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Product Details of [ 2835-77-0 ]

CAS No. :2835-77-0 MDL No. :MFCD00007713
Formula : C13H11NO Boiling Point : -
Linear Structure Formula :C6H4C6H5C(O)NH2 InChI Key :MAOBFOXLCJIFLV-UHFFFAOYSA-N
M.W : 197.23 Pubchem ID :76080
Synonyms :
2-Benzoylaniline

Calculated chemistry of [ 2835-77-0 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.72
TPSA : 43.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 3.19
Log Po/w (WLOGP) : 2.51
Log Po/w (MLOGP) : 2.34
Log Po/w (SILICOS-IT) : 2.68
Consensus Log Po/w : 2.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.53
Solubility : 0.0579 mg/ml ; 0.000293 mol/l
Class : Soluble
Log S (Ali) : -3.77
Solubility : 0.0338 mg/ml ; 0.000171 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.51
Solubility : 0.00612 mg/ml ; 0.000031 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 2835-77-0 ]

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 [ 2835-77-0 ]

* 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 [ 2835-77-0 ]
  • Downstream synthetic route of [ 2835-77-0 ]

[ 2835-77-0 ] Synthesis Path-Upstream   1~11

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Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 27, p. 6561 - 6567
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Reference: [1] Patent: US2009/312575, 2009, A1, . Location in patent: Page/Page column 5
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  • [ 719-59-5 ]
Reference: [1] Letters in Organic Chemistry, 2012, vol. 9, # 7, p. 461 - 464,4
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  • [ 39859-36-4 ]
YieldReaction ConditionsOperation in experiment
96% With sodium perborate; ammonium molibdate; potassium bromide In acetic acid at 0℃; for 3 h; Example A16
(2-Amino-5-bromo-phenyl)-phenyl-methanone
The title compound is known from US 20040127536 A1 and was prepared according to a method developed by D. Roche, K. Prasad, O. Repic, T. J. Blacklock, Tetrahedron Lett. 41, 2083-2085 (2000).
2-Aminobenzophenone (30 g, 152 mmol) was suspended in acetic acid (300 mL).
Potassium bromide (19.9 g, 167 mmol), sodium perborate tetrahydrate (28 g, 183 mmol) and ammonium molybdate tetrahydrate (1.5 g) were added and stirring continued for 3 hours at 0° C.
The dense yellow precipitate which formed was diluted with ice water (300 mL) and then filtered off and washed with ice water and dried.
One obtained 40.3 g (96percent) of a yellow solid. MS: m/z=276 (M).
86% With N-Bromosuccinimide In dichloromethane at -10℃; for 2 h; 2-Aminobenzophenone(5 g, 25.35 mmol) was dissolved in 60 ml of dichloromethane and stirred at -10 ° C for 10 min. N-bromosuccinimide (4.74 g, 26.62 mmol) was added portionwise and the reaction mixture After the reaction was carried out for 2 hours, 30 ml of water was added, extracted with methylene chloride and washed with saturated brine. The organic layer was collected and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using petroleum ether / Ethyl acetate (ν / ν = 20 / 1-10 / 1) to give 6 g of 2-amino-5-bromobenzophenone as a yellow solid in 86percent.
85.71% With N-Bromosuccinimide In dichloromethane; water at -10℃; for 2.16667 h; 2-amino-benzophenone (5g, 25.35mmol) was dissolved in 60ml of dichloromethane, stirred for 10min at -10 cold trap, was added portionwise N- bromosuccinimide (4.74g, after 26.62mmol), reaction was continued for 2 hours in the cold trap, was added 30ml of water, extracted with dichloromethane, washed with brine, and the organic layer was collected, dried over anhydrous sodium sulfate, the organic solvent was distilled off under reduced pressure, the residue was purified by a silica gel column purified by chromatography, using petroleum ether / ethyl acetate (V / V = 20 / 1-10 / 1)to afford 2-amino-5-bromo-benzophenone 6g, as a yellow solid, a yield of 85.71percent
74% With N-Bromosuccinimide In N,N-dimethyl-formamide Intermediate 1-a was synthesized according to Reaction Scheme 1 below. In a 1 L round bottom flask reactor, add 2-aminobenzophenone (50 g, 254 mmol) and 500 mL of dimethylformamide. N-Bromosuccinimide (40.6 g, 228 mmol) is added portionwise to the solid. The reaction is terminated by adding excess water. The solid was separated by column chromatography to obtain & lt; intermediate 1-a & gt ;. (52 g, 74percent)
6.3 g With N-Bromosuccinimide In dichloromethane at -10℃; for 2.5 h; To a solution of (2-Amino-phenyl)-phenyl-methanone (5 g, 25 mmol) in DCM (100 mL) is cooled to -10° C., then NBS (4.512 g, 25 mmol) is added in 30 minutes. After the addition the mixture is stirred at -10° C. for 2 h. The mixture is diluted with DCM, washed with salt NaHCO3 (2*100 mL), salt NaCl (100 mL), dried over anhydrous Na2SO4, filtered and concentrated to give product (6.3 g), which is used for the next step without further purification. TLC (10:1, petrol ether/ethyl acetate) Rf=0.6
80 mg at 0℃; for 16 h; 2-aminophenyl)(phenyl)methanone (500 mg) was reacted with KBr, ammonium molbedate, and sodium per borate in AcOH at 0°C for 16 hours to yield (2-amino-5- bromophenyl)(phenyl)methanone (80 mg).

