Structure of 89-54-3
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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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CAS No. : | 89-54-3 |
Formula : | C7H6ClNO2 |
M.W : | 171.58 |
SMILES Code : | C1=C(N)C=CC(=C1C(O)=O)Cl |
MDL No. : | MFCD00007845 |
InChI Key : | GVCFFVPEOLCYNN-UHFFFAOYSA-N |
Pubchem ID : | 37879 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | 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 | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 42.82 |
TPSA ? Topological Polar Surface Area: Calculated from |
63.32 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.91 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.33 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.63 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.48 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.14 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.1 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.08 |
Solubility | 1.43 mg/ml ; 0.00833 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.26 |
Solubility | 0.941 mg/ml ; 0.00548 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.02 |
Solubility | 1.63 mg/ml ; 0.00948 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 |
-6.4 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 |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 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) |
1.18 |
* 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 |
---|---|---|
60% | In tetrahydrofuran; for 16h; | EXAMPLE 26. Synthesis of 2-ChJoro-5-f2-Fluoro-5-TrifluoromethyI-Benzoylamino)-Benzoic Acid (Intermediate 18)18[0162] 5-Amino-2-chIoro-benzoic acid (0.4 g, 2.32 mmol) was diluted with THF (12 mL), treated with 2-fluoro-5-trifluoromethyl-benzoyl chloride (0.388 g, 2.56 mmol) and stirred for 16h. Solvents were then removed and resulting solids were triturated with DCM. After filtration, the title compound was obtained as a white solid (0.5 g, 60%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With polyphosphoric acid; at 130℃; for 48h; | Into a 1-L round-bottom flask, was placed <strong>[3537-14-2]5-nitropyridine-2,3-diamine</strong> (30 g, 194.65 mmol, 1.00 equiv), 5-amino-2-chlorobenzoic acid (33.4 g, 194.66 mmol, 1.00 equiv), PPA (400 mL). The resulting solution was stirred for 2 days at 130 C. The reaction mixture was cooled with a water/ice bath. The resulting solution was diluted with 400 mL of ice water. The pH value of the solution was adjusted to 7 with sodium hydroxide (5%). The solids were collected by filtration and washed with 3*50 mL water. The solid was dried in an oven under reduced pressure. This resulted in 40 g (71%) of 4-chloro-3-[6-nitro-1H-imidazo[4,5-b]pyridin-2-yl]aniline (I-6) as a yellow solid. |
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