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[ CAS No. 1557267-42-1 ] {[proInfo.proName]}

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Chemical Structure| 1557267-42-1
Chemical Structure| 1557267-42-1
Structure of 1557267-42-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1557267-42-1 ]

CAS No. :1557267-42-1 MDL No. :MFCD29089376
Formula : C26H26FN7O2 Boiling Point : -
Linear Structure Formula :- InChI Key :UOFYSRZSLXWIQB-UHFFFAOYSA-N
M.W : 487.53 Pubchem ID :72734520
Synonyms :
Abivertinib;AC0010

Calculated chemistry of [ 1557267-42-1 ]

Physicochemical Properties

Num. heavy atoms : 36
Num. arom. heavy atoms : 21
Fraction Csp3 : 0.19
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 144.81
TPSA : 98.41 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.71
Log Po/w (XLOGP3) : 4.2
Log Po/w (WLOGP) : 3.98
Log Po/w (MLOGP) : 3.03
Log Po/w (SILICOS-IT) : 3.19
Consensus Log Po/w : 3.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.41
Solubility : 0.00189 mg/ml ; 0.00000387 mol/l
Class : Moderately soluble
Log S (Ali) : -5.98
Solubility : 0.000515 mg/ml ; 0.00000106 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.1
Solubility : 0.00000392 mg/ml ; 0.000000008 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.82

Safety of [ 1557267-42-1 ]

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 [ 1557267-42-1 ]

* 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 [ 1557267-42-1 ]
  • Downstream synthetic route of [ 1557267-42-1 ]

[ 1557267-42-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 814-68-6 ]
  • [ 1557267-42-1 ]
YieldReaction ConditionsOperation in experiment
54% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -5 - 0℃; for 1.5 h; A reactor (30 L) was charged with 4- (3-aminophenoxy) -N- (3-methyl-4- (4-methylpiperazin-1-yl) phenyl) -7H-pyrrolo [2, 3-d] pyrimidin-2-amine (1199 g, 2.77 mol) , DIEA (685 g, 5.30 mol) and THF (13 L) . When the temperature inside the reactor reached -3 , a solution of acryloyl chloride (466.5 g, 5.15 mol) in THF (1 L) was added drop-wise into the reactor over a period of 1 h. The temperature was kept between -5 -0 during the addition. After stirring for another 30 min, a NaOH solution (1 M, 7.5 L) was added slowly to quench the reaction (the temperature kept between -5 -0 ) . The final pH value of the solution was around 9 10. The resulting mixture was stirred for another 3-4 h. The upper THF layer was separated and concentrated under reduced pressure at < 40 . The residue was re-dissolved in ethyl acetate (15 L) . The lower aqueous layer was extracted with ethyl acetate (5 L) . The residue/ethyl acetate solution was combined with the ethyl acetate layers and all were washed with water (5 L x3) and concentrated under reduced pressure to give a crude product ( 1680 g) . The crude material was re-dissolved in EtOH (18 L) at 35-40 and water (12 L) was added with stirring. The resulting solution was allowed to cool to room temperature and was stirred overnight (16 h) . The resulting precipitate was collected and dried under vacuum to afford a second crude product (1010 g) . To further purify this crude product (1010 g) , silica gel chromatography (4: 1 ethyl acetate/EtOH as mobile phase) and two re-crystallizations from EtOH/water (4: 1) were performed to yield the title compound (727 g, 99.2by HPLC, 54yield) as off-white powder. mp: 122.0-123.5 [M+H] +: m/z 488.6 1H NMR and 13C NMR spectral data for N- (3- (2- (3-fluoro-4- (4-methylpiperazin-1-yl) phenylamino) -7H-pyrrolo [2, 3-d] pyrimidin-4-yloxy) phenyl) acrylamide are consistent with those reported in Example 6.
Reference: [1] Patent: WO2017/59702, 2017, A1, . Location in patent: Paragraph 00230
  • 2
  • [ 90213-66-4 ]
  • [ 1557267-42-1 ]
Reference: [1] Patent: WO2017/59702, 2017, A1,
  • 3
  • [ 1557268-80-0 ]
  • [ 1557267-42-1 ]
Reference: [1] Patent: WO2017/59702, 2017, A1,
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