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[ CAS No. 141627-42-1 ] {[proInfo.proName]}

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Chemical Structure| 141627-42-1
Chemical Structure| 141627-42-1
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Product Details of [ 141627-42-1 ]

CAS No. :141627-42-1 MDL No. :MFCD14525623
Formula : C20H19NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :WYALRXZJYXWYGR-UHFFFAOYSA-N
M.W : 353.37 Pubchem ID :22595055
Synonyms :

Calculated chemistry of [ 141627-42-1 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.25
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 100.79
TPSA : 85.26 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.24
Log Po/w (XLOGP3) : 5.2
Log Po/w (WLOGP) : 4.92
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 3.35
Consensus Log Po/w : 3.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.27
Solubility : 0.00189 mg/ml ; 0.00000535 mol/l
Class : Moderately soluble
Log S (Ali) : -6.74
Solubility : 0.0000646 mg/ml ; 0.000000183 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -6.82
Solubility : 0.0000535 mg/ml ; 0.000000151 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.37

Safety of [ 141627-42-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 141627-42-1 ]

* 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 [ 141627-42-1 ]
  • Downstream synthetic route of [ 141627-42-1 ]

[ 141627-42-1 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 100-07-2 ]
  • [ 133238-87-6 ]
  • [ 141627-42-1 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 25℃; for 2 h; Reflux
Stage #2: With water In chlorobenzene
Method-2:45 g (0.2 mole) 2-ri-butyl 5-nitro benzofuran and 44 g of anisoyl chloride in 300 ml of chlorobenzene were taken in round bottom flask at 25°C. The reaction mixture was treated with 40 g of aluminum chloride solution in 300. ml chlorobenzene. The reaction medium was heated under reflux for 2 hours, cooled and diluted with 40 ml of water. The organic phase was separated and washed with water, 5percent sodium hydrogen carbonate solution. The organic phase was evaporated to dryness and the product thus obtained crystallizes rapidly. It was recrystallized from 270 ml of isopropanol and 90percent of 2-n-butyl-3-(4-methoxybenzoyl)-5-nitrobenzofuran.M.P.: 94-96°C, Purity > 96percent (HPLC)
83.5% With tin(IV) chloride In ice-water; 1,1-dichloroethane 59.8 ml (0.50 mole) of tin tetrachloride are added gradually to a solution of 44.5 g (0.2 mole) of 2-n-butyl 5-nitro benzofuran and 44.3 g (0.26 mole) of anisoyl chloride in 308 ml of dichloroethane.
The temperature is maintained at 23° C. and stirring is continued for 24 hours.
The mixture is poured onto 770 ml of ice-water and extracted 3 times with 150 ml of dichloroethane.
The solution is washed with water, 5percent sodium hydrogen carbonate solution and again with water.
It is evaporated to dryness and the product thus obtained crystallizes rapidly [purity on high performance liquid chromatography (HPLC): 91.69percent].
It is recrystallized from 250 ml of isopropanol and 59 g of 2-n-butyl 3-(4-methoxy benzoyl) 5-nitro benzofuran are thus obtained.
Yield: 83.5percent
Purity (HPLC): 96.39percent
M.p.: 95° C.
Reference: [1] Patent: WO2012/32545, 2012, A1, . Location in patent: Page/Page column 32
[2] Journal of the Chinese Chemical Society, 2011, vol. 58, # 7, p. 841 - 845
[3] Patent: US5223510, 1993, A,
[4] Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1077 - 1085
[5] Organic Process Research and Development, 2014, vol. 18, # 1, p. 157 - 162
[6] Organic Process Research and Development, 2013, vol. 17, # 5, p. 863 - 868
  • 2
  • [ 100-09-4 ]
  • [ 133238-87-6 ]
  • [ 141627-42-1 ]
YieldReaction ConditionsOperation in experiment
72.7%
Stage #1: With Methyltrichlorosilane In chlorobenzene at 20 - 40℃; for 4 h;
Stage #2: With ethanol In chlorobenzene at 0℃;
