HCID 22347070, compound → HCID 178480972, compound

Participants

Reaction Steps

Cis-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-fluorophenyl)-1,3-benzothiazol-2-amine was prepared from cis-3-iodo-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.100 g, 0.227 mmol) and N2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzothiazol-2-amine (0.105 g, 0.283 mmol) in a manner similar to that used for cis-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-dlpyrimidin-3-yl}-2-fluorophenyl)-1,3-benzoxazol-2-amine. The compound was formed as an off-white powder (0.051 g, 41%): 1H NMR (DMSO-d6, 400 MHz) δ 10.51 (s, 1H), 8.80 (m, 1H), 8.24 (s, 1H), 7.85 (d, 1H), 7.65 (d, 1H), 7.51 (m, 2H), 7.36 (t, 1H), 7.20 (t, 1H), 4.82 (m, 1H), 3.51-2.25 (m, 14H), 2.15-2.10 (m, 2H), 1.80-1.50 (m, 4H); RP-HPLC (25 to 100% CH3CN in 0.1 N aqueous ammonium acetate over 10 min at 1 mL/min using a Hypersil HS C18, 250×4.6 mm column) tr=7.63 min., 100%; m/z 558 (MH+).

Provenance & Evidence