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[ CAS No. 1785535-58-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1785535-58-1
Chemical Structure| 1785535-58-1
Chemical Structure| 1785535-58-1
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Quality Control of [ 1785535-58-1 ]

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Product Details of [ 1785535-58-1 ]

CAS No. :1785535-58-1 MDL No. :N/A
Formula : C10H9FN2 Boiling Point : -
Linear Structure Formula :- InChI Key :QMQPASUCSXVAAK-UHFFFAOYSA-N
M.W : 176.19 Pubchem ID :105436419
Synonyms :

Calculated chemistry of [ 1785535-58-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.07
TPSA : 38.91 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 1.97
Log Po/w (WLOGP) : 2.69
Log Po/w (MLOGP) : 1.9
Log Po/w (SILICOS-IT) : 2.59
Consensus Log Po/w : 2.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.74
Solubility : 0.319 mg/ml ; 0.00181 mol/l
Class : Soluble
Log S (Ali) : -2.41
Solubility : 0.681 mg/ml ; 0.00387 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.0
Solubility : 0.0174 mg/ml ; 0.0000989 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 1785535-58-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1785535-58-1 ]

* 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.

  • Downstream synthetic route of [ 1785535-58-1 ]

[ 1785535-58-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 348-54-9 ]
  • [ 1785535-58-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 22 h / 20 - 70 °C 2: sodium hydrogencarbonate; iodine / acetonitrile / 3 h / 20 °C 3: caesium carbonate; copper(II) acetylacetonate; ammonium hydroxide / acetylacetone; N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 22 h / 70 °C 1.2: 3 h / 20 °C 2.1: caesium carbonate; copper(II) acetylacetonate; ammonia / N,N-dimethyl-formamide; acetylacetone / 24 h / 90 °C / Inert atmosphere; Sealed tube
  • 2
  • [ 1249745-20-7 ]
  • [ 1785535-58-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; iodine / acetonitrile / 3 h / 20 °C 2: caesium carbonate; copper(II) acetylacetonate; ammonium hydroxide / acetylacetone; N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere; Sealed tube
  • 3
  • [ 2245282-60-2 ]
  • [ 1785535-58-1 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide; copper(II) acetylacetonate; caesium carbonate In N,N-dimethyl-formamide; acetylacetone at 90℃; for 24h; Inert atmosphere; Sealed tube; 2.2 Step 2: preparation of 8-fluoro-4-methyl-quinolin-3-amine A pressure resistant vessel was charged with 8-fluoro-3-iodo-4-methyl-quinoline (1 g,3.5 mmol), 0s2003 (2.3 g, 7.0 mmol), pentane-2,4-dione (0.14 g, 1.4 mmol),copper(ll)acetylacetonate (0.09 g, 0.35 mmol) and N,N-dimethylformamide (7 mL). The resulting mixture was purged with N2, aqueous ammonia (25%, 1 mL, 14 mmol) was then added, and the vessel was sealed and warmed to 90 00 After stirred for 24 h at 90 00 the resulting dark solution was cooled to room temperature, diluted with water and extractedseveral times with ethyl acetate. The combined organic layers were washed with water and brine; dried over Na2SO4, filtrated and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford 8-fluoro-4-methyl-quinolin-3-amine as brown solid.1H NMR (400 MHz, ODd3) 68.51 (s, 1H), 7.63 (d, 1H), 7.40 (dt, 1H), 7.14 (ddd, 1H),3.93 (br s, 2H), 2.43 (s, 3H).
With ammonia; copper(II) acetylacetonate; caesium carbonate In N,N-dimethyl-formamide; acetylacetone at 90℃; for 24h; Inert atmosphere; Sealed tube; 3.2 Step 2: preparation of 8-fluoro-4-methyl-quinolin-3-amine A pressure resistant vessel was charged with 8-fluoro-3-iodo-4-methyl-quinoline (1 g, 3.5 mmol), CS2CO3 (2.3 g, 7.0 mmol), pentane-2, 4-dione (0.14 g, 1.4 mmol), copper(ll)acetylacetonate (0.09 g, 0.35 mmol) and N,N-dimethylformamide (7 mL). The resulting mixture was purged with N2, aqueous ammonia (25%, 1 mL, 14 mmol) was then added, and the vessel was sealed and warmed to 90 °C. After stirred for 24 h at 90 °C, the resulting dark solution was cooled to room temperature, diluted with water and extracted several times with ethyl acetate. The combined organic layers were washed with water and brine; dried over Na2S04, filtrated and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford 8-fluoro-4-methyl-quinolin-3-amine as brown solid. 1H NMR (400 MHz, CDCIs) d 8.51 (s, 1 H), 7.63 (d, 1 H), 7.40 (dt, 1 H), 7.14 (ddd, 1 H), 3.93 (br s, 2H), 2.43 (s, 3H).
  • 4
  • [ 1785535-58-1 ]
  • [ 2245282-62-4 ]
  • [ 2245282-02-2 ]
YieldReaction ConditionsOperation in experiment
