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[ CAS No. 1454682-72-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1454682-72-4
Chemical Structure| 1454682-72-4
Structure of 1454682-72-4 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 1454682-72-4 ]

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Product Details of [ 1454682-72-4 ]

CAS No. :1454682-72-4 MDL No. :MFCD28411374
Formula : C23H29FN6O Boiling Point : -
Linear Structure Formula :- InChI Key :HHCBMISMPSAZBF-UHFFFAOYSA-N
M.W : 424.51 Pubchem ID :71721540
Synonyms :
DP-4978

Calculated chemistry of [ 1454682-72-4 ]

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.39
Num. rotatable bonds : 8
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 123.24
TPSA : 91.83 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.77
Log Po/w (XLOGP3) : 4.7
Log Po/w (WLOGP) : 5.09
Log Po/w (MLOGP) : 3.56
Log Po/w (SILICOS-IT) : 4.53
Consensus Log Po/w : 4.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.29
Solubility : 0.00219 mg/ml ; 0.00000517 mol/l
Class : Moderately soluble
Log S (Ali) : -6.36
Solubility : 0.000187 mg/ml ; 0.00000044 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.94
Solubility : 0.00000049 mg/ml ; 0.0000000012 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.5

Safety of [ 1454682-72-4 ]

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 [ 1454682-72-4 ]

* 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 [ 1454682-72-4 ]
  • Downstream synthetic route of [ 1454682-72-4 ]

[ 1454682-72-4 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 1454682-74-6 ]
  • [ 1454682-77-9 ]
  • [ 1454682-72-4 ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,4-dioxane; water at 50℃; Inert atmosphere Combine l-(3,3-dimethylbutyl)-3-(2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)urea (25.9 g, 68.5 mmol), 7-methyl-2-(methylamino)pyrido[2,3- d]pyrimidin-6-yl trifluoromethanesulfonate (22.09 g, 68.5 mmol), and NaHC03 (17.28 g, 206 mmol) in 1,4-dioxane (500 mL) and water (125 mL) and sparge with argon for 20 minutes. Add tetrakis(triphenylphosphine)palladium (3.96 g, 3.43 mmol) and then heat under argon at 50 °C. Add additional portion of 7-methyl-2-(methylamino)pyrido[2,3-d]pyrimidin-6-yl trifluoromethanesulfonate (300 mg, 0.55 mmol) and continue heating at 50 °C overnight. Cool the mixture to RT, collect the solid by filtration, and wash with water then diethyl ether. Treat the solid with acetonitrile (50 mL) and heat the slurry at 80 °C for 30 minutes. Collect the solid by filtration, wash with acetonitrile and dry under vacuum at 80 °C to obtain a pale yellow solid. Treat the solid with MeOH (50 mL), and heat the mixture at 80 °C for 1 hour. Cool to RT, collect the solid via filtration, wash with MeOH (20 mL), and dry under vacuum to obtain the title compound (22.5 g, 77percent yield) as a pale yellow solid. MS (m/z): 425.2 (M+l).
Reference: [1] Patent: WO2013/134243, 2013, A1, . Location in patent: Page/Page column 22-23
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 2
  • [ 1454682-74-6 ]
  • [ 1454682-79-1 ]
  • [ 1454682-72-4 ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 85℃; Inert atmosphere Method B: Sparge a suspension of l-(3,3-dimethylbutyl)-3-(2-fluoro-4-methyl-5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)urea (4.48 g, 11.8 mmol), 6-bromo-N,7- dimethylpyrido[2,3-d]pyrimidin-2-amine (3.0 g, 11.8 mmol) and K2CO3 (4.91 g, 35.6 mmol) in dioxane (80 mL) and water (20 mL) with argon, treat with tetrakis(triphenylphosphine)palladium (0.685 g, 0.593 mmol) and heat at 85 °C overnight. Remove the dioxane under reduced pressure, treat the mixture with EtOAc and brine, separate the layers, dry the organics over Na2S04, concentrate and purify by silica gel chromatography (40percent to 100percent EtOAc/hexane, 100percent EtOAc, 5percent MeOH/ EtOAc). Treat the material with CH3CN, heat at 80°C for 1 hour, cool to RT and collect the solid via filtration to afford the title compound (3.52 g, 70percent> yield) as a pale yellow solid. MS (m z): 425.2 (M+l).
Reference: [1] Patent: WO2013/134243, 2013, A1, . Location in patent: Page/Page column 22-23
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 3
  • [ 1012880-11-3 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Patent: WO2013/134243, 2013, A1,
[3] Patent: WO2013/134243, 2013, A1,
[4] Patent: WO2013/134243, 2013, A1,
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[7] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 4
  • [ 1454682-73-5 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Patent: WO2013/134243, 2013, A1,
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 5
  • [ 945244-29-1 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Patent: WO2013/134243, 2013, A1,
[3] Patent: WO2013/134243, 2013, A1,
[4] Patent: WO2013/134243, 2013, A1,
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[7] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 6
  • [ 776-53-4 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Patent: WO2013/134243, 2013, A1,
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 7
  • [ 5909-24-0 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Patent: WO2013/134243, 2013, A1,
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 8
  • [ 452-63-1 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Patent: WO2013/134243, 2013, A1,
[3] Patent: WO2013/134243, 2013, A1,
[4] Patent: WO2013/134243, 2013, A1,
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[7] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 9
  • [ 170098-98-3 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Patent: WO2013/134243, 2013, A1,
[3] Patent: WO2013/134243, 2013, A1,
[4] Patent: WO2013/134243, 2013, A1,
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[6] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[7] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 10
  • [ 588-36-3 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Patent: WO2013/134243, 2013, A1,
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 11
  • [ 770-31-0 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Patent: WO2013/134243, 2013, A1,
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 12
  • [ 1454682-75-7 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 13
  • [ 1454682-76-8 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 14
  • [ 1454682-78-0 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 15
  • [ 1256347-64-4 ]
  • [ 1454682-72-4 ]
Reference: [1] Patent: WO2013/134243, 2013, A1,
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 16
  • [ 2987-16-8 ]
  • [ 1454682-72-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
  • 17
  • [ 30564-98-8 ]
  • [ 1454682-72-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
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