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CAS No. : | 330785-83-6 | MDL No. : | MFCD17012696 |
Formula : | C20H25ClN4O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NUTJUOHYJBWTSH-AWEZNQCLSA-N |
M.W : | 420.89 | Pubchem ID : | 52348789 |
Synonyms : |
|
Num. heavy atoms : | 29 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.45 |
Num. rotatable bonds : | 9 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 114.02 |
TPSA : | 96.81 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.23 cm/s |
Log Po/w (iLOGP) : | 3.04 |
Log Po/w (XLOGP3) : | 3.71 |
Log Po/w (WLOGP) : | 2.16 |
Log Po/w (MLOGP) : | 2.02 |
Log Po/w (SILICOS-IT) : | 2.83 |
Consensus Log Po/w : | 2.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.5 |
Solubility : | 0.0133 mg/ml ; 0.0000317 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.43 |
Solubility : | 0.00155 mg/ml ; 0.00000368 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.8 |
Solubility : | 0.000669 mg/ml ; 0.00000159 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 3.56 |
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 |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water monomer / 8.17 h / 25 - 100 °C 2: triethylamine; benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride / N,N-dimethyl-formamide / 14 h / 0 - 5 °C | ||
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water monomer; dimethyl sulfoxide / 20 °C / Cooling with ice 2.1: triethylamine / N,N-dimethyl-formamide / 0.5 h 2.2: 8 h / 20 °C | ||
Multi-step reaction with 3 steps 1: sodium hydroxide / water monomer; dimethyl sulfoxide / 20 °C / Cooling with ice 2: thionyl chloride / 4 h / 80 °C 3: triethylamine / dichloromethane / 20 °C |
Multi-step reaction with 2 steps 1: sodium hydroxide / Heating 2: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 20 °C | ||
Multi-step reaction with 2 steps 1: sodium hydroxide 2: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Example 5 [3737] Preparation of abavinafil [0038] A mixture of 4 _ [(3-chloro-4-methoxybenzyl) amino] _2- [2- (hydroxymethyl) -1-pyrrolidinyl] pyrimidine-5-carboxylate obtained in Example 1 Patent CN00812968.1), 10% aqueous solution of sodium hydroxide 340ml and dimethyl sulfoxide 600ml mixed stirring 15h, The reaction mixture was poured into a 10% aqueous solution of citric acid, The precipitated solid was recrystallized from a mixture of tetrahydrofuran and petroleum ether to give 37 g of a white solid. The solid (37 g) obtained above, <strong>[75985-45-4]2-aminomethylpyrimidine</strong> (13 g), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (19.5 g) 1-hydroxybenzotriazole monohydrate (13.0 g) and DMF (70 ml) was stirred for 8 h, and the reaction mixture was poured into an aqueous solution of sodium hydrogencarbonate. The mixture was extracted with ethyl acetate, washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, Recrystallization from n-heptane 4 - [(3-chloro-4-methoxybenzyl) amino] -2- [2- (hydroxymethyl) -1-pyrrolidinyl] -N- (2-pyrimidinylmethyl) -5- Pyrimidine methanesulfonamide. To give 39.6 g of a pale yellow solid in a yield of 87.0%, purity 99.87% | |
44% | In dichloromethane; at 20℃; | The product of Example 3 (2.0 g, 4.75 mmol), <strong>[75985-45-4]2-aminomethylpyrimidine</strong> (537 mg, 4.75 mmol) was dissolved in dichloromethane (20 ml) and stirred at room temperature overnight.Adding methylene chloride, water extraction, combined organic phase, anhydrous sodium sulfate drying, filtration, concentrated crude product, the silica gel column chromatography purification of white solid 1. 0g,That is, avanafil, the yield of 44%. |
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