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[ CAS No. 96605-66-2 ] {[proInfo.proName]}

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Chemical Structure| 96605-66-2
Chemical Structure| 96605-66-2
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Product Details of [ 96605-66-2 ]

CAS No. :96605-66-2 MDL No. :MFCD04117958
Formula : C15H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :UXWJJVRASIHSQS-MDZDMXLPSA-N
M.W : 260.33 Pubchem ID :11149633
Synonyms :

Calculated chemistry of [ 96605-66-2 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 6
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 77.5
TPSA : 40.62 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.8
Log Po/w (XLOGP3) : 1.7
Log Po/w (WLOGP) : 2.32
Log Po/w (MLOGP) : 1.61
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 2.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.36
Solubility : 1.13 mg/ml ; 0.00434 mol/l
Class : Soluble
Log S (Ali) : -2.17
Solubility : 1.77 mg/ml ; 0.00679 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.252 mg/ml ; 0.000968 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.42

Safety of [ 96605-66-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 96605-66-2 ]

* 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.

  • Upstream synthesis route of [ 96605-66-2 ]
  • Downstream synthetic route of [ 96605-66-2 ]

[ 96605-66-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 105-58-8 ]
  • [ 96605-66-2 ]
YieldReaction ConditionsOperation in experiment
96% With pyrographite; potassium hydroxide In N,N-dimethyl-formamide; acetone at 60℃; for 3 h; (1)Synthesis of Supported KOH/Activated Carbon CatalystThe precursor KOH of the active ingredient is formulated with ultrapure water to a concentration of 0.1-2M.Then add the activated carbon carrier and stir it evenly.After drying in a vacuum dryer at 100°C for about 5 hours,It was then calcined at 150°C for 5 hours.The KOH loading of the catalyst was 15percent.(2)Synthesis of Compounds of Formula IIIn a 1.5-liter reactor, add 10 g of the catalyst of step 1.236 mL of diethyl carbonate was dissolved in 500 mL of a mixed solution of DMF and acetone.After adding 100 g of a compound of Formula III to the mixed solution,While stirring, raise the temperature to 60°C at a rate of 3°C/min.And continue to react under stirring for 3 hours,After the reaction, it is cooled to room temperature, and the catalyst is removed by centrifugal filtration.The residue is extracted two to three times with 500 mL of dichloromethane.The combined organic layers are washed with water,Drying and evaporation of the solvent under reduced pressure yields the compound of formula II as a solid (96percent yield).The purity by HPLC was 99.79percent.
Reference: [1] Patent: CN107793326, 2018, A, . Location in patent: Paragraph 0019; 0020; 0021; 0022; 0023
  • 2
  • [ 64-67-5 ]
  • [ 96605-66-2 ]
YieldReaction ConditionsOperation in experiment
94.5% With pyrographite; potassium hydroxide In N,N-dimethyl-formamide; acetone at 60℃; for 3 h; General procedure: (1)Synthesis of Supported KOH/Activated Carbon CatalystThe precursor KOH of the active ingredient is formulated with ultrapure water to a concentration of 0.1-2M.Then add the activated carbon carrier and stir it evenly.After drying in a vacuum dryer at 100°C for about 5 hours,It was then calcined at 150°C for 5 hours.The KOH loading of the catalyst was 15percent.(2)Synthesis of Compounds of Formula IIIn a 1.5-liter reactor, add 10 g of the catalyst of step 1.236 mL of diethyl carbonate was dissolved in 500 mL of a mixed solution of DMF and acetone.After adding 100 g of a compound of Formula III to the mixed solution,While stirring, raise the temperature to 60°C at a rate of 3°C/min.And continue to react under stirring for 3 hours,After the reaction, it is cooled to room temperature, and the catalyst is removed by centrifugal filtration.The residue is extracted two to three times with 500 mL of dichloromethane.The combined organic layers are washed with water,Drying and evaporation of the solvent under reduced pressure yields the compound of formula II as a solid (96percent yield).The purity by HPLC was 99.79percent