EXAMPLE 133.94 g of chlorobenzene (35 mmol, 7 eq.), 1.05 g of iron chloride (6.5 mmol, 1.3 eq.) and 0.80 g of para-anisic acid (5.25 mmol, 1.05 eq.) are introduced into a 30 ml Schott tube with magnetic stirring at 500 rpm and at ambient temperature.1.09 g of 2-n-butyl-5-nitrobenzofuran (5 mmol, 1 eq.) and 1.12 g of trichloromethylsilane (7.5 mmol, 1.5 eq.) are then added dropwise, and then the reaction mixture is put, with stirring, at a temperature of 40° C. for 4 hours.The reaction mixture is then cooled to 0° C. by means of an ice-bath, and 3 ml of ethanol are added.The mixture is diluted with 25 ml of chlorobenzene and filtered over sintered glass of no. 2 porosity.The filtrate (organic phase) is then washed three times with 25 ml of a 1 N hydrochloric acid solution.The organic phase is dried over magnesium sulfate and then concentrated under reduced pressure.The product is isolated from the crude reaction mixture by separation on a column of silica (silica gel 60 of diameter 0.2 to 0.5 mm), the eluant being a heptane/ethyl acetate mixture going from a ratio of 95:5 to 80:20 during the elution.1.28 g of 2-n-butyl-5-nitro-8-(4'-methoxy)acetophenonebenzofuran (3.64 mmol, which corresponds to a yield of 72.7percent) in the form of a white solid (m.p.=94.7° C.) are then obtained.The NMR characteristics of the resulting product are as follows:1H NMR (200 MHz, CDCl3): δ (ppm)=0.87-0.92 (t, 3H, J=7.2 Hz); 1.30-1.42 (m, 2H); 1.72-1.82 (m, 2H); 2.90-2.95 (t, 2H, J=7.9 Hz); 3.13 (s, 3H); 6.98-7.01 (d, 2H, J=9.3 Hz); 7.55-7.58 (d, 1H, J=9.6 Hz); 7.82-7.85 (d, 2H, J=9 Hz); 8.20-8.24 (dd, 1H, J2=9.2 Hz, J2=2.4 Hz); 8.33-8.34 (d, 1H, J=2.7 Hz).
Reference: [1] Patent: US2008/154049, 2008, A1, . Location in patent: Page/Page column 9
  • 3
  • [ 1256921-45-5 ]
  • [ 141627-42-1 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With iron(III) chloride; tributyl-amine In toluene for 2.5 h; Reflux
Stage #2: With hydrogenchloride In tert-butyl methyl ether
Example 19: Synthesis of 2-n-butyl-3-(4-methoxybenzoyl)-5-nitrobenzofuran (a compound of the formula I, R1 = n-butyl, R2 = OMe) using iron-trichloride (method 2)A flask equipped with a Dean-Stark condenser was charged with 20 ml of dry toluene, 2.00 g (10.7 mmol, 2 equivalents) of tri-n-butylamine, 2.00 g (5.39 mmol) of 2-(2- pentanoyloxy-5-nitrophenyl)-1 -(4-methoxyphenyl)-ethanone (example 2) and 0.05 g (0.30 mmol, 0.05 equivalents) of anhydrous FeCb. The mixture was kept at reflux temperature while some toluene was removed during the reaction. After 2.5 hours RP-HPLC analysis confirmed the quantitative conversion of the starting compound into the title compound. The mixture was taken up in 20 ml of 1 N HCI and 20 ml of MTBE, the organic phase was washed with water and brine, dried over sodium sulphate and evaporated to give the title compound (yield: 1.90 g, 99percent).
92% With tributyl-amine In toluene for 2.5 h; Reflux The iron-doped montmorillonite catalyst was prepared as described in HeIv. Chim. Acta, vol. 70, 577-586 (1987). Dry toluene (15 ml) 2.10 ml (8.89 mmol) of tri-n- butylamine and 0.5 g of the iron-doped montmorillonite catalyst were heated under reflux using a Dean-Stark condenser and 2.20 g (5.92 mmol) of 2-(2-pentanoyloxy-5- nitrophenyl)-1-(4-methoxyphenyl)-ethanone (example 2) dissolved in 5 ml of dry toluene were added. After 2.5 hours LC-MS analysis showed a 100percent conversion of the 2-(2-pentanoyloxy-5-nitrophenyl)-1 -(4-methoxyphenyl)-ethanone and the reaction mixture was cooled to room temperature. The catalyst was filtered off and the organic layer was washed once with 20 ml of 1 N aqueous HCI, 20 ml of water and dried over MgSO4. Yield of the title compound: 1.92 g (92percent)
Reference: [1] Patent: WO2010/136500, 2010, A1, . Location in patent: Page/Page column 35
[2] Patent: WO2010/136502, 2010, A1, . Location in patent: Page/Page column 21
  • 4
  • [ 1257220-33-9 ]
  • [ 141627-42-1 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With titanium tetrachloride; triethylamine In dichloromethane at 38 - 39℃; for 48 h; Inert atmosphere
Stage #2: With hydrogenchloride In dichloromethane; tert-butyl methyl ether; water
Stage #3: With sodium hydrogencarbonate In dichloromethane; tert-butyl methyl ether; water
