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. Author manuscript; available in PMC: 2019 Aug 20.
Published in final edited form as: ChemMedChem. 2018 Jul 11;13(16):1681–1694. doi: 10.1002/cmdc.201800188

Scheme 1. Synthesis of analogs.

Scheme 1.

Synthetic strategy for the preparation of proposed WEE1 inhibitor analogs of AZD1775 (22–35). Reagents and conditions: a) t-butyl carbazate, toluene, reflux, 18 h; b) alkyl halide, BnNEt3CI, K2CO3, MeCN, RT-50°C, 18–48 h or PMB-OH, DEAD, PPh3, THF, RT, 16 h; c) MeNHNH2, THF, RT, 18 h; d) i) DIPEA, THF, reflux, 72 h, ii) TFA, RT-70°C, 2 h or TFA, DCM, RT, 18 h; e) N,N’-diethylethylenediamine, Cul, K2CO3, 1,4-dioxane, 95°C, 18 h; f) i) mCPBA, toluene, RT, 1 h, ii) aniline /amine, DIPEA, toluene, RT, 18 h; g) TFA, reflux, 16 h; h) 4-ToISO2Na, Pd(PPh3)4, MeOH/THF, RT, 2 h.