N-(4-fluoro-2-Methoxy-5-nitrophenyl)-4-(1-Methylindol-3-yl)pyriMidin-2-aMine Chemical Properties

Melting point:

>250°C (dec.)

Boiling point:

639.3±65.0 °C(Predicted)

Density 

1.41±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

DMSO (Slightly, Heated)

pka

2.02±0.10(Predicted)

form 

Solid

color 

Light Yellow to Yellow

InChI

InChI=1S/C20H16FN5O3/c1-25-11-13(12-5-3-4-6-17(12)25)15-7-8-22-20(23-15)24-16-10-18(26(27)28)14(21)9-19(16)29-2/h3-11H,1-2H3,(H,22,23,24)

InChIKey

SZTYQQYYIMVETL-UHFFFAOYSA-N

SMILES

C1(NC2=CC([N+]([O-])=O)=C(F)C=C2OC)=NC=CC(C2C3=C(N(C)C=2)C=CC=C3)=N1

N-(4-fluoro-2-Methoxy-5-nitrophenyl)-4-(1-Methylindol-3-yl)pyriMidin-2-aMine Usage And Synthesis

Uses

N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)-2-pyrimidinamine functions as a reagent in the synthesis of dihydropyrroloquinoline derivatives with anticancer activity as EGFR modulator to inhibit L858R/T790M.

Synthesis

To a 2L three-necked flask was added 1000 mL of 2-pentanol, 50 g of 3-(2-chloropyrimidin-4-yl)-1-methylindole, 42 g of 4-fluoro-2-methoxy-5-nitroaniline, and 3.54 g of p-toluenesulfonic acid at room temperature. The reaction mixture was heated to 80 °C and kept stirring for 6 hours. Upon completion of the reaction, the mixture was cooled to 25 °C to 28 °C, followed by filtration to collect the solid product. The filter cake was washed with preheated 2-pentanol (50 °C) to remove impurities. The resulting solid product was dried in a vacuum oven to give 80.1 g of the final yellow solid product N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine in 99.0% yield.

References

[1] Patent: CN107188888, 2017, A. Location in patent: Paragraph 0061-0063
[2] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 12 - 23
[3] Patent: WO2013/14448, 2013, A1. Location in patent: Page/Page column 138
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 20, p. 8249 - 8267
[5] Patent: CN107043369, 2017, A. Location in patent: Paragraph 0395; 0396; 0397; 0398

N-(4-fluoro-2-Methoxy-5-nitrophenyl)-4-(1-Methylindol-3-yl)pyriMidin-2-aMine(1421372-94-2)Related Product Information

• AZD-9291
• N-(5-Chloro-2-methylphenyl)-7- nitrobenzo[c][1,2,5]oxadiazol-4-amine
• N-(4-CHLOROPHENYL)-2-NITROBENZENAMINE
• 1,4-BenzenediaMine, N1-[2-(diMethylaMino)ethyl]-5-Methoxy-N1-Methyl-N4-[4-(1-Methyl-1H-indol-3-yl)-2-pyriMidinyl]-2-nitro-
• Mutated EGFR-IN-1