Structure of 3073-77-6
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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. : | 3073-77-6 |
Formula : | C4H4N4O2 |
M.W : | 140.10 |
SMILES Code : | C1=C(C=NC(=N1)N)[N+]([O-])=O |
MDL No. : | MFCD00006103 |
InChI Key : | SSHFCFRJYJIJDV-UHFFFAOYSA-N |
Pubchem ID : | 76490 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 35.26 |
TPSA ? Topological Polar Surface Area: Calculated from |
97.62 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.48 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.32 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.03 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.75 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-1.77 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.68 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.89 |
Solubility | 18.3 mg/ml ; 0.13 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.27 |
Solubility | 7.54 mg/ml ; 0.0538 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.65 |
Solubility | 31.5 mg/ml ; 0.225 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 |
-7.38 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 |
2.0 |
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 |
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) |
1.82 |
* 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 |
---|---|---|
95% | With potassium tert-butylate;palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 18h; | Example 16. f4-(4-MethvI-piperazine-l-suIfonvI)-phenvIl-(5-nitro-pyrimidin-2-yl)- amine (11); [0146] 5-Nitro-pyrimidin-2-ylamine (1.78 mmol, 1.0 equiv), l-(4-bromo- benzenesulfonyl)-4-methyl-piperazine (2.68 mmol, 1.5 equiv), Pd(OAc)2 (0.089mmol, 0.05eq), Xantphos (0.178 mmol, 0.1 equiv) and potassium-t-butoxide (3.56 mmol, 2.0 equiv) were suspended in 15 mL of dioxane and refluxed at 100C under an argon atmosphere for 18 h. The mixture was allowed to cool to room temperature, filtered and washed with DCM. The filtrate was concentrated under reduced pressure and a silica plug was run to purify material (5% MeOH/DCM) to afford the title compound as a pale yellow solid (758 mg, 95%). MS (ES+): m/z = 379 (M+H)+. LC retention time: 1.76 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With potassium tert-butylate;palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; for 15h;Heating / reflux; | Example 128. 2-{4-f2-MethvI-6-(5-nitro-pyrimidin-2-ylaminoVpyrimidm-4-yll- piperazin-l-yl}-etlianol (72); [0308] A mixture of 5-nitro-pyrimidin-2-ylamine (0.45 g, 3.2 mmol), compound 71 described in Example 127 (1.0 g, 3.9 mmol), Pd(OAc)2 (50 mg, 0.22 mmol), Xantphos (0.26 g, 0.45 mmol) and potassium tert-butoxide (0.72 g, 6.4 mmol) were suspended in dioxane (15 niL) and heated at reflux under the argon atmosphere for 15 h. The mixture was allowed to cool to room temperature, filtered and washed with DCM. The filtered solid was washed with water and DCM to afford the title compound (0.60 g, 52%), which was used in the next step without further purification. MS (ES+): m/z 361 (M+H)+. |
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