1-Methylpiperazine → HCID 58346572, compound

Participants

Reaction Conditions

Reaction Steps

To 4 mL CH3CN were sequentially added 2-[6-({3-chloro-4-[(6-methylpyridin-2-yl)methoxy]phenyl}amino)-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-2-yl]ethyl methanesulfonate (100 mg, 0.17 mmol), 1-methylpiperazine (0.06 mL, 0.5 mmol), and diisopropylethylamine (0.06 mL, 0.33 mmol). The mixture was stirred at 70° C. for 16 h after which time the mixture was removed from heating, and allowed to cool to rt. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were concentrated under reduced pressure and purified by prep HPLC. The combined fractions were treated with saturated Na2CO3 and dried to afford free base product (43 mg, 43%) as a white solid. 1H-NMR (DMSO-d6) δ 8.43 (s, 1H), 8.34 (s, 1H), 7.95 (s, 1H), 7.77 (d, 1H), 7.73 (d, 1H), 7.51 (dd, 1H), 7.35 (d, 1H), 7.22 (s, 1H), 7.19 (s, 1H), 5.22 (s, 2H), 4.17 (t, 2H), 3.38 (t, 2H), 2.91 (t, 2H), 2.70 (t, 2H), 2.48 (s, 3H), 2.40-2.48 (br s, 4H), 2.25-2.35 (br s, 4H), 2.13 (s, 3H); LCMS RT=2.07-2.24 min, [M+H]+=601.4.

Provenance & Evidence