Structure of 130722-95-1
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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. : | 130722-95-1 |
Formula : | C12H10BrNO |
M.W : | 264.12 |
SMILES Code : | BrC1=CN=CC(OCC2=CC=CC=C2)=C1 |
MDL No. : | MFCD07375004 |
InChI Key : | YSHKYZAWTWKQKK-UHFFFAOYSA-N |
Pubchem ID : | 15389198 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.08 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 62.92 |
TPSA ? Topological Polar Surface Area: Calculated from |
22.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.66 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.01 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.27 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.43 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.52 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.98 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.77 |
Solubility | 0.0451 mg/ml ; 0.000171 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.14 |
Solubility | 0.192 mg/ml ; 0.000726 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.54 |
Solubility | 0.00076 mg/ml ; 0.00000288 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 |
-5.77 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.09 |
* 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 |
---|---|---|
With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 80℃; for 3.5h;Inert atmosphere; | A flask is charged with θ-chloro-i-Boc-indole^-boronic acid (0.839 g, 2.83 mmol), 1- benzyloxy-3-bromo-pyridine (0.500 g, 1.89 mmol), potassium phosphate (1.2 g, 5.67 mmol) and DMF (5 ml_). The flask is evacuated and filled with nitrogen thrice and Pd(PPh3)4 (0.164 g, 0.141 mmol) is added. The flask is evacuated and filled with nitrogen thrice again, and heated to 80 C for 3.5 h. The mixture is then diluted with ethyl acetate and washed with water thrice. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is redissolved in DCM (1 ml_) and trifluoroacetic acid (2 ml.) is added. After 1 h, 4M aqueous NaOH is added and following extraction with DCM, the organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by silica gel flash chromatography (heptane- ethyl acetate, 1 :1) to afford 2-(3-benzyloxy-phenyl)-6-chloro-1 H-indole as a yellow solid. MS (ESI) m/z 335.07 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | Isopropylmagnesium chloride (2 M in THF, 7.63 mL, 15.26 mmol) was added dropwise to a solution of 3-(benzyloxy)-5-bromopyridine (3.10 g, 1 1.74 mmol) in THF (20 mL) at 0 °C. The mixture was stirred at rt for 90 min and a solution of 2-chloro-A/-methoxy-/V-methyl- acetamide (1.78 g, 12.9 mmol) in THF (20 mL) was added dropwise. The mixure was stirred at rt for 1 h. NH4CI (aq, 10 percent) was added and the mixture was extracted with Et20. The combined extracts were washed with brine, dried (Na2S04) and concentrated. The residue was purified by chromatography to give the sub-title compound (1.00 g, 3.82 mmol, 33 percent). |
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