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[ CAS No. 15469-97-3 ] {[proInfo.proName]}

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Chemical Structure| 15469-97-3
Chemical Structure| 15469-97-3
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Product Details of [ 15469-97-3 ]

CAS No. :15469-97-3 MDL No. :MFCD00229427
Formula : C22H18N2 Boiling Point : -
Linear Structure Formula :- InChI Key :NPZDCTUDQYGYQD-UHFFFAOYSA-N
M.W : 310.39 Pubchem ID :618231
Synonyms :

Calculated chemistry of [ 15469-97-3 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 23
Fraction Csp3 : 0.05
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 96.83
TPSA : 17.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.02
Log Po/w (XLOGP3) : 4.79
Log Po/w (WLOGP) : 4.72
Log Po/w (MLOGP) : 3.9
Log Po/w (SILICOS-IT) : 4.36
Consensus Log Po/w : 4.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.23
Solubility : 0.00184 mg/ml ; 0.00000593 mol/l
Class : Moderately soluble
Log S (Ali) : -4.9
Solubility : 0.00394 mg/ml ; 0.0000127 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.99
Solubility : 0.00000315 mg/ml ; 0.0000000102 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.43

Safety of [ 15469-97-3 ]

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 [ 15469-97-3 ]

* 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 [ 15469-97-3 ]
  • Downstream synthetic route of [ 15469-97-3 ]

