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[ CAS No. 288385-99-9 ] {[proInfo.proName]}

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Chemical Structure| 288385-99-9
Chemical Structure| 288385-99-9
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Product Details of [ 288385-99-9 ]

CAS No. :288385-99-9 MDL No. :MFCD11977234
Formula : C10H10FNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :VGDKNHRINLDMIS-UHFFFAOYSA-N
M.W : 227.19 Pubchem ID :22030743
Synonyms :

Calculated chemistry of [ 288385-99-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.49
TPSA : 72.12 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) : -6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 1.44
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 1.06
Log Po/w (SILICOS-IT) : 0.84
Consensus Log Po/w : 1.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.17
Solubility : 1.54 mg/ml ; 0.00677 mol/l
Class : Soluble
Log S (Ali) : -2.56
Solubility : 0.626 mg/ml ; 0.00275 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.93
Solubility : 0.265 mg/ml ; 0.00117 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 288385-99-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 288385-99-9 ]

* 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 [ 288385-99-9 ]
  • Downstream synthetic route of [ 288385-99-9 ]

[ 288385-99-9 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 288385-99-9 ]
  • [ 288385-88-6 ]
Reference: [1] Organic Process Research and Development, 2014, vol. 18, # 1, p. 89 - 102
  • 2
  • [ 288385-96-6 ]
  • [ 288385-99-9 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogenchloride; sodium methylate; sodium In tetrahydrofuran; methanol A solution of sodium methoxide (freshly prepared from sodium (1.71 g) and methanol (35 ml)) was added to a solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (16.2 g, 62 mmol), (prepared as described above), in methanol (200 ml) cooled at 5° C.
The mixture was left to warm to ambient temperature and was stirred for 3 days.
The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and 2N hydrochloric acid (1ml).
The organic layer was concentrated to a total volume of 100 ml and THF (100 ml) and 6N hydrochloric acid (25 ml) were added.
The mixture was stirred for 1 hour at ambient temperature.
The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and water.
The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated.
The residue was purified by column chromatography eluding with ethyl acetate/petroleum ether (3/7) to give 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (12.7 g, 90percent).
MS-ESI: 250 [MNa]+
1H NMR Spectrum: (CDCl3) 2.38 (s, 3H); 4.0 (s, 3H); 4.25 (s, 2H); 7.0 (dd, 1H); 8.05 (d, 1H)
90% With hydrogenchloride; sodium methylate; sodium In tetrahydrofuran; methanol A solution of sodium methoxide (freshly prepared from sodium (1.71 g) and methanol (35 ml)) was added to a solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (16.2 g, 62 mmol), (prepared as described above), in methanol (200 ml) cooled at 5° C.
The mixture was left to warm to ambient temperature and was stirred for 3 days.
The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and 2N hydrochloric acid (1 ml).
The organic layer was concentrated to a total volume of 100 ml and THF (100 ml) and 6N hydrochloric acid (25 ml) were added.
The mixture was stirred for 1 hour at ambient temperature.
The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and water.
The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated.
The residue was purified by column chromatography eluding with ethyl acetate/petroleum ether (3/7) to give 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (12.7 g, 90percent).
MS-ESI: 250 [MNa]+
1H NMR Spectrum: (CDCl3) 2.38 (s, 3H); 4.0 (s, 3H); 4.25 (s, 2H); 7.0 (dd, 1H); 8.05 (d, 1H)
