4-(4-Aminophenoxy)-N-methylpicolinamide Chemical Properties

Melting point:

110-112°C

Boiling point:

476.8±40.0 °C(Predicted)

Density 

1.241±0.06 g/cm3(Predicted)

vapor pressure 

0.001-0.05Pa at 20-109.84℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

13.96±0.46(Predicted)

form 

solid

color 

White to Light yellow to Light orange

InChI

InChI=1S/C13H13N3O2/c1-15-13(17)12-8-11(6-7-16-12)18-10-4-2-9(14)3-5-10/h2-8H,14H2,1H3,(H,15,17)

InChIKey

RXZZBPYPZLAEFC-UHFFFAOYSA-N

SMILES

C1(C(NC)=O)=NC=CC(OC2=CC=C(N)C=C2)=C1

LogP

0.9 at 25℃ and pH7

Surface tension

71.71mN/m at 883.8mg/L and 20.1℃

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

4-(4-Aminophenoxy)-N-methylpicolinamide Usage And Synthesis

Chemical Properties

Light-Brown Solid

Uses

Sorafenib intermediate

Synthesis

To a solution of 4-aminophenol (1 g, 9.2 mmol) in DMF (20 mL) was added 1M potassium ier/-butoxide in THF (9.7 mL, 9.7 mmol) at room temperature. After 2h, (4-chloro(2-pyridyl))-N- methyl carboxamide (1.6 g, 9.2 mmol) and potassium carbonate (0.64 g, 4.6 mmol) were added, and then the reaction mixture was heated to 80 °C for 6h. After cooling, the reaction mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with brine (20 mL) and dried over magnesium sulfate. The solvent was removed in vacuo. The residue was purified by column chromatography to afford 4-(4-Aminophenoxy)-N-methylpicolinamide (2.2 g, 80 %) as a light-brown solid.

References

[1] Patent: WO2005/82853, 2005, A1. Location in patent: Page/Page column 209
[2] Patent: CN108409648, 2018, A. Location in patent: Paragraph 0043; 0044
[3] Patent: CN105085388, 2018, B. Location in patent: Paragraph 0028; 0033; 0036; 0039; 0042; 0045; 0048
[4] Patent: CN107915676, 2018, A. Location in patent: Paragraph 0012-0014

4-(4-Aminophenoxy)-N-methylpicolinamide(284462-37-9)Related Product Information

• Sorafenib
• Sorafenib Impurity 35
• Sorafenib Impurity 43
• 1-(4-chloro-3-(trifluoromethyl)phenyl)urea
• Trimebutine maleate
• PYRIDINE-2-CARBOXAMIDE
• N,N-Dimethylformamide
• N-Methylformamide
• SORAFENIB N-OXIDE
• Sorafenib tosylate
• N-Methyl-4-chloropyridine-2-carboxamide
• 4-Chloro-alpha,alpha,alpha-trifluoro-m-toluidine
• 1,4-Benzoquinoneimine
• Sorafenib related compound 10
• 4-HYDROXYPHENYLFORMAMIDE
• Sorafenib IMpurity
• Sorafenib related coMpound 8
• Sorafenib Related Compound 21