Structure of 630125-91-6
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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. : | 630125-91-6 |
Formula : | C14H20F3N3 |
M.W : | 287.32 |
SMILES Code : | NC1=CC=C(CN2CCN(CC)CC2)C(C(F)(F)F)=C1 |
MDL No. : | MFCD09909923 |
InChI Key : | ZYWCDXFRHUHFNV-UHFFFAOYSA-N |
Pubchem ID : | 59134564 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 20 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.57 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 81.16 |
TPSA ? Topological Polar Surface Area: Calculated from |
32.5 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.72 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.14 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.67 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.32 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.5 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.47 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.93 |
Solubility | 0.339 mg/ml ; 0.00118 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.45 |
Solubility | 1.01 mg/ml ; 0.00351 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.9 |
Solubility | 0.0363 mg/ml ; 0.000126 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) |
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) |
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 |
-6.53 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) |
2.03 |
* 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 |
---|---|---|
63% | With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 15h; | To a solution of 100 mg (0.69 mmol) of <strong>[10601-99-7]3-ethynyl benzoic acid</strong> in 5 mL of dry N,N-dimethylformamide, 164 mg (0.57 mmol) of 4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)aniline (prepared as described in J. Med. Chem., (2010) 53, 4701-4719) 242 mg (0.75 mmol) of TBTU and 0.14 mL (0.82 mmol) of DIPEA were added consecutively. After 15 h under stirring at room temperature the mixture was poured into aqueous NaHC03 and extracted twice with ethylacetate. The organic phase was then washed with brine, dried over Na2S04 and evaporated to dryness. A flash- chromatography on silica gel (DCM-MeOH-NH3 7N in methanol 9/1/0.04), afforded 149 mg of the title compound (63%). 1H NMR (600 MHz, DMSO-d6) delta ppm 0.99 (t, J=7.14 Hz, 3 H) 2.19 - 2.46 (m, 10 H) 3.57 (s, 3 H) 6.61 (br. s., 2 H) 7.60 (t, J=7.88 Hz, 1 H) 7.64 (d, J=2.20 Hz, 1 H) 7.72 (d, J=8.61 Hz, 1 H) 7.80 (dt, J=7.83, 1.21 Hz, 1 H) 7.91 - 7.98 (m, 1 H) 8.05 (dd, J=8.52, 1.92 Hz, 1 H) 8.12 (s, 1 H) 8.16 (t, J=1.47 Hz, 1 H) 8.21 (d, J=2.20 Hz, 1 H) 10.59 (s, 1 H) 12.08 (br. s., 1 H) HRMS (ESI) calcd for C29H28N7OF3 [M+H]+ 548.2380, found 548.2392. |
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