Structure of 2365-85-7
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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. : | 2365-85-7 |
Formula : | C7H6FNO2 |
M.W : | 155.13 |
SMILES Code : | O=C(O)C1=CC=C(F)C(N)=C1 |
MDL No. : | MFCD00130055 |
InChI Key : | WFSPEVFSRUTRCN-UHFFFAOYSA-N |
Pubchem ID : | 75396 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 37.76 |
TPSA ? Topological Polar Surface Area: Calculated from |
63.32 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.95 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.41 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.53 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.32 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.92 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.03 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.03 |
Solubility | 1.46 mg/ml ; 0.00938 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.34 |
Solubility | 0.702 mg/ml ; 0.00453 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.68 |
Solubility | 3.27 mg/ml ; 0.0211 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 |
-6.25 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 |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
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) |
1.15 |
* 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 |
---|---|---|
100% | With thionyl chloride; at 0℃; for 12h;Reflux; | To a stirred solution of 3-amino-4-fluoro-benzoic acid (25 g, 161 mmol) in methanol (300 mL) was added thionyl chloride (30 mL, 403 mmol) dropewise at 0° C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3.x.100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-amino-4-fluoro-benzoic acid methyl ester (27.5 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8FNO2 (M+H)+: 170.16, observed: 169.9 |
89% | With sulfuric acid; for 20h;Reflux; | Step 1: Preparation of methyl 3-amino-4-fluorobenzoate (54) To a mixture of 3-amino-4-fluorobenzoic acid (1 g, 6.45 mmol) in MeOH (20 ml), conc. H2SO4 (0.687 ml, 12.89 mmol) was added drop wise, and the reaction was refluxed for 20 hours. After cooling to room temperature the solvent was evaporated and the residue was partitioned between aq. NaHCO3 sat. sol. and ethyl acetate; the organic phase was washed with brine, dried over Na2SO4 and evaporated to dryness affording methyl 3-amino-4-fluorobenzoate as a brown solid (0.970 g, 5.73 mmol, 89percent yield, MS/ESI+170.0 [MH]+) (43) |
290 mg | With sulfuric acid;Reflux; | 3-amino-4-fluorobenzoic acid (0.5g) was dissolved in methanol (lOml), then concentrated sulfuric acid (lml) was added. The reaction solution was heated to reflux until the reaction is complete. Then the reaction mixture was cooled down and poured into water, the pH of the resultant solution was adjusted to 8 by 2N NaOH solution. The product was extracted to EtOAc layer and the solvent was stripped off. 290mg of methyl 3-amino-4- fluorobenzoate was obtained. |
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