90% With hydrogenchloride; sodium methylate; sodium In tetrahydrofuran; methanol A solution of sodium methoxide (freshly prepared from sodium (1.71 g) and methanol (35 ml)) was added to a solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (16.2 g, 62 mmol), (prepared as described above), in methanol (200 ml) cooled at 5° C.
The mixture was left to warm to ambient temperature and was stirred for 3 days.
The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and 2N hydrochloric acid (1 ml).
The organic layer was concentrated to a total volume of 100 ml and THF (100 ml) and 6N hydrochloric acid (25 ml) were added.
The mixture was stirred for 1 hour at ambient temperature.
The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and water.
The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated.
The residue was purified by column chromatography eluding with ethyl acetate/petroleum ether (3/7) to give 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (12.7 g, 90percent). MS-ESI: 250 [MNa]+
1H NMR Spectrum: (CDCl3) 2.38 (s, 3H); 4.0 (s, 3H); 4.25 (s, 2H); 7.0 (dd, 1H); 8.05 (d, 1H)
Reference: [1] Patent: US2003/199491, 2003, A1,
[2] Patent: US2003/212055, 2003, A1,
[3] Patent: US2003/207878, 2003, A1,
  • 3
  • [ 121247-16-3 ]
  • [ 288385-99-9 ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate In methanol for 3 h; Heating / reflux A mixture of 1-(2,3-difluoro-6-nitrophenyl) -propan-2-one (183 g) and potassium carbonate (100 g) in methanol (1L) was heated at reflux for 3 h. The reaction mixture was then cooled and concentrated in vacuo to remove most of the methanol. The residue was diluted with ethyl acetate (1L), filtered and washed with water. The separated aqueous layer was neutralized with 2N HCl and extracted with ethyl acetate (2x500 mL). The combined organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo to give a brown solid. The solid was triturated with diethyl ether and filtered to provide 1-(2-fluoro-3-methoxy-6-nitrophenyl)-propan-2-one (121 g, 71 percent) as a yellow solid. LC/MS; (M+H)+ = 228.2
Reference: [1] Patent: WO2004/9542, 2004, A2, . Location in patent: Page 34; 35
  • 4
  • [ 67-56-1 ]
  • [ 121247-16-3 ]
  • [ 288385-99-9 ]
Reference: [1] Organic Process Research and Development, 2014, vol. 18, # 1, p. 89 - 102
[2] Patent: EP2940031, 2015, A1, . Location in patent: Paragraph 0131
  • 5
  • [ 771-69-7 ]
  • [ 288385-99-9 ]
Reference: [1] Organic Process Research and Development, 2014, vol. 18, # 1, p. 89 - 102
[2] Patent: EP2940031, 2015, A1,
  • 6
  • [ 1022112-32-8 ]
  • [ 288385-99-9 ]
Reference: [1] Organic Process Research and Development, 2014, vol. 18, # 1, p. 89 - 102
[2] Patent: EP2940031, 2015, A1,
  • 7
  • [ 288385-99-9 ]
  • [ 649736-31-2 ]
YieldReaction ConditionsOperation in experiment
96% at 20 - 180℃; for 1.25 h; Heating / reflux A mixture of 1-(2-fluoro-3-methoxy-6-nitrophenyl)-propan-2-one from previous step (454 mg, 21 mmol) and pyridinium chloride (0.9 g, 7.8 mmol) was stirred at 180 C for 75 min. The reaction was cooled to room temperature, diluted with 1N HCl (3mL) and ethyl acetate (10 mL) and filtered. The filtrate was washed with brine (2x), dried and concentrated in vacuo to give 1-(2-fluoro-3-hydroxy-6-nitrophenyl)-propan-2-one (410 mg, 96 percent) as a grey solid, which was used without further purification for the next step. LC/MS; (M+H)+ = 214. 1H NMR (CDCl3): δ 2.37 (s, 3H), 4.22 (s, 2H), 6.95 (dd, 1H), 7.95 (d, 1H, J= 9.35 Hz)
Reference: [1] Patent: WO2004/9542, 2004, A2, . Location in patent: Page 35
[2] Organic Process Research and Development, 2014, vol. 18, # 1, p. 89 - 102
  • 8
  • [ 288385-99-9 ]
  • [ 7705-07-9 ]
  • [ 288385-93-3 ]
Reference: [1] Patent: US2003/199491, 2003, A1,
[2] Patent: US2003/212055, 2003, A1,
  • 9
  • [ 288385-99-9 ]
  • [ 288385-93-3 ]
Reference: [1] Patent: EP2940031, 2015, A1, . Location in patent: Paragraph 0132
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