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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
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Structure of 5335-40-0
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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. : | 5335-40-0 |
Formula : | C7H7ClO4S2 |
M.W : | 254.71 |
SMILES Code : | O=S(C1=CC=CC(S(=O)(C)=O)=C1)(Cl)=O |
MDL No. : | MFCD04037968 |
InChI Key : | CQEFJGDLGWJIRV-UHFFFAOYSA-N |
Pubchem ID : | 220330 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅲ |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 52.62 |
TPSA ? Topological Polar Surface Area: Calculated from |
85.04 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.32 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.58 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.18 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.68 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.56 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.6 |
Solubility | 0.64 mg/ml ; 0.00251 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.98 |
Solubility | 0.269 mg/ml ; 0.00106 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.25 |
Solubility | 0.142 mg/ml ; 0.000556 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 |
No |
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 |
-6.73 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 |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.35 |
* 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 |
---|---|---|
3-Methanesulfonyl-benzenesulfonyl chloride was prepared according to a previously described procedure (Tetrahedron 59 (2003) 1317-1325). 3-Methanesulfonyl- phenylamine (1 gm, 4.8 mmol) was dissolved in CH3CN (40 mL). The solution was cooled in an ice bath (0 - 5 0C) and 4 mL of acetic acid and 2 mL of concentrated HCl were added. To the mixture was added NaNO2 (397 mg, 5.76 mmol, in 3 mL water) over 10 min at 5 0C. After stirring 20 min, SO2 gas was bubbled in over 30 min (~ 200 drops) keeping the reaction mixture < 7 0C. A solution of CuCl2 (840 mg, 6.24 mmol) in water (2.5 mL) was added and the mixture was allowed to warm and stir for 16 h at RT. The mixture was concentrated in vacuo and the remaining mixture was diluted with I N HCl and extracted with EtOAc (3 x 100 mL). The combined organic layer was washed with brine, dried (MgSO4), and evaporated in vacuo to provide 1.2 gm of 3- methanesulfonyl-benzenesulfonyl chloride as a pale yellow solid. 1H-NMR (CDCl3): delta 8.62 (t, IH, J = 1.6 Hz), 8.33-8.36 (m, 2H), 7.92 (t, IH, J = 8.0 Hz), 7.28 (s, IH), and 3.18 (s, 3H). | ||
Into a 100-mL round-bottom flask, was placed a solution of <strong>[35216-39-8]3-(methylsulfonyl)benzenamine</strong>(200 mg, 1.17 mmol) in HC1 (6 M, 5 mL). This was followed by the addition of a solution ofNaNO2 (97 mg, 1.41 mmol) in water (0.5 mL) dropwise with stirring at 0C. The resultingsolution was stirred for 20 mm at 0C. The above mixture was added to a saturated solution of SO2 in AcOH (5 mL) dropwise with stirring at 0C. Then to the above was added CuC12 (157 mg, 1.17 mmol). The resulting solution was stirred for 1 h at RT and then was quenched by the addition of 10 mL of water. The resulting solution was extracted with 3x10 mL of DCM and theorganic layers combined and dried over anhydrous Na2504, then concentrated under vacuum.This resulted in 250 mg (84%) of the title compound as a light yellow solid. The crude productwas used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Reference Example 240 5-(2-Fluorophenyl)-1-[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrole-3-carbaldehyde To a solution (48 mL) of <strong>[881674-56-2]5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde</strong> (475 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 302 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (1.66 g) was added dropwise and the mixture was stirred for 30 min, [3-(methylsulfonyl)benzene]sulfonyl chloride (1.28 g) was added, and the mixture was further stirred for 15 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:3?2:3), and crystallized from diisopropyl ether· ethyl acetate mixed solvent (4:1) to give the title compound as colorless crystals (yield 576 mg, 56%). 1H-NMR(CDCl3) delta:3.03(3H,s), 6.69(1H,d,J=1.8Hz), 6.97-7.02(1H,m), 7.19-7.22(2H,m), 7.43-7.50(1H,m), 7.63-7.75(2H,m), 7.99-8.00(1H,m), 8.14(1H,d,J=1.8Hz), 8.16-8.19(1H,m), 9.91(1H,s). | |
In tetrahydrofuran; | Reference Example 240 5-(2-Fluorophenyl)-1-[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrole-3-carbaldehyde To a solution (48 mL) of <strong>[881674-56-2]5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde</strong> (475 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 302 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (1.66 g) was added dropwise and the mixture was stirred for 30 min, [3-(methylsulfonyl)benzene]sulfonyl chloride (1.28 g) was added, and the mixture was further stirred for 15 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:3?2:3), and crystallized from diisopropyl ether-ethyl acetate mixed solvent (4:1) to give the title compound as colorless crystals (yield 576 mg, 56%). 1H-NMR(CDCl3) delta:3.03(3H, s), 6.69(1H, d, J=1.8Hz), 6.97-7.02(1H, m), 7.19-7.22(2H, m), 7.43-7.50(1H, m), 7.63-7.75(2H,m),7.99-8.00(1H,m),8.14(1H,d,J=1.8Hz),8.16-8.19(1H,m),9.91(1H,s). |
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