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[ CAS No. 112522-64-2 ] {[proInfo.proName]}

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Chemical Structure| 112522-64-2
Chemical Structure| 112522-64-2
Structure of 112522-64-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 112522-64-2 ]

CAS No. :112522-64-2 MDL No. :
Formula : C15H15N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VAZAPHZUAVEOMC-UHFFFAOYSA-N
M.W : 269.30 Pubchem ID :2746
Synonyms :
N-acetyldinaline;CI-994;CI994, CI-994, CI 994, PD123654, PD-123654, PD 123654, Tacedinaline, acetyldinaline;Acetyldinaline;PD-123654;Goe-5549

Calculated chemistry of [ 112522-64-2 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 3.0
Molar Refractivity : 79.37
TPSA : 84.22 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) : -7.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.7
Log Po/w (XLOGP3) : 1.25
Log Po/w (WLOGP) : 2.11
Log Po/w (MLOGP) : 1.84
Log Po/w (SILICOS-IT) : 1.49
Consensus Log Po/w : 1.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.41
Solubility : 1.04 mg/ml ; 0.00388 mol/l
Class : Soluble
Log S (Ali) : -2.62
Solubility : 0.651 mg/ml ; 0.00242 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.94
Solubility : 0.00306 mg/ml ; 0.0000114 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.62

Safety of [ 112522-64-2 ]

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

Application In Synthesis of [ 112522-64-2 ]

* 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 [ 112522-64-2 ]
  • Downstream synthetic route of [ 112522-64-2 ]

