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[ CAS No. 78281-72-8 ] {[proInfo.proName]}

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Chemical Structure| 78281-72-8
Chemical Structure| 78281-72-8
Structure of 78281-72-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 78281-72-8 ]

CAS No. :78281-72-8 MDL No. :MFCD08067732
Formula : C15H14N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QEFAQIPZVLVERP-UHFFFAOYSA-N
M.W : 254.28 Pubchem ID :151075
Synonyms :
AL 6515;AHR 9434;Nevanac
Chemical Name :2-(2-Amino-3-benzoylphenyl)acetamide

Calculated chemistry of [ 78281-72-8 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 73.4
TPSA : 86.18 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 1.95
Log Po/w (WLOGP) : 1.54
Log Po/w (MLOGP) : 1.45
Log Po/w (SILICOS-IT) : 2.2
Consensus Log Po/w : 1.75

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.85
Solubility : 0.36 mg/ml ; 0.00142 mol/l
Class : Soluble
Log S (Ali) : -3.38
Solubility : 0.105 mg/ml ; 0.000413 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.5
Solubility : 0.00799 mg/ml ; 0.0000314 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.03

Safety of [ 78281-72-8 ]

Signal Word:Danger Class:9
Precautionary Statements:P264-P270-P273-P280-P301+P312+P330-P302+P352+P312-P305+P351+P338+P310-P332+P313-P391-P501 UN#:3077
Hazard Statements:H302+H312-H315-H318-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 78281-72-8 ]

* 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 [ 78281-72-8 ]
  • Downstream synthetic route of [ 78281-72-8 ]

[ 78281-72-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 78281-61-5 ]
  • [ 78281-72-8 ]
YieldReaction ConditionsOperation in experiment
86% at 20℃; for 0.166667 h; Example 11Preparation of 2-amino-3-benzoylbenzeneacetamide (i.e. nepafenac, compound of formula I).This example illustrates the use of the compound (IV) Form B obtained according to the process of the invention, for preparing nepafenac.100 g of wet Raney-Ni catalyst was loaded in the filter reactor and purged with nitrogen or argon. The catalyst was washed twice with water and once with THF (the washings were done opening the bottom valve and applying argon or nitrogen pressure in the reactor). Then 25.0 g of 2-amino-3-benzoyl-α-(methylthio)benzeneacetamide (83.2 mmol; obtained in Example 3) were dissolved in a mixture of 330 mL of THF and 80 mL of water and the resulting solution was added in one portion through the addition funnel. The reaction mixture was vigorously stirred at room temperature for 10 min. The yellow solution was unloaded from the vessel and the catalyst was washed twice with 250 mL of THF. The THF solutions were combined and distilled until a volume of 250 mL. Then, 200 mL of 2-propanol were charged twice and distilled until a remaining volume of 250 mL. The solution was allowed to cool crystallizing a yellow solid which was collected by filtration. The product was dried yielding 18.2 g of yellow crystals in needle-like shape (Yield: 86percent).Analytical data: HPLC purity: 99.6percent before the purification, 99.8percent after the purification; No chlorination by-products were observed by HPLC; XRD: See FIG. 5; IR: See FIG. 6.
78.8% With Raney nickel In tetrahydrofuran at -5 - 5℃; for 0.5 h; Take 20.02g of the solid obtained in the second step, add 800mL of THF, cool down to -5 ~ 5 °C, and add 200.06g of Raney Nickel after treatment (Raney Nickel treatment: wash first with 3 X 200ml water, Then wash with 3X 200ml THF). After 0.5h of reaction, add 200ml of saturated sodium chloride solution, stand for layering, pour the upper layer liquid, filter to remove Raney Nickel, divide the filtrate into water layer, and spin down the organic layer. The spin-dried product was recrystallized by adding 500 ml of isopropanol, decrystallized at -5 ~ 5 °C for 2 hours, filtered, and dried to give 13.38 g of yellow needles. The purity by HPLC was 99.84percent and the yield was 78.8 percent.
13 g With Raaney nickel In tetrahydrofuran; water at 20℃; for 0.25 h; To a solution of 2-amino-3-benzoyl-α-(methylthio)phenylacetamide (26 gm) in tetrahydrofuran (340 mL) and water (80 mL), Raney nickel (wet 208 g) was added at room temperature. The mixture was stirred for 15 min and filtered through a hydrflo bed. The filtrate was concentarted under reduced pressure and the obtained solid was dissolved in isopropyl alcohol (780 mL) at about 75°-80°C. The solution was allowed to cool to room remperature and the resultant precipitate was filtered was dried at about 50-55° C under reduced pressure to afford nepafenac as yellow solid (13 g).
Reference: [1] Patent: US2009/312575, 2009, A1, . Location in patent: Page/Page column 5-6
[2] Patent: CN106928103, 2017, A, . Location in patent: Paragraph 0039; 0047; 0054; 0055
[3] Journal of Medicinal Chemistry, 1990, vol. 33, # 8, p. 2296 - 2304
[4] Patent: US4313949, 1982, A,
[5] Letters in Organic Chemistry, 2012, vol. 9, # 7, p. 461 - 464,4
[6] Patent: WO2014/207769, 2014, A1, . Location in patent: Page/Page column 14
  • 2
  • [ 2835-77-0 ]
  • [ 78281-72-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 8, p. 2296 - 2304
[2] Letters in Organic Chemistry, 2012, vol. 9, # 7, p. 461 - 464,4
  • 3
  • [ 173262-94-7 ]
  • [ 78281-72-8 ]
Reference: [1] Patent: US5475034, 1995, A,
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