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CAS No. : | 1597403-47-8 | MDL No. : | |
Formula : | C22H24Cl2N2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 451.34 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 30 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 10 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 116.12 |
TPSA : | 76.66 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.62 cm/s |
Log Po/w (iLOGP) : | 3.43 |
Log Po/w (XLOGP3) : | 4.84 |
Log Po/w (WLOGP) : | 3.99 |
Log Po/w (MLOGP) : | 2.69 |
Log Po/w (SILICOS-IT) : | 4.15 |
Consensus Log Po/w : | 3.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.32 |
Solubility : | 0.00214 mg/ml ; 0.00000475 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.18 |
Solubility : | 0.000296 mg/ml ; 0.000000655 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -7.52 |
Solubility : | 0.0000137 mg/ml ; 0.0000000304 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 3.32 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
65% | With potassium carbonate In tetrahydrofuran; water at 20℃; for 0.5h; | trans-ISRIB: 2-(4-Chlorophenoxy)-N-[(lr,4r)-4-[2-(4-chlorophenoxy )acetamido] cyclohexyl] acetamide trans-ISRIB: 2-(4-Chlorophenoxy)-N-[(lr,4r)-4-[2-(4-chlorophenoxy )acetamido] cyclohexyl] acetamide [0409] To a mixture of (lr,4r)-cyclohexane-l,4-diamine (20 mg, 0.18 mmol) in tetrahydrofuran:water (1 : 1, 1 ml) were sequentially added potassium carbonate (73 mg, 0.53 mmol) and 4-chlorophenoxyacetyl chloride (56 μ, 0.36 mmol). Upon addition of the acid chloride, a white solid immediately formed. The reaction mixture was vigorously stirred at ambient temperature for 30 min. Water (2.5 ml) was added. The mixture was vigorously vortexed then centrifuged, and the water was decanted. This washing protocol was repeated with potassium bisulfate (1% aq, 2.5 ml), water (2.5 ml), and diethyl ether (2 x 2.5 ml). The resulting wet white solid was dried by partially dissolving in dichloromethane/methanol (10/1, 10 ml) and gravity filtering through an Autochem 4.5 mL reaction tube. The residual undissolved product was extracted from the wet filter cake by adding dichloromethane (4 x 4.5 ml) and gravity filtering. The combined filtrate was concentrated using rotary evaporation to afford 51 mg (65%) of the title compound as a white solid. XH NMR (400 MHz, DMSO-d6) δ 7.91 (d, J= 8.1 Hz, 2H), 7.31 (d, J= 9.0 Hz, 4H), 6.94 (d, J= 9.0 Hz, 4H), 4.42 (s, 4H), 3.55 (br. s., 2H), 1.73 (br. d, J= 5.9 Hz, 4H), 1.30 (quin, J= 10.5 Hz, 4H); LC-MS: m/z = 451 [M+H, 35C1 x 2]+, 453 [M+H, 35C1, 37C1]+. |