[ 112522-64-2 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 1299346-13-6 ]
  • [ 112522-64-2 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With trifluoroacetic acid In dichloromethane at 0 - 23℃; for 2 h;
Stage #2: With sodium hydrogencarbonate In water
To a 0 °C solution of tert-butyl (2-(4-acetamidobenzamido)phenyl) carbamate 1.5 (3.5 g, 9.5 mmol) in dry dichloromethane (55 mL) was added trifluoroacetic acid (22 mL) dropwise. The mixture was allowed to slowly warm to 23 °C for 2 hours until the reaction was complete. The solvents were removed in vacuo. The reaction mixture was diluted with water and the pH was adjusted to ~8 with a saturated aqueous solution of sodium bicarbonate. The resulting precipitate was filtered, washed with water and ether, and dried under vacuum to afford 4-acetamido-N-(2-aminophenyl)benzamide 1.6 as an off-white solid. Yield 1.6 = 2.4 g (96percent).1H NMR (500 Hz, d6-DMSO) δ 10.18 (s, 1H), 9.54 (s, 1H), 7.93 (d, J = 8.5Hz, 2H), 7.69 (d, J = 8.5Hz, 2H), 7.15 (d, J = 7.5Hz, 1H), 6.96 (t, J= 7.5Hz, 1H), 6.78 (d, J = 7.5Hz, 1H), 6.59 (t, J = 7.5Hz, 1H), 4.88 (s, 2H), 2.08 (s, 3H). MS (ESI+): m/z 269.9 [M+H]+.
96% With trifluoroacetic acid In dichloromethane at 0 - 23℃; for 2 h; To a 0° C. solution of tert-butyl (2-(4-acetamidobenzamido)phenyl) carbamate 1.5 (3.5 g, 9.5 mmol) in dry dichloromethane (55 mL) was added trifluoroacetic acid (22 mL) dropwise. The mixture was allowed to slowly warm to 23° C. for 2 hours until the reaction was complete. The solvents were removed in vacuo. The reaction mixture was diluted with water and the pH was adjusted to 8 with a saturated aqueous solution of sodium bicarbonate. The resulting precipitate was filtered, washed with water and ether, and dried under vacuum to afford 4-acetamido-N-(2-aminophenyl)benzamide 1.6 as an off-white solid. Yield 1.6=2.4 g (96percent). 1H NMR (500 Hz, d6-DMSO) δ 10.18 (s, 1H), 9.54 (s, 1H), 7.93 (d, J=8.5 Hz, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.15 (d, J=7.5 Hz, 1H), 6.96 (t, J=7.5 Hz, 1H), 6.78 (d, J=7.5 Hz, 1H), 6.59 (t, J=7.5 Hz, 1H), 4.88 (s, 2H), 2.08 (s, 3H). MS (ESI+): m/z 269.9 [M+H]+.
84% With trifluoroacetic acid In dichloromethane at 0 - 23℃; To a 0 °C solution of Boc protected benzamide 5 (18 g, 48.7mmol) in dry DCM (250 mL) was added TFA (100 mL) portion wise. The mixture was allowed to slowly warm to 23 °C. After stirring for 2 h, TLC showed that the reaction was complete. The TFA was removed in vacuo and the reaction mixture was diluted with water and the pH was adjusted to ~8 with sat. NaHCC>3. The resulting precipitate was filtered, washed with water, ether and dried under vacuum to afford 4-acetamido-N-(2- aminophenyl)benzamide 6 as an off-white solid.Yield: (11.5 g, 84percent). TLC : good, Rf = 0.3 (10percent MeOH in DCM) lU NMR (DMSO-d6, 500 MHz) δ 10.18(s, IH), 9.54 (s, IH), 7.93 (d, 2H, 7=9.0 Hz), 7.69 (d, 2H, 7=8.0 Hz), 7.15 (d, IH, 7=7.5 Hz), 6.96 (t, IH, 7=8.0 Hz), 6.78 (d, IH, 7=8.0 Hz), 6.59 (t, IH, 7=7.5 Hz), 4.87 (br s, 2H), 2.08 (s, 3H);MS: 270[M+1]+; HPLC: 97.71percent at 210nm.
Reference: [1] Patent: WO2012/3413, 2012, A1, . Location in patent: Page/Page column 34
[2] Patent: US2013/102677, 2013, A1, . Location in patent: Paragraph 0127; 0128; 0129
[3] Patent: WO2011/53876, 2011, A1, . Location in patent: Page/Page column 51; 52
  • 2
  • [ 556-08-1 ]
  • [ 95-54-5 ]
  • [ 112522-64-2 ]
YieldReaction ConditionsOperation in experiment
66% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16 h; To the extent possible, the procedure set forth in Thomas, M. et al., Bioorganic & Medicinal Chemistry 2008, 16, 8109-8116, was followed as described herein. To a stirred solution of 4-acetamido benzoic acid 7.4 (2.5 g, 13.95 mmol, 1.0 eq.) in N,N-dimethylformamide (50 mL) was added o-phenyldiamine 7.7 (4.53 g, 41.9 mmol, 3.0 eq.), followed by N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (3.48 g, 18.14 mmol, 1.3 eq.) and catalytic 4-(dimethylamino)pyridine (0.18 g, 1.47 mmol, 0.1 eq.). The reaction mixture was stirred at room temperature for 16 hours. The solvents were removed under reduced pressure at 58° C. The crude residue was diluted with dichloromethane (100 mL) and kept in the refrigerator overnight. The resulting precipitate was filtered, washed with hot dichloromethane (100 mL), and dried under vacuum to afford 4-acetamido-N-(2-aminophenyl)benzamide 7.6 as an off-white solid. Yield 7.6=2.48 g (66percent).
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 17, p. 8109 - 8116
[2] Patent: US2013/102677, 2013, A1, . Location in patent: Paragraph 0149; 0150
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 23, p. 5543 - 5546
[4] Patent: WO2012/3413, 2012, A1, . Location in patent: Page/Page column 40
  • 3
  • [ 1353653-79-8 ]
  • [ 112522-64-2 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydrogencarbonate In ethanol; water for 1.5 h; The dried solid of 4-acetamido-N-(2-aminophenyl)benzamide trifluoroacetate salt was suspended in a solution of 1 : 1 EtOH:H20 (320mL). Saturated NaHC03 solution (lOOmL) was added slowly to adjust the pH to 8. The resultant slurry was stirred for 1.5 hours. The precipitates were filtered and washed with water (2 X 60mL). After drying at 40°C in vacuo for 16h, 4-acetamido-N-(2-aminophenyl)benzamide (21.3g, 92percent yield, 97.0percent HPLC purity) was isolated as crystalline Form B (white solid).1HNMR (400 Hz, d6-DMSO) δ: 10.22 (s, 1H), 9.58 (s, 1H), 7.94 (d, J= 8.8 Hz, 2H), 7.70 (d, J = 8.8 Hz, 2H), 7.16 (dd, J = 1.2 Hz, 8.0 Hz, 1H), 6.97 (app dt, J= 1.6 Hz, 8.4 Hz, 1H), 6.79 (dd, J = 1.2 Hz, 8.0 Hz, 1H), 6.6 ( app dt, J= 1.6 Hz, 8.4 Hz, 2H), 4.90 (s, 2H), 2.10 (s, 3H).
Reference: [1] Patent: WO2012/3413, 2012, A1, . Location in patent: Page/Page column 52-53
  • 4
  • [ 95-54-5 ]
  • [ 112522-64-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 6, p. 3352 - 3360
  • 5
  • [ 146651-75-4 ]
  • [ 112522-64-2 ]
Reference: [1] Patent: WO2012/3413, 2012, A1,
[2] Patent: WO2012/3413, 2012, A1,
[3] Patent: WO2011/53876, 2011, A1,
[4] Patent: US2013/102677, 2013, A1,
  • 6
  • [ 88-74-4 ]
  • [ 112522-64-2 ]
Reference: [1] Patent: WO2012/3413, 2012, A1,
[2] Patent: WO2012/3413, 2012, A1,
[3] Patent: WO2011/53876, 2011, A1,
[4] Patent: US2013/102677, 2013, A1,
  • 7
  • [ 54614-93-6 ]
  • [ 112522-64-2 ]
Reference: [1] Patent: WO2012/3413, 2012, A1,
[2] Patent: WO2012/3413, 2012, A1,
[3] Patent: WO2011/53876, 2011, A1,
[4] Patent: US2013/102677, 2013, A1,
  • 8
  • [ 95-54-5 ]
  • [ 112522-64-2 ]
Reference: [1] Patent: WO2012/3413, 2012, A1,
[2] Patent: WO2012/3413, 2012, A1,
[3] Patent: US2013/102677, 2013, A1,
  • 9
  • [ 1075719-58-2 ]
  • [ 489-91-8 ]
  • [ 124-38-9 ]
  • [ 112522-64-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 17, p. 8109 - 8116
  • 10
  • [ 1075719-57-1 ]
  • [ 489-91-8 ]
  • [ 124-38-9 ]
  • [ 41833-13-0 ]
  • [ 112522-64-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 17, p. 8109 - 8116
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