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[ CAS No. 914306-50-6 ] 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole

Cat. No.: A193706
Chemical Structure| 914306-50-6
Chemical Structure| 914306-50-6
Structure of 914306-50-6 * Storage: Sealed in dry,Room Temperature
Purity Size Price USA Stock *0-1 Day Global Stock *5-7 Days Quantity
95% 100mg $33.00 Inquiry Inquiry
95% 250mg $56.00 Inquiry Inquiry
95% 1g $147.00 Inquiry Inquiry

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* Storage: Sealed in dry,Room Temperature

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Product Details of [ 914306-50-6 ]

CAS No. :914306-50-6 MDL No. :MFCD27923076
Formula : C21H24N2 Boiling Point : -
Linear Structure Formula :- InChI Key :DGCQHTACQZUATF-UHFFFAOYSA-N
M.W : 304.43 Pubchem ID :58037491
Synonyms :

Calculated chemistry of [ 914306-50-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.29
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 98.16
TPSA : 17.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.44
Log Po/w (XLOGP3) : 5.59
Log Po/w (WLOGP) : 5.79
Log Po/w (MLOGP) : 4.44
Log Po/w (SILICOS-IT) : 5.18
Consensus Log Po/w : 4.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.53
Solubility : 0.000894 mg/ml ; 0.00000294 mol/l
Class : Moderately soluble
Log S (Ali) : -5.73
Solubility : 0.000572 mg/ml ; 0.00000188 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.08
Solubility : 0.0000255 mg/ml ; 0.0000000838 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.72

Safety of [ 914306-50-6 ]

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 [ 914306-50-6 ]

* 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 [ 914306-50-6 ]

[ 914306-50-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 591-50-4 ]
  • [ 914306-50-6 ]
YieldReaction ConditionsOperation in experiment
78% With tetrakis(triphenylphosphine) palladium(0) In toluene at 120℃; for 16 h; Inert atmosphere In the same procedure as in Synthesis Example 2, the compound 2 was prepared from a solution containing the compound 1 (28.5 g, 125 mmol), tetrahydrofuran (125ml), the n-BuLi-hexane solution (74.9 ml, mole number of n-BuLi in the solution: 125 mmol, molarity (mole number of n-BuLi/solution amount): 1.67M) and zinc chloride (28.4 g, 208 mmol) dissolved in tetrahydrofuran (208 ml). After preparing the compound 2, the compound 2 was put into a three-necked flask, to which an oil-sealed rotary pump was connected through a solvent trap that is cooled using a solvent of dry ice/acetone. The three-necked flask was heated to about 40 degrees C under reduced pressure to remove the solvent (310 ml) from the reaction system (the solvent removal step). A removal amount of the solvent herein is an amount collected by the solvent trap. Subsequently, nitrogen was put into the reaction system to return to the normal pressure. Toluene (104 ml) was put into the reaction system (toluene addition step). Next, iodobenzene (21.3g, 104 mmol) and Pd(PPh3)4 (2.89 g, 2.5 mmol) were added thereto and reacted at 120 degrees C for 16 hours under nitrogen atmosphere. [0151] A relationship of the solvent amounts in the reaction system in Synthesis Example 4 is shown in Table 1. Herein, a relationship between the total volume VA [liter] of tetrahydrofuran (i.e., the ether solvent having at most 5 carbon atoms) and the mole number Nf2 [mol] of iodobenzene is represented below according the same calculation as in Synthesis Example 3 as shown in Table 1. The relationship of the numerical formula (3) was satisfied. Further, a relationship between a volume VB [liter] of toluene (i.e., an aromatic hydrocarbon solvent having 7 carbon atoms) and a mole number Nf2 [mol] of iodobenzene is represented below as shown in Table 1. The relationship of the numerical formula (5) was satisfied. There is a possibility that n-hexane (i.e., an aliphatic hydrocarbon having 6 carbon atoms) is contained in the reaction system even after the solvent removal step in Synthesis Example 4. However, since the volume of n-hexane after the solvent removal step is less than the volume of toluene subsequently added, the relationship of the numerical formula (5) is still satisfied even in consideration of n-hexane. The same applies to Examples 3 and 4 described later. Accordingly, Synthesis Example 4 was conducted under the reaction condition of satisfying the relationships of the numerical formulae (3) and (5). [0152] After the reaction, a small amount of water was added to the sample to deactivate the reaction. The mixture was diluted with dichloromethane (300 ml). An aqueous solution of tetrasodium ethylenediaminetetraacetate dihydrate (129.9 g, 312 mmol) was added to the diluted mixture and stirred in a separating funnel. An aqueous sodium hydroxide was further added thereto to adjust an aqueous phase to pH10 or more. A dichloromethane phase was collected. The aqueous phase was extracted with dichloromethane several times. The extract was dried over anhydrous magnesium sulfate, filtrated and concentrated. The obtained product was refined by silica-gel chromatography (toluene:ethyl acetate=95:5 (volume ratio)) and was further recrystallized in a mixture solvent of hexane/ethyl acetate to obtain a white solid. The compound 4 was identified according to 1H-NMR and FD-MS. Yield: 24.7 g Yield Rate: 78percent
Reference: [1] Patent: EP2662365, 2013, A1, . Location in patent: Paragraph 0142; 0143; 014; 0150; 0151; 0152; 0173-0176; 0189
  • 2
  • [ 107-20-0 ]
  • [ 153998-83-5 ]
  • [ 914306-50-6 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydrogencarbonate In isopropyl alcoholReflux N-(2,6-diisopropylphenyl)benzimidamide (13.60 g, 48.5 mmol), 2-chloroacetaldehyde (12.28 ml, 97 mmol), and sodium hydrogen carbonate (8.15 g, 97 mmol) were combined in 2-propanol (250 ml) and heated at reflux overnight, turning brown. The suspension was cooled to room temperature and filtered through celite, washing with DCM. The filtrate was reduced under vacuum purified by column chromatography, yielding 2 in quantitative yield.
Reference: [1] Patent: US2018/319830, 2018, A1, . Location in patent: Paragraph 0142
  • 3
  • [ 24544-04-5 ]
  • [ 914306-50-6 ]
Reference: [1] European Journal of Organic Chemistry, 2013, # 27, p. 6137 - 6145
[2] Patent: EP2662365, 2013, A1,
[3] Patent: US2018/319830, 2018, A1,
  • 4
  • [ 100-47-0 ]
  • [ 914306-50-6 ]
Reference: [1] Patent: US2018/319830, 2018, A1,
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