 mg, 0.603 mmol) and 1,4?-bipiperidine (190 mg, 1.129 mmol) in DMAC (1 mL) was microwaved at 150 C. for 10 min after which time the reaction was cooled and concentrated to dryness to be used in the next step as crude (3-([1,4?-bipiperidin]-1?-ylmethyl)phenyl)boronic acid. |
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