Structure of 83933-17-9
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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. : | 83933-17-9 |
Formula : | C5H4BrNOS |
M.W : | 206.06 |
SMILES Code : | O=C(C1=CC(Br)=CS1)N |
MDL No. : | MFCD09859843 |
InChI Key : | WPIFYCRDSOUHLT-UHFFFAOYSA-N |
Pubchem ID : | 12836067 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 40.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
71.33 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.4 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.5 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.61 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.94 |
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 |
1.57 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.41 |
Solubility | 0.806 mg/ml ; 0.00391 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.61 |
Solubility | 0.511 mg/ml ; 0.00248 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.11 |
Solubility | 1.58 mg/ml ; 0.00769 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 |
-6.49 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 |
---|---|---|
91% | With copper diacetate; acetonitrile In ethanol at 78℃; for 5 h; | General procedure: To a 25 mL round-bottom flask equipped with a magnetic stirrer were added aldoximes (5 mmol), copper(II) acetate (45 mg, 0.25 mmol),acetonitrile (10 mg, 0.25 mmol) and EtOH (15 mL). The mixture was stirred for 4–8 h at 78 °C or for 12 h at room temperature. After removal of the solvent, the residue was purified by column chromatography to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydroxylamine hydrochloride; caesium carbonate In water; dimethyl sulfoxide at 125℃; for 14 h; | General procedure: Aldehyde (0.5mmol), NH2OH·HCl (0.6mmol) and Cs2CO3 (0.6mmol) were stirred at 125°C for 48h in a 3:1 mixture of DMSO–H2O (2mL) under air. The progress of the reaction was monitored by TLC using ethyl acetate and hexane as eluent. After completion, the reaction mixture was cooled to room temperature and treated with water (1mL). The resulting mixture was extracted with ethyl acetate (3×5mL). Drying (Na2SO4) and evaporation of the solvent gave a residue that was purified on silica gel column chromatography using ethyl acetate and hexane. The purified products were identified by 1H NMR spectra and the melting points comparison with the literature data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2 h; Stage #2: With ammonia In water; N,N-dimethyl-formamide at 0 - 20℃; for 5 h; |
A solution of 4 bromo-thiophene-2-carbo xylic acid (2.Og, 9.66mmol), l-ethyl-3-(3'- dimethylaminopropyl)carbodiimide hydrochloride (2.04g, 10.63mmol) and 1 -hydroxybenzotriazole hydrate (1.44g, 10.63mmol) in DMF (2OmL) is stirred at room temperature for 2 hours. The reaction mixture is then cooled to O0C and aq. NH3 (ImL, 17.3mmol) is added. The mixture is stirred at room temperature for an additional 5 hours, then water is added to the reaction mixture and the resultant precipitate is collected by filtration and washed with IM NaOH, H2O and petroleum ether. The title compound is isolated as a white solid (1.56g, 78percent). |
8 g | With N-hydroxybenzotriazole ammonium salt; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile | A) 4-bromothiophene-2-carboxamide [0504] To a solution of 4-bromothiophene-2-carboxylic acid (15 g), HOBt ammonium salt (16.5 g) and triethylamine (20.08 mL) in acetonitrile (250 mL) was added EDCI hydrochloride (16.87 g), and the mixture was stirred overnight. The reaction mixture was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8.0 g). 1H NMR (300 MHz, CDCl3) δ 5.87 (2H, brs), 7.43 (2H, q, J = 1.4 Hz) |
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