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[ CAS No. 694499-26-8 ] {[proInfo.proName]}

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Chemical Structure| 694499-26-8
Chemical Structure| 694499-26-8
Structure of 694499-26-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 694499-26-8 ]

CAS No. :694499-26-8 MDL No. :MFCD09909924
Formula : C13H18F3N3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZMWAZMYBMAAMAW-UHFFFAOYSA-N
M.W : 273.30 Pubchem ID :46838908
Synonyms :

Calculated chemistry of [ 694499-26-8 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.54
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 76.36
TPSA : 32.5 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 1.77
Log Po/w (WLOGP) : 2.28
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 2.13
Consensus Log Po/w : 2.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.69
Solubility : 0.564 mg/ml ; 0.00206 mol/l
Class : Soluble
Log S (Ali) : -2.07
Solubility : 2.32 mg/ml ; 0.0085 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.5
Solubility : 0.0868 mg/ml ; 0.000318 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.92

Safety of [ 694499-26-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 694499-26-8 ]

* 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 [ 694499-26-8 ]
  • Downstream synthetic route of [ 694499-26-8 ]

[ 694499-26-8 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 853297-04-8 ]
  • [ 694499-26-8 ]
YieldReaction ConditionsOperation in experiment
60% With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran at 5 - 20℃; 400mL THF was added to a 2L reaction kettle, cooled to -5 ° C or less, was added portionwise aluminum hydrideLithium 50g (l. 33mol, 4. Oeq), stirred lOmin, continue to -5 ° C or less, and began dropping aluminum trichloride10g (0. 0667mol, 0. 2eq) in THF solution. Keeping the temperature below 5 ° C, then stirred for 30min after beginning coupled step dropsThe product amide 96g (0. 334mol, 1. Oeq) was dissolved in 500mL THF solution, the temperature is still below 5 ° C, after increases room temperatureStirring. Disappearance of starting materials monitored by TLC the reaction was complete. Cooled to 0 ° C or less, and began dropping water to quench the reaction. Filtered and the filtrateRotary done crude was crystallized from toluene once in pure 60. 5g, Yield: 60percent
50%
Stage #1: With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 65℃; for 6 h; Inert atmosphere
Stage #2: With sodium hydroxide In water; toluene at 20℃; for 1.5 h;
To a solution of vitride (3 equiv) in toluene (6times) under nitrogen atmosphere was slowly added lot wise [4-amino-2-(trifluoromethyl) phenyl] -(4-methylpiperazin-l- yl)methanone (1 equiv) at room temperature during 2h (exothermic). After stirring for 4h at 65°C, slowly added 8percent aq. NaOH solution (12 equiv) during lh at room temperature. Resulting solution was stirred for 30minutes, extracted with toluene, combined toluene layers were dried over Na2S04 and concentrated. Crystallization form boiling hexane afforded the title compound (50percent yield).
Reference: [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 20, p. 7150 - 7163
[2] Patent: CN105461659, 2016, A, . Location in patent: Paragraph 0032; 0033; 0034; 0065; 0066; 0067
[3] Patent: WO2015/186137, 2015, A1, . Location in patent: Page/Page column 19
[4] Patent: WO2005/51366, 2005, A2, . Location in patent: Page/Page column 62
[5] Patent: WO2005/51366, 2005, A2, . Location in patent: Page/Page column 62
  • 2
  • [ 109-01-3 ]
  • [ 876322-73-5 ]
  • [ 694499-26-8 ]
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 6, p. 1146 - 1155
  • 3
  • [ 709045-30-7 ]
  • [ 694499-26-8 ]
Reference: [1] Patent: WO2004/52884, 2004, A1, . Location in patent: Page 54
[2] Patent: WO2005/51366, 2005, A2, . Location in patent: Page/Page column 60-61
[3] Organic Process Research and Development, 2008, vol. 12, # 6, p. 1146 - 1155
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 6, p. 595 - 600
[5] Patent: WO2005/51366, 2005, A2, . Location in patent: Page/Page column 60-61
  • 4
  • [ 89976-12-5 ]
  • [ 694499-26-8 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 5, p. 1669 - 1672
[2] Patent: WO2013/162727, 2013, A1,
[3] Patent: US2014/31354, 2014, A1,
[4] Patent: WO2015/106292, 2015, A1,
[5] Bioorganic Chemistry, 2016, vol. 68, p. 112 - 123
[6] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 86 - 106
[7] Patent: CN106749278, 2017, A,
[8] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 8801 - 8815
[9] Patent: US2017/305920, 2017, A1,
[10] Patent: WO2018/102751, 2018, A1,
  • 5
  • [ 694499-22-4 ]
  • [ 694499-26-8 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 5, p. 1669 - 1672
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 3033 - 3047
[3] Patent: WO2013/162727, 2013, A1,
[4] Patent: US2014/31354, 2014, A1,
[5] Patent: WO2015/106292, 2015, A1,
[6] Bioorganic Chemistry, 2016, vol. 68, p. 112 - 123
[7] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 86 - 106
[8] Patent: CN106749278, 2017, A,
[9] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 8801 - 8815
[10] Patent: US2017/305920, 2017, A1,
[11] Patent: WO2018/102751, 2018, A1,
  • 6
  • [ 320-37-6 ]
  • [ 694499-26-8 ]
Reference: [1] Patent: WO2015/186137, 2015, A1,
[2] Patent: WO2005/51366, 2005, A2,
  • 7
  • [ 433-97-6 ]
  • [ 694499-26-8 ]
Reference: [1] Patent: WO2015/186137, 2015, A1,
[2] Patent: WO2005/51366, 2005, A2,
  • 8
  • [ 98187-15-6 ]
  • [ 694499-26-8 ]
Reference: [1] Patent: WO2015/186137, 2015, A1,
[2] Patent: WO2005/51366, 2005, A2,
  • 9
  • [ 630125-84-7 ]
  • [ 694499-26-8 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 6, p. 595 - 600
[2] Patent: WO2005/51366, 2005, A2,
  • 10
  • [ 853297-03-7 ]
  • [ 694499-26-8 ]
Reference: [1] Patent: WO2005/51366, 2005, A2,
  • 11
  • [ 109-01-3 ]
  • [ 694499-26-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 3033 - 3047
[2] Patent: WO2015/106292, 2015, A1,
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 8801 - 8815
  • 12
  • [ 65934-74-9 ]
  • [ 694499-26-8 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 6, p. 595 - 600
  • 13
  • [ 654-70-6 ]
  • [ 694499-26-8 ]
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 6, p. 1146 - 1155
  • 14
  • [ 350-96-9 ]
  • [ 694499-26-8 ]
Reference: [1] Patent: WO2005/51366, 2005, A2,
  • 15
  • [ 109-01-3 ]
  • [ 393-06-6 ]
  • [ 694499-26-8 ]
Reference: [1] Patent: CN105461659, 2016, A,
  • 16
  • [ 694499-26-8 ]
  • [ 1257628-77-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 879 - 894
  • 17
  • [ 694499-26-8 ]
  • [ 1421227-52-2 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 5, p. 1669 - 1672
  • 18
  • [ 694499-26-8 ]
  • [ 1421227-58-8 ]
  • [ 1421227-53-3 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 5, p. 1669 - 1672
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