Structure of 6574-97-6
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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. : | 6574-97-6 |
Formula : | C7H3Cl2N |
M.W : | 172.01 |
SMILES Code : | C1=CC=C(C(=C1C#N)Cl)Cl |
MDL No. : | MFCD00016372 |
InChI Key : | OHDYZVVLNPXKDX-UHFFFAOYSA-N |
Pubchem ID : | 736567 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-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 | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 41.18 |
TPSA ? Topological Polar Surface Area: Calculated from |
23.79 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.84 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.9 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.87 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.63 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.08 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.66 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.18 |
Solubility | 0.114 mg/ml ; 0.000665 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.06 |
Solubility | 0.15 mg/ml ; 0.000871 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.71 |
Solubility | 0.0335 mg/ml ; 0.000195 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) |
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 |
-5.29 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) |
1.58 |
* 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 |
---|---|---|
36% | With hydroxylamine hydrochloride; triethylamine; In ethanol; at 50℃; for 16h; | To a solution of <strong>[6574-97-6]2,3-<strong>[6574-97-6]dichlorobenzonitrile</strong></strong> (500 mg, 3.30 mmol) in 10 ml ethanol was added hydroxylammonium chloride (303 mg, 4.0 mmol) and triethylamine (382 mg, 4.0 mmol) and then the reaction mixture was stirred 16 h at 50 °C. After cooling to RT, the solvent was evaporated and the crude was solved in ethyl acetate and dichloromethane and extracted with water. The organic phase was dried over magnesium sulfate, filtered and evaporated under vacuum to yield the title compound (225 mg, 36 percent of theory). LC-MS (method 2B): RT = 1.66min, m/z = 205 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Examples of aromatic nitriles (I) which can be prepared by the process according to the present invention are:para-chloro-benzonitrile;meta-chloro-benzonitrile;ortho-chloro-benzonitrile;2-fluoro-benzonitrile;2,3-di-chloro-benzonitrile;3,4-di-chloro-benzonitrile;2,3,4-tri-chloro-benzonitrile;2,4,5-tri-chloro-benzonitrile;3,4,5-tri-chloro-benzonitrile;... | ||
Process according to claim 1, characterized in that the following nitriles (I) are prepared:para-chloro-benzonitrile;meta-chloro-benzonitrile;ortho-chloro-benzonitrile;2-fluoro-benzonitrile;2,3-di-chloro-benzonitrile;3,4-di-chloro-benzonitrile;2,3,4-tri-chloro-benzonitrile;2,4,5-tri-chloro-benzonitrile;3,4,5-tri-chloro-benzonitrile;... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With sodium carbonate; In methanol; | EXAMPLE 56C 3-Amino-2-carbomethoxy-7-chloro-benzthiophene The product from Example 56B (1.7 g, 10 mmol) was treated with 1 eq of methyl thioglycolate and 1 eq sodium carbonate in methanol as described in Example 41A to give after chromatography (4:1 hexane/EtOAc) the title compound in 12percent yield. 1H NMR (300 MHz, CDCl3) d 3.81 (s, 3H), 5.90 (bs, 2H), 7.34 (t, J=8 Hz, 1H), 7.48 (dd, J=8.1 Hz, 1H), 7.56 (dd, J=8,1 Hz, 1H). MS (DCI/NH3) m/e 259 (M+NH4)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In trichlorophosphate; | EXAMPLE 56B 2,3-Dichlorobenzonitrile The product from Example 56A (9.4 g, 50 mmol) in 150 mL POCl3 was heated for 2 h at 95° C. The soln was cooled and concentrated. The residue was partitioned between EtOAc and 10percent aq potassium carbonate. The layers were separated and the EtOAc layer was washed 2*50 mls with water, with brine, dried (MgSO4) and concentrated to give a 96percent yield (8.2g, m.p. 60°-61° C.) of the benzonitrile. 1H NMR (300 MHz, CDCl3 7.34 (t, J=8 Hz, 1H), 7.62 (dd, J=8,1 Hz, 1H), 7.71 (dd, J=8,1 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium fluoride; tetramethlyammonium chloride; In sulfolane; at 210℃; for 8h;Inert atmosphere; | Take dried 2L flask was refluxed for four devices, under nitrogen, into sulfolane 1200g, 280g of potassium fluoride, tetramethylammonium chloride 50g, 2,3- <strong>[6574-97-6]dichlorobenzonitrile</strong> 688g, open stirring slowly raised to 210 reaction was incubated 8h, the control sample, the end of the reaction raw material ?1percent.The reaction solution was added to a short column distillation, to give 2-fluoro-3-chlorobenzonitrile 560g, content ?99percent, yield 90percent. |