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[ CAS No. 878671-94-4 ] {[proInfo.proName]}

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Chemical Structure| 878671-94-4
Chemical Structure| 878671-94-4
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Product Details of [ 878671-94-4 ]

CAS No. :878671-94-4 MDL No. :MFCD11109543
Formula : C13H13N Boiling Point : -
Linear Structure Formula :- InChI Key :NYKSBMRQNSCVMO-UHFFFAOYSA-N
M.W :183.25 Pubchem ID :53482112
Synonyms :

Calculated chemistry of [ 878671-94-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.23
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.82
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.13
Log Po/w (XLOGP3) : 3.4
Log Po/w (WLOGP) : 3.24
Log Po/w (MLOGP) : 2.99
Log Po/w (SILICOS-IT) : 3.27
Consensus Log Po/w : 3.01

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.58
Solubility : 0.0481 mg/ml ; 0.000263 mol/l
Class : Soluble
Log S (Ali) : -3.63
Solubility : 0.0434 mg/ml ; 0.000237 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.31
Solubility : 0.00891 mg/ml ; 0.0000486 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 878671-94-4 ]

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 [ 878671-94-4 ]

* 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 [ 878671-94-4 ]
  • Downstream synthetic route of [ 878671-94-4 ]

[ 878671-94-4 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 2298-07-9 ]
  • [ 411235-57-9 ]
  • [ 878671-94-4 ]
YieldReaction ConditionsOperation in experiment
95.3% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 6 h; Inert atmosphere Bromo-1-naphthylamine (3) (0.50 g, 2.25 mmol), cyclopropylboronic acid (0.212 g, 2.47 mmol)Tetrakistriphenylphosphine palladium (0.26 g, 0.23 mmol), potassium phosphate (1.67 g, 7.87 mmol) was weighed out in a 50 mL round bottom flask,A mixed solvent of dioxane and water (25/1, 26 mL) was added, and the mixture was heated in an oil bath at 90 ° C. for 6 hours after being substituted by nitrogen for three times.The reaction mixture was cooled to room temperature and the insoluble material was filtered off. The solvent was evaporated under reduced pressure, 50 mL of water was added and the mixture was extracted with ethyl acetate (2 × 10 mL)The organic layer was washed twice with saturated brine, dried over anhydrous sodium sulfate and concentrated by filtration to obtain the intermediate 4.Purple-black oil, yield: 95.3percent.
83.6% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃; for 12 h; Inert atmosphere 4-bromo-1-naphthylamine II (90mmol, 20.0g), cyclopropyl boronic acid III (116mmol, 10.0g), potassium (300mmol, 64.0g) phosphate and tetrakistriphenylphosphine palladium (6mmol, 7.0g) 100mL of toluene and added to 4mL of water mixed solvent, reacted under nitrogen at 100 12h, when the reaction mixture was cooled to room temperature, the reaction mixture was added 100mL of water, extracted three times with ethyl acetate, dried over sodium sulfate was added . Half an hour later filtered by vacuum distillation to give 13.8g of intermediate compoundWas IV, a yield of 83.6percent '
83.6% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃; for 12 h; Inert atmosphere Bromo-1-naphthylamine (10) (20.0 g, 90 mmol),Cyclopropylboronic acid (10.0 g, 116 mmol),(64.0 g, 300 mmol) and tetrakistriphenylphosphine palladium (7.0 g, 6 mmol) were added to a mixed solvent of 100 mL of toluene and 4 mL of water,And the reaction was carried out at 100 ° C for 12 hours under a nitrogen atmosphere (the reaction was complete by TLC).After completion of the reaction, the reaction solution was cooled, 100 mL of an aqueous solution was added to the reaction solution, and the mixture was extracted three times with ethyl acetate and dried over sodium sulfate. Filtered and distilled under reduced pressure to obtain 13.8 g of intermediate 4-cyclopropyl-1-naphthylamine (11) in a yield of 83.6percent.
80 g With potassium phosphate; palladium diacetate In water; toluene at 110℃; for 3 h; Inert atmosphere Example 1. 4-cyclopropyl-l-naphthylamine [066] To a four necked flask that equipped with a mechanical stirrer, a reflux condenser and a thermometer added 4-bromo-l-naphthylamine (90 g, 40.5 mmol), cyclopropyl boronic acid (38.4 g, 44.6 mmol), anhydrous potassium phosphate (258 g, 122 mmol), toluene (800 mL) and water (30 mL) to form a mixture, stirred the mixture followed by adding cyclohexylphosphine (11.5 g, 4.1 mmol) and palladium acetate (3.65 g, 1.62 mmol) under nitrogen atmosphere to form a reaction mixture. The reaction mixture was heated to 110°C and stirred at 110°C for 3 hours, then was added with water (800 mL), separated the organic layer, extracted the aqueous phase with ethyl acetate (300 mL><2) and dried the combined organic phases with anhydrous sodium sulfate. After removing the desiccant, the filtrate was reduced under vacuum pressure to obtain 4-cyclopropyl-l-naphthylamine 80 g.

