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[ CAS No. 849217-60-3 ] {[proInfo.proName]}

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Chemical Structure| 849217-60-3
Chemical Structure| 849217-60-3
Structure of 849217-60-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 849217-60-3 ]

CAS No. :849217-60-3 MDL No. :MFCD22045581
Formula : C17H15FN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :FSFMBVMXIPQPMJ-UHFFFAOYSA-N
M.W : 314.31 Pubchem ID :57810197
Synonyms :

Calculated chemistry of [ 849217-60-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.18
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 83.81
TPSA : 78.43 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 3.3
Log Po/w (WLOGP) : 2.86
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 2.61
Consensus Log Po/w : 2.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.86
Solubility : 0.0436 mg/ml ; 0.000139 mol/l
Class : Soluble
Log S (Ali) : -4.62
Solubility : 0.00749 mg/ml ; 0.0000238 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.42
Solubility : 0.00119 mg/ml ; 0.0000038 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.85

Safety of [ 849217-60-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 849217-60-3 ]

* 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 [ 849217-60-3 ]
  • Downstream synthetic route of [ 849217-60-3 ]

[ 849217-60-3 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 849217-48-7 ]
  • [ 123-30-8 ]
  • [ 849217-60-3 ]
YieldReaction ConditionsOperation in experiment
88% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In ISOPROPYLAMIDE at 20℃; for 3 h; To a solution of 4-aminophenol (2.93 g, 26.9 mmol) and 1- (4-FLUORO-PHENYLCARBAMOYL)-CYCLOPROPANECARBOXYLIC acid (5.00 g, 22.4 mmol) in DMA (30 mL) was added EDCI (5.15 g, 26.9 mmol). The mixture was stirred vigorously until the reaction was complete (-3 h). With vigorous stirring, the reaction mixture was then poured into a flask containing sat. aqueous NAHCO3 solution (200 mL). The stirring was continued for 1 h. The resulting suspension was then filtered. The solid was washed with water (50 mL), chloroform (50 ML) and dried under vacuum, affording 1- (4-FLUORO- phenylcarbamoyl) -cyclopropanecarboxylic acid (6.22g, 88percent yield) as a powder (>95percent purity by HPLC AND 1H NMR).
88% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl acetamide will1- (3-Dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride(5.15 g, 26.9 mmol)Aminophenol (2.93 g, 26.9 mmol) and1- (4-fluorophenylcarbamoyl) cyclopropanecarboxylic acid (5.00 g, 22.4 mmol)In N, N-dimethylacetamide (30 mL).The reaction was stirred until the reaction was complete and the mixture was poured into saturated aqueous sodium bicarbonate(200 ml) and stirred for 1 hour.The residue was filtered, washed with water (50 ml) and then with chloroform (50 ml)Drying tooN- (4-fluorophenyl) -N'-(4-hydroxyphenyl) -cyclopropane-1,1-dicarboxamide(6.22 g, yield: 88percent).
88% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In ISOPROPYLAMIDE at 20℃; for 3 h; To a solution of 4-aminophenol (2.93 g, 26.9 mmol) and 1- (4-FLUORO-PHENYLCARBAMOYL)-CYCLOPROPANECARBOXYLIC acid (5.00 g, 22.4 mmol) in DMA (30 mL) was added EDCI (5.15 g, 26.9 mmol). The mixture was stirred vigorously until the reaction was complete (-3 h). With vigorous stirring, the reaction mixture was then poured into a flask containing sat. aqueous NAHCO3 solution (200 mL). The stirring was continued for 1 h. The resulting suspension was then filtered. The solid was washed with water (50 mL), chloroform (50 ML) and dried under vacuum, affording 1- (4-FLUORO- phenylcarbamoyl) -cyclopropanecarboxylic acid (6.22g, 88percent yield) as a powder (>95percent purity by HPLC AND 1H NMR).
87.9% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3 h; General procedure: To a solution of the intermediate 9 (1.0g, 4.48mmol) and substituted aminophenol (5.38mmol) in DMF (15mL) was added EDCI (1.03g, 5.38mmol). The solution was stirred at room temperature for 3h. Then water (50mL) was added to precipitate white solid, adjusting pH to 4.0–5.0 by 1M HCl. The white solid was filtered off, washed and dried in vacuum to afford 10a-b [45]. 5.3.1 N-(4-fluorophenyl)-N-(4-hydroxyphenyl)cyclopropane-1,1-dicarboxamide (10a) Yield: 87.9percent; MS (ESI) m/z: 315.4 [M+H]+. 1H NMR (400MHz, DMSO-d6) δ: 10.17 (s, 1H, CONH), 9.73 (s, 1H, CONH), 9.23 (s, 1H, OH), 7.83–6.68 (m, 8H, Ar-H), 1.48 (s, 4H, CH2CH2).

