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CAS No. : | 209984-56-5 | MDL No. : | MFCD12828734 |
Formula : | C26H23F2N3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QSHGISMANBKLQL-OWJWWREXSA-N |
M.W : | 463.48 | Pubchem ID : | 11454028 |
Synonyms : |
DBZ;Dibenzazepine;Deshydroxy LY-411575.;Iminostilbene;YO-01027
|
Chemical Name : | (S)-2-(2-(3,5-Difluorophenyl)acetamido)-N-((S)-5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)propanamide |
Num. heavy atoms : | 34 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.19 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 126.51 |
TPSA : | 78.51 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.59 cm/s |
Log Po/w (iLOGP) : | 2.95 |
Log Po/w (XLOGP3) : | 3.57 |
Log Po/w (WLOGP) : | 3.65 |
Log Po/w (MLOGP) : | 3.15 |
Log Po/w (SILICOS-IT) : | 4.36 |
Consensus Log Po/w : | 3.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.89 |
Solubility : | 0.00594 mg/ml ; 0.0000128 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.9 |
Solubility : | 0.00577 mg/ml ; 0.0000125 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -8.62 |
Solubility : | 0.0000011 mg/ml ; 0.0000000024 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.32 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 4 - 17h; | D; 7.1 Synthesis of 5-(S)-[N'(3,5-Difluorophenylacetyl)-L-alaninyl]amino-7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one GENERAL PROCEDURE D Fourth EDC Coupling Procedure A round bottom flask was charged with the corresponding carboxylic acid (1.0 eq.), hydroxybenzotriazole hydrate (1.1 eq.) and the corresponding amine (1.0 eq.) in THF under nitrogen atmosphere. An appropriate amount (1.1 eq for free amines and 2.2 eq. for hydrochloride amine salts) of base, such as Hunig's base was added to the well stirred mixture followed by EDC (1.1 eq.). After stirring from 4 to 17 hours at room temperature the solvent was removed at reduced pressure, the residue taken up in ethyl acetate (or similar solvent) and water, washed with saturated aqueous sodium bicarbonate solution, 1 N HCl, brine, dried over anhydrous sodium sulfate and the solvent removed at reduced pressure to provide the product.; Example 7-1 Synthesis of 5-(S)-[N'(3,5-Difluorophenylacetyl)-L-alaninyl]amino-7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one Following General Procedure D above using N-(3,5-difluorophenylacetyl)-L-alanine (Example B) and 5-amino-7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one hydrochloride (Example 7-A), the title compound was prepared as a colorless solid. The diastereomers were purified by HPLC (Bulk OD-25) using 15% EtOH in heptane as eluent and a flow rate of 1.5 ml/min. Isomer 1: retention time of 11.4 minutes. NMR data was as follows: 1H-nmr (CDCl3): δ = 7.62-7.33. (m, 8H), 6.79 (m, 2H), 6.71 (m,1H), 6.47 (m,1H), 5.24 (d 1H), 4.70 (m,1H), 3.48 (s, 2H), 3.34 (s, 3H), 1.42 (d, 3H). Optical Rotation: [α]20 = - 125 (at) 589 nm (c = 1, MeOH). C26H23F2N3O3 (MW = 463.49); mass spectroscopy (MH+) 463. Anal. Calcd for C26H23F2N3O3; C, 67.38 H, 5.00 N, 9.06. Found: C, 67.49 H, 5.06 N, 8.93. |