Structure of 334018-52-9
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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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CAS No. : | 334018-52-9 |
Formula : | C14H18BClO4 |
M.W : | 296.55 |
SMILES Code : | O=C(OC)C1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1Cl |
MDL No. : | MFCD06659928 |
InChI Key : | SPVAFOQLYCMOAO-UHFFFAOYSA-N |
Pubchem ID : | 22493932 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 20 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.5 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 79.21 |
TPSA ? Topological Polar Surface Area: Calculated from |
44.76 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.39 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.43 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.06 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.42 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.06 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.84 |
Solubility | 0.043 mg/ml ; 0.000145 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.01 |
Solubility | 0.029 mg/ml ; 0.000098 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.68 |
Solubility | 0.0062 mg/ml ; 0.0000209 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) |
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 |
-5.7 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.91 |
* 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 |
---|---|---|
76% | A mixture of the product of step 3 (16 g), <strong>[334018-52-9]methyl 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate</strong> (12 g, CAS 334018-52-9) and K3PO4 (16 g) in THF (200 ml.) was stirred at r.t. for 10 min. Then, [1,1'-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (complex with dichloromethane, "Pd(dppf)Cl2-CH2Cl2", 1.5 g, CAS 95464- 05-4) was added and the mixture was refluxed overnight under N2. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on silica gel to afford the product (13 g, 76%). 1 H NMR (400 MHz, CDCl3): delta 7.89 (d, 1 H), 7.60 (s, 1 H), 7.47 (d, 1 H), 7.35-7.33 (m, 3H), 6.49 (s, 1 H), 3.97 (s, 3H), 3.03-2.77 (m, 3H), 2.48-2.36 (m, 1 H). |
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