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[ CAS No. 5925-93-9 ] {[proInfo.proName]}

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Chemical Structure| 5925-93-9
Chemical Structure| 5925-93-9
Structure of 5925-93-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5925-93-9 ]

CAS No. :5925-93-9 MDL No. :MFCD00267506
Formula : C8H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :OZLMBXPYRDASTP-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :242778
Synonyms :

Calculated chemistry of [ 5925-93-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.53
TPSA : 49.81 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 : Yes
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 1.58
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 1.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.05 mg/ml ; 0.00797 mol/l
Class : Soluble
Log S (Ali) : -2.24
Solubility : 0.766 mg/ml ; 0.0058 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.48
Solubility : 0.442 mg/ml ; 0.00334 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.14

Safety of [ 5925-93-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 UN#:3439
Hazard Statements:H301+H311+H331-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5925-93-9 ]

* 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 [ 5925-93-9 ]
  • Downstream synthetic route of [ 5925-93-9 ]

[ 5925-93-9 ] Synthesis Path-Upstream   1~29

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Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3366
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  • [ 56-81-5 ]
  • [ 55706-57-5 ]
Reference: [1] J. Annamalai Univ., 1933, vol. 2, p. 227,236
  • 3
  • [ 32315-10-9 ]
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  • [ 39576-82-4 ]
Reference: [1] Heterocycles, 2012, vol. 85, # 6, p. 1417 - 1426
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  • [ 503-38-8 ]
  • [ 39576-82-4 ]
Reference: [1] Synlett, 2006, # 1, p. 65 - 68
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  • [ 124-38-9 ]
  • [ 62484-16-6 ]
YieldReaction ConditionsOperation in experiment
99% With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 110℃; for 24 h; Autoclave General procedure: Table 5: To a DMSO‑d6 solution (1 mL) of 2-aminobenzonitrile 4a (1 mmol) in a stainless steel autoclave was added a catalyst (0.01 mmol) under an argon atmosphere. The autoclave was sealed, heated at 110°C and then pressurized with CO2 of 2 MPa. The cyclization reaction of 4a proceeded by the magnetic stirring of the resulting mixture at 110°C for 3 h. After the reaction the autoclave was cooled in an ice bath and depressurized. The chemical yield of quinazoline-2,4(1H,3H)-dione 5a was determined by integrating 1HNMR with reference to an internal standard (3,5-dimethoxybenzylalcohol), which was added to the reaction mixture. Table 6: DMSO solution (6 mL) of 4 (6 mmol) was treated for the carboxylative cyclization of 4 with CO2 according to the procedure of Table 5. After the reaction, the autoclave was cooled in an ice bath and depressurized, and the reaction mixture was added to water (60 mL). The precipitation was collected by filtration, washed with water and diethyl ether, and then dried in vacuo at 35°C for 15 h to give the pure product 5.
97% With {Eu[N(SiMe3)2](μ-O:κ2-C6H5C(O)NC6H3(iPr)2)(THF)}2; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 100℃; for 24 h; In anhydrous, anaerobic, argon protection,0.0999 g (7.5 x 10-5 mol) of {L2Eu [N (SiMe3) 2] THF} 2 was added to the reaction flask,An additional 11.2 μL (7.5 × 10 -5 mol) DBU was added, under the protection of carbon dioxide bag,2 mL of dimethyl sulfoxide was added, followed by addition of 0.2643 g (1.5 × 10 -3 mol) of 2-amino-5-methylbenzonitrile, and the mixture was stirred in a constant temperature bath at 100 ° C. After 24 hours,Add 5mL 2mol / L hydrochloric acid quenching reaction, suction filtration, successively with 3 × 5mL hydrochloric acid,The solid was washed with toluene and diethyl ether, the residual solvent was removed by suction and the solid was dried to give the product in 97percent yield.
89% With fibrous nanosilica functionalized with sodium tripolyphosphate and 3-aminopropyltriethoxysilane In neat (no solvent) at 70℃; for 0.833333 h; Autoclave; Green chemistry General procedure: 2-aminobenzonitrile (1 mmol) and KCC-1/STPP NPs (0.7 mg) were mixed together. The autoclave was closed, purged twice with CO2 gas, pressurized to 1.5 MPa of CO2, and heated at 70°C for 50 min. Then, the reactor was cooled to ambient temperature and the resulting mixture was transferred to a 50 mL round-bottom flask. During completion, the reaction progress was monitored by TLC. Following its completion, EtOH was added to the reaction mixture and the catalyst was separated by filtration. Afterwards, the solvent was removed from the solution under reduced pressure and the resulting product was purified by recrystallization using n-hexane/ethyl acetate. The products are known and their sample characterization data is presented in the Supplemental Materials.
88% at 70℃; for 1 h; Autoclave General procedure: 2-aminobenzonitrile (1mmol), and KCC-1/IL NPs (0.0007g) were added. The autoclave was closed, purged twice with CO2 gas, pressurized with 0.8MPa of CO2 and then heated at 70°C for 60min. Then the reactor was cooled to ambient temperature, and the resulting mixture was transferred to a 50mL round bottom flask. Upon completion, the progress of the reaction was monitored by TLC when the reaction was completed, EtOH was added to the reaction mixture and the KCC-1/IL NPs were separated by distillation under vacuum. Then the solvent was removed from solution under reduced pressure and the resulting product purified by recrystallization using n-hexane/ethyl acetate.

