444731-75-3

Light Beige to Beige Solid

N-(2-Chloro-4-pyrimidinyl)-N,2,3-trimethyl-2H-indazol-6-amine is an impurity of Pazopanib (P210925), an oral angiogenesis inhibitor targeting VEGFR and PDGFR.

A flask was charged with N,2,3-trimethyl-2H-indazol-6-amine (1 eq.), 2,4-dichloropyrimidine (1.5 eq.), sodium bicarbonate (2 eq.) and N, N-dimethylformamide. The reaction mixture was stirred at 85 °C until completion of the reaction. Then, water was added and stirred for 3 h. Product crystals were collected by filtration, washed with water, and then dried to get N-(2-chloropyriMidin-4-yl)-N,2,3-triMethyl-2H-indazol-6-aMine as off-white/beige powder (Yield: 97%).

[1] Patent: WO2003/106416, 2003, A2. Location in patent: Page 45-46
[2] Patent: US2015/329526, 2015, A1. Location in patent: Paragraph 0039
[3] Patent: US2008/293691, 2008, A1. Location in patent: Page/Page column 10
[4] Patent: WO2007/143483, 2007, A2. Location in patent: Page/Page column 33
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1108 - 1110