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[ CAS No. 356068-94-5 ] {[proInfo.proName]}

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Chemical Structure| 356068-94-5
Chemical Structure| 356068-94-5
Structure of 356068-94-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 356068-94-5 ]

CAS No. :356068-94-5 MDL No. :MFCD16038046
Formula : C22H25FN4O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SRSGVKWWVXWSJT-ATVHPVEESA-N
M.W : 396.46 Pubchem ID :5329106
Synonyms :
SU11654;PHA 291639E;PHA 291639

Calculated chemistry of [ 356068-94-5 ]

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.36
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 118.11
TPSA : 77.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.14
Log Po/w (XLOGP3) : 2.39
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 4.62
Consensus Log Po/w : 2.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.69
Solubility : 0.0812 mg/ml ; 0.000205 mol/l
Class : Soluble
Log S (Ali) : -3.65
Solubility : 0.0881 mg/ml ; 0.000222 mol/l
Class : Soluble
Log S (SILICOS-IT) : -6.88
Solubility : 0.0000521 mg/ml ; 0.000000132 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.47

Safety of [ 356068-94-5 ]

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 [ 356068-94-5 ]

* 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 [ 356068-94-5 ]
  • Downstream synthetic route of [ 356068-94-5 ]

[ 356068-94-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 7154-73-6 ]
  • [ 356068-93-4 ]
  • [ 356068-94-5 ]
YieldReaction ConditionsOperation in experiment
77% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 2 h; 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (100 g) and dimethylformamide (500 ml) were stirred and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (221 g), 1-(2-aminoethyl) pyrrolidine (45.6 g) and triethylamine (93 ml) were added. The mixture was stirred for 2 hours at ambient temperature. The solid product was collected by vacuum filtration and washed with ethanol. The solids were slurry-washed by stirring in ethanol (500 ml) for one hour at 64 C and cooled to room temperature. The solids were collected by vacuum filtration, washed with ethanol, and dried under vacuum to give 5-[5-fluoro-2-oxo-1,2-dihydro-indol- (3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide (101.5 g, 77 percent yield). 1H-NMR (dimethylsulfoxide-d6) δ 1.60 (m, 4H, 2xCH2), 2.40, 2.44 (2xs, 6H, 2xCH3), 2.50 (m, 4H, 2xCH2), 2.57, 3.35 (2xm, 4H, 2XCH2), 7.53, 7.70, 7.73, 7.76 (4xm, 4H, aromatic and vinyl), 10.88 (s, 1H, CONH), 13.67 (s, 1H, pyrrole NH). MS m/z 396 [M+1].
77% With benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2 h; 5-[5-Fluoro-2-oxo- 1 ,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl- IH- pyrrole-3 -carboxylic acid (100 g) and dimethylformamide (50OmL) were stirred and EPO <DP n="19"/>benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafluorophosphate (221 g), l-(2-aminoethyl)pyrrolidine (45.6 g) and triethylamine (93 niL) were added. The mixture was stirred for 2 hours at ambient temperature. The solid product was collected by vacuum filtration and washed with ethanol. The solids were slurry- washed by stirring in ethanol (500 mL) for one hour at 64° C. and cooled to room temperature. The solids were collected by vacuum filtration, washed with ethanol, and dried under vacuum to give 5-[5-fluoro-2-oxo-l,2-dihydro-indol-(3Z)- ylidenemethyl)-2,4-dimethyl-lH-pyrrole-3-carboxylic acid (2-pyrrolidin-l-yl-ethyl)- amide (101.5 g, 77percent yield).
Reference: [1] Patent: WO2004/76410, 2004, A2, . Location in patent: Page 12
[2] Patent: WO2007/34272, 2007, A1, . Location in patent: Page/Page column 17-18
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 7, p. 1116 - 1119
  • 2
  • [ 253870-02-9 ]
  • [ 356068-94-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 7, p. 1116 - 1119
  • 3
  • [ 2199-59-9 ]
  • [ 356068-94-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 7, p. 1116 - 1119
  • 4
  • [ 86770-31-2 ]
  • [ 356068-94-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 7, p. 1116 - 1119
  • 5
  • [ 342642-56-2 ]
  • [ 56341-41-4 ]
  • [ 356068-94-5 ]
Reference: [1] Patent: WO2004/76410, 2004, A2, . Location in patent: Page 11
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