Structure of 59674-85-0
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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. : | 59674-85-0 |
Formula : | C8H7N3O2 |
M.W : | 177.16 |
SMILES Code : | O=C(N1)NC2=C(C=CC(N)=C2)C1=O |
MDL No. : | MFCD13191696 |
InChI Key : | YJVIGCMCVAFCCB-UHFFFAOYSA-N |
Pubchem ID : | 401837 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 49.59 |
TPSA ? Topological Polar Surface Area: Calculated from |
91.74 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.66 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.09 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.04 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.48 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.41 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.56 |
Solubility | 4.83 mg/ml ; 0.0273 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.57 |
Solubility | 4.76 mg/ml ; 0.0268 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.78 |
Solubility | 0.293 mg/ml ; 0.00166 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) |
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 |
-7.32 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 |
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) |
1.76 |
* 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 |
---|---|---|
at 150℃; for 20.0h; | General procedure: Anthranilic acids (3, 29.1 mmol, 1 eq) and urea (582.8 mmol, 20 eq) were poured into 100 mL round bottom flask. Then, the reaction mixture was heated at 150 oC for 20 h. The reaction was monitored by TLC. After the reaction was completed, it cooled down to room temperature. Then, 60 mL water was poured and the reaction mixture was heated at 100 oC for 1 h. The reaction mixture was cooled in ice bath and the white solid was precipitated. The white solid was filtered and washed with water and hexane. The residue (4, 28.3 mmol, 97%) was dried in vacuo and used next step without further purification. The chemical yield of first reaction was usually around 90%. The compound 4 (28.3 mmol, 1 eq) was dissolved in triethylamine (56.6 mmol, 2 eq). Then, POCl3 (254.5 mmol, 9 eq) was slowly added to the reaction mixture. The reaction mixture was heated at 115 oC for 17 h. The reaction was monitored by TLC. After the completion of the reaction, the reaction solvents were evaporated with toluene several times. The residue was diluted with water and extracted with ethyl acetate several times. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude 5 (25.2 mmol) was used in next step without further purification. The crude 5 (25.2 mmol) was dissolved in 2 N NaOH solution (75.6 mmol, 38 mL, 3 eq) and was stirred at room temperature for 20 h. The reaction mixture was cooled to room temperature. Acetic acid (75.6 mmol, 3 eq) was added to the reaction mixture. The aqueous phase was extracted with ethyl acetate and the combined organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford crude 6 (19.4 mmol), which was used in next step without further purification. To a 25 mL round bottom flask were added crude 6 (0.93 mmol), anilines (7, 2.8 mmol, 3 eq), and DMF (3.1 mL). The reaction mixture was stirred at 85 oC for 16 h. The reaction mixture was cooled to room temperature and precipitates were formed. The precipitates were washed with water and hexane thoroughly. The residue (8, 0.88 mmol, 94%) was dried in vacuo. If the precipitates were not formed, the reaction mixture was purified by prep HPLC (Shim-pack PREP-ODS, H2O:CH3CN:CH3OH=40:30:30 to H2O:CH3CN:CH3OH=1:49.5:49.5, flow rate=12 mL/min, 40 oC, λ=254 nm, retention time : 30 min). The chemical yields for each final products are described below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; trichlorophosphate; at 115℃; for 17.0h; | General procedure: Anthranilic acids (3, 29.1 mmol, 1 eq) and urea (582.8 mmol, 20 eq) were poured into 100 mL round bottom flask. Then, the reaction mixture was heated at 150 oC for 20 h. The reaction was monitored by TLC. After the reaction was completed, it cooled down to room temperature. Then, 60 mL water was poured and the reaction mixture was heated at 100 oC for 1 h. The reaction mixture was cooled in ice bath and the white solid was precipitated. The white solid was filtered and washed with water and hexane. The residue (4, 28.3 mmol, 97%) was dried in vacuo and used next step without further purification. The chemical yield of first reaction was usually around 90%. The compound 4 (28.3 mmol, 1 eq) was dissolved in triethylamine (56.6 mmol, 2 eq). Then, POCl3 (254.5 mmol, 9 eq) was slowly added to the reaction mixture. The reaction mixture was heated at 115 oC for 17 h. The reaction was monitored by TLC. After the completion of the reaction, the reaction solvents were evaporated with toluene several times. The residue was diluted with water and extracted with ethyl acetate several times. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude 5 (25.2 mmol) was used in next step without further purification. The crude 5 (25.2 mmol) was dissolved in 2 N NaOH solution (75.6 mmol, 38 mL, 3 eq) and was stirred at room temperature for 20 h. The reaction mixture was cooled to room temperature. Acetic acid (75.6 mmol, 3 eq) was added to the reaction mixture. The aqueous phase was extracted with ethyl acetate and the combined organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford crude 6 (19.4 mmol), which was used in next step without further purification. To a 25 mL round bottom flask were added crude 6 (0.93 mmol), anilines (7, 2.8 mmol, 3 eq), and DMF (3.1 mL). The reaction mixture was stirred at 85 oC for 16 h. The reaction mixture was cooled to room temperature and precipitates were formed. The precipitates were washed with water and hexane thoroughly. The residue (8, 0.88 mmol, 94%) was dried in vacuo. If the precipitates were not formed, the reaction mixture was purified by prep HPLC (Shim-pack PREP-ODS, H2O:CH3CN:CH3OH=40:30:30 to H2O:CH3CN:CH3OH=1:49.5:49.5, flow rate=12 mL/min, 40 oC, λ=254 nm, retention time : 30 min). The chemical yields for each final products are described below. |
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