Hydrochloric Acid → (E)-1-(3-(3-(Hex-1-enyl)imidazo[1,2-b]pyridazin-6-ylamino)propyl)pyrrolidin-2-one hydrochloride

Participants

Reaction Steps

Prepared from the product of step A and (E)-1-hexeneboronic acid according to general procedure 2. The free-base was converted to the HCl salt with 2N HCl in Et2O to provide the title compound (68 mg, 52%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.90 (s, 1H), 7.86 (d, J=9.8 Hz, 1H), 7.16 (d, J=9.8 Hz, 1H), 6.89 (dt, J=6.1, 16.2 Hz, 1H), 6.68 (d, J=16.2 Hz, 1H), 3.50 (t, J=7.0 Hz, 2H), 3.44-3.40 (m, 4H), 2.38-2.32 (m, 4H), 2.09-2.03 (m, 2H), 1.98-1.93 (m, 2H), 1.56-1.50 (m, 2H), 1.46-1.40 (m, 2H), 0.98-0.96 (t, J=6.3 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 177.8, 157.1, 139.0, 133.3, 130.1, 121.2, 120.6, 117.9, 114.3, 41.3, 39.9, 34.3, 32.4, 32.1, 26.9, 23.3, 18.9, 14.3 (one signal overlapping with solvent); HPLC tR=11.4 min (Luna), 97.3%; ES-MS: (M+H)=342 m/z.

Provenance & Evidence