Structure of 5570-18-3
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 5570-18-3 |
Formula : | C6H8BNO2 |
M.W : | 136.94 |
SMILES Code : | NC1=CC=CC=C1B(O)O |
MDL No. : | MFCD01074645 |
Boiling Point : | No data available |
InChI Key : | DIRRKLFMHQUJCM-UHFFFAOYSA-N |
Pubchem ID : | 2773216 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 40.67 |
TPSA ? Topological Polar Surface Area: Calculated from |
66.48 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.7 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-1.04 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.36 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-1.44 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.43 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.51 |
Solubility | 4.25 mg/ml ; 0.031 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.67 |
Solubility | 2.9 mg/ml ; 0.0212 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.9 |
Solubility | 17.3 mg/ml ; 0.126 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) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.64 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 |
1.0 |
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 |
2.0 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) |
1.47 |
* 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 |
---|---|---|
39% | With [Rh(OH)(cod)]2; surfactant TPGS-750-M; potassium carbonate; In water; at 20℃; for 24h;Green chemistry; | General procedure: In a 5 mL microwave vial containing alpha,beta-unsaturated ethyl ester (100mg, 1.00equiv), boronic ester (2.00 equiv), potassium carbonate (2.00 equiv) and [RhOH(COD)]2 (0.05 equiv) was added 2% wt. TPGS-750-M solution in water (3 mL). The mixture was stirred vigorously at ambient temperature for the indicated time. The reaction mixture was then extracted with ethyl acetate. The organic phase was subsequently dried over MgSO4, filtrated and reduced under vacuum. The crude product was purified by column chromatography on silica (eluent: 0-10% methanol in dichloromethane) to yield the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); In tetrahydrofuran; water; at 60℃; for 16h;Inert atmosphere; | Degassed THF (30 ml) and water (6 ml) were added to a 250 ml flask containing <strong>[18442-22-3]7-bromochroman-4-one</strong> (5 g, 22 mmol), 2-(aminophenyl)boronic acid (3.02 g, 22 mmol), K3P04(9.35 g, 44 mmol), and chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl) [2-(2?-amino- 1,1 ?-biphenyl)jpalladium(II) (866 mg, 1.1 mmol). The mixture was placed under an argon atmosphere, and evacuated and purged with nitrogen three times. The reaction was heated at 60 C for 16 h, then cooled to room temperature and the solvent was evaporated under reduced pressure. The resulting crude product was diluted with water (50 ml), extracted with ethylacetate (x2), dried over anhydrous magnesium sulfate, filtered and concentrated under reducedpressure. The resulting residue was purified by column chromatography on silica (0-60%EtOAc/hexanes) to afford 7-(2-aminophenyl)chroman-4-one: MS ESI calcd. for C15H14N02 [M+ Hj 240, found 240. |
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