7-(benzyloxy)-N-(4-bromo-2-fluorophenyl)-6-methoxyquinazolin-4-amine Chemical Properties

Melting point:

244-246 °C

Boiling point:

541.1±50.0 °C(Predicted)

Density 

1.488

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

5.44±0.30(Predicted)

InChI

InChI=1S/C22H17BrFN3O2/c1-28-20-10-16-19(11-21(20)29-12-14-5-3-2-4-6-14)25-13-26-22(16)27-18-8-7-15(23)9-17(18)24/h2-11,13H,12H2,1H3,(H,25,26,27)

InChIKey

UPEHYJHYPMGWJC-UHFFFAOYSA-N

SMILES

N1=C2C(C=C(OC)C(OCC3=CC=CC=C3)=C2)=C(NC2=CC=C(Br)C=C2F)N=C1

7-(benzyloxy)-N-(4-bromo-2-fluorophenyl)-6-methoxyquinazolin-4-amine Usage And Synthesis

Synthesis

General procedure for the synthesis of 7-(benzyloxy)-N-(4-bromo-2-fluorophenyl)-6-methoxyquinazolin-4-amine from 4-bromo-2-fluoroaniline and 7-benzyloxy-4-chloro-6-methoxyquinazoline: 6.5 M hydrogen chloride (2.54 mL) was added to a 2-propanol (160 mL) solution containing 4-bromo-2-fluoroaniline (4.51 g, 15.0 mmol) and 7-benzyloxy-4- chloro-6-methoxyquinazoline (2.40 g, 16.5 mmol) in a solution of 2-propanol (160 mL). Subsequently, the reaction mixture was heated to reflux and kept for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the precipitated solid product was collected by filtration. The solid was washed sequentially with 2-propanol and ether and finally dried under vacuum overnight to afford the target compound 7-(benzyloxy)-N-(4-bromo-2-fluorophenyl)-6-methoxyquinazolin-4-amine (7.9 g, 94% yield) as a white solid.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 11, p. 3222 - 3226
[2] Patent: WO2005/13998, 2005, A1. Location in patent: Page/Page column 75
[3] Patent: US2010/75916, 2010, A1. Location in patent: Page/Page column 16
[4] Patent: WO2005/97134, 2005, A2. Location in patent: Page/Page column 16-17; figure 2
[5] Patent: US2009/238808, 2009, A1

7-(benzyloxy)-N-(4-bromo-2-fluorophenyl)-6-methoxyquinazolin-4-amine(768350-54-5)Related Product Information

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