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[ CAS No. 330785-83-6 ] {[proInfo.proName]}

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Chemical Structure| 330785-83-6
Chemical Structure| 330785-83-6
Structure of 330785-83-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 330785-83-6 ]

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 :

Calculated chemistry of [ 330785-83-6 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.56

Safety of [ 330785-83-6 ]

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:

Application In Synthesis of [ 330785-83-6 ]

* 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.

  • Downstream synthetic route of [ 330785-83-6 ]

[ 330785-83-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 330785-83-6 ]
  • [ 330784-47-9 ]
YieldReaction ConditionsOperation 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

  • 2
  • ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidinecarboxylate [ No CAS ]
  • [ 75985-45-4 ]
  • [ 330784-47-9 ]
YieldReaction ConditionsOperation 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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