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[ CAS No. 6373-46-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 6373-46-2
Chemical Structure| 6373-46-2
Chemical Structure| 6373-46-2
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Product Details of [ 6373-46-2 ]

CAS No. :6373-46-2 MDL No. :MFCD00025318
Formula : C13H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :FIIDVVUUWRJXLF-UHFFFAOYSA-N
M.W : 199.25 Pubchem ID :22860
Synonyms :

Calculated chemistry of [ 6373-46-2 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 61.83
TPSA : 35.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.13
Log Po/w (XLOGP3) : 3.11
Log Po/w (WLOGP) : 2.7
Log Po/w (MLOGP) : 2.69
Log Po/w (SILICOS-IT) : 2.68
Consensus Log Po/w : 2.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.43
Solubility : 0.0743 mg/ml ; 0.000373 mol/l
Class : Soluble
Log S (Ali) : -3.52
Solubility : 0.0604 mg/ml ; 0.000303 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.71
Solubility : 0.00393 mg/ml ; 0.0000197 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 6373-46-2 ]

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 [ 6373-46-2 ]

* 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.

  • Upstream synthesis route of [ 6373-46-2 ]
  • Downstream synthetic route of [ 6373-46-2 ]

[ 6373-46-2 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 6373-46-2 ]
  • [ 1215-59-4 ]
Reference: [1] Liebigs Annalen der Chemie, 1987, p. 765 - 770
  • 2
  • [ 6373-46-2 ]
  • [ 52068-30-1 ]
YieldReaction ConditionsOperation in experiment
95% With sodium nitrite In hydrogenchloride; water A.
4-Benzyloxyphenylhydrazine hydrochloride
A solution of sodium nitrite (3.8 g, 0.055 mol in 20 mL of H2 O), is added dropwise to an ice cold stirring suspension of 4-benzyloxyaniline (13.0 g, 0.055 mol in 150 mL of concentrated HCl).
The reaction mixture is stirred for 90 minutes at -8° to 10° C.
A solution of SnCl2.2H2 O (32.0 g, 0142 mol in 50 mL concentrated HCl) is added and stirred for 1 hour at 0° C.
The reaction mixture is removed from the ice bath and is stirred at room temperature for 20 hours.
The mixture is then filtered and washed with water to give 13.0 g (95percent yield) of product, m.p. 182°-185° C.
Reference: [1] Patent: US5229516, 1993, A,
  • 3
  • [ 6373-46-2 ]
  • [ 52068-30-1 ]
YieldReaction ConditionsOperation in experiment
95% With sodium nitrite In hydrogenchloride; water A.
4-Benzyloxyphenylhydrazine hydrochloride
A solution of sodium nitrite (3.8 g, 0.055 mol in 20 mL of H2 O), is added dropwise to an ice cold stirring suspension of 4-benzyloxyaniline (13.0 g, 0.055 mol in 150 mL of concentrated HCl).
The reaction mixture is stirred for 90 minutes at -8° to 10° C.
A solution of SnCl2 *2H2 O (32.0 g, 0142 mol in 50 mL concentrated HCl) is added and stirred for i hour at 0° C.
The reaction mixture is removed from the ice bath and is stirred at room temperature for 20 hours.
The mixture is then filtered and washed with water to give 13.0 g (95percent yield) of product, m.p. 182°-185° C.
Reference: [1] Patent: US5420289, 1995, A,
  • 4
  • [ 6373-46-2 ]
  • [ 52068-30-1 ]
Reference: [1] Patent: EP596983, 1995, B1,
  • 5
  • [ 13675-18-8 ]
  • [ 6373-46-2 ]
  • [ 146631-00-7 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
  • 6
  • [ 6373-46-2 ]
  • [ 4495-66-3 ]
  • [ 198479-63-9 ]
YieldReaction ConditionsOperation in experiment
23% With triethylamine In N,N-dimethyl-formamide at 125℃; for 6 h; In a 250 mL round bottom flask, 4-(benzyloxy)aniline (8.8 g, 44.34 mmol, 3.00 equiv) was added to a solution of 1-[4-(benzyloxy)phenyl]propan-1-one (4.3 g, 17.89 mmol, 1.00 equiv) in DMF/TEA (40/4.3 mL).
The resulting solution was stirred for 6 hours at 125° C.
The reaction was then quenched by the addition of water.
The resulting mixture was extracted with ethyl acetate (20 mL*3) and the organic layers were combined, washed with brine and dried over anhydrous sodium sulfate.
The organic solvent was removed under reduced pressure and the residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1:5).
This resulted in 1.7 g (23percent) of 5-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-methyl-1H-indole as a light brown solid.
Reference: [1] Patent: US2018/72711, 2018, A1, . Location in patent: Paragraph 0432; 0435
  • 7
  • [ 6373-46-2 ]
  • [ 198479-63-9 ]
Reference: [1] Patent: US6583170, 2003, B1,
[2] Patent: US5985910, 1999, A,
[3] Patent: US6005102, 1999, A,
[4] Patent: US5780497, 1998, A,
[5] Patent: EP802184, 1997, A1,
[6] Patent: EP802184, 1997, A1,
  • 8
  • [ 1048697-94-4 ]
  • [ 6373-46-2 ]
  • [ 198479-63-9 ]
YieldReaction ConditionsOperation in experiment
80.5% for 6 h; Reflux 1- (4-benzyloxyphenyl) -2- (4-benzyloxy-phenylamino) -1-propanone (12.3g, 0.028mol), 4- benzyloxyaniline (14.0g, 0.070mol) placed in 500mL flask, ethylene glycol monomethyl ether as a solvent, refluxed 6h. The solvent was distilled off under reduced pressure, the residue was stirred with ethanol, suction filtered to give 9.5 g of a brown solid, yield 80.5percent. m.p.151-152 . ESI-MS: m / z420 ([M + H] +). 1H-NMR (400MHz, CDCl3) δ7.89 (s, 1H), 7.45 (m, 14H), 7.28 (d, J = 2.6Hz, 1H), 7.11 (d, J = 8.4Hz, 2H), 6.97 ( dd, J1 = 8.5Hz, J2 = 1.5Hz, 1H), 5.18 (s, 2H), 5.15 (s, 2H), 2.43 (s, 3H).
Reference: [1] Patent: CN105801564, 2016, A, . Location in patent: Paragraph 0026; 0030; 0041; 0042
  • 9
  • [ 6373-46-2 ]
  • [ 198479-63-9 ]
Reference: [1] Patent: US5880137, 1999, A,
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