Structure of 22246-13-5
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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. : | 22246-13-5 |
Formula : | C9H10N2O |
M.W : | 162.19 |
SMILES Code : | O=C1NC2=C(C=C(N)C=C2)CC1 |
MDL No. : | MFCD00559318 |
InChI Key : | NFWVCYWFUIFIKU-UHFFFAOYSA-N |
Pubchem ID : | 4912759 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 50.95 |
TPSA ? Topological Polar Surface Area: Calculated from |
55.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.25 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.66 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.59 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.84 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.37 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.94 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.63 |
Solubility | 3.79 mg/ml ; 0.0234 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.39 |
Solubility | 6.55 mg/ml ; 0.0404 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.8 |
Solubility | 0.258 mg/ml ; 0.00159 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 |
-6.82 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 |
1.0 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) |
1.46 |
* 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 |
---|---|---|
14 mg; 14 mg | Example 287: Preparation of 4-(cyclopropylamino)-2-((2-oxo-l,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile and 2-(cyclopropylamino)-4-((2-oxo-l,2,3>4- tetrahydroquinolin-6-yl)amino)pyrimidine-5-carbonitrile.2,4-Dichloropyrimidine-5-carbonitrile (0.100 g, 0.575 mmol), cyclopropanamine (0.040 ml, 0.575 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.1 10 ml, 0.632 mmol) were mixed in acetonitrile (2 ml). The mixture was microwaved at 70 °C for 10 min and then concentrated. 6- amino-3,4-dihydroquinolin-2(l H)-one (0.093 g, 0.575 mmol) and acetic acid (0.035 g, 0.575 mmol) were added. The mixture was microwaved at 1 10 °C for 20 min and then concentrated. 14 mg of 4-(cyclopropylamino)-2-((2-oxo- l ,2,3,4-tetrahydroquinolin-6-yl)amino)pyrimidine-5- carbonitrile and 14 mg of 2-(cyclopropylamino)-4-((2-oxo-l ,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile were recovered after automated reverse phasechromatography (water-MeCN). MS calcd for [Ci7Hi6N60+H]+: 321.15 found 321.00. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 80℃; for 72h; | To a stirred solution of <strong>[475216-25-2]4-fluoro-N-methyl-3-nitrobenzamide</strong>2 (500 mg) in N-methyl-2- pyrrolidinone (5 ml) were added 6-amino-3,4-dihydroquinolin-2(iH)-one24 (450 mg) and N,Ndiisopropylethylamine (489 mg). The reaction mixture was heated at 80 C for 3 days. LC-MS analysis indicated that the reaction was incomplete. The reaction mixture was heated at 120 Cfor 1 day. The reaction mixture was cooled to room temperature and ethyl acetate (10 ml) and water (3 ml) were added. An orange precipitate formed. The precipitate was collected by filtration, washed with ethyl acetate, and dried in vacuo to give N-methyl-3-nitro-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)amino)benzamide as an orange solid (825 mg, 96 %). MS (ISP):341.0 ([M+H]j. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h; | Into a 40- mL vial was placed a mixture of 6-amino-7-fluoro-3,4-dihydroquinolin-2(lH)-one (180 mg, 1.00 mmol, 1.00 equiv), N,N-dimethylformamide (5 mL), <strong>[4080-54-0]3-ethylisonicotinic acid</strong> (166 mg, 1.10 mmol, 1.10 equiv), N-ethyl-N-isopropylpropan-2-amine (387 mg, 3.00 mmol, 3.00 equiv) and l-((dimethylamino)(dimethyliminio)methyl)-lH-[l,2,3]triazolo[4,5-b]pyridine 3- oxide hexafluorophosphate(V) (570 mg, 1.50 mmol, 1.50 equiv). The reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was filtered and the filtrate was purified by prep-HPLC. This resulted in 260 mg (88%) of 3-ethyl-N-(2-oxo-l,2,3,4- tetrahydroquinolin-6-yl)isonicotinamide. LC-MS (ES) [M+l]+ m/z: 296.1. Tl NMR (DMSO-i, 300 MHz) was consistent with a compound having the structure of 3-ethyl-N-(2- oxo-l,2,3,4-tetrahydroquinolin-6-yl)isonicotinamide. |
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