Reference: [1] Tetrahedron, 2007, vol. 63, # 13, p. 2811 - 2823
[2] Patent: US2006/94754, 2006, A1, . Location in patent: Page/Page column 11
[3] Organic Letters, 2010, vol. 12, # 12, p. 2841 - 2843
[4] Chemical Communications, 2010, vol. 46, # 29, p. 5244 - 5246
[5] European Journal of Organic Chemistry, 2017, vol. 2017, # 31, p. 4600 - 4608
[6] Patent: CN107056771, 2017, A, . Location in patent: Paragraph 0107-0109
[7] Patent: CN105541825, 2016, A, . Location in patent: Paragraph 0064; 0065; 0066; 0067; 0068; 0069
[8] ChemMedChem, 2018, vol. 13, # 13, p. 1363 - 1368
[9] Tetrahedron Letters, 2006, vol. 47, # 49, p. 8693 - 8697
[10] Journal of Medicinal Chemistry, 2011, vol. 54, # 19, p. 6514 - 6530
[11] Synthetic Communications, 2009, vol. 39, # 2, p. 215 - 219
[12] Patent: KR2017/139895, 2017, A, . Location in patent: Paragraph 0395-0401
[13] Molecular Crystals and Liquid Crystals, 2007, vol. 462, # 1, p. 159 - 167
[14] Patent: WO2005/9967, 2005, A2, . Location in patent: Page/Page column 58
[15] Patent: WO2014/154762, 2014, A1, . Location in patent: Page/Page column 36-37
[16] Patent: US2014/296230, 2014, A1, . Location in patent: Paragraph 0141-0143
[17] Patent: WO2014/159837, 2014, A1, . Location in patent: Page/Page column 76
[18] ChemMedChem, 2015, vol. 10, # 7, p. 1153 - 1156
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YieldReaction ConditionsOperation in experiment
100% at 0 - 20℃; 2-benzoyl-4-bromoaniline
Pathway 2: 2-aminobenzophenone (1 eq., 5 mmol, 0.986 g) is dissolved in dichloromethane at 0° C. N-bromosuccinimide (1 eq., 5 mmol, 0.890 g) is then added in small portions. The temperature of the reaction mixture is allowed to return to ambient temperature over approximately two hours. The reaction mixture is then evaporated and 2-benzoyl-4-bromoaniline is quantitatively obtained.
1H NMR (400 MHz, CDCl3) δ: 7.64-7.63 (d, J=7.2 Hz, 2H, 2′), 7.56 (s, 1H, 6), 7.55-7.54 (d, J=2.4 Hz, 1H, 4′), 7.50-7.47 (t, J=7.6 Hz, 2H, 3′), 7.38-7.35 (q, J=8.8-2.4 Hz, 1H, 4), 6.66-6.64 (d, J=8.4 Hz, 1H, 3), 6.09 (s, 2H, NH2).
MS (ES) m/z 276 (M+H+), 198, 105.
Reference: [1] Patent: US2016/83355, 2016, A1, . Location in patent: Paragraph 0340; 0341; 0342; 0343
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Reference: [1] Angewandte Chemie - International Edition, 2005, vol. 44, # 11, p. 1654 - 1657
[2] Angewandte Chemie - International Edition, 2005, vol. 44, # 19, p. 2947 - 2951
[3] Advanced Functional Materials, 2013, vol. 23, # 18, p. 2329 - 2337
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Reference: [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 10, p. 2343 - 2348
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Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 23, p. 8436 - 8439
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Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 31, p. 7972 - 7975[2] Angew. Chem., 2013, vol. 125, # 31, p. 8130 - 8133
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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
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Reference: [1] Patent: WO2008/112913, 2008, A1,
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