Reference: [1] Patent: WO2005/30140, 2005, A2, . Location in patent: Page/Page column 205
[2] Patent: CN106632028, 2017, A, . Location in patent: Paragraph 0079; 0084; 0085
[3] Patent: WO2005/30140, 2005, A2, . Location in patent: Page/Page column 205
[4] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 212 - 228
  • 2
  • [ 849217-59-0 ]
  • [ 849217-60-3 ]
YieldReaction ConditionsOperation in experiment
95% With cyclohexa-1,4-diene In ethanol for 2 - 5 h; Heating / reflux To a refluxing mixture of cyclopropane-l, L-DICARBOXYLIC acid (4-benzyloxy- phenyl) -amide (4-fluoro-phenyl) -amide (46 g, 113 mmol), 10percent Pd/C (2 g) in EtOH (400 mL) was added dropwise 1,4-cyclohexadiene (62.7 mL, 678 mmol). Stirring was continued for 2-5 h until the reaction was complete. The mixture was cooled to rt, filtered through celite, and washed with EtOH. The solution was then concentrated under reduced pressure. To the flask containing the crude product was added CHC13 (200 mL). The resulting suspension was stirred for 15 min at rt. The solid was filtered, and dried in the air to give cyclopropane-l, L-DICARBOXYLIC acid (4-fluoro-phenyl) -amide (4-hydroxy- phenyl) -amide (34.4 g, 95percent, yield).
95% With cyclohexa-1,4-diene In ethanol for 2 - 5 h; Heating / reflux To a refluxing mixture of cyclopropane-l, L-DICARBOXYLIC acid (4-benzyloxy- phenyl) -amide (4-fluoro-phenyl) -amide (46 g, 113 mmol), 10percent Pd/C (2 g) in EtOH (400 mL) was added dropwise 1,4-cyclohexadiene (62.7 mL, 678 mmol). Stirring was continued for 2-5 h until the reaction was complete. The mixture was cooled to rt, filtered through celite, and washed with EtOH. The solution was then concentrated under reduced pressure. To the flask containing the crude product was added CHC13 (200 mL). The resulting suspension was stirred for 15 min at rt. The solid was filtered, and dried in the air to give cyclopropane-l, L-DICARBOXYLIC acid (4-fluoro-phenyl) -amide (4-hydroxy- phenyl) -amide (34.4 g, 95percent, yield).
Reference: [1] Patent: WO2005/30140, 2005, A2, . Location in patent: Page/Page column 205
[2] Patent: WO2005/30140, 2005, A2, . Location in patent: Page/Page column 205
  • 3
  • [ 208121-91-9 ]
  • [ 123-30-8 ]
  • [ 849217-60-3 ]
YieldReaction ConditionsOperation in experiment
87% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3 h; 4-Aminophenol (15, 0.59 g, 5.38 mmol) and Intermediate 3 (1 g, 4.48 mmol) were dissolved in 15 mL of DMF, EDC.HCl (1.03 g, 5.38 mmol) was added thereto, and the mixture was stirred at room temperature for 3 h.After the reaction was completed, water was added to the reaction solution to precipitate a white solid, and 1N HCl was added to adjust the pH to 4.0 to 5.0. After stirring for 15 minutes, the mixture was filtered, and the filter cake was washed with water until neutral, and dried under vacuum to obtain 1.23 g of a white solid. The yield was 87.9. percent.
Reference: [1] Patent: CN107793363, 2018, A, . Location in patent: Paragraph 0144; 0145; 0146; 0147; 0148; 0149
  • 4
  • [ 123-30-8 ]
  • [ 849217-60-3 ]
Reference: [1] Patent: US2018/244667, 2018, A1, . Location in patent: Paragraph 0075-0076
  • 5
  • [ 371-40-4 ]
  • [ 849217-60-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 212 - 228
[2] Patent: CN106632028, 2017, A,
[3] Patent: CN107793363, 2018, A,
[4] Patent: US2018/244667, 2018, A1,
[5] Patent: WO2005/30140, 2005, A2,
[6] Patent: WO2005/30140, 2005, A2,
  • 6
  • [ 598-10-7 ]
  • [ 849217-60-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 212 - 228
[2] Patent: CN106632028, 2017, A,
[3] Patent: WO2005/30140, 2005, A2,
[4] Patent: WO2005/30140, 2005, A2,
  • 7
  • [ 849217-48-7 ]
  • [ 849217-60-3 ]
Reference: [1] Patent: US2018/244667, 2018, A1,
[2] Patent: WO2005/30140, 2005, A2,
  • 8
  • [ 6914-71-2 ]
  • [ 849217-60-3 ]
Reference: [1] Patent: US2018/244667, 2018, A1,
  • 9
  • [ 1345847-71-3 ]
  • [ 849217-60-3 ]
Reference: [1] Patent: US2018/244667, 2018, A1,
  • 10
  • [ 113020-21-6 ]
  • [ 849217-60-3 ]
Reference: [1] Patent: US2018/244667, 2018, A1,
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