Structure of 73721-78-5
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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. : | 73721-78-5 |
Formula : | C9H8N2O5 |
M.W : | 224.17 |
SMILES Code : | O=C(O)C1=C([N+]([O-])=O)C=CC=C1NC(C)=O |
MDL No. : | MFCD08276267 |
InChI Key : | HHNTZMHFBQIQAK-UHFFFAOYSA-N |
Pubchem ID : | 153453 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.11 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 56.54 |
TPSA ? Topological Polar Surface Area: Calculated from |
112.22 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.92 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.66 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.06 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.14 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-1.29 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.3 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.66 |
Solubility | 4.91 mg/ml ; 0.0219 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.59 |
Solubility | 0.573 mg/ml ; 0.00255 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.55 |
Solubility | 6.36 mg/ml ; 0.0284 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) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.2 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 |
0.0 |
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 |
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) |
2.19 |
* 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 |
---|---|---|
35% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; at 20.0℃; for 24.0h;Inert atmosphere; | Step 3. Synthesis of rac-2-Acetamido-N-(2,6-dioxopiperidin-3-yi)-6-nitrobenzamide [00302] The starting acid (3.10 g, 13.8 mmol) was mixed with hydroxybenzotriazole (HOBt, 2.12 g of the hydrate, 13.8 mmol) and l-ethyl-3-(3-dimethylaminopropyl)- carbodiimide hydrochloride (EDC, 2.54 g, 13.3 mmol), under a nitrogen atmosphere. N,N- dimethylformamide (DMF, 21.4 mL) was added and the mixture was stirred for 30 minutes at room temperature. rac-3-Aminopiperidine-2,6-dione hydrochloride (5.01 g, 30.4 mmol) was added, followed by Nu,Nu-diisopropylethylamine (DIEA, 9.63 mL, 55.3 mmol). The reaction mixture was stirred at 20C, while monitoring by HPLC. After 24 hours, the reaction mixture showed approximately 40% conversion to the desired product containing some remaining starting acid, but no amine. Then, the reaction mixture was slowly poured into 200 mL water with vigorous stirring. After 20 minutes, a white precipitate began to form. The mixture was placed in the refrigerator for 18 hours. Then, the precipitate was isolated by filtration. The filter cake was washed with 50 mL ether, and air dried to provide the title compound (1.60 g, 4.79 mmol, 35%) as a white powder. XH NMR (300 MHz, DMSO-d6) delta 1 1.16 (s, 1H), 9.40 (s, 1H), 9.34 (d, J = 8.0 Hz, 1H), 8.53 (d, J = 7.5 Hz, 1H), 7.89 (dd, J = 8.2, 0.98 Hz, 1H), 7.66 (t, J = 8.3 Hz, 1H), 4.79 (m, 1H), 2.85(m, 1H), 2.59 (m, 1H), 2.21 (m, 1H), 2.20 (s, 3H), 2.03 (m, 1H). MS (ESI-) calc. for [Ci4H14N406-H]" 333.3, found 333.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Alkaline conditions; | Reaction of compound 1 with acetyl chloride andbase, such as Et3N, Hunig?s Base, or imidazole in eitheracetonitrile or tetrahydrofuran at either room temperature orC. provided compound la. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 2191.5h; | Acetic anhydride was selected as an acylation and dehydration reagent. Initially, compound 1 was refluxed in neat acetic anhydride (4.8 equivalents), followed by cooling and filtration to provide compound 2, which contained 5 wt % of acetic acid and was converted to an acetylated compound 1 ,2-acetamido-6-nitrobenzoic acid 1 a, over a three month period under ambient storage in a glass bottle. In order to improve the stability of compound 2, the amount of acetic anhydride was reduced to 2.2 equivalents and isopropyl acetate was used as an alternative solvent. |