Triethylamine → HCID 178462648, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (509 μL, 3.62 mmol) was added to a solution of 4-(4-ethylpiperazin-1-yl)-benzene-1,2-diamine as the tetra-hydrochloride salt in anhydrous DMF (4 mL). After five minutes, a solution of [4-(5-formyl-1H-pyrazol-3-yl)phenyl]carbamic acid tert-butyl ester in anhydrous DMF (2 mL) was added to the diamine. The reaction flask was left open to the air and heated to 65° C. After twelve hours the reaction was concentrated in vacuo and the residue purified on reverse phase HPLC using water-acetonitrile gradient (0.1% TFA) to provide the product (87 mg, 99% yield) as a light purple solid. Note that the BOC group was removed under the purification conditions: 1H NMR (400 MHz, CDCl3): δ 7.90 (m, 2H), 7.71 (d, J=8.8 Hz, 1H), 7.46 (m, 2H), 7.42 (dd, J=9.2, 2.0 Hz, 1H), 7.41 (s, 1H), 7.30 (d, J=2.4 Hz, 1H), 4.01 (bd, J=12.0 Hz, 2H), 3.74 (bd, J=10.4 Hz, 2H), 3.35-3.27 (m, 4H), 3.23 (m, 2H), 1.44 (t, J=7.2 Hz, 3H); MS (EI) for C22H25N7: 388.2 (MH+).

Provenance & Evidence