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Chemical Structure| 425638-74-0
Chemical Structure| 425638-74-0
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Product Details of [ 425638-74-0 ]

CAS No. :425638-74-0 MDL No. :MFCD16627975
Formula : C10H8ClN3O Boiling Point : -
Linear Structure Formula :- InChI Key :HBENSHGDVIJNBK-UHFFFAOYSA-N
M.W : 221.64 Pubchem ID :18770867
Synonyms :

Calculated chemistry of [ 425638-74-0 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.23
TPSA : 68.87 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 1.35
Log Po/w (WLOGP) : 1.31
Log Po/w (MLOGP) : 0.78
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 1.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.43
Solubility : 0.831 mg/ml ; 0.00375 mol/l
Class : Soluble
Log S (Ali) : -2.4
Solubility : 0.886 mg/ml ; 0.004 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.95
Solubility : 0.0251 mg/ml ; 0.000113 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 425638-74-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 425638-74-0 ]

* 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 [ 425638-74-0 ]
  • Downstream synthetic route of [ 425638-74-0 ]

[ 425638-74-0 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 607-68-1 ]
  • [ 141-97-9 ]
  • [ 425638-74-0 ]
YieldReaction ConditionsOperation in experiment
54%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 1 h;
Stage #2: for 0.5 h; Reflux
Stage #3: for 0.333333 h;
Λ/, ν-dimethylaniline (33.4 g, 276 mmol, 1 .0 eq) was added dropwise to a solution of 2,4 (1 H, 3H)-quinazolinedione (50 g, 276 mmol, 1 .0 eq) in POCI3 (300 ml) and the mixture was heated to reflux for 3 hrs. The solution was cooled to room temperature, poured onto ice water and the resulting precipitate was filtered off and washed with water. The solid was dissolved in EtOAc and washed with water and brine. The organic fraction was dried over Na2S04, filtered, concentrated under reduced pressure, and washed with petroleum ether to give the corresponding dichloro-derivative (20 g, 34percent yield).Ethyl-3-oxobutanoate (31.2 g, 240 mmol, 2.0 eq) was added dropwise to a suspension of NaH (6 g, 156 mmol, 1 .3 eq) in THF (520 ml) at 0 °C. After stirring at 0 °C for 1 h and removal of THF under reduced pressure, a solution of 2,4-dichloroquinazoline (24 g, 120 mmol, 1.0 eq) in toluene (350 ml) was added and the reaction mixture was heated to reflux for 30 min. After removal of toluene under reduced pressure, NH4OH (320 ml) was added. After stirring for 20 min, the mixture was concentrated to remove NH4OH. EtOAc (100 ml) and water (50 ml) were added to the mixture, that was filtered to give 2-(2- chloroquinazolin-4-yl)acetamide (14.4 g, 54 percent yield).1 -Methylpiperazine (34 g, 339 mmol, 5.0 eq) was added to a solution of 2-(2- chloroquinazolin-4-yl)acetamide (14.4 g, 65 mmol, 1.0 eq) in NMP (250 ml) and stirred at 50 °C for 30 min. After cooling to room temperature, EtOAc (100 ml) was added and the suspension was filtered to give 2-(2-(4-methylpiperazin-1 -yl)quinazolin-4-yl)acetamide (10.5 g, 55 percent yield).fert-BuOK (215 ml_, 121 mmol, 3.0 eq) was added to a solution of 2-(2-(4-methylpiperazin- 1 -yl)quinazolin-4-yl)acetamide (10.5 g, 36.8 mmol, 1.0 eq) and Intermediate 2 (10.5 g, 40.5 mmol, 1.1 eq) in anhydrous THF (250 ml) at room temperature and the mixture was stirred for about 30 min, quenched with water, extracted with EtOAc, washed with brine, dried over Na2S04, concentrated and purified by column chromatography (silicagel) to give the methyl-ester of intermediate 8 (1 1 g, 60 percent yield).
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 20, p. 6193 - 6196
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 17, p. 6028 - 6039
[3] Patent: WO2013/4709, 2013, A1, . Location in patent: Page/Page column 54-55
[4] Patent: US2003/69424, 2003, A1,
  • 2
  • [ 86-96-4 ]
  • [ 425638-74-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 17, p. 6028 - 6039
[2] Patent: WO2013/4709, 2013, A1,
  • 3
  • [ 607-68-1 ]
  • [ 425638-74-0 ]
Reference: [1] Patent: US2011/152243, 2011, A1,
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