Structure of 65195-35-9
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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. : | 65195-35-9 |
Formula : | C7H9N3O2 |
M.W : | 167.17 |
SMILES Code : | O=C(C1=CN=CN=C1N)OCC |
MDL No. : | MFCD01028678 |
InChI Key : | OBBDJDIJXFWRJK-UHFFFAOYSA-N |
Pubchem ID : | 12454717 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 42.52 |
TPSA ? Topological Polar Surface Area: Calculated from |
78.1 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.56 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.63 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.24 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.27 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.32 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.49 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.45 |
Solubility | 6.0 mg/ml ; 0.0359 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.85 |
Solubility | 2.39 mg/ml ; 0.0143 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.77 |
Solubility | 2.86 mg/ml ; 0.0171 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 |
-6.87 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) |
1.64 |
* 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 |
---|---|---|
59% | for 2h;Heating / reflux; | Compound 21 (0.72 g, 4.3 mmol) was mixed with 8 mL of acetic anhydride and the reaction mixture was stirred under reflux for 2 h until no starting material was observed by TLC (4:1 EtOAc/hexanes). The reaction mixture was concentrated in vacuo and the product was purified by flash chromatography (CH2Cl21EtOAc) to yield 0.53 g of compound 22 in 59% yield. |
59% | for 2h;Reflux; | Ethyl 4-acetamidopyrimidine-5-carboxylate (22): Compound 21 (0.72 g, 4.3 mmol) was mixed with 8 mL of acetic anhydride and the reaction mixture was stirred under reflux for 2 h until no starting material was observed by TLC (4:1 EtOAc/hexanes). The reaction mixture was concentrated in vacuo and the product was purified by flash chromatography (CH2Cl2/EtOAc) to yield 0.53 g of compound 22 in 59% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sulfuric acid; for 72h;Heating / reflux; | Compound 20 (1.0 g, 7.2 mmol) was mixed with 15 mL of EtOH and 1 mL of H2SO4 (conc.). The suspension was left stirring under reflux conditions for 72 h. The solvent was removed under reduced pressure and the residue was poured over ice, stirred for 1 h and neutralized with Na2CO3 (sat.). The product was extracted into CHCl3 (3×70 mL) and combined organic layers were washed with brine and dried over Na2SO4. Concentration under reduced pressure gave 0.76 g of compound 21 in 63% yield. |
63% | With sulfuric acid; for 72h;Reflux; | Ethyl 4-aminopyrimidine-5-carboxylate (21): Compound 20 (1.0 g, 7.2 mmol) was mixed with 15 mL of EtOH and 1 mL of H2SO4 (conc.). The suspension was left stirring under reflux conditions for 72 h. The solvent was removed under reduced pressure and the residue was poured over ice, stirred for 1 h and neutralized with Na2CO3 (sat.). The product was extracted into CHCl3 (3×70 mL) and combined organic layers were washed with brine and dried over Na2SO4. Concentration under reduced pressure gave 0.76 g of compound 21 in 63% yield. |
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