Structure of 13165-35-0
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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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CAS No. : | 13165-35-0 |
Formula : | C8H5ClN2O2 |
M.W : | 196.59 |
SMILES Code : | O=C(N1)NC2=C(C=CC(Cl)=C2)C1=O |
MDL No. : | MFCD00563867 |
InChI Key : | QEXAYZARVWHJJA-UHFFFAOYSA-N |
Pubchem ID : | 246858 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-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 | 2.0 |
Molar Refractivity | 50.2 |
TPSA ? Topological Polar Surface Area: Calculated from |
65.72 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.17 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.4 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.87 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.19 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.84 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.49 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.51 |
Solubility | 0.607 mg/ml ; 0.00309 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.38 |
Solubility | 0.812 mg/ml ; 0.00413 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.76 |
Solubility | 0.0339 mg/ml ; 0.000173 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 |
-6.51 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 |
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) |
1.61 |
* 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 |
---|---|---|
62% | Stage #1: With 2,2'-iminobis[ethanol] In water for 0.0333333 h; Autoclave Stage #2: at 100℃; for 12 h; Autoclave |
Weigh 0.763 g (5 mmol) of 2-amino-4-chlorobenzonitrile was placed in a polytetrafluoroethylene liner of a stainless steel reactor and3 mL of a diethanolamine aqueous solution having a concentration of 1.33 mol / L was added and stirred for 2 minutes , The carbon dioxide was heated and the temperature was raisedto 100 ° C, and the carbon dioxide pressure was adjusted to 1 MPa for the carboxylation reaction under stable conditions for 12 hours.Antiupon end, the reaction system was cooled to room temperature slowly released unreacted carbon dioxide, was added 10mL of deionized water and stirreddispersion product, resulting precipitate was filtered and washed with a small amount of distilled water, and then 15mL / wash three times with methyl tert-butyl ether Andthe product was dried at a temperature of 100 ° C to give the product 7-chloroquinazoline-2,4 (1H, 3H) -dione in a yield of 62percent. |
62% | With {Eu[N(SiMe3)2](μ-O:κ2-C6H5C(O)NC6H3(iPr)2)(THF)}2; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 100℃; for 24 h; | In anhydrous, anaerobic, argon protection,0.0999 g (7.5 x 10-5 mol) of {L2Eu [N (SiMe3) 2] THF} 2 was added to the reaction flask,An additional 11.2 μL (7.5 × 10 -5 mol) of DBU,Under the protection of carbon dioxide bag, add 2mL dimethyl sulfoxide,Further, 0.2949 g (1.5 x 10-3 mol) of 2-amino-4-chlorobenzonitrile was added,The reaction was stirred in a constant temperature bath at 100 ° C.After 24h, add 5mL2mol / L hydrochloric acid to quench the reaction, and then suction filtered,The solid was washed with 3 × 5 mL of hydrochloric acid, then with toluene and then with diethyl ether. The residual solvent was removed and the solid was dried to give the product in 62percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 200℃; for 1 h; | Step A: Preparation of 7-chloro-1H-quinazoline-2,4-dione. A mixture of 2-amino-4-chlorobenzoic acid (2.00 g, 11.6 mmol) and urea (2.80 g, 46.6 mmol) was heated to 200° C. for 1 h. The mixture was allowed to cool to room temperature and the resulting mass was triturated well with water. The product was collected by filtration (2.30 g, 100percent). The MS and NMR data are in agreement with those that have been previously described: Organic Process Research and Development, 2003, 7, 700-706. 1H NMR (600 MHz, DMSO-d6): 12.00 (br s, 2H), 8.59-8.53 (m, 1H), 7.93-7.80 (m, 2H). |
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