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CAS No. : | 871026-44-7 | MDL No. : | MFCD22124520 |
Formula : | C26H25ClF3N5O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZYQXEVJIFYIBHZ-UHFFFAOYSA-N |
M.W : | 547.96 | Pubchem ID : | 11620908 |
Synonyms : |
|
Num. heavy atoms : | 38 |
Num. arom. heavy atoms : | 21 |
Fraction Csp3 : | 0.27 |
Num. rotatable bonds : | 11 |
Num. H-bond acceptors : | 8.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 137.91 |
TPSA : | 101.3 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.52 cm/s |
Log Po/w (iLOGP) : | 3.79 |
Log Po/w (XLOGP3) : | 4.4 |
Log Po/w (WLOGP) : | 7.07 |
Log Po/w (MLOGP) : | 2.93 |
Log Po/w (SILICOS-IT) : | 4.62 |
Consensus Log Po/w : | 4.56 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.69 |
Solubility : | 0.00111 mg/ml ; 0.00000203 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.24 |
Solubility : | 0.000312 mg/ml ; 0.00000057 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -9.27 |
Solubility : | 0.000000294 mg/ml ; 0.0000000005 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 3.71 |
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; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 120h; | Example 158 Production of N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxy-3-methylbutanamide A mixture of 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (150 mg), 3-hydroxy-3-methylbutyric acid (68 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (166 mg), 1-hydroxybenzotriazole monohydrate (133 mg), triethylamine (0.40 mL) and N,N-dimethylformamide (5.0 mL) was stirred at room temperature for 5 days. Water was added to the reaction system and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified by basic silica gel column chromatography (eluent, ethyl acetate --> ethyl acetate:methanol=9:1). Crystallization from ethyl acetate-diisopropyl ether gave the title compound (122 mg) as colorless crystals. 1H-NMR (CDCl3) delta: 1.33 (6H, s), 2.49 (2H, s), 2.65-2.77 (1H, m), 3.57-3.68 (2H, m), 4.44-4.53 (2H, m), 6.61 (1H, d, J= 3.0 Hz), 6.93-7.01 (1H, m), 7.07 (1H, d, J= 9.0 Hz), 7.09-7.15 (1H, m), 7.19 (1H, d, J= 3.0 Hz), 7.23-7.35 (2H, m), 7.40-7.45 (1H, m), 7.77 (1H, dd, J= 9.0, 2.7 Hz), 8.08 (1H, d, J= 2.7 Hz), 8.52 (1H, s), 8.66 (1H, s). melting point: 167-169°C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: isopropyl alcohol / 12 h / 80 °C 2: hydrogenchloride / tetrahydrofuran; water / 20 h / 60 °C 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / tetrahydrofuran; water / 20 h / 60 °C 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 2: platinum on carbon; hydrogen / ethyl acetate / 2 h / 20 °C 3: isopropyl alcohol / 12 h / 80 °C 4: hydrogenchloride / tetrahydrofuran; water / 20 h / 60 °C 5: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 2: platinum on carbon; hydrogen / ethyl acetate / 2 h / 20 °C 3: isopropyl alcohol / 12 h / 80 °C 4: hydrogenchloride / tetrahydrofuran; water / 20 h / 60 °C 5: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: isopropyl alcohol / 12 h / 80 °C 2: hydrogenchloride / tetrahydrofuran; water / 20 h / 60 °C 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: platinum on carbon; hydrogen / ethyl acetate / 2 h / 20 °C 2: isopropyl alcohol / 12 h / 80 °C 3: hydrogenchloride / tetrahydrofuran; water / 20 h / 60 °C 4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 96 h / 40 °C 2: isopropyl alcohol / 12 h / 80 °C 3: hydrogenchloride / tetrahydrofuran; water / 20 h / 60 °C 4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C |