With trimethylaluminum In toluene at 20 - 90℃; for 64h; 2.5 Step 5: preparation of 2-benzyl-N-(8-fluoro-4-methyl-3-q uinolyl)-2 ,4-d imethyl-pent-4-enamide To a suspension of methyl 2-benzyl-2,4-dimethyl-pent-4-enoate (0.10 g, 0.5 mmol) and 8-fluoro-4-methyl-quinolin-3-amine (0.08 g, 0.5 mmol) in toluene (1 mL) was added trimethyl aluminium (2 M in toluene, 0.3 mL, 0.6 mmol) at room temperature. The resulting mixture was warmed to 90°C and stirred for 64 h at this temperature. The reaction was then cooled to roomtemperature and added into aq. NaOH (1 M) solution. The mixture was extracted with ethyl acetate, the organic layer was washed with brine, dried over Na2504, filtrated and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford 2- benzyl-N-(8-fluoro-4-methyl-3-quinolyl)-2,4-dimethyl-pent-4-enamide as yellow solid, m.p. 105- 109 °C.1H NMR (400 MHz, CDCI3) 68.83 (s, 1H), 7.73 (d, 1H), 7.53-7.48 (m, 1H), 6.99-7.45 (m, 7H), 4.99 (s, 1 H), 4.89 (s, 1 H), 3.35 (d, 1 H), 3.02 (d, 1 H), 2.66 (d, 1 H), 2.29 (s, 3H), 2.22(d, 1H), 1.86 (s, 3H), 1.42 (s, 3H)19F NMR (377 MHz CDCI3) 6-124.67 (s, iF)
With trimethylaluminum In toluene at 90℃; for 64h; 3.5 Step 5: preparation of 2-benzyl-N-(8-fluoro-4-methyl-3-quinolyl)-2,4-dimethyl-pent-4-enamide To a suspension of methyl 2-benzyl-2,4-dimethyl-pent-4-enoate (0.10 g, 0.5 mmol) and 8-fluoro-4-methyl-quinolin-3-amine (0.08 g, 0.5 mmol) in toluene (1 ml.) was added trimethyl aluminium (2 M in toluene, 0.3 ml_, 0.6 mmol) at room temperature. The resulting mixture was warmed to 90°C and stirred for 64 h at this temperature. The reaction was then cooled to room temperature and added into aq. NaOH (1 M) solution. The mixture was extracted with ethyl acetate, the organic layer was washed with brine, dried over Na2S04, filtrated and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford 2- benzyl-N-(8-fluoro-4-methyl-3-quinolyl)-2,4-dimethyl-pent-4-enamide as yellow solid, m.p. 105- 109 °C. 1H NMR (400 MHz, CDCIs) d 8.83 (s, 1 H), 7.73 (d, 1 H), 7.53-7.48 (m, 1 H), 6.99-7.45 (m, 7H), 4.99 (s, 1 H), 4.89 (s, 1 H), 3.35 (d, 1 H), 3.02 (d, 1 H), 2.66 (d, 1 H), 2.29 (s, 3H), 2.22 (d, 1 H), 1.86 (s, 3H), 1.42 (s, 3H) 19F NMR (377 MHz CDCIs) d -124.67 (s, 1 F)
  • 5
  • [ 1785535-58-1 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With 1-methyl-1H-imidazole In dichloromethane at 20℃; for 0.00216667h; 5.2 To a solution of 8-fluoro-4-methyl-quinolin-3-amine (5.27 g, 29.9 mmol) and 1 -methylimidazole (6.77 g, 81 .6 mmol) in DCM (90 ml.) was added a solution of (S)-2-benzyl-4,4,4-trifluoro-2- methyl-butanoyl chloride in DCM (as prepared above) over a period of -10 min. The resulting brown solution was stirred at ambient temperature for 2 h. The reaction mixture was diluted with additional DCM and washed with water and brine. The organic layer was dried over Na2S04, filtered and concentrated in vacuo to afford a dark yellow oil. The residue was purified by medium pressure chromatography (silica gel, cyclohexane:EtOAc) to afford (S)-2-benzyl- 4,4,4-trifluoro-N-(8-fluoro-4-methyl-3-quinolyl)-2-methyl-butanamide as off white solid. [a]° : -128° (CHC , c = 1 .00), (e.r. 95:5 {retention time minor enantiomer: 1 .71 min, retention time major enantiomer: 0.71 min, Daicel SFC CHIRALPAK ID, CC>2/iPrOH}) 1H NMR (400 MHz, CDCIs) d 8.51 (s, 1 H), 7.76 (d, 1 H), 7.49-7.54 (m, 1 H), 7.32-7.42 (m, 4H), 2.20-2.22 (dd, 2H), 7.03 (s, 1 H), 3.22-3.35 (m, 2H), 2.67 (d, 1 H), 2.35 (s, 3H), 2.22-2.31 (m, 1 H), 1 .59 (s, 3H). 19F NMR (400 MHz, CDCIs) d 60.03 (s, 3F), 124.18 (s, 1 F).
  • 6
  • [ 1785535-58-1 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With 1-methyl-1H-imidazole In dichloromethane at 20℃; for 2h; 8.6 The oil obtained above was taken up in dichloromethane (3 ml.) and slowly added to a solution of 8-fluoro-4-methyl-quinolin-3-amine (0.44 g, 2.5 mmol) and N-methyl imidazole (0.56 g, 6.8 mmol) in dichloromethane (4 ml.) at ambient temperature. The resulting solution was stirred for 2h at ambient temperature. Additional dichloromethane was then added and the solution was washed with water, brine, dried over Na2S04, filtrated and concentrated in vacuo. The brown residue was purified by medium pressure chromatography (silica gel, cyclohexane/ethyl acetate) to afford the title compound as yellow solid, m.p. 134-136°C. 1H NMR (400 MHz, CDCIs) d 8.75 (s, 1 H), 7.68 (d, 1 H), 7.46 (td, 1 H), 7.06-7.40 (m, 7H), 3.22 (d, 1 H), 2.61 (d, 1 H), 2.24 (s, 3H), 2.13 (dd, 1 H), 1 .79-1 .96 (m, 1 H), 1.49 (dd, 1 H), 1 .41 (s, 3H), 1.02 ppm (dd, 6H). [a]° : -103° (CHC , c = 1.00), (e.r. 93:7 {retention time minor enantiomer: 4.28 min, retention time major enantiomer: 3.10 min Daicel SFC CHIRALPAK IF, CC>2/EtOH})
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