Structure of 18595-18-1
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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. : | 18595-18-1 |
Formula : | C9H11NO2 |
M.W : | 165.19 |
SMILES Code : | C1=C(C(=CC=C1C(OC)=O)C)N |
MDL No. : | MFCD00025206 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | 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 | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 47.09 |
TPSA ? Topological Polar Surface Area: Calculated from |
52.32 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.86 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.67 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.37 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.64 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.44 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.4 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.52 |
Solubility | 4.94 mg/ml ; 0.0299 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.35 |
Solubility | 7.46 mg/ml ; 0.0452 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.49 |
Solubility | 0.531 mg/ml ; 0.00321 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 |
-6.83 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) |
1.29 |
* 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 |
---|---|---|
Intermediate 1 B Methyl 3-(7-bromoimidazo[1 ,2-a]pyridine-3-carboxamido)-4- methylbenzoateA mixture comprising 7-bromoimidazo[1 ,2-a]pyridine-3-carboxylic acid (Intermediate 1 A step 3) (750 mg, 3.1 1 mmol) and thionyl chloride (5 ml, 68.5 mmol) under N2 was heated at reflux for 2hrs. The mixture was concentrated in vacuo and azeotroped with toluene. Methyl 3-amino-4-methylbenzoate (514 mg, 3.1 1 mmol) (pre-dried at 45C) was added followed by pyridine (5 ml) and the mixture was stirred at room temperature under N2 overnight. The reaction mixture was diluted with EtOAc and washed with sat. NaHC03, brine, H20, dried (MgS04) and concentrated in vacuo. Purification by chromatography on silica eluting with 50-100% EtOAc in iso-hexane afforded the title compound as an orange solid;LC-MS: Rt 0.94 mins; MS m/z 390/391/392 {M+H}+; Method 2minl_C_v0031 H NMR (400MHz, DMSO-d6) δ 10.0 (1 H, s), 9.4 (1 H, d), 8.6 (1 H, s), 8.2 (1 H, d), 8.0(1 H, d), 7.8 (1 H, d), 7.5 (1 H, d), 7.3 (1 H, d), 3.9 (3H, s), 2.4 (3H, s |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 16.0h; | To a stirred solution of I (1.0 g, 4.9 mmol) in DMF (2 mL) was added HATU (2.3g, 6.1 mmol),DIPEA (1.6 mL, 9 mmol) and II (0.808 g, 4.9 mmol). The reaction mixture was allowed to stir at RT for16 h. Reaction was then diluted with water and extracted with ethyl acetate (50 mL x 3). Brine washingwas given to the organic layer and dried over Na2SO4. Combined organic layers were concentrated undervacuum and purified by using normal phase silica column chromatography to obtain III (0.815 g, 47%).LCMS: 352 [M+1]+ |
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