Structure of 20712-12-3
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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. : | 20712-12-3 |
Formula : | C7H8BrNO |
M.W : | 202.05 |
SMILES Code : | OCC1=CC(Br)=CC=C1N |
MDL No. : | MFCD08234509 |
Boiling Point : | No data available |
InChI Key : | GDCWZYRWKSOYGQ-UHFFFAOYSA-N |
Pubchem ID : | 11030874 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 44.67 |
TPSA ? Topological Polar Surface Area: Calculated from |
46.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.74 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.39 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.38 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.64 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.63 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.56 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.35 |
Solubility | 0.91 mg/ml ; 0.0045 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.96 |
Solubility | 2.19 mg/ml ; 0.0108 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.73 |
Solubility | 0.381 mg/ml ; 0.00188 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) |
Yes |
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 |
-6.55 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) |
1.12 |
* 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 |
---|---|---|
83% | With potassium tert-butylate; cobalt(II) diacetate tetrahydrate; In toluene; at 110℃; for 12h;Inert atmosphere; | The reaction vessel was charged with 2-amino-5-bromobenzyl alcohol 1s (202.0 mg, 1.0 mmol), acetophenone 2a (120.2 mg, 1.0 mmol), Co(OAc)2 4H2O (19.9 mg, 0.08 mmol) and KOtBu (112.0 mg, 1.0 mmol).Under an argon atmosphere, 2 mL of toluene was added and heated at 110 C for 12 h.After cooling to room temperature, 10 mL of water was added, and the mixture was extracted with EtOAc (3 x 10 mL).The combined organic phases were concentrated under reduced pressure.The residue was then purified by flash column chromatography (petroleum ether:ethyl acetate 100:1, v/v) to give 3s as a white solid (234.9 mg, 83% yield). |
80% | With C22H24N6O2Ru(1+)*Cl(1-); potassium hexamethylsilazane; In toluene; at 110℃; for 12h;Inert atmosphere; | Add 2-amino-5-bromobenzyl alcohol 2q (201.0mg, 1.0mmol), acetophenone 3a (120.2mg, 1.0 mmol), complex 1a (10.8mg, 0.02mmol) and KHMDS (1mL, 1.0mmol). Under a nitrogen atmosphere, 2 mL of toluene was added and heated at 110 C. for 12 h. After cooling to room temperature, 10 mL of water was added, and the mixture was extracted with EtOAc (3×10 mL). The combined organic phase was concentrated under reduced pressure. The residue was then purified by flash column chromatography (petroleum ether: ethyl acetate 100:1, v/v) to obtain 4q (226 mg, 80%) as a white solid. |
With C22H24N6O2Ru(1+)*Cl(1-); potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 110℃; for 12h;Inert atmosphere; | General procedure: A mixture of 2-aminophenylmethanol (2a) (123.2 mg, 1.0 mmol),acetophenone (3a) (120.2 mg, 1.0 mmol), complex 1a (10.8 mg,0.02 mmol), and KHMDS (1.0 mL, 1.0 M in THF) in 2 mL of toluene wasstirred at 110 C for 12 h under a nitrogen atmosphere. After cooling toambient temperature, 10 mL water was added and the mixture wasextracted with EtOAc (3 × 10 mL). The combined organic layer wasdried over anhydrous Na2SO4 and concentrated under reduced pressure.The resulting residue was subjected to purification by flash columnchromatography on alumina (petroleum ether: ethyl acetate 100: 1, v/v)to afford 4a as a white solid (190.9 mg, 93% yield), which was identifiedby NMR analysis. |
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