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CAS No. : | 1201923-48-9 | MDL No. : | MFCD28359281 |
Formula : | C22H23FN2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TWQAEDUMDUDFGX-INIZCTEOSA-N |
M.W : | 398.43 | Pubchem ID : | 58282788 |
Synonyms : |
|
Num. heavy atoms : | 29 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.32 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 109.33 |
TPSA : | 75.71 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) : | -6.09 cm/s |
Log Po/w (iLOGP) : | 3.35 |
Log Po/w (XLOGP3) : | 3.72 |
Log Po/w (WLOGP) : | 3.6 |
Log Po/w (MLOGP) : | 3.24 |
Log Po/w (SILICOS-IT) : | 3.79 |
Consensus Log Po/w : | 3.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.43 |
Solubility : | 0.0147 mg/ml ; 0.000037 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.0 |
Solubility : | 0.00397 mg/ml ; 0.00000997 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.59 |
Solubility : | 0.000102 mg/ml ; 0.000000256 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 3.34 |
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 |
---|---|---|
67.2% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.5 h; Cooling with ice | To an ice cooled mixture of [(S)-2-(3-fluoro-phenyl)-1-hydroxymethyl-ethyl]carbamic acid tert-butyl ester (1.214 g, 4.5 mmol), triphenyl phosphine (1.359 g, 5.18 mmol), phthalimide (0.762 g, 5.18 mmol) and tetrahydrofuran (15 mL) was added a solution of diisopropyldiazodicarboxylate (1.048 g, 5.18 mmol) in tetrahydrofuran (5 mL). The mixture was stirred for 30 minutes at room temperature and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with dichloromethane-ethyl acetate (90:10) to give [(S)-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(3-fluoro-phenyl)-ethyl]carbamic acid tert-butyl ester as a white solid. (Yield 1.205 g, 67.2percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 12 h; | To a solution of 1 ,1-dimethylethyl 1 ,1-dimethylethyl {(1 S)-2-(1 ,3-dioxo-1 ,3-dihydro-2/-/-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (9.0 g, 22.6 mmol) in DCM (200 ml.) at RT was added 4M HCI in dioxane (56 ml_, 226 mmoles). After 12h, the solution was filtered and washed with DCM (50 ml.) affording the title compound (7.8 g,99percent) as a white HCI salt: LCMS (ES) m/z 349 (M+H)+. |
99% | With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 12 h; | To a solution of 1 ,1-dimethylethyl 1 ,1-dimethylethyl {(1 S)-2-(1 ,3-dioxo-1 ,3-dihydro- 2/-/-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (9.0 g, 22.6 mmol) in DCM (200 mL) at RT was added 4M HCI in dioxane (56 mL, 226 mmoles). After 12h, the solution was filtered and washed with DCM (50 mL) affording the title compound (7.8 g, 99percent) as a white HCI salt: LCMS (ES) m/z 349 (M+H)+. |
3.1 g | With hydrogenchloride In 1,4-dioxane; methanol at 20℃; for 2 h; | Step B 2-[(2S)-2-amino-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione [1.0]-hydrogen chloride To a solution of tert-butyl[(1S)-1-(3-fluorobenzyl)-2-hydroxyethyl]carbamate (9.40 g, 34.9 mmol), triphenylphosphine (9.15 g, 34.9 mmol), and phthalimide (5.14 g, 34.9 mmol) in tetrahydrofuran (100 mL, 1000 mmol) at room temperature was added diethyl azodicarboxylate (17.9 mL, 45.4 mmol). The reaction was stirred at room temperature for 2 hr and then concentrated under reduced pressure. The residue was purified by combi-flash chromatography eluted with EtOAc/hexane (0-40percent) to give the desired intermediate. LCMS found: 399.0 (M+1). To the solution of the purified intermediate in methanol (20 mL, 400 mmol) was added 4.0 M hydrogen chloride in dioxane (30 mL, 100 mmol). The mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure to give 3.1 g (26percent total yield for the two steps) of the final product, 2-[(2S)-2-amino-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione [1.0]-Hydrogen chloride, as white solid. LC/MS found: 299.0 (M+H)+. |
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