Reference: [1] Tetrahedron, 2018, vol. 74, # 24, p. 2914 - 2920
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 14, p. 2555 - 2559
[3] Patent: CN105153048, 2017, B, . Location in patent: Paragraph 0118; 0119
[4] Catalysis Science and Technology, 2016, vol. 6, # 5, p. 1435 - 1441
[5] RSC Advances, 2015, vol. 5, # 31, p. 24670 - 24674
[6] Inorganic Chemistry, 2012, vol. 51, # 23, p. 13001 - 13008
[7] Catalysis Science and Technology, 2014, vol. 4, # 6, p. 1608 - 1614
[8] Phosphorus, Sulfur and Silicon and the Related Elements, 2018, vol. 193, # 8, p. 535 - 544
[9] Catalysis Communications, 2015, vol. 72, p. 91 - 96
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  • [ 68-12-2 ]
  • [ 62484-16-6 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 6, p. 1193 - 1196
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  • [ 617-84-5 ]
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Reference: [1] Organic Letters, 2009, vol. 11, # 6, p. 1193 - 1196
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  • [ 2941-78-8 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3366
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Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3366
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YieldReaction ConditionsOperation in experiment
99%
Stage #1: With hydrogenchloride; tin(ll) chloride In ethanol; water at 20 - 30℃; for 1 h;
Stage #2: With sodium hydroxide In ethanol; water
5-Methyl-2-nitrobenzonitrile (1.92 g, 11.84 mmol) was added in portions to a stirred solution of SnCl2 (11.22 g, 59.2 mmol) in conc. HCl (12 mL) and EtOH (12 mL).
The reaction temperature was maintained at 20-30° C. using an ice bath.
The reaction mixture was then stirred at room temperature for 1 h and poured into an ice cold aqueous solution of NaOH (6N, app. 30 mL) to neutralize to pH7.
The product was extracted into EtOAc, washed with brine, dried over MgSO4 and concentrated to provide the title product (1.56 g, 99percent) as a yellow-brown solid. 1H NMR (400 MHz, DMSO-d6) δ 2.21 (s, 3H), 5.79 (bs, 2H), 6.68-6.71 (d, 1H), 7.10-7.13 (dd, 1H), 7.15 (s, 1H).
13C NMR (DMSO-d6) δ 20.13, 93.99, 116.12, 118.94, 125.38, 132.32, 135.76, 150.21. MS 133 (MH+).
78.4% With sodium dithionite In water; acetonitrile at 0 - 25℃; for 0.5 h; [0055] To a solution of 5-methyl-2-nitrobenzonitrile from Example 2, (25.7 g, 0.158 mol) in 643 mL of acetonitrile was added sodium dithionate (128.5 g, 0.739 mol), followed by addition of 600 mL of deionized water at 0° C. The reaction mixture was stirred for 30 minutes at 25° C. The aqueous layer was extracted with ethyl acetate three times, and the combined organic layers were dried over sodium sulfate and evaporated under vacuum to afford a crude yellow solid, which was dried under high vacuum for 24 hours to give 16.4 g of substantially pure title compound (78.4percent). 1H NMR (CDCl3): δ 2.23 ppm (s, 3H, CH3), 6.65 (d, J=8.4 Hz, aromatic), 7.18 (s, aromatic), 7.14 (d, J=8.4 Hz, aromatic).
Reference: [1] Patent: US2008/306053, 2008, A1, . Location in patent: Page/Page column 60
[2] Tetrahedron, 1994, vol. 50, # 18, p. 5515 - 5525
[3] Patent: US2004/92739, 2004, A1, . Location in patent: Page 4
[4] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 2, p. 345 - 349
[5] Chemische Berichte, 1905, vol. 38, p. 3555
[6] Journal of Organic Chemistry, 1978, vol. 43, # 2, p. 220 - 224
[7] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 892 - 913
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Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 39, p. 12248 - 12249
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  • [ 583-68-6 ]
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YieldReaction ConditionsOperation in experiment
