Structure of 114780-06-2
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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. : | 114780-06-2 |
Formula : | C8H9ClN2O |
M.W : | 184.62 |
SMILES Code : | O=C(N(C)C)C1=NC=CC(Cl)=C1 |
MDL No. : | MFCD06655680 |
Boiling Point : | No data available |
InChI Key : | UIYJJRGPGYNXNE-UHFFFAOYSA-N |
Pubchem ID : | 4962252 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H319-H317 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 47.14 |
TPSA ? Topological Polar Surface Area: Calculated from |
33.2 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.73 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.27 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.44 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.84 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.4 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.33 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.02 |
Solubility | 1.75 mg/ml ; 0.00949 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.57 |
Solubility | 5.01 mg/ml ; 0.0271 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.7 |
Solubility | 0.368 mg/ml ; 0.00199 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 |
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 |
-6.52 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) |
1.48 |
* 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 |
---|---|---|
With triethylamine; In tetrahydrofuran; dichloromethane; at 0 - 20℃; | Step 1.Synthesis of 4-Chloro-pyridine-2-carboxylic acid dimethylamide: A solution of 4-chloro-pyridine-2-carbonyl chloride (1 eq) in dichloromethane was cooled to 0 C., whereupon triethylamine (2 eq) was added followed by dimethylamine (2 eq, 2M solution in THF).The solution was allowed to warm to room temperature and let stir overnight.It was then washed with 1M NaOH. The separated organic layer is dried over MgSO4, filtered, and concentrated to yield the desired product. HPLC, 1.82 min; MS: MH+=185.6 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 2.Synthesis of 4-(4-Amino-3-nitro-phenoxy)-pyridine-2-carboxylic acid dimethylamide: A mixture containing 4-amino-3-nitrophenol (1 eq) and potassium bis(trimethylsilyl)amide (2 eq) was stirred in dimethylformamide for 2 hours at room temperature.To this mixture was added <strong>[114780-06-2]4-Chloro-pyridine-2-carboxylic acid dimethylamide</strong> (1 eq) and potassium carbonate (1.2 eq) and then it was stirred at 90 C. for 3 days.The reaction mixture was then concentrated before partitioning between ethyl acetate and water.The organic layer was separated, washed with brine, dried, filtered and concentrated in vacuum to give brown solid.Purification by flash chromatography with ethyl acetate and hexane (1:1) gave the desired product as a yellow syrup. HPLC, 1.69 min; MS: MH+=303.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In tetrahydrofuran; at 0 - 20℃; for 5h;Inert atmosphere; | [0136] The acid chloride 2 (500 mg, 2.87 mmol) was added portion wise to dimethylamine (2.0 M) in tetrahydrofuran (100 mL) at 0 00 under argon. The mixture was stirred at 0 00 for 1 hour then at room temperature for 4 hours, concentrated to near dryness, and dissolved in ethyl acetate (50 mL). The organics were washed with brine, dried over sodium sulfate, and concentrated. The crude reaction mixture was purified by column chromatography (dichloromethane/methanol) to provide the 4-chloro-N,N- dimethylpyridine-2-carboxamide 3b (459 mg, 2.7 mmol, 94%) as a yellow, crystalline solid. 1H NMR (DMSO-d6, 400 MHz): d 2.83 (5, 6H); 7.71 (dd, J = 2.2, 5.1 Hz, 1H); 8.02 (d, J = 2.2, 1H); 8.65 (d, J = 5.1 Hz, 1H); MS (APOI+, Mi-i) 184.68. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70%; 69% | [0137] A solution of 4-aminophenol (256 mg, 2.35 mmol) in dry N,Ndimethylformamide (40 mL) was treated with potassium tert-butoxide (274 mg, 2.44 mmol), and the reddish-brown mixture was stirred at room temperature for 1 hour. The contents were treated with 3a and 3b (400 mg, 2.35 mmol) and potassium carbonate (974 mg, 7.05 mmol) and then heated to 80 C under argon for 4 h. The mixture was cooled to room temperature and poured into ethyl acetate (100 mL) and brine (400 mL). The combined organics were washed with brine, dried over sodium sulfate, and concentrated. The crude reaction mixture was purified by column chromatography (dichloromethane/methanol) to afford the desired 4-(4-aminophenoxy)-N- methylpyridine-2-carboxamide 4a (400 mg, 1 .65 mmol, 70%) and 4-(4- aminophenoxy)-N,N-dimethylpyridine-2-carboxamide (69%) 4b after column as a light-brown solid. |