Structure of 433939-27-6
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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. : | 433939-27-6 |
Formula : | C6H4BrFO |
M.W : | 191.00 |
SMILES Code : | OC1=CC(F)=CC(Br)=C1 |
MDL No. : | MFCD07783710 |
Boiling Point : | No data available |
InChI Key : | JCPJGUPQZDEZQH-UHFFFAOYSA-N |
Pubchem ID : | 21904636 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 36.12 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.72 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.36 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.71 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.67 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.48 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.39 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.0 |
Solubility | 0.189 mg/ml ; 0.00099 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.43 |
Solubility | 0.718 mg/ml ; 0.00376 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.96 |
Solubility | 0.211 mg/ml ; 0.00111 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 |
-5.79 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 |
2.0 |
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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.42 |
* 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 |
---|---|---|
77% | With potassium carbonate; In acetonitrile; at 85℃; for 1h; | Example 15. Synthesis of 1-546-1. Into a 50-mL round-bottom flask, was placed <strong>[55876-84-1]methyl 5-(bromomethyl)picolinate</strong> (500 mg, 2.17 mmol, 1.00 equiv), 3-bromo-5-fluorophenol (440 mg, 2.30 mmol, 1.06 equiv), CH3CN (6 mL), and potassium carbonate (900 mg, 6.52 mmol, 3.00 equiv). The resulting solution was stirred for 60 min at 85°C. The mixture was concentrated under vacuum and the residue was diluted with 20 mL of H20. The resulting solution was extracted with 3x20 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 0.62 g (77percent) of methyl 5-((3-bromo-5- fluorophenoxy)methyl)picolinate as a yellow solid.LC-MS: ( + |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With potassium carbonate; In acetone; at 60℃; for 16h; | A solution of <strong>[19047-31-5]2-chloro-N-cyclopropylacetamide</strong> (2.8 g, 20.9 mmol), 3-bromo- 5-fluorophenol (4.0 g, 20.9 mmol) and K2CO3 (4.3 g, 31.4 mmol) in 40 mL of acetone was heated at 60 C for 16 h. The mixture was filtered and concentrated to give a residue, which was purified by column chromatography (PE/EA, 3/1) to give the title compound (4.3 g, 71%) as a yellow solid, m/e 288 (M+H)+. |
71% | With potassium carbonate; In acetone; at 60℃; for 16h; | Example 84 2-(3-Bromo-5-fluorophenoxy)-N-cyclopropylacetamide A solution of <strong>[19047-31-5]2-chloro-N-cyclopropylacetamide</strong> (2.8 g, 20.9 mmol), 3-bromo-5- fluorophenol (4.0 g, 20.9 mmol) and K2CO3 (4.3 g, 31.4 mmol) in 40 mL of acetone was heated at 60 C for 16 h. The mixture was filtered and concentrated to give a residue, which was purified by column chromatography (PE/EA, 3/1) to give the title compound (4.3 g, 71%) as a yellow solid, m/e 288 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With sodium hydroxide; In water; at 120℃; for 120h; | To 3-bromo-5-fluoro-phenol (9.0 g, 47 mmol), and 1-chloro-2-methyl-propan-2-ol (5.116 g, 47.12 mmol), aqueous sodium hydroxide (37.69 g, 94.24 mmol) was added and the reaction mixture was heated at 120° C. for 5 days in a pressure vessel. The reaction was cooled and then extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified on 220 g of silica gel utilizing a gradient of 0 to 10percent ethyl acetate in dichloromethane. The impure product was repurified on 220 g of gold silica gel utilizing a gradient of 0 to 10percent ethyl acetate in dichloromethane to yield 1-(3-bromo-5-fluoro-phenoxy)-2-methyl-propan-2-ol (4.75 g, 18.0 mmol, 38percent). ESI-MS m/z calc. 262.00046. found 263.0 (M+1)+. Retention time: 1.57 minutes (3 min run). |
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