N,N-Dimethylethylenediamine → HCID 22346698, compound

Participants

Reaction Steps

The representative procedure for amide formation was used in the reaction of methyl 2-[4-amino-3-(4-{[(2,3-dichlorophenyl)sulfonyl]amino}-3-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]acetate (0.035 g, 0.067 mmol) with N,N-dimethylethylenediamine (1 mL). Purification by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min using an 8μ Hypersil HS C18, 250×21 mm column, Rt 6.85-7.45 min) afforded N1-[2-(dimethylamino)ethyl]-2-[4-amino-3-(4-{[(2,3-dichlorophenyl)sulfonyl]amino)-3-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl}acetamide as an off-white solid (0.008 g, 0.014 mmol): 1H NMR (DMSO-d6, 400 MHz) δ 10.20 (br, 1H), 8.22 (m, 2H), 7.96 (d, 1H), 7.80 (d, 1H), 7.45 (t, 1H), 7.31 (m, 3H), 6.90 (br, 2H), 4.96 (s, 2H), 3.40 (m, 2H), 2.75 (m, 2H), 2.07 (s, 6H); MS: (M−H)− 579.

Provenance & Evidence