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[ CAS No. 198904-84-6 ] {[proInfo.proName]}

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Chemical Structure| 198904-84-6
Chemical Structure| 198904-84-6
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Product Details of [ 198904-84-6 ]

CAS No. :198904-84-6 MDL No. :MFCD09701469
Formula : C17H19N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 297.35 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 198904-84-6 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.24
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 86.87
TPSA : 63.58 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.97
Log Po/w (XLOGP3) : 3.15
Log Po/w (WLOGP) : 3.61
Log Po/w (MLOGP) : 2.08
Log Po/w (SILICOS-IT) : 3.26
Consensus Log Po/w : 3.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.68
Solubility : 0.0627 mg/ml ; 0.000211 mol/l
Class : Soluble
Log S (Ali) : -4.16
Solubility : 0.0208 mg/ml ; 0.00007 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.58
Solubility : 0.000788 mg/ml ; 0.00000265 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.86

Safety of [ 198904-84-6 ]

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 [ 198904-84-6 ]

* 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 [ 198904-84-6 ]
  • Downstream synthetic route of [ 198904-84-6 ]

[ 198904-84-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 24424-99-5 ]
  • [ 198904-84-6 ]
YieldReaction ConditionsOperation in experiment
93.2% With sodium hydroxide In tetrahydrofuran; 4-(pyridin-2-yl)benzaldehyde hydrazone EXAMPLE 6
Production of N-(tert-butoxycarbonyl)-N'-[4-(pyridin-2-yl)phenylmethylidene]hydrazine
In a 100 ml four neck flask were placed 4-(pyridin-2-yl)benzaldehyde hydrazone (2.2 g, 12.0 mmol) obtained in Example 4, THF (50 ml) and 0.5M aqueous sodium hydroxide solution (10 ml), and a solution of di-tert-butyl dicarbonate (5.2 g, 23.8 mmol) in THF (5 ml) was added dropwise at 30° C. over 20 minutes with stirring.
The mixture was heated to 55-60° C. and vigorously stirred for 3 hours.
The reaction mixture was analyzed by HPLC. As a result, N-(tert-butoxycarbonyl)-N'-[4-(pyridin-2-yl)phenylmethylidene]hydrazine was confirmed to have been produced in a 93.2percent yield.
The reaction mixture was concentrated under reduced pressure, and the crystalline residue was washed with a small amount of cold methanol and recrystallized from toluene to give N-(tert-butoxycarbonyl)-N'-[4-(pyridin-2-yl)phenylmethylidene]hydrazine (yield 2.1 g).
Various spectrum data of the obtained N-(tert-butoxycarbonyl)-N'-[4-(pyridin-2-yl)phenylmethylidene]hydrazine are shown in the following.
melting point:169.2-171.5° C.; IR(XBr)cm-1: 3308, 1712, 1612, 1586, 1528, 1510, 1468, 1434, 1394, 1360, 1310, 1246, 1158, 780.
1 H-NMR(CDCl3, ppm) δ: 1.55(s,9H), 7.24(m,1H), 7.75(m,2H), 7.78(d,2H), 7.87(s,1H), 8.00(d,2H), 8.16(s,1H), 8.70(m,1H).
Reference: [1] Patent: US6147218, 2000, A,
  • 2
  • [ 127406-56-8 ]
  • [ 870-46-2 ]
  • [ 198904-84-6 ]
YieldReaction ConditionsOperation in experiment
91.1% for 4 h; Heating / reflux Synthesis of tert-butyl 2-(4-(pyridin-2-yl)benzylidene)hydrazinecarboxylate (XII, Y1a = H).; A mixture of 4-(pyridin-2-yl)benzaldehyde X (17.7 g, 96.6 mmol) and tert-butyl carbazate (12.2 g, 92.3 mmol) in ethanol (125 mL) was kept at reflux under nitrogen for 4 hours (hrs). The reaction mixture was cooled to 40°C and ice (60 g) was added, The resulting mixture was stirred for 20 minutes (min). The precipitate was collected by filtration, washed with water and dried in a vacuum oven (60 °C) to give the product XII, wherein Y1a = H (25.0 g, 91.1 percent).
Reference: [1] Patent: EP2003120, 2008, A1, . Location in patent: Page/Page column 33
[2] Organic and Biomolecular Chemistry, 2013, vol. 11, # 39, p. 6806 - 6813
[3] Organic Process Research and Development, 2002, vol. 6, # 3, p. 323 - 328
[4] Patent: US6765097, 2004, B1, . Location in patent: Page column 14-15
[5] Patent: WO2010/149356, 2010, A1, . Location in patent: Page/Page column 14; 15
[6] Molecules, 2015, vol. 20, # 5, p. 9229 - 9241
[7] Patent: CN106543073, 2017, A, . Location in patent: Paragraph 0040; 0041
  • 3
  • [ 24424-99-5 ]
  • [ 198904-84-6 ]
Reference: [1] Patent: US6147218, 2000, A,
  • 4
  • [ 127406-56-8 ]
  • [ 198904-84-6 ]
Reference: [1] Patent: US6147218, 2000, A,
  • 5
  • [ 87199-17-5 ]
  • [ 198904-84-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 39, p. 6806 - 6813
[2] Organic Process Research and Development, 2002, vol. 6, # 3, p. 323 - 328
[3] Molecules, 2015, vol. 20, # 5, p. 9229 - 9241
  • 6
  • [ 109-04-6 ]
  • [ 198904-84-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 39, p. 6806 - 6813
[2] Organic Process Research and Development, 2002, vol. 6, # 3, p. 323 - 328
[3] Molecules, 2015, vol. 20, # 5, p. 9229 - 9241
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