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[ CAS No. 115279-57-7 ] {[proInfo.proName]}

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Chemical Structure| 115279-57-7
Chemical Structure| 115279-57-7
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Product Details of [ 115279-57-7 ]

CAS No. :115279-57-7 MDL No. :MFCD09909912
Formula : C10H12N2 Boiling Point : -
Linear Structure Formula :- InChI Key :VXDPOGVDHHJTDY-UHFFFAOYSA-N
M.W : 160.22 Pubchem ID :10057801
Synonyms :

Calculated chemistry of [ 115279-57-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.87
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 : No
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 1.83
Log Po/w (WLOGP) : 2.08
Log Po/w (MLOGP) : 1.74
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 1.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.29
Solubility : 0.821 mg/ml ; 0.00513 mol/l
Class : Soluble
Log S (Ali) : -2.5
Solubility : 0.511 mg/ml ; 0.00319 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.94
Solubility : 0.186 mg/ml ; 0.00116 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 115279-57-7 ]

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 [ 115279-57-7 ]

* 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 [ 115279-57-7 ]
  • Downstream synthetic route of [ 115279-57-7 ]

[ 115279-57-7 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 71825-51-9 ]
  • [ 115279-57-7 ]
YieldReaction ConditionsOperation in experiment
95% With tin(ll) chloride In ethyl acetate for 2.5 h; Reflux which is subsequently reduced to the amine 2-3.
95% With tin(ll) chloride In ethyl acetate for 2.5 h; Reflux 10556] The above reaction scheme illustrates the synthesis of a compound of the invention 2-13. Methylation of starting material 2-1 yields compound 2-2, which is subsequently reduced to the amine 2-3. In a separate reaction, compound 2-4 is converted to a salt, such as an HC1 salt, which is then reacted, for example, with 2-nitrovinyl-hydroxylamine to yield compound 2-6. Further cyclization yields compound 2-7. Halogenation with a reagent such as POd3 results in compound 2-8, which can be coupled with intermediate 2-3 to yield 2-9. The nitro moiety of 2-9 is subsequently reduced to an amine, and a further reaction with 4-nitrophenyl carbonochloridate results in the heterocycle 2-11. The desired compound 2-13 is then prepared by coupling to the benzoxazolyl boronate 2-12, for example in a Suzuki coupling.
95% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; To a suspension of 4-nitrophenylacetonitrile 1 (1.0 equiv, 4.50 g, 27.8 mmol), tetrabutyl ammonium bromide (TBAB, 0.448 g, 1.39 mmol, 0.05 equiv) and iodomethane (11.8 g, 83.4 mmol, 3.0 equiv) in dichloromethane (DCM, 40.0 mL) was added sodium hydroxide (2.78 g, 69.5 mmol, 2.5 equiv) in water (40.0 mL) dropwise.
After stirring at room temperature for 8 h, the organic layer was separated, washed with brine, dried with anhydrous Na2SO4 and concentrated in vacuo.
Then the residue was subjected to flash column chromatography using EA/PE (1:14-1:7) as eluent to furnish the di-methylated product as a white crystal. Yield: 83percent; ESI-MS: m/z = 191 [M+H]+.
The di-methylated product (4.38 g, 23.1 mmol) and 10percent Pd/C (10percent of the substrate, w/w) were shacked in methanol (60.0 mL) and the mixture was stirred at room temperature under H2 (balloon) atmosphere overnight.
After this time, Pd/C was filtered and the filtrate was concentrated in vacuo to provide 2 as a colorless oil, which slowly solidified and was used for the next step without purification. Yield: 95percent. ESI-MS: m/z = 161 [M+H]+.
93% With iron; ammonium chloride In ethanol at 120℃; for 6 h; A solution of 9.4 g (0.35 mol) of iron powder, 37.2 g (0.694 mol) of ammonium chloride solution (37.2 g of ammonium chloride / 40 ml of water) was added successively to 22 g (0.115 mol) of intermediate 4 dissolved in 300 ml of absolute ethanol, 120 ° C reflux reaction 6h,The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was dried by filtration. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 1 : LO, V: V), was light yellow oily liquid intermediates 5 17.23g, yield 93 ,
89% With tin(ll) chloride In ethyl acetate at 20℃; 2-methyl-2-(4-nitro-phenyl)-propionitrile was dissolved in ethyl acetate (20ml) and treated with stannous chloride dihydrate (3.52g, 15.86mmol). After stirring overnight at room temperature, the reaction mixture was basified with aqueous sodium carbonate. The organic layer was separated, washed with water, dried and concentrated to oil. The crude compound was purified by column chromatography over silica gel using ethyl acetate/pet ether (1:9) as eluent to give 2-(4-aminophenyl)-2-methyl propionitrile (0.45g, 89percent) as oil.
80% With hydrogen In methanol at 20℃; for 2.5 h; 10percent Pd/C (300 mg) was added to a solution of 2-methyl-2-(4-nitro-phenyl)- propionitrile (3.00 g; 15.8 mmol), prepared as in l(A), in MeOH (65 mL). The mixture was hydrogenated at 1 bar at room temperature for 2.5 hours, the catalyst was filtered off and the filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (2.40 g; 80percent yield).LCMS (RT): 0.78 min (Method A); MS (ES+) gave m/z: 161.1 (MH+).
74% With hydrogen In tetrahydrofuran; methanol at 20℃; for 10 h; 2-Methyl-2-(4-nitrophenyl)propanenitrile (Compound of step 1, 16 g, 84.1 mmol) and Raney- Ni (4.16 g) were shaken in THF-MeOH [(1:1), 160 mL] under 40 psi of hydrogen for 10 hours at RT, After completion of reaction, the catalyst was filtered-off and the solvent was evaporated to dryness. The crude product was purified by column chromatography (silica gel, ethyl acetate in hexane) to obtain the title compound as oil.Yield: 10 g (74 percent); 1H NMR (DMSO-d6, 300 MHz): δ 7.091-7.119 (d, 2H, J= 8.4Hz), 6.533- 6.561 (d, 2H, J= 8.4Hz), 5.135 (s, 2H), 1.568 (s, 6H); MS: m/z 161 (M+).
74% With hydrogen In tetrahydrofuran; methanol at 20℃; for 10 h; Step 2:
2-(4-Aminophenyl)-2-methylpropanenitrile
2-Methyl-2-(4-nitrophenyl)propanenitrile (Compound of step 1, 16 g, 84.1 mmol) and Raney-Ni (4.16 g) were shaken in THF-MeOH [(1:1), 160 mL] under 40 psi of hydrogen for 10 hours at RT, After completion of reaction, the catalyst was filtered-off and the solvent was evaporated to dryness.
The crude product was purified by column chromatography (silica gel, ethyl acetate in hexane) to obtain the title compound as oil.
Yield: 10 g (74percent); 1H NMR (DMSO-d6, 300 MHz): δ 7.091-7.119 (d, 2H, J=8.4 Hz), 6.533-6.561 (d, 2H, J=8.4 Hz), 5.135 (s, 2H), 1.568 (s, 6H); MS: m/z 161 (M+).
3.5 g With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 15 h; 2-methyl-2-(4-nitrophenyl) propanenitrile (4.5 g, 23.6 mmol) was added to a reaction vessel, to which were successively added Pd/C (450 mg) and 50 mL ethyl acetate. The system was vacuumed and hydrogen was introduced. The resulting mixture is reacted at room temperature for 15 hrs. The resulting reaction was filtered with Celite, and washed with ethyl acetate. The resulting filtrate was concentrated to obtain a colorless oil of 2-(4-aminophenyl)-2-methyl propanenitrile (3.5 g).
3.5 g With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 15 h; 10208] 2-methyl-2-(4-nitrophenyl) propanenitrile (4.5 g,23.6 mmol) was added to a reaction vessel, to which were successively added Pd/C (450 mg) and 50 mE ethyl acetate. The system was vacuumed and hydrogen was introduced. The resulting mixture is reacted at room temperature for 15 hrs. The resulting reaction was filtered with Celite, and washed with ethyl acetate. The resulting filtrate was concentrated to obtain a colorless oil of 2-(4-aminophenyl)-2-methyl propanenitrile (3.5 g).

Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4834 - 4848
[2] Patent: US2009/137595, 2009, A1,
[3] Patent: WO2012/116237, 2012, A2, . Location in patent: Page/Page column 119
[4] Patent: US2015/320727, 2015, A1, . Location in patent: Paragraph 0555; 0556
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7585 - 7596
[6] Patent: CN104411706, 2016, B, . Location in patent: Paragraph 0201-0202
[7] Patent: WO2006/123145, 2006, A1, . Location in patent: Page/Page column 50
[8] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 17, p. 2203 - 2214
[9] Patent: WO2008/117175, 2008, A2, . Location in patent: Page/Page column 98
[10] Patent: WO2011/1212, 2011, A1, . Location in patent: Page/Page column 38
[11] Patent: US2012/108627, 2012, A1, . Location in patent: Page/Page column 16
[12] Acta Chemica Scandinavica (1947-1973), 1954, vol. 8, p. 1203,1207[13] Acta Chemica Scandinavica (1947-1973), 1955, vol. 9, p. 210,214
[14] Journal of Medicinal Chemistry, 1979, vol. 22, # 12, p. 1460 - 1464
[15] Patent: WO2006/65646, 2006, A1, . Location in patent: Page/Page column 21-22
[16] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 1027 - 1030
[17] Patent: WO2005/54238, 2005, A1, . Location in patent: Page/Page column 99
[18] Patent: WO2008/64093, 2008, A2, . Location in patent: Page/Page column 18
[19] Patent: WO2013/23119, 2013, A1, . Location in patent: Page/Page column 28
[20] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00641
[21] Patent: US2015/30588, 2015, A1, . Location in patent: Page/Page column 74
[22] Patent: EP2896622, 2015, A1, . Location in patent: Paragraph 0135; 0136
[23] Patent: US2015/239885, 2015, A1, . Location in patent: Paragraph 0207; 0208
[24] Patent: US9295673, 2016, B2, . Location in patent: Page/Page column 359
[25] Patent: CN103254203, 2016, B, . Location in patent: Paragraph 0065; 0087; 0088
[26] Patent: US9358229, 2016, B2, . Location in patent: Page/Page column 19; 20
[27] Patent: WO2006/122806, 2006, A2, . Location in patent: Page/Page column 49
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Reference: [1] Patent: US2012/108583, 2012, A1, . Location in patent: Page/Page column 29
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  • [ 101184-73-0 ]
  • [ 115279-57-7 ]
Reference: [1] Patent: WO2007/119055, 2007, A1,
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Reference: [1] Acta Chemica Scandinavica (1947-1973), 1954, vol. 8, p. 1203,1207[2] Acta Chemica Scandinavica (1947-1973), 1955, vol. 9, p. 210,214
[3] Patent: CN103254203, 2016, B,
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