Structure of 13210-29-2
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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. : | 13210-29-2 |
Formula : | C7H7NO2 |
M.W : | 137.14 |
SMILES Code : | CC(C1=NC=CC=C1O)=O |
MDL No. : | MFCD08062669 |
InChI Key : | DYFSAZGSIBFUAI-UHFFFAOYSA-N |
Pubchem ID : | 14088947 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 36.45 |
TPSA ? Topological Polar Surface Area: Calculated from |
50.19 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.66 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.07 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.99 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.48 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.17 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.88 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.74 |
Solubility | 2.48 mg/ml ; 0.0181 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.72 |
Solubility | 2.64 mg/ml ; 0.0193 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.76 |
Solubility | 2.41 mg/ml ; 0.0175 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 |
-6.38 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) |
1.27 |
* 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 |
---|---|---|
77% | Stage #1: With triethylamine In tetrahydrofuran at 60 - 65℃; for 5 h; Stage #2: With Methyl formate In tetrahydrofuran at 5 - 20℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 10℃; |
Example 2; 3-methyl-N4[(1S)-3-methyl-1-([(4S,7R)-7-methyl-3-oxo-1-(2-pyridinylsulfonyl) hexahydro-1H-azepin-4-yl]amino}carbonyl)butyl]furo[3,2-b]pyridine-2-carboxamide; Preparation of 3-methylfuro[3,2-b]pyridine-2-carboxylic acid (6-1); Under nitrogen, charge the flask with 3 M methyl magnesium chloride in THF (600 mL, 1.80 mol, 5.0 equiv) and THF (500 mL). Heat the solution to 60-65° C. and add a solution of 3-hydroxypicolinic acid (1) (50 g, 0.36 mole), triethylamine (50 mL, 0.36 mole) in THF (250 mL) to the reaction mixture over approximately 3 h. Continue heating at reflux for 2 h. Cool the reaction to 5-10° C. and add methyl formate (44 mL) keeping the reaction temperature less than 20° C. At 10° C., add 10percent aqueous HCl to a pH 34. Transfer to separatory funnel and allow the layers to separate. Remove the top organic phase and extract the aqueous phase with THF (250 mL). Combine the organic phases combined and concentrate to 13-15 volumes and add water (170 mL). Continue with the vacuum distillation until all the THF has been removed. Cool the solution to 10° C., stir 0.5 h, filter and dry 1-(3-hydroxypyridin2-yl)ethanone (2) as the tan solid (38.1 g, 77percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: for 6.16667 h; Cooling with ice water bath; Reflux Stage #2: With water; ammonium chloride In diethyl ether; benzeneCooling with ice water bath; Saturated solution |
l-(3-Hydroxypyridin-2-yl)ethanone (50) A flame-dried 250 mL round bottom flask was charged with methylmagnesium iodide in ether (67.0 ml, 200 mmol). This solution was stirred in an ice-H2O bath as 2-cyanopyridin-3-yl acetate (49) (6.5 g, 40 mmol) in benzene (45 mL) was cannulated in over a period of 40 min. The resulting mixture was refluxed for 5.5 hrs, then cooled in an ice-H2O bath and cautiously quenched with <n="64"/>saturated NH4Cl aqueous solution. The aqueous layer was cautiously neutralized with 2N HCl aqueous solution and then extracted with EtOAc (2X). The combined organic layer was washed with brine (IX) and dried over anhydrous Na2SO4. Purification by combi- flash column chromatography (EtOAc/Hexanes) gave l-(3-hydroxypyridin-2-yl)ethanone (50) (3.6 g, 65percent yield) as a light yellow solid. 1H NMR (400 MHz, DMS0-d6) δ ppm 11.58 (1 H, s), 8.27 (1 H, dd, J=4.3, 1.6 Hz), 7.61 (1 H, dd, J=8.4, 4.3 Hz), 7.47 (1 H, dd, J=8.4, 1.6 Hz), 2.69 (3 H, s). |
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