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CAS No. : | 144657-66-9 | MDL No. : | MFCD11045434 |
Formula : | C13H14N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GFZQRKMUXOECFL-UHFFFAOYSA-N |
M.W : | 246.26 | Pubchem ID : | 11806939 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.31 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 67.32 |
TPSA : | 61.19 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.38 cm/s |
Log Po/w (iLOGP) : | 2.33 |
Log Po/w (XLOGP3) : | 2.0 |
Log Po/w (WLOGP) : | 2.63 |
Log Po/w (MLOGP) : | 1.55 |
Log Po/w (SILICOS-IT) : | 1.72 |
Consensus Log Po/w : | 2.05 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.73 |
Solubility : | 0.456 mg/ml ; 0.00185 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.91 |
Solubility : | 0.302 mg/ml ; 0.00123 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.94 |
Solubility : | 0.283 mg/ml ; 0.00115 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.23 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H317 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
89% | With triethylamine In dichloromethane at 20℃; | A round-bottom flask was charged with Int-15 (6.6 g, 45 mmol), (BoC)2O (10.7 g, 50 mmol), 4-dimethylaminopyridine (55 mg, 0.45 mmol), triethylamine (13 g, 130 mmol), and DCM (50 mL). The mixture was stirred at room temperature overnight, concentrated to dryness, and purified by flash column chromatography to afford product Int-16 (9.8 g, 89percent). |
82% | With dmap In acetonitrile at 20℃; for 6.5 h; | To a suspension of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (304 mg, 2.08 mmol; commerciallyavailable from, for example, Enamine) and di-tett-butyl dicarbonate (0.580 mL, 2.50 mmol) inacetonitrile (5 mL) was added DMAP (28 mg, 0.23 mmol) and the reaction mixture stirred at rt under nitrogen for 6.5 h before being left to stand overnight. The reaction mixture was concentrated in vacuo to give a brown solid which was dissolved in dichloromethane (3 mL) and loaded onto a 25 g SNAP silica cartridge and purified by flash chromatography eluting with a gradient of 3O-5Opercent ethylacetate in cyclohexane. The required fractions were combined and concentrated in vacuo before the residue was dissolved in dichloromethane (6 mL), transferred to a tarred vial, concentrated under a stream of nitrogen and dried in vacuo to give a white solid; ter1butyl 3-formyl-1H-pyrrolo[2,3- b]pyridine-1-carboxylate (420.7 mg, 1.71 mmol, 82 percent yield).LCMS (2 mm high pH) Rt = 0.97 mi m/z= 247 for [MH] |
0.779 g | With dmap In acetonitrile at 20℃; | General procedure: To a solution of an appropriate indole, azaindole or alternative heterocycles (1.0 eq) and di-ferf-butyl dicarbonate (1eq. to 2 eq., more in particular 1.2 eq) in acetonitrile was added DMAP (0.1 to 0.5 eq. more in particular 0.1 eq). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with a saturated sodium bicarbonate solution. The phases were separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with a saturated ammonium chloride solution, water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The BOC-protected compound was used in the next step without further purification. |
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