[ 15469-97-3 ] Synthesis Path-Upstream   1~14

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Reference: [1] Synthetic Communications, 1989, vol. 19, # 13-14, p. 2551 - 2566
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  • [ 527-73-1 ]
Reference: [1] Inorganic Chemistry Communications, 2017, vol. 78, p. 32 - 36
[2] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 253 - 256
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YieldReaction ConditionsOperation in experiment
95.6%
Stage #1: With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.5 h; Large scale
Stage #2: at 0 - 15℃; for 16 h; Large scale
Compound XIII (880g, 12.9mol, 1.0eq.) In the autoclave 50L, 12L DMF were dissolved, cooled To below 0 °C, triethylamine (1308g, 12.9mol, 1.0eq. ) The reaction was kept 30min, 0 ° C solution of the following threePhenyl chloride (3605.0g, 12.9mol, 1.0eq. ) In DMF (16L), drops Bi, 15 ° C overnight with stirring 16 h. Thereaction mixture was poured into water, large amount of solid precipitated, suction filtered, the filter cake washedwith water, drained, dried to obtain compound XIV-1 White The solid 3835.1g, Yield: 95.6percent.
91%
Stage #1: With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.5 h;
Stage #2: at 0 - 20℃;
1-trityl-midazol (Compound 28, Scheme 19) was prepared by adding Et3N (5.1 ml, 36.7 mmol) at 0° C. to a stirred solution of the imidazole Compound 27 (2.5 grams, 36.7 mmol) dissolved in 75 ml DMF. After 30 minutes of stirring, trityl-chloride (10.3 grams, 36.7 mmol) dissolved in DMF (45 ml) was added slowly to the reaction mixture, and the reaction mixture was allowed to reach room temperature while stirred continuously for over night. Thereafter the reaction mixture was quenched with cold water (1 L) to precipitate a solid, which was collected by filtration and recrystallized from hexane/DCM to afford Compound 28 as a white solid (91percent yield).1H NMR (500 MHz, CDCl3)-δ: 7.47 (s, 1H), 7.33-7.30 (m, 9H), 7.16-7.12 (m, 6H), 7.07 (s, 1H), 6.83 (s, 1H).
90% With ammonium chloride; triethylamine In dichloromethane Example 22
Synthesis of 1-tritylimidazole (5)
To a solution of trityl chloride (5.58 g, 20.0 mmol.) in dry methylene chloride (100 ml) cooled down to 0° C. and stirred under Ar, was added dropwise over 1.5 hours a solution of imidazole (1.36 g, 20.0 mmol.) and triethylamine (2.7 mml, 20 mmol.) in 50 ml dry methylene chloride.
At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred under Ar at that temperature overnight.
The reaction mixture was then washed with 20 ml of a 10percent solution of ammonium chloride, then with 20 ml of distilled water.
The organic phase was dried over magnesium sulfate and evaporated in vacuo to yield quantitatively a white solid.
Recrystallization from methylene chloride/hexanes yielded 5.60 g of (5) (yield=90percent after recrystallization).
m.p. 214° C.; 1H NMR (200 MHz, CDCl3) δ7.43 (m, 1H, NCHN), 7.3-7.4 (m, 9H, 3*C6H5), 7.1-7.2 (m, GH, 3*C6H5), 7.0 (m, 1H, Ph3CNCH=CH), 6.81 (m, 1H, Ph3CNCH=CH); 13C NMR (50 MHz, CDCl3) δ142.3, 139.0, 129.6, 128.2, 128.3, 121.6.
90% With ammonium chloride; triethylamine In dichloromethane Example 22
Synthesis of 1-tritylimidazole (5) STR73
To a solution of trityl chloride (5.58 g, 20.0 mmol.) in dry methylene chloride (100 ml) cooled down to 0° C. and stirred under Ar, was added dropwise over 1.5 hours a solution of imidazole (1.36 g, 20.0 mmol.) and triethylamine (2.7 mml, 20 mmol.) in 50 ml dry methylene chloride.
At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred under Ar at that temperature overnight.
The reaction mixture was then washed with 20 ml of a 10percent solution of ammonium chloride, then with 20 ml of distilled water.
The organic phase was dried over magnesium sulfate and evaporated in vacuo to yield quantitatively a white solid.
Recrystallization from methylene chloride/hexanes yielded 5.60 g of (5) (yield=90percent after recrystallization).
m.p. 214° C.; 1 H NMR (200 MHz, CDCl3) δ 7.43 (m, 1H, NCHN), 7.3-7.4 (m, 9H, 3xC6 H5), 7.1-7.2 (m, 6H, 3xC6 H5), 7.0 (m, 1H, Ph3 CNCH=CH), 6.81 (m, 1H, Ph3 CNCH=CH); 13 C NMR (50 MHz, CDCl3) δ 142.3, 139.0, 129.6, 128.2, 128.3, 121.6.
90% With ammonium chloride; triethylamine In dichloromethane Example 22
Synthesis of 1-tritylimidazole (5) STR70
To a solution of trityl chloride (5.58 g, 20.0 mmol.) in dry methylene chloride (100 ml) cooled down to 0° C. and stirred under Ar, was added dropwise over 1.5 hours a solution of imidazole (1.36 g, 20.0 mmol.) and triethylamine (2.7 mml, 20 mmol) in 50 ml dry methylene chloride.
At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred under Ar at that temperature overnight.
The reaction mixture was then washed with 20 ml of a 10percent solution of ammonium chloride, then with 20 ml of distilled water.
The organic phase was dried over magnesium sulfate and evaporated in vacuo to yield quantitatively a white solid.
Recrystallization from methylene chloride/hexanes yielded 5.60 g of (5) (yield=90percent after recrystallization).
m.p. 214° C.; 1 H NMR (200 MHz, CDCl3) δ7.43 (m, 1H, NCHN), 7.3-7.4 (m, 9H, 3*C6 H5), 7.1-7.2 (m, 6H, 3*C6 H5), 7.0 (m, 1H, Ph3 CNCH=CH), 6.81 (m, 1H, Ph3 CNCH=CH); 13 C NMR (50 MHz, CDCl3) δ142.3, 139.0, 129.6, 128.2, 128.3, 121.6.

