Structure of 1122-72-1
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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. : | 1122-72-1 |
Formula : | C7H7NO |
M.W : | 121.14 |
SMILES Code : | O=CC1=NC(C)=CC=C1 |
MDL No. : | MFCD00006291 |
InChI Key : | AHISYUZBWDSPQL-UHFFFAOYSA-N |
Pubchem ID : | 70737 |
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 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 34.59 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.96 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.07 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.05 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.2 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.13 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.96 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.08 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.68 |
Solubility | 2.53 mg/ml ; 0.0209 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.27 |
Solubility | 6.51 mg/ml ; 0.0537 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.31 |
Solubility | 0.589 mg/ml ; 0.00486 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) |
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 |
-6.29 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) |
1.01 |
* 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 sodium sulfate; In methanol; at 20℃; for 24h;Inert atmosphere; | General procedure: To a solution of (S)-2-aminomethyl-1-N-Cbz-pyrrolidine (1.17g, 5mmol) and pyridine-2-carboxaldehyde (0.535g, 5mmol) in methanol was added some anhydrous Na2SO4, and the reaction mixture was stirred at room temperature for 24 hours, then the mixture was filtered and washed with methanol. Subsequently, NaBH4 (0.756g, 4eq) in small portions were added into the combined filtrates and the resulting mixture was stirring for 12 hours at room temperature before adding enough water to quench the reaction. After evaporation of all volatiles under reduced pressure, the aqueous layer was further extracted with CH2Cl2, the combined organic layers were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to give yellow oil of 2a. (1.51g, 93% yield for two steps).1H NMR (CDCl3, 400 MHz): delta 8.44 (s, 1H), 7.60-7.40 (m, 1H), 7.38-7.15 (m, 6H), 7.14-7.00 (m, 1H), 5.03 (dd, J = 18Hz, 12.4 Hz, 2H), 4.15-3.61 (m, 3H), 3.44-3.25( m, 2H), 2.94-2.66 (m, 1H), 2.64-2.42 (m, 1H), 2.28 (s, 1H), 1.98-1.68 (m, 4H). 13C NMR (100 MHz, CDCl3): delta 158.69, 154.31, 148.21, 135.93, 135.38, 127.41, 126.94, 126.85, 126.76, 121.13, 121.05, 120.86, 65.74, 56.79, 54.15, 51.51, 45.89, 28.67, 22.82. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With chitosan; In neat (no solvent); at 75℃; for 0.1h;Microwave irradiation; Green chemistry; | General procedure: An equimolar mixture of <strong>[54396-44-0]2-methyl-3-(trifluoromethyl)aniline</strong> (0.351 g, 0.002 mol), corresponding aldehyde (0.002 mol), dimethyl phosphite (0.18 ml, 0.002 mol) and chitosan catalyst (10 molpercent) were taken in a reaction glass tube, degassed for 10 min and microwave irradiated at 180 W for 2 min at 60 °C. The progress of the reaction was monitored by TLC using petroleum ether and ethyl acetate (3:7) as solvent. After completion of the reaction, the mixture was diluted with ethyl acetate, washed with water (2 x 15 ml) followed by brine (1 x 10 ml), dried over Na2SO4 and evaporated to dryness. The crude mass was purified by column chromatography on silicagel (100-200 mesh) by using a 7:3 mixture of ethyl acetate in hexane to afford the pure alpha-aminophosphonates. |
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