Example 15: Synthesis of 2-n-butyl-3-(4-methoxybenzoyl)-5-nitrobenzofuran (a compound of the formula I, R1 = n-butyl, R2 = OMe) (method 3)Under argon atmosphere 0.56 g (3.26 mmol, 1.2 equivalents) of 2-tert.-butyl-1 ,1 ,3,3,- tetramethylguanidine were added at 5-15°C to 1.00 g (2.69 mmol) of 2-(2- pentanoyloxy-5-nitrophenyl)-1 -(4-methoxyphenyl)-ethanone (example 2) dissolved in 5 ml of dry dichloromethane. After stirring for 20 min, 20 ml of 0.5 M aqueous HCI solution and 50 ml of MTBE were added. The organic phase was dried with sodium sulphate and evaporated to give quantitatively the crude 2-(2-hydroxy-5-nitrophenyl)- 1 -(4-methoxyphenyl)-1 ,3-heptandione (a compound of the formula VIII, R1 = n-butyl; R2 = OMe) which was further purified by RP-chromatography to yield 0.7 g (70percent) of the pure material. This 1 ,3-diketone was reacted with 0.38 g of thethylamine (3.8 mmol, 2 equivalents) and 0.44 g of TiCI4 (2.2 mmol, 1.2 equivalents) in dichloromethane exactly as described in example 11 to give 0.65 g (98percent based on 1 ,3-diketone) of the title compound.
Reference: [1] Patent: WO2010/136500, 2010, A1, . Location in patent: Page/Page column 33
  • 5
  • [ 1256921-44-4 ]
  • [ 638-29-9 ]
  • [ 141627-42-1 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: at 20℃; for 14 h; Inert atmosphere
Stage #2: With titanium tetrachloride; triethylamine In dichloromethane at 40℃;
Example 13: One-pot-synthesis of 2-n-butyl-3-(4-methoxybenzoyl)-5-nitrobenzofuran (a compound of the formula I, R1 = n-butyl, R2 = OMe) from the potassium salt (example 1 ) using titanium tetrachloride (method 2)0.23 g (1.89 mmol, 1.1 equivalents) of valeroyl chloride (a compound of the formula V, R2 = n-butyl) were added at room temperature to a stirred suspension of 0.56 g (1.72 mmol) of 2-(2-hydroxy-5-nitrophenyl)-1-(4-methoxyphenyl)-ethanone potassium salt (example 1 ) in 10 ml of dry dichloromethane. After 14 hours 0.21 g (2.07 mmol, 1.2 equivalents) of triethylamine and then 1.89 ml of a 1 M solution of TiCI4 in dichloromethane (1.89 mmol, 1.1 equivalents) were added. After stirring the mixture at 40°C over night LC-MS analysis confirmed nearly complete conversion. The reaction mixture was diluted with 10 ml of 1 N aqueous HCI and 30 ml of MTBE. The organic phase was separated and washed thoroughly with 2 N aqueous NaOH at 40°C for 20 minutes, then with 10 ml of 1 N aqueous HCI at room temperature and brine, dried over sodium sulphate and evaporated to dryness. The residue crystallized to give 0.48 g (79percent) of the title compound.
Reference: [1] Patent: WO2010/136500, 2010, A1, . Location in patent: Page/Page column 32
  • 6
  • [ 1137261-90-5 ]
  • [ 33543-55-4 ]
  • [ 141627-42-1 ]
YieldReaction ConditionsOperation in experiment
70% at 70 - 100℃; for 17 h; O-4-nitrophenylhydroxylamine (100 mg), was suspended in 0.5 ml acetic acid and 1-(4-methoxyphenyl)-heptane-1 ,3-dione was added. The mixture was stirred at 700C for 3h and then at 1000C for an additional 14h. The mixture was cooled to room temperature and the solvent evaporated under vacuum. Yield 70 percent of 2- butyl-3-(4-methoxybenzoyl)-5-nitrobenzofuran.
70% at 70 - 100℃; for 17 h; O-4-nitrophenylhydroxylamine prepared according to Example 1 (100 mg), was suspended in 0.5 ml acetic acid and 1-(4-methoxyphenyl)-heptane-1 ,3-dione was added. The mixture was stirred at 700C for 3h and then at 100°C for an additional 14h. The mixture was cooled to room temperature and the solvent evaporated under vacuum. Yield 70 percent of 2-butyl-3-(4-methoxybenzoyl)-5-nitrobenzofuran
Reference: [1] Patent: WO2009/44143, 2009, A2, . Location in patent: Page/Page column 36
[2] Patent: WO2010/116140, 2010, A1, . Location in patent: Page/Page column 48
  • 7
  • [ 856758-03-7 ]
  • [ 100-66-3 ]
  • [ 141627-42-1 ]
  • [ 856758-04-8 ]
Reference: [1] Patent: WO2005/66149, 2005, A1, . Location in patent: Page/Page column 9; 11
  • 8
  • [ 100-02-7 ]
  • [ 141627-42-1 ]
Reference: [1] Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1077 - 1085
  • 9
  • [ 956-75-2 ]
  • [ 141627-42-1 ]
Reference: [1] Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1077 - 1085
  • 10
  • [ 1393093-65-6 ]
  • [ 141627-42-1 ]
Reference: [1] Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1077 - 1085
  • 11
  • [ 1393093-66-7 ]
  • [ 141627-42-1 ]
Reference: [1] Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1077 - 1085
  • 12
  • [ 1393093-67-8 ]
  • [ 141627-42-1 ]
Reference: [1] Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1077 - 1085
  • 13
  • [ 1393093-68-9 ]
  • [ 141627-42-1 ]
Reference: [1] Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1077 - 1085
  • 14
  • [ 142-61-0 ]
  • [ 141627-42-1 ]
Reference: [1] Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1077 - 1085
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