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[ CAS No. 277299-70-4 ] {[proInfo.proName]}

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Chemical Structure| 277299-70-4
Chemical Structure| 277299-70-4
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Product Details of [ 277299-70-4 ]

CAS No. :277299-70-4 MDL No. :MFCD09795980
Formula : C12H14N2O Boiling Point : -
Linear Structure Formula :- InChI Key :HBWBJCSXUJIDGN-UHFFFAOYSA-N
M.W :202.25 Pubchem ID :11735829
Synonyms :

Calculated chemistry of [ 277299-70-4 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 61.29
TPSA : 37.79 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) : -5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 2.58
Log Po/w (WLOGP) : 2.09
Log Po/w (MLOGP) : 2.46
Log Po/w (SILICOS-IT) : 3.04
Consensus Log Po/w : 2.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.2
Solubility : 0.129 mg/ml ; 0.000637 mol/l
Class : Soluble
Log S (Ali) : -3.02
Solubility : 0.192 mg/ml ; 0.00095 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.0
Solubility : 0.0202 mg/ml ; 0.0000998 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 277299-70-4 ]

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 [ 277299-70-4 ]

* 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 [ 277299-70-4 ]
  • Downstream synthetic route of [ 277299-70-4 ]

[ 277299-70-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 141-97-9 ]
  • [ 60481-51-8 ]
  • [ 277299-70-4 ]
YieldReaction ConditionsOperation in experiment
76% With sodium bicarbonate; sodium acetate In diethyl ether; acetic acid f
1-(3,4-Dimethylphenyl)-3-methyl-3-pyrazolin-5-one
A solution of 3,4-dimethylphenylhydrazine hydrochloride (17.7 g; 0.1 mol.), ethyl acetoacetate (13.0 g; 0.1 mol.) and sodium acetate (8.2 g; 0.1 mol.) in glacial acetic acid (250 mL) was stirred and heated under reflux for 24 h.
The mixture was cooled and evaporated and the residue dissolved in diethyl ether (IL) and carefully washed with sat. aqu. sodium hydrogen carbonate (5*200 mL).
The ethereal layer was evaporated to afford the title compound (15.4 g; 76percent).
1H NMR (300 MHz, d6-DMSO) δ11.30 (br s, 1H), 7.49 (d, J=1.4 Hz, 1H), 7.43 (dd, J=8.2 Hz, 1H), 7.14 (d, J=8.2 Hz, 1H), 5.31 (s, 1H), 2.20 (s, 3H), 2.22 (s, 3H), 2.08 (s, 3H); MS(ES) m/z 203 [M+H].
76% With sodium acetate In acetic acid for 24 h; Heating / reflux A solution of 3,4-dimethylphenylhydrazine hydrochloride (17.7 g; 0.1 mol.), ethyl acetoacetate (13.0 g; 0.1 mol.) and sodium acetate (8.2 g; 0.1 mol.) in glacial acetic acid; (250 mL) was stirred and heated under reflux for 24 h. [0378] The mixture was cooled and evaporated and the residue dissolved in diethyl ether (1L) and carefully washed with sat. aqu. sodium hydrogen carbonate (5.x.200 mL). The ethereal layer was evaporated to afford the title compound (15.4 g; 76percent). 1H NMR (300 MHz, d6-DMSO) δ 11.30 (br s, 1H), 7.49 (d, J=1.4 Hz, 1H), 7.43 (dd, J=8.2 Hz, 1H), 7.14 (d, J=8.2 Hz, 1H), 5.31 (s, 1H), 2.20 (s, 3H), 2.22 (s, 3H), 2.08 (s, 3H); MS(ES) m/z 203 [M+H].
76% for 24 h; Reflux A solution of 3,4-dimethylphenylhydrazine hydrochloride (17.7 g; 0.1 mol.), ethyl acetoacetate (13.0 g; 0.1 mol.) and sodium acetate (8.2 g; 0.1 mol.) in glacial acetic acid; (250 mL) was stirred and heated under reflux for 24h. The mixture was cooled and evaporated and the residue dissolved in diethyl ether (1L) and carefully washed with saturated aqueous sodium hydrogen carbonate (5 x 200 mL). The ethereal layer was evaporated to afford the title compound (15.4 g; 76percent).
Reference: [1] Patent: US2004/53299, 2004, A1,
[2] Patent: US2004/19190, 2004, A1, . Location in patent: Page 17
[3] Patent: WO2016/35018, 2016, A1, . Location in patent: Page/Page column 13
  • 2
  • [ 141-97-9 ]
  • [ 13636-53-8 ]
  • [ 277299-70-4 ]
Reference: [1] Patent: US6552008, 2003, B1,
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