Structure of 424792-57-4
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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. : | 424792-57-4 |
Formula : | C7H6F2O2S |
M.W : | 192.18 |
SMILES Code : | FC1=C(C=C(C=C1)[S](=O)(=O)C)F |
MDL No. : | MFCD04037934 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 39.45 |
TPSA ? Topological Polar Surface Area: Calculated from |
42.52 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.39 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.66 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.29 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.38 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.98 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.14 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.38 |
Solubility | 0.799 mg/ml ; 0.00416 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.17 |
Solubility | 1.31 mg/ml ; 0.00681 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.27 |
Solubility | 0.103 mg/ml ; 0.000536 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 |
-6.29 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 |
0.55 |
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) |
1.98 |
* 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 |
---|---|---|
94% | With potassium hydroxide; In water; for 3.0h;Heating / reflux; | 2. Preparation of 2-Fluoro- 1 -methoxy-4-(methylsulfonyl)benzene 2009330; Carried out over two equal batches. A solution of 85% potassium hydroxide (824 g, 12.51 mol) in methanol (5 L) was added in 500 niL portions over a period of 2 h to a refluxing solution of l,2-difluoro-4-(methylsulfonyl)benzene 2008101 (2.00 kg, 10.4 mol) in methanol (5 L). Upon complete addition, the reaction mixture was heated at reflux for a further 1 h before being allowed to cool to room temperature. The mixture was then concentrated under reduced pressure and water (10 L) was added to the residue. The resultant precipitate was collected by filtration, washed with water (5 L) and dried to give 2-fluoro-l-methoxy-4-(methylsulfonyl)benzene 2009330 (2.0 kg, 94%) as a white solid, mp 98-1010C. 1H NMR (300 MHz, CDCl3) δ 3.05 (s, 3H), 3.96 (s, 3H), 7.09 (app t, IH), 7.63 (dd, IH), 7.70 (dd, IH). |
85% | With potassium hydroxide; for 1.33333h;Reflux; | Step 2: 2-Fluoro-4-methanesulfonyl-1-methoxy-benzene; A solution of potassium hydroxide (85%; 824 mg, 12.5 mmol) in methanol (5 mL) was added to a refluxing solution of 1,2-difluoro-4-methanesulfonyl-benzene (2.00 g, 10.4 mmol) in methanol (10 mL) over 20 min. The resulting mixture was heated at reflux for 1 h and then cooled to room temperature. The solvent was evaporated, water was added, and the resulting precipitate was filtered off, washed with water, and dried in vacuo to give 2-fluoro-4-methanesulfonyl-1-methoxy-benzene (1.8 g, 85%) as a white solid which was used directly in the next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 120℃; | Intermediate 641 -(2-Fluoro-4-methanesulfonylphenyl)-1 H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong>A mixture of 1 H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong> (500 mg), 1 ,2-difluoro-4- methanesulfonylbenzene (1 .2 g), and N,N-diisopropyl-ethyl-amine (4 mL) in N,N- dimethylformamide (6 mL) is heated to 120 °C overnight. The crude product is purified by HPLC. LC (method 20): tR = 1 .69 min; Mass spectrum (APCI): m/z = 285 [M+H]+. | |
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 120℃; | 1-(2-Fluoro-4-methanesulfonylphenyl)-1H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong> A mixture of 1H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong> (500 mg), 1,2-difluoro-4-methanesulfonylbenzene (1.2 g), and N,N-diisopropyl-ethyl-amine (4 mL) in N,N-dimethylformamide (6 mL) is heated to 120° C. overnight. The crude product is purified by HPLC. LC (method 20): tR=1.69 min; Mass spectrum (APCI): m/z=285 [M+H]+. |
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