Reference: [1] Patent: CN104086553, 2016, B, . Location in patent: Paragraph 0065-0068
[2] Patent: US2010/16610, 2010, A1, . Location in patent: Page/Page column 28
[3] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 253 - 256
[4] Tetrahedron, 1999, vol. 55, # 13, p. 4109 - 4122
[5] Patent: US6476216, 2002, B1,
[6] Patent: US6160109, 2000, A,
[7] Patent: US5734041, 1998, A,
[8] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 903 - 906
[9] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 1, p. 2 - 6
[10] European Journal of Organic Chemistry, 2011, # 30, p. 6092 - 6099
[11] Heterocycles, 1985, vol. 23, # 11, p. 2895 - 2906
[12] Arzneimittel-Forschung/Drug Research, 1992, vol. 42, # 6, p. 832 - 835
[13] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 857 - 860
[14] Patent: US5039691, 1991, A,
[15] ChemMedChem, 2010, vol. 5, # 6, p. 899 - 910
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YieldReaction ConditionsOperation in experiment
82.7% With pyridine In acetonitrile EXAMPLE 11
Preparation of 1-triphenylmethylimidazole
A mixture of pyridine (15 ml), diphenyl phosphite (2.34 g, 10 mmole), imidazole (0.68 g, 10 mmole) and triphenylmethanol (2.08 g, 8 mmole) was refluxed for 3 hours.
Pyridine was removed under reduced pressure, and the residue was extracted with dichloromethane.
The extract was washed with a 5percent aqueous hydroxide solution and water in order, dried and evaporated.
Recrystallization of the residue (2.23 g) from acetonitrile gave 2.05 g of 1-triphenylmethylimidazole as colorless needles.
Yield, 82.7percent. M.P., 221°-223° C.
Elementary analysis: Calcd. for C22 H18 N2: C, 85.13percent; H, 5.85percent; N, 9.03percent. Found: C, 85.20percent; H, 6.03percent; N, 9.21percent.
Reference: [1] Patent: US4216333, 1980, A,
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Reference: [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 9, p. 1360 - 1369
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Reference: [1] Patent: US6051573, 2000, A,
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Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 15, p. 5498 - 5507
  • 8
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Reference: [1] Arzneimittel-Forschung/Drug Research, 1992, vol. 42, # 6, p. 832 - 835
  • 9
  • [ 288-32-4 ]
  • [ 95953-45-0 ]
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Reference: [1] Journal of the American Chemical Society, 1986, vol. 108, # 22, p. 7023 - 7027
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  • [ 3473-63-0 ]
  • [ 76-83-5 ]
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  • [ 142822-28-4 ]
  • [ 33769-07-2 ]
Reference: [1] Tetrahedron, 1992, vol. 48, # 21, p. 4327 - 4346
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Reference: [1] Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 57 - 59
[2] Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 57 - 59
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YieldReaction ConditionsOperation in experiment
69%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Sealed tube
Stage #2: With hexachloroethane In tetrahydrofuran; hexane at -78℃; Inert atmosphere
Example 1
Synthesis of 2-chloroimidazole (2-cim)
To a 300-mL, three-neck, round-bottom flask equipped with a magnetic stirrer and argon inlet, were added N-tritylimidazole (3.14 g, 0.01 mol) and anhydrous THF (140 mL).
The stirrer was started, and the solution was cooled to -78° C. (acetone/dry ice).
n-BuLi (2.5 M in hexanes, 8.0 mL, 0.02 mol) was added via syringe resulting in reddish solution.
This solution was stirred for 60 min whereupon hexachloroethane (5.0 g, 0.021 mol) in THF (25 mL) was added in portions.
The reaction mixture was stirred for 1 additional hour and then quenched with saturated aqueous ammonium chloride (100 mL).
The cooling bath was removed, and when the reaction flask reached room temperature the contents were transferred to a 500 mL separatory funnel, and extracted with ethyl acetate (50 mL*2).
The organic layer was separated, washed with water and brine, and dried over anhydrous sodium sulfate.
After filtration, the solvents were evaporated under reduced pressure resulting in a slightly yellow solid.
The solid was refluxed with 5percent acetic acid in methanol (75 mL) for 24 hours.
Upon evaporation of the solvent, water was added to the residue.
Extraction with hexanes effectively removed the triphenylmethane impurity.
Evaporation of water in vacuo afforded off-white solid as pure 2-chloroimidazole (2-cim, 0.70 g, 69percent overall yield from N-triylimidazole).
Reference: [1] Patent: US2011/282067, 2011, A1, . Location in patent: Page/Page column 2-3
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Reference: [1] Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 57 - 59
[2] Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 57 - 59
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989, p. 95 - 99
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989, p. 95 - 99
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