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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
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Structure of 15017-52-4
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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.
4.5
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CAS No. : | 15017-52-4 |
Formula : | C7H5BrFNO2 |
M.W : | 234.02 |
SMILES Code : | O=[N+](C1=CC(CBr)=CC=C1F)[O-] |
MDL No. : | MFCD03412241 |
Boiling Point : | No data available |
InChI Key : | OAMKMERAYXDUEW-UHFFFAOYSA-N |
Pubchem ID : | 10868208 |
GHS Pictogram: |
![]() |
Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅱ |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 48.06 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.82 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.56 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.41 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.9 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.92 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.11 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.18 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.05 |
Solubility | 0.21 mg/ml ; 0.000897 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.01 |
Solubility | 0.226 mg/ml ; 0.000968 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.32 |
Solubility | 0.112 mg/ml ; 0.000478 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 |
-6.02 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 |
3.0 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) |
1.96 |
* 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 |
---|---|---|
80% | In acetonitrile; at 20℃; for 4h; | 34A: 2-(4-fluoro-3-nitrophenyl)acetonitrile To a solution of 4-(bromomethyl)-l-fluoro-2-nitrobenzene (1 g, 4.27 mmol) in acetonitrile (5 mL) was added tetraethylammonium cyanide (0.801 g, 5.13 mmol). The resulting deep green solution was stirred at RT for 4 h. The solvent was then removed in vacuo, purification via flash chromatography gave 34A (light yellow oil, 617 mg, 3.43 mmol, 80 % yield). LC-MS Anal. Calc'd for C8H5F 2O2 180.03, did not show paretn ion, Tr = 0.74 min (Method B). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | To a solution of diethyl N-Boc-aminomalonate (1.5 g, 5.45 mmol, 1 eq) in freshly distilled DMF (20 mL) was added sodium hydride (60% in oil, 0.261 g, 1.2 eq) portionwise. Then, 4-fluoro-3-nitrobenzyl bromide (1.53 g, 1.2 eq) was added and the solution stirred at room temperature during one day. The reaction mixture was hydrolysed with 70 mL of water and extracted with 3*50 mL of CH2Cl2. The combined organic layers were dried over MgSO4 and the solvent removed under vacuum. Crude product was purified by flash chromatography on silica gel with petroleum ether/ethyl acetate (9/1) to afford the diester as yellow oil in 59 % yield (1.38 g). 1H NMR (300 MHz, CDCl3) δ 1.30 (t, 3JHH= 7.5 Hz, 6H, H2’), 1.48 (s, 9H, H14), 3.68 (s, 2H, H4), 4.17-4.37 (m, 4H, H1’), 5.76 (br s, 1H, H11), 7.20 (dd, 3JHF= 10.4 Hz, 3JHH = 8.6 Hz, 1H, H9), 7.30-7.35 (m, 1H, H6), 7.77 (dd, 3JHH =7.3, 4JHF = 2.2 Hz, 1H, H10). 13C NMR (75.5 MHz, CDCl3) δ 14.0 (C2’), 28.1 (C14), 37.2 (C4), 62.9 (C1’), 66.8 (C2), 80.8 (C13), 118.2 (d, 2JCF = 21.4 Hz, C9), 127.3 (C6), 132.6 (C5), 136.8 (d, 3JCF = 7.7 Hz, C10), 137.1 (d, 2JCF = 9.2 Hz, C7), 154.0 (C12), 154.8 (d, 1CF = 264,1 Hz, C8), 167.1 (C1+C3). 19F NMR (CDCl3) δ -119.91. HRMS (ESI) calculated for C19H25N2O8FNa [M+Na+] 451.1493; found 451.1502. IR (cm-1) ν 3436, 2981, 1730, 1713, 1538, 1157. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With 18-crown-6 ether; potassium iodide; In N,N-dimethyl-formamide; at 20℃; | A mixture of 4-(bromomethyl)-1 -fluoro-2-nitrobenzene (18 g, 76.9 mmol), KCN (10 g, 153.8 mmol), Kl (1 .3 g, 7.69 mmol) and 18-Crown-6 (10 g, 38.5 mmol) in DMF (100 mL) was stirred at r.t. overnight. The resulting mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated to give the crude product which was purified by flash chromatography (silica gel, 0-30% EtOAc in PE) to afford the title compound (6.6 g, 47% yield). LCMS (ESI) m/z calcd for C8H5FN202: 180.03. Found: 181 .37 (M+1)+. |
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