Structure of 3800-06-4
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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.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 3800-06-4 |
Formula : | C13H10FNO |
M.W : | 215.22 |
SMILES Code : | NC1=C(C=CC=C1)C(=O)C1=CC=C(F)C=C1 |
MDL No. : | MFCD06658166 |
InChI Key : | FFFXIQFESQNINT-UHFFFAOYSA-N |
Pubchem ID : | 9837287 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 60.68 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.09 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.1 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.39 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.07 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.74 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.08 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.87 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.73 |
Solubility | 0.0398 mg/ml ; 0.000185 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.97 |
Solubility | 0.0229 mg/ml ; 0.000106 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.79 |
Solubility | 0.00349 mg/ml ; 0.0000162 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) |
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 |
-5.21 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 |
1.0 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) |
1.6 |
* 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 |
---|---|---|
96% | methanesulfonic acid; In isopropyl alcohol; at 80 - 87℃; for 8h; | 92 g of <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropionate</strong> and 130.3 g of 2-amino-4'-fluorobenzophenone and 58.2 g of methanesulfonic acid were added to 1100 g of 2-propanol, and 2-propanol was distilled off at 80 to 87C. After distilling off 984 g of 2-propanol over 5 hours, 6.85 g of <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropionate</strong> was added and the mixture was heated at 80C for 3 hours.. An analysis of the mixture with HPLC showed disappearance of 2-amino-4'-fluorobenzophenone as a raw material. 1100 g of toluene was added into the reaction solution, and the reaction solution was washed with 602 g of 4% aqueous solution of sodium hydroxide and then 262 g of 2% aqueous solution of sodium hydroxide.. The reaction solution was further washed with 206 g of 5% brine solution, and then dried over 21 g of anhydrous magnesium sulfate.. An analysis of the toluene solution with HPLC showed that 186.5 g of methyl 2-cyclopropyl-4-(4'-fluorophenyl)quinoline-3-carboxylate was produced (converted yield: 96%). |
Example-2Preparation of methyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylateTo the solution of 2-amino-4'-fluorobenzophenone (100 g) in methanol (500 ml) added Methyl 3-cyclopropyl-3-oxopropanoate (132 g), sulfuric acid (5 ml) and stirred for 15 minutes at 25 C. Heated the reaction mixture to 65 C. for 22 hrs. Distilled off the methanol completely under reduced pressure. Cooled the reaction mixture to 25 C., added water (500 ml) and stirred for 30 minutes. Cooled the reaction mixture to 0 C. and pH adjusted to 6.0 with sodium carbonate solution. Stirred the reaction mixture for 45 minutes at 25 C. Filtered the cake and washed with water. Spin dry the compound for 60 minutes. To this compound added methanol (150 ml) and stirred for 1 hr at 25 C. Filtered the solid and washed with methanol (50 ml). Dried the obtained solid to get the title compound.Yield: 141.6 g; MR: 123-125 C.;Purity by HPLC: 99.69% |
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