Structure of 799293-85-9
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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. : | 799293-85-9 |
Formula : | C7H5BrN2S |
M.W : | 229.10 |
SMILES Code : | NC1=NC=CC2=C1C(Br)=CS2 |
MDL No. : | MFCD08275115 |
InChI Key : | NRVPVUKWJYSNTO-UHFFFAOYSA-N |
Pubchem ID : | 18450797 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 51.72 |
TPSA ? Topological Polar Surface Area: Calculated from |
67.15 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.8 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.21 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.65 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.01 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.1 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.36 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.26 |
Solubility | 0.126 mg/ml ; 0.000552 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.25 |
Solubility | 0.127 mg/ml ; 0.000556 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.47 |
Solubility | 0.0776 mg/ml ; 0.000339 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) |
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 |
-6.13 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) |
2.43 |
* 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 |
---|---|---|
EXAMPLE 543B 3-bromofuro[3,2-c]pyridin-4-amine The desired product was prepared by substituting Example 543A for 3-bromo-4-chlorothieno[3,2-c]pyridine in Example 1B. MS (ESI(+)) m/e 213, 215 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.1% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere; | General procedure: A solution of 3-bromothieno[3,2-c]pyridin-4-amine (3 g, 13 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol) and (4-phenoxyphenyl)boronic acid (3.06 g, 14.3 mmol) in toluene (20 mL) was degassed with nitrogen for 5 min followed by addition of EtOH (4 mL), H2O (2 mL) and Na2CO3 (3.5 g, 32.5 mmol) under continuous flow of nitrogen. The reaction mixture was stirred at 90 C for 2 h. The reaction mixture was cooled, filtered through Celite, diluted with water (45 mL), and extracted with (3 * 60 mL) ethyl acetate. The combined organic layers were dried over sodium sulfate and were concentrated in vacuo, the crude product was purified on a silica gel column using (20-80% ethyl acetate/hexanes) as eluent to afford 10 (4.0 g, 96%) as a white solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of 3-bromo-thieno[3,2-c]pyridin-4-ylamine (80 mg, 0.35 mmol) in DME (3.2 mL) and water (0.32 mL), CS2CO3 (342 mg, 1.05 mmol) and 2-fluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (207 mg, 0.87 mmol) were added. The mixture was sonicated for 5 minutes before adding Pd(dppf)Cl2 (20 mg) and microwave heating at 100 C for 1.5 h. The mixture was diluted with AcOEt and washed with a saturated solution of NaHC03 and brine. The organic layer was dried with Na2SO4 and evaporated to dryness. The residue was purified by flash column chromatography over silica gel eluting with DCM-MeOH 2%. 3-(3-amino-2-fluoro-phenyl)-thieno[3,2-c]pyridin-4-ylamine was so isolated (68 mg). HPLC (254 nm): Rt: 4.55 min. HRMS (ESI) calcd for G3H11 FN3S [M+H]+ 260.0652, found 260.0654. 1H NMR (500 MHz, DMSO-d6) delta ppm 5.38 (s, 4 H) 6.52 (ddd, J=7.44, 6.37, 1.45 Hz, 1 H) 6.88 (td, J=8.27, 1.60 Hz, 1 H) 6.99 (t, J=7.70 Hz, 1 H) 7.26 (d, J=5.64 Hz, 1 H) 7.51 (s, 1 H) 7.81 (d, J=5.64 Hz, 1 H). |
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