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[ CAS No. 289499-45-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 289499-45-2
Chemical Structure| 289499-45-2
Structure of 289499-45-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 289499-45-2 ]

CAS No. :289499-45-2 MDL No. :
Formula : C24H27Cl3FN5O3 Boiling Point : -
Linear Structure Formula :- InChI Key :JZZFDCXSFTVOJY-UHFFFAOYSA-N
M.W : 558.86 Pubchem ID :156413
Synonyms :
CI-1033 dihydrochloride;PD-183805 dihydrochloride;PD 183805;CI-1033;Canertinib (hydrochloride)

Calculated chemistry of [ 289499-45-2 ]

Physicochemical Properties

Num. heavy atoms : 36
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.29
Num. rotatable bonds : 10
Num. H-bond acceptors : 7.0
Num. H-bond donors : 2.0
Molar Refractivity : 147.74
TPSA : 88.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 5.51
Log Po/w (WLOGP) : 5.84
Log Po/w (MLOGP) : 3.11
Log Po/w (SILICOS-IT) : 4.33
Consensus Log Po/w : 3.76

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.45
Solubility : 0.000201 mg/ml ; 0.000000359 mol/l
Class : Poorly soluble
Log S (Ali) : -7.13
Solubility : 0.0000415 mg/ml ; 0.0000000742 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.22
Solubility : 0.00000339 mg/ml ; 0.0000000061 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.64

Safety of [ 289499-45-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 289499-45-2 ]

* 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.

  • Downstream synthetic route of [ 289499-45-2 ]

[ 289499-45-2 ] Synthesis Path-Downstream   1~1

YieldReaction ConditionsOperation in experiment
1 Preparation of N-[4-(3-chloro-4-fluorophenylamino)-7-(3-morpholin-4-ylpropoxy)-quinazolin-6-yl]-acrylamide Dihydrochloride Form M. EXAMPLE 1 Preparation of N-[4-(3-chloro-4-fluorophenylamino)-7-(3-morpholin-4-ylpropoxy)-quinazolin-6-yl]-acrylamide Dihydrochloride Form M. A 6 l three-necked flask equipped wich a mechanical stirrer, a reflux condenser and a dropping funnel is supplied with 300 g N-[4-(3-chloro-4-fluorophenylamino)-7-(3-morpholin-4-ylpropoxy)-quinazolin-6-yl]-acrylamide and 4 l abs. ethanol. With stirring, the suspension is heated to 35° C. A mixture of 100 ml conc. hydrochloric acid and 100 ml water is then added dropwise thereto within 30 s and the reaction mixture further heated to 74° C. At 40° C, a clear solution results, at about 50° C. the solution becomes turbid and the crystallisation commences. With stirring, one allows the reaction mixture to cool slowly to room temperature and then cools further in an icebath for 2 h to 2° C. The precipitated crystals are filtered off with suction and dried in a circulating drying cabinet for 40 h at 60° C. Thereafter, the product is carefully sieved through a 0.5 mm Kressner sieve. One obtains 314.2 g of product. Water according to Karl Fischer: 2.84%. Elementary analysis: (C24H25ClFNSO3*2HCl*H2O)
3 Preparation of N-[4-(3-chloro-4-fluorophenylamino)-7-(3-morpholin-4-ylpropoxy)-quinazolin-6-yl]-acrylamide Dihydrochloride Form B EXAMPLE 3 Preparation of N-[4-(3-chloro-4-fluorophenylamino)-7-(3-morpholin-4-ylpropoxy)-quinazolin-6-yl]-acrylamide Dihydrochloride Form B A Suspension of 250 g N-[4-(3-chloro-4-fluorophenylamino)-7-(3-morpholin-4-ylpropoxy)-quinazlon-6-yl]-acrylamide dihydrochloride form A in 2.6 l water is heated, with stirring, to 50° C. The slightly turbid solution is sucked through a Buchner funnel (porosity a) and the filtrate cooled to room temperature without stirring. After standing overnight in a refrigerator at 4° C., the precipitated product is filtered off with suction, washed out with 100 ml water and dried in a vacuum desiccator over calcium chloride at 20 mbar for 3 days. The product obtained is sieved over a 1 mm Kresner sieve. One obtains 212.2 g of product. Water according to Karl Fischer: 8.6% Elementary analysis: (C24H2ClFN5O3*2HCl*3H2O)
4 Preparation of N-[4-(3-chloro-4-fluorophenylamino)-7-(3-morpholin-4-ylpropoxy)-quinazolin-6-yl]-acrylamide Dihydrochloride Form H EXAMPLE 4 Preparation of N-[4-(3-chloro-4-fluorophenylamino)-7-(3-morpholin-4-ylpropoxy)-quinazolin-6-yl]-acrylamide Dihydrochloride Form H 2 g N-[4-(3-Chloro-4-fluorophenylamino)-7-(3-morpholin-4-ylpropoxy)-quinazolin-6-yl]-acrylamide dihydrochloride form B are dissolved in 80 ml abs. methanol at room temperature. The solution is filtered into a crystallisation dish and kept open under an extractor up to the complete evaporation of the solvent (7 days). Water according to Karl Fischer: 19.95% Elementary analysis: (C24H2ClFNFO3*2HCl*7H2O)
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Reason: Free-salt