Reference: [1] Chemical Biology and Drug Design, 2016, vol. 88, # 2, p. 241 - 253
[2] Patent: CN105175414, 2017, B, . Location in patent: Paragraph 0040
[3] Patent: CN105566237, 2016, A, . Location in patent: Paragraph 0060; 0061; 0062
[4] Patent: CN106083847, 2016, A, . Location in patent: Paragraph 0133; 0134; 0170; 0171
[5] Patent: WO2006/26356, 2006, A2, . Location in patent: Page/Page column 35-36
[6] Patent: WO2014/198241, 2014, A1, . Location in patent: Paragraph 065-066
[7] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4424 - 4433
  • 2
  • [ 878671-93-3 ]
  • [ 878671-94-4 ]
YieldReaction ConditionsOperation in experiment
87% With ammonium chloride; zinc In tetrahydrofuran; waterReflux 21.32g (0.1mol) 4- cyclopropyl-1-nitro-naphthalene 1,32.69g (0.5mol) zinc powder and 26.75g (0.5mol) NH 4 Cl was added a mixed solution of 60mL of water and 150mLTHF dubbed in followed by stirring under reflux until TLC showed completion of the reaction (usually takes 10 hours or so). After completion of the reaction, the reaction mixture was cooled to room temperature, the solid was removed by suction filtration (Celite filter aid) and the filtrate was poured into 500mL of ice water with stirring, and stirring was continued for 5 minutes, 300mL × 3CH 2 Cl 2 extracted. The combined organic phase was extracted, washed 500mL5percent brine, dried over anhydrous Na 2 SO 4, the solvent was distilled off on a rotary evaporator, the residue was purified by silica gel column chromatography, that is, pure 2 red liquid, 15.94g, 87percent yield. Example 1 is consistent its HNMR and implementation
73% With hydrogen In ethanol [00356] A solution of l-cycloρroρyl-4-nitronaphtha]ene (5g, 23mmol) in ethanol (20OmL) was stirred under hydrogen in the presence of Pd/C (10percent net, 1.8g). The reaction mixture was shaken overnight, filtered over celite, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield l-amino-4-cyclopropylnaphthalene (3.1g, 73percent).
73% With hydrogen In ethanol A solution of l-cyclopropyl-4-nitro-naphthalene (5 g, 23 mmol) in ethanol (200 mL) was stirred under hydrogen in the presence of Pd/C (10percent net, 1.8 g). The reaction mixture was shaken overnight, then filtered over celite. The solvent was evaporated, and the residue was purified by silica gel chromatography to yield l-amino-4-cyclopropyl- naphthalene (3.1 g, 73percent).
73% With hydrogen In ethanol STEP C: l-Amino-4-cyclopropylnaphthalene A solution of l-cyclopropyl-4-nitronaphthalene (5 g, 23 mmol) in ethanol (200 mL) was stirred under hydrogen in the presence of Pd/C (10percent net, 1.8 g). The reaction mixture was shaken overnight, filtered over celite, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield l-amino-4-cyclopropylnaphthalene (3.1 g, 73percent).

Reference: [1] Patent: CN105622427, 2016, A, . Location in patent: Paragraph 0025-0026
[2] Patent: WO2009/70740, 2009, A2, . Location in patent: Page/Page column 89-90
[3] Patent: WO2006/26356, 2006, A2, . Location in patent: Page/Page column 20-21
[4] Patent: WO2011/85009, 2011, A2, . Location in patent: Page/Page column 36-37
[5] Patent: WO2014/8295, 2014, A1, . Location in patent: Paragraph 0345-0348
[6] Patent: CN105985295, 2016, A, . Location in patent: Paragraph 0045; 0046; 0047
[7] Patent: CN106478531, 2017, A, . Location in patent: Paragraph 0028; 0035
  • 3
  • [ 25033-19-6 ]
  • [ 878671-94-4 ]
Reference: [1] Patent: WO2011/85009, 2011, A2,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: CN105985295, 2016, A,
[4] Patent: CN106478531, 2017, A,
  • 4
  • [ 90-11-9 ]
  • [ 878671-94-4 ]
Reference: [1] Patent: WO2011/85009, 2011, A2,
[2] Patent: WO2014/8295, 2014, A1,
  • 5
  • [ 878671-94-4 ]
  • [ 878671-96-6 ]
Reference: [1] Patent: WO2011/85009, 2011, A2,
[2] Patent: CN105566237, 2016, A,
  • 6
  • [ 878671-94-4 ]
  • [ 1151516-14-1 ]
Reference: [1] Patent: WO2011/85009, 2011, A2,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
[4] Patent: WO2014/8295, 2014, A1,
[5] Patent: WO2014/8295, 2014, A1,
[6] Patent: CN105985295, 2016, A,
  • 7
  • [ 878671-94-4 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/198241, 2014, A1,
  • 8
  • [ 878671-94-4 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/198241, 2014, A1,
[4] Patent: CN105985295, 2016, A,
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