Structure of 129799-15-1
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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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CAS No. : | 129799-15-1 |
Formula : | C11H20N2O4 |
M.W : | 244.29 |
SMILES Code : | N1(C(=O)OC(C)(C)C)C(C(=O)OC)CNCC1 |
MDL No. : | MFCD01861779 |
InChI Key : | BRXKHIPPSTYCKO-UHFFFAOYSA-N |
Pubchem ID : | 2756818 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.82 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 69.4 |
TPSA ? Topological Polar Surface Area: Calculated from |
67.87 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.7 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.41 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.39 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.22 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.11 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.61 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.28 |
Solubility | 12.7 mg/ml ; 0.0521 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.4 |
Solubility | 9.68 mg/ml ; 0.0396 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.13 |
Solubility | 18.2 mg/ml ; 0.0743 mol/l |
Class? Solubility class: Log S scale |
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 |
No |
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) |
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 |
-7.5 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 |
1.0 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) |
3.01 |
* 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 |
---|---|---|
84% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 40℃; for 1.5h; | A suspension of <strong>[1214196-85-6]1-Boc-piperazine-2-carboxylic acid</strong> (9, 2.0 g, 8.69 mmol), EDCI (1.99 g, 10.42 mmol) and DMAP (0.32 g,2.61 mmol) in MeOH/CH2Cl2 (1:1) was stirred at 40 C for 1.5 hr, then the resulting solution was cooled down to room temperature and stirred for another 4 hrs. After removing the solvent, the residue was dissolved in CH2Cl2. The solution was washed with H2O (50 mL x 3). The combined aqueous was re-extracted with CH2Cl2 (40 mL x 3). All of the organics were combined, washed with 1 N NaHCO3 (50 mL x 3) and brine, and finally dried over Na2SO4. The product, a colorless liquid, was purified via flash chromatography, eluted with CH2Cl2 then 10% MeOH/CH2Cl2. Rf= 0.7 (10% MeOH/CH2Cl2, stained by phosphomolybdic acid (PMA)); yield - 84% |
79% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 - 40℃; for 21.5h;Inert atmosphere; | A 50 mL rb flask equipped with an air condenser, rubber septum and a magnetic stir bar was set under Ar atmosphere and charged with 500 mg of 1 -(/tv7-b utoxy carbonyl)piperazine-2- carboxylic acid (2.17 mmol, 1 equiv.), 80.0 mg of DMAP (0.651 mmol, 0.3 equiv.), 500 mg of EDCI (2.61 mmol, 1.2 equiv.), 10 mL of CH2CI2 and 3 mL of dry methanol. The reaction mixture was stirred at 40 C for 1.5 h and then the reaction was allowed to cool to rt. After stirring for 20 h, the reaction mixture was concentrated and the residue was dissolved in CH2CI2. The CH2CI2 solution was washed with water (3x). The water solutions were combined and the product was back-extracted with CH2CI2 (3x). Then the combined organics were washed with sat. NaHC03 solution, brine and dried over Na2S04. The crude product (661 mg) was purified on silica gel column using 0 to 5 % MeOH in CH2CI2 as eluent affording 419 mg (79 %) of the product 41 as a colorless oil. |
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