Structure of 15400-58-5
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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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CAS No. : | 15400-58-5 |
Formula : | C8H10N2O4 |
M.W : | 198.18 |
SMILES Code : | COC1=NC=C(C(=N1)OC)C(=O)OC |
MDL No. : | MFCD11617311 |
InChI Key : | HDQHTPWKNFCTDN-UHFFFAOYSA-N |
Pubchem ID : | 15050416 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.38 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 46.3 |
TPSA ? Topological Polar Surface Area: Calculated from |
70.54 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.22 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.66 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.28 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.08 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.73 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.76 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.54 |
Solubility | 5.75 mg/ml ; 0.029 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.72 |
Solubility | 3.8 mg/ml ; 0.0192 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.99 |
Solubility | 2.03 mg/ml ; 0.0103 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 |
-7.04 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) |
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 |
---|---|---|
To a suspension of Sodium hydride (120 mg, 3.00 mmol) in THF (15 mL) activated molecular sieves (0.3 nm, beads about 2 mm) were added. Then, N- hydroxyethanimidamide (commercially available from ABCR, 222 mg, 3.00 mmol) dissolved in THF (8 mL) was added.After 15 min. Methyl 2,4-bis(methyloxy)-5-pyrimidinecarboxylate (Prep32, 540 mg, 2.72 mmol) dissolved in THF (12 mL) was added. After 10 min. N,N-Dimethylformamide (DMF) (7.00 mL) was added and the reaction mixture was stirred at 60 0C for 4 h. The reaction mixture was filtered and concentrated under reduced pressure to obtain a red oil (195mg).The residue was dissolved in HCI 4M in dioxane (15mL, psiOmmol) and heated at 9OC for2h. Solvents were evaporated under vaccum to obtain 170mg of the title compound as brown solid. MS (ES) (mlz): 196.12 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a suspension of 2,4-Bis(methyloxy)-5-pyrimidinecarboxylic acid (Prep31 , 1.000 g, 5.43 mmol) in N,N-Dimethylformamide (DMF) (35 ml.) at 0 0C N,N'-Carbonyldiimidazole (1.321 g, 8.15 mmol) was added and the mixture was stirred for 1 hour at 0 0C, then left stirring at rt. After 4 h Triethylamine (2.271 ml_, 16.29 mmol) and N,N'-Carbonyldiimidazole (1.321 g, 8.15 mmol), were added to the white suspension. After other 4 h, N, N'- Carbonyldiimidazole (1.321 g, 8.15 mmol) of another batch was added to the suspension. The reaction was left overnight at rt. The solution was then concentrated in vacuo and methanol was added. The solution was stirred at reflux for 2 h. Then the mixture was evaporated in vacuo, the residue was dissolved in DCM and washed with NaHCC>3 sat. sol. and then with H2O. Organic phase was dried with Na2SO4 anhydrous, filtered and evaporated in vacuo to obtain 550 mg of the title compound, which was used in the following step whitout further purification. MS (ES) {mlz): 199.2 [M+H]+. |
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