Structure of 64690-19-3
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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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CAS No. : | 64690-19-3 |
Formula : | C13H22N2 |
M.W : | 206.33 |
SMILES Code : | C1=C(NCCCCCCCC)C=CN=C1 |
MDL No. : | MFCD09743883 |
InChI Key : | RHDWCSIBVZKRRU-UHFFFAOYSA-N |
Pubchem ID : | 3017535 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.62 |
Num. rotatable bonds | 8 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 67.19 |
TPSA ? Topological Polar Surface Area: Calculated from |
24.92 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.94 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.25 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.66 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.28 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.47 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.32 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.56 |
Solubility | 0.0562 mg/ml ; 0.000272 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.48 |
Solubility | 0.00676 mg/ml ; 0.0000328 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.3 |
Solubility | 0.00103 mg/ml ; 0.00000498 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) |
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) |
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) |
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 |
-4.54 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<3.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.67 |
* 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 |
---|---|---|
78.5% | at 130℃; for 2 h; Large scale | Into 200L reactor was pumped n-octylamine 100kg,30kg of 4-chloropyridine hydrochloride and 10kg of sodium fluoride were added, the temperature was raised to 130 ° C, and the mixture was stirred for 2 hours while keeping warm,Decompression recovery n-octylamine, while hot sodium carbonate aqueous solution to adjust the pH to about 7, adding ethyl acetate 120kg, separating the aqueous layer, the organic layer was cooled, filtered,Dried to give 4-octylaminopyridine 32.3kg,Purity was 99.3percent, yield was 78.5percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | at 120 - 200℃; for 7 h; | 5.0 g (0.0333 mol) of 4-chlororpyridine hydrochloride,And 0.55 g (0.0333 mol) of n-OCtylaminehydrochloride,The mixture is stirred and heated from 120 ° C to 180 ° C, heated to 200 ° C and held for 7 hours. The reaction was confirmed by thin-layer chromatography, and after completion, it was cooled and cooled to 100 ° C. To the reaction solution was added 20 ml of water and the mixture was cooled with stirring.To the reaction mixture was added 35percent aqueous solution of sodium hydroxide to make it alkaline. The mixture was extracted three times with 20 ml of di-dichloromethane (MC). The organic layer was collected, washed with 10 ml of cold water, washed with saturated brine, dehydrated with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, 14 ml of hexane was added to the residue solid, and the mixture was refluxed and cooled. The resulting crystals were filtered, dried under reduced pressure at room temperature. [0103] 6.4 g of octylaminopyridine base (yield: 93.0percent, MP 65-69 ° C) was obtained through the above-mentioned procedure. |
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