Structure of Cbz-DL-Pip-OH
CAS No.: 28697-07-6
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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. : | 28697-07-6 |
Formula : | C14H17NO4 |
M.W : | 263.29 |
SMILES Code : | O=C(C1N(C(OCC2=CC=CC=C2)=O)CCCC1)O |
MDL No. : | MFCD01863568 |
InChI Key : | ZSAIHAKADPJIGN-UHFFFAOYSA-N |
Pubchem ID : | 4431026 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 19 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.43 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 73.2 |
TPSA ? Topological Polar Surface Area: Calculated from |
66.84 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.29 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.1 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.73 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.57 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.28 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.79 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.7 |
Solubility | 0.526 mg/ml ; 0.002 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.13 |
Solubility | 0.193 mg/ml ; 0.000734 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.36 |
Solubility | 1.15 mg/ml ; 0.00436 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 |
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) |
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 |
-6.42 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 |
0.56 |
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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.74 |
* 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 |
---|---|---|
93% | With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 20℃; for 18h; | EXAMPLE 36; 2-(2-methylpiperidin-2-yl)-1H-benzimidazole-4-carboxamide; EXAMPLE 36A; 1-benzyl 2-methyl piperidine-1,2-dicarboxylate A solution of 1-[(benzyloxy)carbonyl]piperidine-2-carboxylic acid (5 g) and iodomethane (2.5 mL) in DMF (40 mL) was treated with potassium bicarbonate (3.8 g) and stirred at room temperature for 18 hrs. The reaction mixture was concentrated and the residual oil was partitioned between ethyl acetate and water. The organic phase was concentrated and the residue was purified by flash chromatography (silica gel, ethyl acetate/hexanes) to provide Example 36A (4.88 g, Yield: 93%). MS (DCI/NH3) m/z 278 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | To a solution of 9.41 g (1 eq.) l-(Benzyloxycarbonyl)-2-piperidinecarboxylic acid in 200 mL DCM 0.6 g HOBt (0.11 eq.) and 7.45 g (1.1 eq.) EDC hydrochloride were added and the mixture was stirred vigorously at ambient temperature for 1.5 h. To the solution was added 40 mL methanol. The mixture was stirred overnight, extracted with water, and the organic phase dried over magnesium sulfate. The dry solution was filtered and concentrated in vacuum. The resulting residue was purified by chromatography (ethyl acetate/nTieptane 1 : 1), yielding 6.6 g of the title compound as colorless oil (yield 61%). |
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