Structure of 6268-43-5
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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. : | 6268-43-5 |
Formula : | C11H10N4O |
M.W : | 214.22 |
SMILES Code : | O=C(NC1=NC=CC=C1)NC1=NC=CC=C1 |
MDL No. : | MFCD00233705 |
Boiling Point : | No data available |
InChI Key : | FOQXHWCMYZXOGZ-UHFFFAOYSA-N |
Pubchem ID : | 80445 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 60.75 |
TPSA ? Topological Polar Surface Area: Calculated from |
66.91 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.59 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.26 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.74 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.72 |
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 |
1.21 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.25 |
Solubility | 1.2 mg/ml ; 0.00558 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.26 |
Solubility | 1.17 mg/ml ; 0.00545 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.23 |
Solubility | 0.0126 mg/ml ; 0.000059 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
Yes |
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 |
-6.71 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 |
0.55 |
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) |
2.15 |
* 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% | With iron(II,III) oxide; ferric hydroxide; In para-xylene; at 140℃; for 60.0h; | 1 ,3-di(Pyridin-2-yl)urea (5a) was synthesised via the reaction of triphosgene (1 .0 g, 3.37 mmol) with 2-aminopyridine (6a) (1.576 g, 16.74 mmol) in the presence of DMAP (2.44 g, 20.01 mmol) in 0H2012(15.0 mL) at room temperature for 36 h. 5a was equally synthesised via Fe(OH)3Fe304-catalysed(0.060 g, 0.052 mmol) reaction of 2-aminopyridine (6a) (0.376 g, 4.0 mmol) with urea (3b) (0.120 g,2.0 mmol) in p-xylene at 140 00 for 2.5 days and obtained in 62% (0.266 g, 1.24 mmol) yield.26 White crystals; m.p. 175 c 130-NMR (100 MHz, DMSO-d6): : 152.4, 151.9, 147.3, 138.4, 118.1, 112.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diethylene glycol dimethyl ether; cesium fluoride; at 100℃; for 20.0h;Schlenk technique; Glovebox; | General procedure: In the glove box, add aniline (1mmol), CsF (2mol), and diglyme (3mL) to the 10ml Schlenk bottle, and replace the air with CO2. Connect the Schlenk bottle with a CO2 balloon, and then PMHS with a syringe (4.5 mmol) was poured into a reaction flask and placed in an oil bath and stirred at 100 C for 20 hours. After the reaction was completed, the temperature was lowered to room temperature, and then poured into 30 mL of H2O, and a large amount of precipitate was immediately obtained, and then a large amount of solid powder was obtained by suction filtration. The solid powder was washed with n-hexane (3 x 5 mL) to remove unreacted raw materials, and then ethyl acetate was used. (3 x 10 mL) washed the solid powder. The ethyl acetate layer was collected, dried over anhydrous magnesium sulfate, and then subjected to vacuum rotary evaporation to obtain a pure product in an isolated yield of 96%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 20℃; | General procedure: To a stirred solution of various amines (2.0 equiv.) in 5 mLdichloromethane was added bis(trichloromethyl) carbonate (0.4 equiv.) andtriethylamine (2.0 equiv.). After stirring for 3 ~ 8 h atroom temperature, the solution was concentrated under reduced pressure andthe resulting residue was purified by flash chromatography on silica gel togive 39-40, 43-45 as whitesolids (44 ~ 87% yield).1,3-bis(4-morpholino-3-(trifluoromethyl)phenyl)urea 39 (81%yield). | |
With dmap; In dichloromethane; at 20℃; for 36.0h; | 1 ,3-di(Pyridin-2-yl)urea (5a) was synthesised via the reaction of triphosgene (1 .0 g, 3.37 mmol) with 2-aminopyridine (6a) (1.576 g, 16.74 mmol) in the presence of DMAP (2.44 g, 20.01 mmol) in 0H2012(15.0 mL) at room temperature for 36 h. 5a was equally synthesised via Fe(OH)3Fe304-catalysed(0.060 g, 0.052 mmol) reaction of 2-aminopyridine (6a) (0.376 g, 4.0 mmol) with urea (3b) (0.120 g,2.0 mmol) in p-xylene at 140 00 for 2.5 days and obtained in 62% (0.266 g, 1.24 mmol) yield.26 White crystals; m.p. 175 c 130-NMR (100 MHz, DMSO-d6): : 152.4, 151.9, 147.3, 138.4, 118.1, 112.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With 1-butyl-3-methyl-1H-imidazole-2(3H)-selenone; oxygen; at 90℃; under 9750.98 Torr; for 6.0h;Ionic liquid; Autoclave; | General procedure: 5 mmol of aniline, 0.46 mmol of selenium-containing catalyst, and 0.25 g [BMIM]BF4 were sealed in a 100 mL stainless steel autoclave. The reactor was pressurized with 0.2 Mpa oxygen and 1.1 Mpa carbon monoxide and then placed in an oil bath preheated to 90 C; after 6 h of the reaction time, the apparatus was degassed, and the 1,3-diaryl urea was separated from [BMIM]BF4 by adding acetone and water to the reaction mixtures. Purification by column chromatography on silica gel or recrystallization gave the urea product. Products were identified by NMR measurements and/or comparison with authentic samples. |
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