Reference: [1] Patent: CN107793326, 2018, A, . Location in patent: Paragraph 0019; 0020; 0021; 0022; 0023; 0024; 0025
  • 3
  • [ 4637-24-5 ]
  • [ 200630-96-2 ]
  • [ 96605-66-2 ]
YieldReaction ConditionsOperation in experiment
100% at 180℃; for 0.166667 h; microwave irradiation Acetamidoacetophenone (0. 2 g, 1. 13 mmol) in ME2CO (2 mL) was treated with KOH (63 mg, 1. 13 mmol) and then iodoethane (0. 45 mL, 5. 64 mmol). After stirring at room temperature overnight the reaction mixture was concentrated to dryness. The residue was redissolved in EtOAc and was washed with H20 and brine, and was dried on MGS04. The solvent was evaporated to yield N-(3-acetyl-phenyl)-N-ethyl-acetamide as an orange powder (0. 23 g, 100 percent) : mp 203-204 °C ; 1H-NMR (CD30D) : No. 1. 11 (t, 3H, J= 7. 0 Hz, CH3), 1. 82 (s, 3H, CH3), 3. 31 (s, 3H, CH3), 3. 77 (q, 2H, J = 7. 0, 14. 0 Hz, CH2) 7. 56 (d, 1H, J=8. 0 Hz, Ph-H), 7. 65 (t, 1H, J= 8 Hz, Ph-H), 7. 88 (s, 1H, Ph-H) and 8. 06 (d, 1H, J = 8 Hz, Ph-H) ; MS (ESF) m/z 205. 91 [M], C12H15NO2 requires 205. 25. This material (0. 23G, 1. 13 mmol), redissolved in MECN (2 mL), was treated with N,N- dimethylformamide dimethylacetal (150 UL, 1. 12 mmol) at 180 °C FOR 10 min in a microwave reactor (SmithCreator, Personal Chemistry Ltd.). The solvent was evaporated and the residue was filtered and washed with EtOAc/PE (1 : 3) to afford N [3- (3- DIMETHYLAMINO-ACRYLOYL)-PHENYL]-N-ETHYL-ACETAMIDE as an orange solid (0. 30 g, 100 percent). 1H-NMR (CD30D) : 61. 11 (t, 3H, J= 7. 0 Hz, CH3), 1. 82 (s, 3H, CH3), 2. 04 (s, 6H, CH3), 3. 76 (q, 2H, J= 7. 0, 14. 0 Hz, CH2), 5. 87 (d, 1H, J= 12. 0 Hz, CH), 7. 39 (d, 1H, J= 8. 0 Hz, Ph-H), 7. 55 (t, 1H, J= 8. 0 Hz, 5-H), 7. 76 (s, 1H, Ph-H), 7. 89 (d, 1H, J= 12. 0 Hz, CH), 7. 93 (d, 1H, J = 8. 0 Hz, Ph-H) ; MS (ESI+) m/z 261. 32 [M+H]+, C15H20N2O2 requires 260. 33. A solution of this material (0. 228 g, 0. 88 mmol), 4-hydroxy-phenyl guanidine nitrate (0. 188 g, 0. 88 mmol) and NAOH (35 mg, 0. 88 mmol) in MeCN (2 mL) was heated at 190 °C for 15 min in the microwave reactor. The solvent was evaporated and the residue was purified by Si02 gel chromatography (EtOAc/PE, 1 : 1) to afford the title compound as a yellow solid (117 mg, 38 percent). IH-NMR (CD30D) : No.1. 16 (t, 3H, J= 7 Hz, CH3), 3. 35 (s, 3H, CH3), 3. 38 (q, 2H, J= 7. 0, 14. 0 Hz, CH2), 6. 77 (d, 2H, J= 9. 0 Hz, Ph-H), 7. 27 (d, 1H, J= 5. 0 Hz, pyrimidine-H), 7. 42 (d, 1H, J= 8. 0 Hz, Ph-H), 7. 48 (d, 2H, J= 9. 0 Hz, Ph-H), 7. 62 (t, 1H, J= 8. 0 Hz, Ph-H), 8. 6 (s, 1H, Ph-H), 8. 14 (d, 1H, J=8. 0 Hz, Ph-H), 8. 41 (d, 1H, J= 5. 0 Hz, pyrimidine-H).
91% for 5 h; Reflux The N, N- dimethylformamide dimethyl acetal (39ml, 0.293mol) and N- ethyl -N- [3- (3- acetylphenyl)] acetamide (V) (20g, 0.0974mol ) the reaction was stirred at reflux for 5h, atmospheric distillation to recover the unreacted N, N- dimethylformamide dimethyl acetal.The residue after rotary evaporation, the residue was recrystallized from n-hexane to give the crude product N- ethyl -N- [3- (3- dimethylamino-1-oxo-2-propenyl) phenyl] ethanone amide (VI) (23.1g, 91percent yield).
Reference: [1] Patent: WO2005/12262, 2005, A1, . Location in patent: Page/Page column 45-46
[2] Patent: CN105622615, 2016, A, . Location in patent: Paragraph 0128; 0129; 0130; 0131
  • 4
  • [ 75-03-6 ]
  • [ 96605-66-2 ]
Reference: [1] Patent: WO2011/7180, 2011, A1, . Location in patent: Page/Page column 12
  • 5
  • [ 7463-31-2 ]
  • [ 96605-66-2 ]
Reference: [1] Patent: WO2011/7180, 2011, A1,
[2] Patent: CN105622615, 2016, A,
  • 6
  • [ 98-86-2 ]
  • [ 96605-66-2 ]
Reference: [1] Patent: CN105622615, 2016, A,
  • 7
  • [ 121-89-1 ]
  • [ 96605-66-2 ]
Reference: [1] Patent: CN105622615, 2016, A,
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