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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+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 93-11-8
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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. : | 93-11-8 |
Formula : | C10H7ClO2S |
M.W : | 226.68 |
SMILES Code : | O=S(C1=CC=C2C=CC=CC2=C1)(Cl)=O |
MDL No. : | MFCD00004087 |
InChI Key : | OPECTNGATDYLSS-UHFFFAOYSA-N |
Pubchem ID : | 7125 |
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: | Ⅱ |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 57.03 |
TPSA ? Topological Polar Surface Area: Calculated from |
42.52 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.94 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.52 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.85 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.56 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.38 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.65 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.3 |
Solubility | 0.115 mg/ml ; 0.000506 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.06 |
Solubility | 0.198 mg/ml ; 0.000873 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.62 |
Solubility | 0.00543 mg/ml ; 0.0000239 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 |
-5.89 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.9 |
* 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 |
---|---|---|
95.8% | With trichlorophosphate; In chloroform; at 90℃; for 9h; | 1) 346 g (1.5 mol) of sodium 2-naphthalenesulfonate and 770 g (5 mol) of phosphorus oxytrichloride were successively added to 2.25 mol of chloroform to obtain a reaction solution a;2) The reaction liquid a obtained in the step 1) is reacted at a temperature of 90 C for 9 hours to obtain a mixed liquid b;3) the step 2) obtained by the mixture b continued to steam out the excess of phosphorus oxychloride and chloroform, followed by washing, filtration, vacuum distillation, in 2 - naphthalene sulfonyl chloride.It was calculated that the product yield of the 2-naphthalenesulfonyl chloride was 95.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In dichloromethane; | To a solution of 2-naphthalene sulfonyl chloride (3 g, 13.23 mmol) and serine benzylester (3.07 g, 13.23 mmol) in 120 mL CH2 Cl2 was added Et3 N (5.53 mL, 13.23 mmol) at 0 C. The reaction was stirred at room temperature for 1 hr and washed with a saturated (sat.) solution of KHSO4, brine, and dried over Na2 SO4. The organic layer was concentrated in vacuo to give the naphthylsulfonamide (93%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With triethylamine; In dichloromethane; at 0 - 20℃; | 2-Naphtalenesulphonyl chloride (20.07g, 97.39mmol) was added in one portion to a solution of intermediate B (17.53g, 88.54mmol) and Et3N (24.7ml, 177.07mmol) in anhydrous DCM (270ml) at O0C under N2, giving a light brown solution which was allowed to warm to r.t. overnight. The reaction mixture was diluted with DCM (200ml) and sat. NaHCO3 (200ml). The organic phase was separated and washed with H2O (2 x 200ml), dried (Na2SO4), filtered and concentrated in vacuo to give a pale yellow oil. Trituration with TME and heptane gave a solid which was isolated by filtration and washed with heptane to give the title compound as a white solid (27.99g, 82%). LCMS purity 100%, m/z 389 [M+H]+, 1H NMR (300 MHz, CDCI3) δ: 1.35 (9H, s), 1.82 (2H, m), 1.96 (1 H, m), 3.29-3.34 (2H, m), 3.41-3.56 (2H, m), 5.12 (1 H, br s), 7.62- 7.68 (2H, m), 7.85 (1 H, m), 7.93 (1 H, d), 7.99-8.02 (2H, m), 8.47 (1 H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N-methyl-acetamide; | Step 1 Synthesis of 3-[2-(2-naphthalenesulfonylamino)ethoxy]benzonitrile: 163 mg of <strong>[120351-94-2]3-(2-aminoethoxy)benzonitrile</strong> and 0.5 ml of diisopropylethylamine were dissolved in 10 ml of dimethylformamide. A solution of 250 mg (1.1 mmol) of 2-naphthalenesulfonyl chloride in dimethylformamide was added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. The title compound was obtained by the same isolation process as that of step 1 in Example 1 with ethyl acetate as the extractant. Yield: 320 mg (0.91 mmol) (91 %) H-NMR (CDCl3) delta 3.45 (2H, dt), 4.00(2H, t), 5.05(1H, br), 6.96 (1H, s),6.97 (1H, d), 7.20 (1H, d), 7.30 (1H, t), 7.59-7.70 (2H, m), 7.82-7.98(4H, m), 8.46 (1H, s) |
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