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CAS No. : | 919486-40-1 | MDL No. : | MFCD24038757 |
Formula : | C20H20ClN5O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OZRMEKAUZBKTTC-UHFFFAOYSA-N |
M.W : | 397.86 | Pubchem ID : | 10340781 |
Synonyms : |
|
Chemical Name : | 4-(Benzylamino)-2-((3-chloro-4-hydroxyphenethyl)amino)pyrimidine-5-carboxamide |
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.15 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 109.55 |
TPSA : | 113.16 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.89 cm/s |
Log Po/w (iLOGP) : | 2.91 |
Log Po/w (XLOGP3) : | 3.99 |
Log Po/w (WLOGP) : | 2.67 |
Log Po/w (MLOGP) : | 2.17 |
Log Po/w (SILICOS-IT) : | 2.87 |
Consensus Log Po/w : | 2.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.77 |
Solubility : | 0.00679 mg/ml ; 0.0000171 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.07 |
Solubility : | 0.00034 mg/ml ; 0.000000855 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -7.56 |
Solubility : | 0.000011 mg/ml ; 0.0000000276 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 2.78 |
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 |
---|---|---|
29% | With 1-methyl-pyrrolidin-2-one; diisopropylamine at 100℃; for 1h; | |
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 110℃; for 1h; | 1 Example 1 To 8 ml NMP solution of 750 mg of 4-benzylamino-2-methylsulfonylpyrimidine-5-carboxamide were added 765 mg of 2-(3-chloro-4-hydroxyphenyl)ethylamine hydrochloride and 1.07 ml of diisopropylethylamine, followed by stirring at 110°C for 1 hour. The reaction mixture was cooled down to room temperature, and then mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (chloroform:methanol:aqueous ammonia) and the resulting crude crystals were recrystallized (methanol-ethyl acetate) to obtain 280 mg of 4-benzylamino-2-[2-(3-chloro-4-hydroxyphenyl)ethyl]amino}pyrimidine-5-carboxamide as colorless crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 91 percent / N-methylpyrrolidinone; m-chloroperbenzoic acid / 3 h 2: 29 percent / diisopropylamine; N-methylpyrrolidinone / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 98 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; NH4OH / dimethylformamide; H2O / 16 h / 20 °C 2: 91 percent / N-methylpyrrolidinone; m-chloroperbenzoic acid / 3 h 3: 29 percent / diisopropylamine; N-methylpyrrolidinone / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 96 percent / ethyldiisopropylamine / acetonitrile / 5 h / 20 °C 2: 100 percent / NaOH / methanol; tetrahydrofuran / 5 h / 50 °C 3: 98 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; NH4OH / dimethylformamide; H2O / 16 h / 20 °C 4: 91 percent / N-methylpyrrolidinone; m-chloroperbenzoic acid / 3 h 5: 29 percent / diisopropylamine; N-methylpyrrolidinone / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 100 percent / NaOH / methanol; tetrahydrofuran / 5 h / 50 °C 2: 98 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; NH4OH / dimethylformamide; H2O / 16 h / 20 °C 3: 91 percent / N-methylpyrrolidinone; m-chloroperbenzoic acid / 3 h 4: 29 percent / diisopropylamine; N-methylpyrrolidinone / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 96 percent / ethyldiisopropylamine / acetonitrile / 5 h / 20 °C 2: 100 percent / NaOH / methanol; tetrahydrofuran / 5 h / 50 °C 3: 98 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; NH4OH / dimethylformamide; H2O / 16 h / 20 °C 4: 91 percent / N-methylpyrrolidinone; m-chloroperbenzoic acid / 3 h 5: 29 percent / diisopropylamine; N-methylpyrrolidinone / 1 h / 100 °C |
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