Structure of 345-18-6
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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. : | 345-18-6 |
Formula : | C6H3ClFNO2 |
M.W : | 175.54 |
SMILES Code : | C1=C(C(=CC=C1Cl)F)[N+](=O)[O-] |
MDL No. : | MFCD00069418 |
Boiling Point : | No data available |
InChI Key : | DIAWBHLTWNWYGR-UHFFFAOYSA-N |
Pubchem ID : | 67660 |
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 | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 40.23 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.82 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.46 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.39 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.81 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.9 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.77 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.87 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.77 |
Solubility | 0.297 mg/ml ; 0.00169 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.99 |
Solubility | 0.178 mg/ml ; 0.00102 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.67 |
Solubility | 0.375 mg/ml ; 0.00214 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 |
-5.67 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) |
1.79 |
* 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 |
---|---|---|
0.6 g; 1.2 g | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; | Step 5: synthesis of cis-4- [(4-chloro-2-nitrophenyl)amino] -1 -methylcyclohexanol A mixture of <strong>[233764-32-4]4-amino-1-methylcyclohexanol</strong> (2.9 g, 22.3 mmol), 4-chloro-1-fluoro-2-nitro- benzene (3.9 g, 22.3 mmol) and K2C03 (9.2 g, 66.9 mmol) in DMF (40 mL) was stined under argon at RT overnight. The resulting mixture was diluted with EA (200 mL) and then washed by saturated NH4C1 solution. The resulting organic layer was concentrated in vacuo. The residuewas purified by column chromatography on silica gel (EA: PE = 1:19 to 1:4) to afford 0.6 g of cis-4- [(4-chloro-2-nitrophenyl)amino] -1 -methylcyclohexanol, 1.2 g of trans-4- [(4-chloro-2- nitrophenyl)amino]-1-methylcyclohexanol, and 3.2 g of the mixture of cis-isomer and transisomer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.6 g; 1.2 g | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | Step 5: synthesis of cis-4-[(4-chloro-2-nitrophenyl)amino]-1-methylcyclohexanol A mixture of <strong>[233764-32-4]4-amino-1-methylcyclohexanol</strong> (2.9 g, 22.3 mmol), 4-chloro-1-fluoro-2-nitro-benzene (3.9 g, 22.3 mmol) and K2CO3 (9.2 g, 66.9 mmol) in DMF (40 mL) was stirred under argon at RT overnight. The resulting mixture was diluted with EA (200 mL) and then washed by saturated NH4Cl solution. The resulting organic layer was concentrated in vacuo. The residue was purified by column chromatography on silica gel (EA:PE=1:19 to 1:4) to afford 0.6 g of cis-4-[(4-chloro-2-nitrophenyl)amino]-1-methylcyclohexanol, 1.2 g of trans-4-[(4-chloro-2-nitrophenyl)amino]-1-methylcyclohexanol, and 3.2 g of the mixture of cis-isomer and trans-isomer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.6 g; 1.2 g; 3.2 g | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | A mixture of <strong>[233764-32-4]4-amino-1-methylcyclohexanol</strong> (2.9 g, 22.3 mmol), 4-chloro-1-fluoro-2-nitro-benzene (3.9 g, 22.3 mmol) and K2CO3 (9.2 g, 66.9 mmol) in DMF (40 mL) was stirred under argon at RT overnight. The resulting mixture was diluted with EA (200 mL) and then washed by saturated NH4Cl solution. The resulting organic layer was concentrated in vacuo. The residue was purified by column chromatography on silica gel (EA:PE=1:19 to 1:4) to afford 0.6 g of cis-4-[(4-chloro-2-nitrophenyl)amino]-1-methylcyclohexanol, 1.2 g of trans-4-[(4-chloro-2-nitrophenyl)amino]-1-methylcyclohexanol, and 3.2 g of the mixture of cis-isomer and trans-isomer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate; In N,N-dimethyl-formamide; at 140.0℃; for 0.23333299999999998h;Microwave irradiation; | Add 1 mmol of 4-bromo-1-naphthalenesulfonamide and 1.1 mmol of 2-nitro-4-chlorofluorobenzene to a reaction tube containing 1.5 mmol of anhydrous potassium carbonate and 5 mL of N,N-dimethylformamide (DMF) Medium, then cover the reaction tube cover,After microwave irradiation for 14 minutes at 140 C, it was cooled to room temperature, opened and acidified. The organic phase was extracted with ethyl acetate and dried over anhydrous sodium sulfate.The filtrate was dehydrated under reduced pressure and column chromatography.The eluent is petroleum ether and acetone. Made a yellow solid,Yield: 90%; |
With potassium carbonate; In N,N-dimethyl-formamide; at 140.0℃; for 0.2h;Microwave irradiation; | General procedure: A mixture of benzenesulfonamides (1, 1.0 mmol), halogenated nitrobenzene(2, 1.0 mmol) and K2CO3 (1.1 mmol) were dissolved in DMF in a microwave tube. Then, the reaction mixture was irradiated in a microwave apparatus at 140 C for 12 minutes. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by column chromatography on silica gel to the desired products 3. |
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