Structure of 26510-52-1
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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. : | 26510-52-1 |
Formula : | C10H11NO3 |
M.W : | 193.20 |
SMILES Code : | O=C(OCC)CC(C1=NC=CC=C1)=O |
MDL No. : | MFCD00094022 |
InChI Key : | FQHXWZMJALFSJJ-UHFFFAOYSA-N |
Pubchem ID : | 2736461 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 50.14 |
TPSA ? Topological Polar Surface Area: Calculated from |
56.26 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.53 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.26 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.22 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.08 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.77 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.17 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.82 |
Solubility | 2.93 mg/ml ; 0.0152 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.04 |
Solubility | 1.76 mg/ml ; 0.00912 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.86 |
Solubility | 0.265 mg/ml ; 0.00137 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 |
-6.58 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) |
1.7 |
* 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 |
---|---|---|
95% | In pyridine; at 20℃; for 16h; | Ethyl picolinoylacetate (4.7 g, 24.3 mmol) and the product of Preparation 1 (5.0 g, 36.5 mmol) are mixed in 10 ML of pyridine. The reaction mixture is stirred overnight at RT and then evaporated to a solid mass. The crude mixture is purified by MPLC on silica gel (40% EtOAc/Hexanes) to give the title compound, 6.63 g (95%), as a liquid. MS ES+ m/e 276. 1 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With pyridine; at 20℃; for 20h; | B. Preparation of 3-(2-Oxo-pyrrolidin-l-ylimino)-3-(pyridin-2-yl)-propionic acid ethyl ester; Place l-aminopyrrolidin-2-one hydrochloride (Zubek, A. Z. Chem., 1969, 9(2), 58; 155.6 g, 1.14 mol) in a 3 L flask equipped with mechanical stirrer and nitrogen inlet. Add 3-oxo-3-pyridin-2-yl-propionic acid ethyl ester (Preparation 2, Part A; 200 g, 1.04 mol) and pyridine (400 mL). Stir the reaction mixture at room temperature for 20 h.Dilute the mixture with water (500 mL) and extract with toluene (2 x 500 mL). Combine EPO <DP n="19"/>the organic layers, dry (sodium sulfate), filter, and concentrate in vacuo to yield 280 g (98%) of the subtitled compound as a dark oil. MS (ES) m/z = 276 (M+H). |
98% | With pyridine; at 20℃; for 20h; | Place L-AMINOPYRROLIDIN-2-ONE hydrochloride (Zubek, A. Z. CHEM., 1969, 9 (2), 58; 155.6 g, 1.14 mol) in a 3 L flask equipped with mechanical stirrer and nitrogen inlet. Add 3-oxo-3-pyridin-2-yl-propionic acid ethyl ester (200 g, 1.04 mol) then pyridine (400 mL). Stir the reaction mixture at room temperature for 20 h. Dilute the mixture with water (500 mL), and-extract with toluene (2 x 500 mL). Combine the organic layers, dry (sodium sulfate), filter and concentrate in vacuo to yield the subtitled compound as a dark oil (280 g, 98%). MS ES+ M/E 276 (M+1). |
98% | In pyridine; at 20℃; for 20h; | Place l-aminopyrrolidin-2-one hydrochloride (Zubek, A. Z. Chem., 1969, 9 (2), 58 ; 155. 6 g, 1.14 mol) in a 3 L flask equipped with mechanical stirrer and nitrogen inlet. Add 3-oxo-3-pyridin-2-yl-propionic acid ethyl ester (Preparation 3-A ; 200 g, 1.04 mol) and pyridine (400 mL). Stir the reaction mixture at room temperature for 20 h. Dilute the mixture with water (500 mL) and extract with toluene (2 x 500 mL). Combine the organic layers, dry (sodium sulfate), filter, and concentrate in vacuo to yield 280 g (98%) of the subtitled compound as a dark oil. MS ES+ m/e 276 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With acetic acid; at 115℃; for 12h;Inert atmosphere; | (a) Ethyl 3-oxo-3-(pyridin-2-yl)propanoate (500 mg, 2.6 mmol) was taken in AcOH (50 mL) in a 250 mL round bottom flask under N2. To it was added <strong>[4922-98-9]3-phenyl-1H-1,2,4-triazol-5-amine</strong> (497 mg, 3.1 mmol). The reaction mixture was heated at 115 °C for 12 h. The reaction mixture was then evaporated to dryness using toluene as an azeotropic solvent and triturated with diethyl ether. This was finally dried under high vacuum which afforded 66b as a deep brown solid (300 mg, 40percent). This was then used in the next step without any further purification. LCMS(ESI) m/z 288.02 [M-H+]; 57percent (purity). |
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