Structure of 3749-51-7
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 3749-51-7 |
Formula : | C6H7NO2 |
M.W : | 125.13 |
SMILES Code : | O=C1C=C(O)C=C(C)N1 |
MDL No. : | MFCD01860849 |
InChI Key : | WKGSLYHMRQRARV-UHFFFAOYSA-N |
Pubchem ID : | 54691419 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 34.05 |
TPSA ? Topological Polar Surface Area: Calculated from |
53.09 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.12 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.06 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.39 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.49 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.58 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.07 |
Solubility | 10.6 mg/ml ; 0.0849 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.6 |
Solubility | 31.2 mg/ml ; 0.249 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.7 |
Solubility | 2.49 mg/ml ; 0.0199 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 |
-7.11 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) |
1.51 |
* 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 phosphorus(V) oxybromide; In chloroform; at 140℃; for 4.5h; | Reference Example 5: Synthesis of 2,4-dibromo-6-methylpyridine A mixture of 2,4-dihydroxy-6-methylpyridine (5.0 g) and phosphorus oxybromide (68.7 g) was stirred at 140C for 4.5 h. The reaction mixture was cooled to room temperature, followed by addition of chloroform, and then the mixture was poured into ice water. The layers were separated, and then aqueous layer was extracted with chloroform. The organic layer was washed with water and saturated aqueous sodium hydrogencarbonate and dried with anhydrous sodium sulfate, then the desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting solids were recrystallized with methanol and ethyl acetate to obtain 2,4-dibromo-6-methylpyridine (2.2 g). MS: CI+ (m/z) 250 (M++1) 1H-NMR (200 MHz, CDCl3): delta7.80-7.84 (m, 1H), 7.63-7.67 (m, 1H), 2.45 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of 4-hydroxy-6-methyl-2-oxo-l,2-dihydropyridine (3-2; 20.1 g; 161 mmol) in NMP (1.6 L) was added <strong>[327056-73-5]3-chloro-5-fluorobenzonitrile</strong> (3-1; 25 g; 161 mmol) and potassium carbonate (44.4 g; 321 mmol). The resulting solution stirred at 12O0C overnight. The reaction mixture was cooled to ambient temperature and diluted with 4 L of ice- water. The aqueous layer was acidified to pH 5 to precipitate out the product. The precipitate was collected via filtration, washed with water, and air dried. The crude solid product was triturated in 5% methanol/dichloromethane and filtered to give a solid. The solid was triturated with 1 : 1 ethyl acetate :hexane, stirred, and filtered to afford the title product as a tan solid. MS M+l = 261.0. lH NMR (CD3OD): 2.30 (s, 3H), 5.62 (s, IH), 6.05 (s, IH), 7.55 (s, IH), 7.0 (s, IH), 7.76 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium acetate; In ethanol; at 78℃; for 1h;Green chemistry; | General procedure: Isatin 1 (3 mmol), malononitrile (3 mmol), 4-hydroxy-6-methylpyridin-2(1H)-one 2 (3 mmol) were refluxed for 60 minin ethanol (5 ml) with sodium acetate (10 mol%) or in pyridine (without any catalyst). After the reaction was finished, the solid was filtered,washed with ice ethanol and dried to isolate pure products 3. For their characteristics, see Online Supplementary Materials. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium acetate; In ethanol; for 1h;Reflux; | General procedure: Aldehyde 1 (3 mmol), malononitrile (3 mmol), 4-hydroxy-6-methylpyridin-2(1H)-one (3 mmol) and AcONa (0.3 mmol) were refluxed in 5 mL of ethanol for 1 h. After the reaction was finished, the solid was filtered, washed with cold ethanol and dried to isolate pure substituted 2-amino-7-methyl-5-oxo-4-phenyl-5,6-dihydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles 2a-i. |
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