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[ CAS No. 755039-55-5 ] {[proInfo.proName]}

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Chemical Structure| 755039-55-5
Chemical Structure| 755039-55-5
Structure of 755039-55-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 755039-55-5 ]

CAS No. :755039-55-5 MDL No. :MFCD10698781
Formula : C14H19ClN4O Boiling Point : -
Linear Structure Formula :- InChI Key :RDOMCFLYXZACAX-SNVBAGLBSA-N
M.W : 294.78 Pubchem ID :24820413
Synonyms :

Calculated chemistry of [ 755039-55-5 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.64
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 86.14
TPSA : 49.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.02
Log Po/w (XLOGP3) : 2.98
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 1.86
Consensus Log Po/w : 2.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.64
Solubility : 0.0683 mg/ml ; 0.000232 mol/l
Class : Soluble
Log S (Ali) : -3.68
Solubility : 0.0617 mg/ml ; 0.000209 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.48
Solubility : 0.0978 mg/ml ; 0.000332 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.26

Safety of [ 755039-55-5 ]

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 [ 755039-55-5 ]

* 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 [ 755039-55-5 ]
  • Downstream synthetic route of [ 755039-55-5 ]

[ 755039-55-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 755039-55-5 ]
  • [ 876126-60-2 ]
  • [ 755038-02-9 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 7, p. 764 - 769
[2] Patent: US2008/177066, 2008, A1, . Location in patent: Page/Page column 57; 60
[3] Patent: US2006/35902, 2006, A1, . Location in patent: Page/Page column 7
  • 2
  • [ 755039-55-5 ]
  • [ 755038-02-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 40, p. 9378 - 9381
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7785 - 7795
  • 3
  • [ 512-56-1 ]
  • [ 755039-54-4 ]
  • [ 755039-55-5 ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate In 1,4-dioxane at 90℃; for 6 h; Inert atmosphere Compound IV (260 mg, 0.93 mmol) was dissolved in dioxane (5 ml).Trimethylphosphate (650 mg, 4.6 mmol) and K2CO3 (192 mg, 1.39 mmol) were added, and the reaction mixture was stirred under 2 at 90 °C for 6hr until the starting material was consumed. The reaction mixture was diluted with water and extracted with EtOAc. The solvent was removed, and the residue was purified by silica gel column chromatography (PE: EtOAc=l : l) to give intermediate B as a white solid (270 mg, 86 percent). 3/4 NMR (CDCI3) δ: 7.7 (s, 1H), 4.34 (m, 1H), 4.25 (m, 1H), 3.33 (s, 3H), 2.1-1.6 (m, 10H) and 0.86 ppm (t, 3H).
Reference: [1] Patent: WO2011/79114, 2011, A1, . Location in patent: Page/Page column 54; 55
  • 4
  • [ 755039-54-4 ]
  • [ 80-48-8 ]
  • [ 755039-55-5 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In acetone for 2 h; Reflux; Inert atmosphere Step 11 (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one; (7R)-2-Chloro-8-cyclopentyl-7-ethyl-7,8-dihydro-5H-pteridin-6-one In (3.50 g, 12.50 mmol) was dissolved in 80 mL of acetone followed by the addition of methyl p-toluenesulfonate (3.40 g, 18.70 mmol) and potassium carbonate (3.45 g, 25 mmol). The resulting mixture was heated to reflux for 2 hours with stirring and then cooled down to room temperature. The reaction mxiture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one 1o (3.40 g, yield: 93.0percent) as a white solid. MS m/z (ESI): 295.4 [M+1]
93% With potassium carbonate In acetone for 2 h; Reflux Step 11
(7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one
(7R)-2-Chloro-8-cyclopentyl-7-ethyl-7,8-dihydro-5H-pteridin-6-one 1n (3.50 g, 12.50 mmol) was dissolved in 80 mL of acetone followed by the addition of methyl p-toluenesulfonate (3.40 g, 18.70 mmol) and potassium carbonate (3.45 g, 25 mmol).
The resulting mixture was heated to reflux for 2 hours with stirring and then cooled down to room temperature.
The reaction mixture was filtered and the filtrate was concentrated under reduced pressure.
The resulting residue was purified by silica gel column chromatography to obtain the title compound (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one 1o (3.40 g, yield: 93.0percent) as a white solid.MS m/z (ESI): 295.4 [M+1]
Reference: [1] Patent: EP2481739, 2012, A1, . Location in patent: Page/Page column 21-22
[2] Patent: US2012/184543, 2012, A1, . Location in patent: Page/Page column 24
  • 5
  • [ 755039-54-4 ]
  • [ 74-88-4 ]
  • [ 755039-55-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 40, p. 9378 - 9381
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 7, p. 764 - 769
[3] ChemBioChem, 2016, vol. 17, # 8, p. 759 - 767
[4] Patent: US2006/46989, 2006, A1, . Location in patent: Page/Page column 14
[5] Patent: WO2006/21378, 2006, A1, . Location in patent: Page/Page column 37
[6] Patent: WO2006/18182, 2006, A1, . Location in patent: Page/Page column 47; 59
[7] Patent: WO2006/18185, 2006, A2, . Location in patent: Page/Page column 47; 59
[8] Patent: US2006/35903, 2006, A1, . Location in patent: Page/Page column 15
[9] Patent: US2008/177066, 2008, A1, . Location in patent: Page/Page column 57; 59-60
[10] Patent: US2004/176380, 2004, A1, . Location in patent: Page/Page column 10
[11] Patent: WO2004/76454, 2004, A1, . Location in patent: Page/Page column 28
[12] Patent: US2006/35902, 2006, A1, . Location in patent: Page/Page column 6
[13] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7785 - 7795
  • 6
  • [ 755039-54-4 ]
  • [ 616-38-6 ]
  • [ 755039-55-5 ]
Reference: [1] Patent: US2006/35902, 2006, A1, . Location in patent: Page/Page column 7
  • 7
  • [ 755039-53-3 ]
  • [ 755039-55-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 40, p. 9378 - 9381
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 7, p. 764 - 769
[3] ChemBioChem, 2016, vol. 17, # 8, p. 759 - 767
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7785 - 7795
  • 8
  • [ 755039-52-2 ]
  • [ 755039-55-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 40, p. 9378 - 9381
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 7, p. 764 - 769
[3] ChemBioChem, 2016, vol. 17, # 8, p. 759 - 767
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7785 - 7795
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