Structure of 39093-93-1
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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. : | 39093-93-1 |
Formula : | C4H9NO2S |
M.W : | 135.18 |
SMILES Code : | O=S1(CCNCC1)=O |
MDL No. : | MFCD05861623 |
InChI Key : | NDOVLWQBFFJETK-UHFFFAOYSA-N |
Pubchem ID : | 6484228 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 34.91 |
TPSA ? Topological Polar Surface Area: Calculated from |
54.55 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.79 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-1.05 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.3 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.41 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.21 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.02 |
Solubility | 130.0 mg/ml ; 0.962 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
0.39 |
Solubility | 334.0 mg/ml ; 2.47 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.93 |
Solubility | 15.7 mg/ml ; 0.116 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) |
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 |
-7.87 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 |
2.0 |
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) |
1.94 |
* 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 |
---|---|---|
With 1-methyl-pyrrolidin-2-one; N-ethyl-N,N-diisopropylamine; at 135℃; for 27.0h; | (1) A mixture of <strong>[79055-52-0]2,4-dibromo-6-methylpyridine</strong> (0.50 g), thiomorpholine 1,1-dioxide (0.32 g), N,N-diisopropylethylamine (0.70 mL), and N-methylpyrrolidone (2.0 mL) was stirred at 135C for 27 h. The reaction mixture was cooled to room temperature, followed by addition of water, and the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, then the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate = 1:1 - ethyl acetate) to obtain 4-(2-bromo-6-methylpyridin-4-yl)thiomorpholine 1,1-oxide (0.11 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In water; at 100℃; for 16h;Inert atmosphere; | [1357] 4-(1,1-dioxidothiomorpholino)benzaldehyde : To a solution of 4-fluorobenzaldehyde (0.4 g, 3.22 mmol, 1.0 eq.) and thiomorpholine 1,1-dioxide (0.65 g, 4.83 mmol, 1.5 eq.) in water (20.0 mL) was added K2CO3 (0.67 g, 4.83 mmol, 1.5 eq.). The mixture was stirred at 100C. for 16 h under N2 atmosphere. TLC (30% EtOAc in hexane) showed the reaction was completed. The reaction was cooled to room temperature and was extracted with EtOAc (2100 mL). The organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure to get the crude. The crude product was purified by flash column chromatography using 25-30% EtOAc in hexane as an eluent to give 4-(1,1-dioxidothiomorpholino)benzaldehyde. LC-MS (m/z)=240.1[M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.12 (s, 4H), 3.95 (s, 4H), 7.14 (d, J=8.8 Hz, 2H), 7.74 (d, J=8.8 Hz, 2H), 9.74 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.56% | With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃;Inert atmosphere; Sealed tube; | Methyl 4-bromo-2,6-dichloro-benzoate (70 mg, 246.54 umol), 1,4-thiazinanel,1-dioxide hydrochloride (50.78 mg, 295.84 umol), diacetoxypalladium (2.77 mg, 12.33 umol), binap (9.21 mg, 14.79 umol), Cesium carbonate (240.98 mg, 739.61 umol) in toluene (5 mL) was added to a nitrogen-filled sealed tube, and the subsequent reaction mixture was stirred at 100 C. overnight, TLC showed that the starting material was consumed, then the reaction mixture was diluted with DCM, and filtered to collect the filtrate. The crude material was purified by silica gel column (PE:EA=4:1) to afford methyl 2,6-dichloro-4-(1,1-dioxo-1,4-thiazinan-4-yl)benzoate (63 mg, 186.28 umol, 75.56% yield) LC-MS (Agilent LCMS 1260-6120, Column: Waters X-Bridge C18 (50 mm*4.6 mm*3.5 μm); Column Temperature: 40 C.; Flow Rate: 1.5 mL/min; Mobile Phase: from 95% [water+10 MmNH4HCO3] and 5% [CH3CN] to 5% [water+10 MmNH4HCO3] and 95% [CH3CN] in 2 min, then under this condition for 2 min. Purity is 100%. Rt=2.362 min; MS Calcd.: 337.0; MS Found: 337.8 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 6.80 (s, 2H), 3.95 (s, 3H), 3.92-3.85 (m, 4H), 3.13-3.05 (m, 4H). |
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