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[ CAS No. 112279-72-8 ] {[proInfo.proName]}

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Chemical Structure| 112279-72-8
Chemical Structure| 112279-72-8
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Product Details of [ 112279-72-8 ]

CAS No. :112279-72-8 MDL No. :MFCD09030643
Formula : C6H4BrF2N Boiling Point : -
Linear Structure Formula :- InChI Key :UEVLRVBHLWKNEN-UHFFFAOYSA-N
M.W : 208.00 Pubchem ID :14621037
Synonyms :

Calculated chemistry of [ 112279-72-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.46
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 2.13
Log Po/w (WLOGP) : 3.16
Log Po/w (MLOGP) : 3.1
Log Po/w (SILICOS-IT) : 2.66
Consensus Log Po/w : 2.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.92
Solubility : 0.253 mg/ml ; 0.00121 mol/l
Class : Soluble
Log S (Ali) : -2.31
Solubility : 1.02 mg/ml ; 0.00492 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.073 mg/ml ; 0.000351 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 112279-72-8 ]

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 [ 112279-72-8 ]

* 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 [ 112279-72-8 ]
  • Downstream synthetic route of [ 112279-72-8 ]

[ 112279-72-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 4519-40-8 ]
  • [ 112279-72-8 ]
YieldReaction ConditionsOperation in experiment
100% With N-Bromosuccinimide In N,N-dimethyl-formamide for 1 h; Cooling with ice To a solution of 2,3-difluoroaniline (G-1) (38.0 ml, 375 mmol) in anhydrous dimethylformamide (20 ml) was added NBS (70.1 g, 394 mmol) with ice-cooling, then the reaction mixture was stirred for 1 hour. To the reaction solution was added water, then the reaction solution was extracted with ethyl acetate. The extraction was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to give Compound (G-2) (81.9 g, quant.) as an oil.Compound (G-2);Method C: Rt=1.81 min, 207.65 (ES+)
68% With N-Bromosuccinimide In acetonitrile at 35℃; for 2 h; 4-Bromo-2,3-difluoroaniline
To a solution of 2,3-difluoroaniline (1 equiv.), N-bromosuccinimide (1 equiv.) in acetonitrile (1 M).
The mixture was stirred at 35° C. for 2 h, and then reduced in vacuo to afford a residue.
The residue was poured into water and extracted with ethyl acetate, then concentrated to give the crude product, which was purified by silica gel chromatography to afford the desired product 4-bromo-2,3-difluoroaniline (68percent).
34% With tetra-N-butylammonium tribromide In acetonitrile at 20℃; for 3 h; Step 1: 4-bromo-2,3-difluoroanilinThe procedure for preparing this compound was based on that described in International Patent Publication No. WO 2010/091272. To a 100 mL round bottom flask, 2,3-difluoroaniline (1 g, 0.0077 mol) and ACN (30 mL) were added. To the flask was added the solution of tetrabutylammonium tribromide (3.71 g, 0.0077 mol, in 10 mL of ACN). The reaction mixture was stirred at room temperature for 3 h. The reaction mass was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine and evaporated under reduced pressure to get the crude product. The crude product was purified by column chromatography using 60-12 silica gel and 30percent ethyl acetate in hexane to get the title compound [0.55 g, 34percent]. The obtained product was immediately taken to the next step.
30%
Stage #1: at 0℃; for 5 h;
Stage #2: With sodium hydroxide In water
Example 124: Preparation of N-{4-(4-bromo-2,3-difluoro-phenylamino)-7-[2- (2-dimethylamino-acetylamino)-ethoxy]-quinazolin-6-yl}-acrylamide<124-1> 4-bromo-2,3-difluoro-phenylamine; 2,3-difluoro-phenylamine (13.45 g, 104.2 mmol) was diluted with acetic acid (180 mi), bromine (2.6 mi) diluted with acetic acid (5 mi) was slowly added thereto at 0 "C , and the solution was stirred for 5 hours. The resulting solution was distilled under a reduced pressure to remove the solvent, basified by adding 50percent sodium hydroxide solution (250 mi), and extracted with dichloromethane (200 mi) twice. The separated organic layer was dried over magnesium sulfate, filtered and distilled under a reduced pressure to obtain the title compound 6.46 g (yield: 30percent). 1H NMR (CDCl3) δ: 7.08-7.02 (m, IH), 6.49-6.42 (m, IH), 3.72 (bs,2H).

Reference: [1] Patent: US2012/253040, 2012, A1, . Location in patent: Page/Page column 35
[2] Patent: US2016/96841, 2016, A1, . Location in patent: Paragraph 0380
[3] Patent: WO2012/58671, 2012, A1, . Location in patent: Page/Page column 88-89
[4] Patent: WO2007/55514, 2007, A1, . Location in patent: Page/Page column 142
[5] Patent: US2010/204477, 2010, A1, . Location in patent: Page/Page column 30
[6] Patent: US2009/48305, 2009, A1, . Location in patent: Page/Page column 30
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