Structure of 3515-49-9
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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. : | 3515-49-9 |
Formula : | C14H18N2 |
M.W : | 214.31 |
SMILES Code : | C1(CC2CCNCC2)=CNC3=C1C=CC=C3 |
MDL No. : | MFCD01718591 |
InChI Key : | HKYWCJOLDLYIOL-UHFFFAOYSA-N |
Pubchem ID : | 19026 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.43 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 71.9 |
TPSA ? Topological Polar Surface Area: Calculated from |
27.82 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.26 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.57 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.33 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.37 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.64 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.63 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.07 |
Solubility | 0.182 mg/ml ; 0.000847 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.8 |
Solubility | 0.338 mg/ml ; 0.00158 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.9 |
Solubility | 0.00267 mg/ml ; 0.0000125 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) |
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 |
-5.78 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.72 |
* 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 |
---|---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In chloroform; water; | EXAMPLE 6 3-Chloro-4-[(4-piperidyl)-methyl]-quinoline The operation is as in Example 1, but starting from 13.4 g of <strong>[3515-49-9]4-(3-indolyl-methyl)-piperidine</strong> and 0.54 g of triethylbenzylammonium chloride in 130 ml of chloroform and 19.5 g of sodium hydroxide in solution in 39 ml of water. 4.2 g of 3-chloro-4-[(4-piperidyl)-methyl]-quinoline are finally obtained in the form of the dihydrochloride melting above 260 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydroxide; In 1,4-dioxane; water; at 20.0℃; for 16.0h; | To a solution of <strong>[3515-49-9]3-(piperidin-4-ylmethyl)-1H-indole</strong> (0.500 g, 2.33 mmol) in 1,4-dioxane (5 mL) was added NaOH (1.0 M aqueous solution, 5.00 mL, 5.00 mmol). A solution of Boc2O (0.509 g, 2.33 mmol) in 1,4-dioxane (5.00 mL) was added dropwise. The mixture was stirred at ambient temperature for about 16 h. The organic phase was separated, washed with water and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with a gradient of 0-25% EtOAc in heptane to give tert-butyl 4-((1H-indol-3-yl)-methyl)piperidine-1-carboxylate (0.661 g, 90% yield): LC/MS (Table 1, Method a) Rt=2.80 min; no ionization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | 3-(Pyridin-4-ylmethyl)-1H-indole (5.00 g, 24.0 mmol) and acetic acid (25 mL) were added to platinum(IV) oxide (1.00 g, 4.40 mmol, Johnson Matthey) in a 250 mL stainless steel pressure bottle and stirred for about 2 hr under about 30 psi hydrogen at ambient temperature. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved with EtOAc and then washed with saturated aqueous Na2CO3. The organic layer became turbid. A small amount of MeOH was added to form a clear solution. The organic layer was washed with 2 N aqueous NaOH and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting solid was triturated with Et2O and then dried to give 3-(piperidin-4-ylmethyl)-1H-indole (4.35 g, 73% yield): LC/MS (Table 1, Method a) Rt=1.51 min; MS m/z: 215.12 (M+H)+. |
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