60% for 1.25 h; Heating / reflux Combine 2-bromo-4-methyl-phenylamine (8.00 g, 43.0 mmol), CuCN (4.62 g, 51.6 mmol), and NMP [(30.] 0 ml) and stir at reflux. After 75 minutes, cool to ambient temperature, pour the mixture onto ice chips and stir for 1 hour. Remove the resulting precipitate by vacuum filtration. Dissolve the precipitate in NH40H and extract with dichloromethane. Combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using [DICHLOROMETHANE/HEXANES] (75: 25) to give 3.39 g (60percent) of an orange solid: mass spectrum (ion spray): m/z = 133.1 (M+1).
Reference: [1] Patent: WO2004/14895, 2004, A1, . Location in patent: Page 61
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Reference: [1] Journal of the American Chemical Society, [2] Journal of the American Chemical Society, 2009, vol. 131, p. 7238 - 7239
[3] Advanced Synthesis and Catalysis, 2012, vol. 354, # 16, p. 2899 - 2904
  • 14
  • [ 150893-79-1 ]
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Reference: [1] Synlett, 2006, # 1, p. 65 - 68
  • 15
  • [ 75-16-1 ]
  • [ 156149-46-1 ]
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  • [ 1262111-18-1 ]
Reference: [1] European Journal of Organic Chemistry, 2010, # 34, p. 6588 - 6599
  • 16
  • [ 3113-72-2 ]
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Reference: [1] Tetrahedron, 1994, vol. 50, # 18, p. 5515 - 5525
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 892 - 913
  • 17
  • [ 4315-12-2 ]
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Reference: [1] Tetrahedron, 1994, vol. 50, # 18, p. 5515 - 5525
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 892 - 913
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Reference: [1] Synlett, 2006, # 1, p. 65 - 68
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Reference: [1] Synlett, 2006, # 1, p. 65 - 68
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  • [ 38939-88-7 ]
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Reference: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 2, p. 345 - 349
  • 21
  • [ 620-22-4 ]
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Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3555
[2] Journal of Organic Chemistry, 1978, vol. 43, # 2, p. 220 - 224
  • 22
  • [ 106-49-0 ]
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Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 16, p. 2899 - 2904
  • 23
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Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 64, p. 401 - 409
  • 24
  • [ 38818-49-4 ]
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Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 892 - 913
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Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3366
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Reference: [1] Journal of the Chemical Society, 1959, p. 1633
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Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3555
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Reference: [1] Journal of Organic Chemistry, 1978, vol. 43, # 2, p. 220 - 224
[2] Australian Journal of Chemistry, 1992, vol. 45, # 7, p. 1119 - 1134
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YieldReaction ConditionsOperation in experiment
90% With water; potassium carbonate In water at 150℃; for 0.5 h; Microwave irradiation General procedure: Adapted from a literature procedure,1 the appropriate organonitrile (1.0 eq.) and K2CO3(0.2eq.)wereaddedtoamicrowavetubewithastir-barwithdeionizedwater(8.5mLpermmolsubstrate).Afterirradiationundermicrowaveat150°Cfor30minutes,thereactionmixturewascooled,extractedwithEtOAc(320mL),thecombinedphasesdriedoverMgSO4andexcesssolventremovedinvacuo.TheresiduewaspurifiedbyFCC,ifrequired,togivethetitlecompound.
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 1, p. 135 - 144
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