Structure of 116091-63-5
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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. : | 116091-63-5 |
Formula : | C10H13NO4S |
M.W : | 243.28 |
SMILES Code : | O=S(C1=CC(CC(C)=O)=CC=C1OC)(N)=O |
MDL No. : | MFCD07782136 |
InChI Key : | MQQJFLHZXQRKKJ-UHFFFAOYSA-N |
Pubchem ID : | 14179759 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 58.71 |
TPSA ? Topological Polar Surface Area: Calculated from |
94.84 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.13 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.08 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.55 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.09 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.7 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.71 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.41 |
Solubility | 9.42 mg/ml ; 0.0387 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.63 |
Solubility | 5.76 mg/ml ; 0.0237 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.84 |
Solubility | 0.352 mg/ml ; 0.00145 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 |
-7.73 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.21 |
* 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 |
---|---|---|
74% | With ammonia In tetrahydrofuran; water | Example 6 - comparative; A method of preparation of tamsulosin (II) according to the prior art in comparison with the method with included steps according to the invention 1. The method according to the prior art; 1. 1. Chlorosulfonation in two steps according to US 4,731, 478 (1988); 1.2. VII yield 40percent yield 74percent III total yield 30percent |
63 g | With ammonium hydroxide In ethyl acetate at -5 - 20℃; for 2 h; | Chlorosulfonic acid (426 g, 3.656 mol) was cooled to -10 ~ (-15) ° C. 4-methoxyphenylacetone (100 g, 0.609 mol) was added at a rate such that the temperature of the reaction mixture did not exceed 5 ° C.After addition of the whole amount of methoxyphenylacetone, the reaction mixture was allowed to warm to room temperature.The mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into a stirred mixture of ice (1500 g) and water (1600 ml).The formed crystals were filtered off and washed with cold water (200 ml).The crystals were dissolved in ethyl acetate (300 ml). Ammonia water (600 ml) was cooled to -5 ° C, and the above ethyl acetate solution was gradually added at a constant rate so that the temperature did not exceed 5 ° C.The mixture was then allowed to warm to room temperature and stirred overnight. The resulting crystals were filtered off and washed with water (200 ml) and ethanol (100 ml).The crystals of the crude product were recrystallized from ethanol to give 63 g of the title compound. |
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