2,2-Dimethyl-1,3-propanediamine → 2-(3-Amino-2,2-dimethylprop-1-ylamino)-4-methoxyquinoline

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A mixture of 2-chloro-4-methoxyquinoline (0.63 g, 3.25 mmol) and 2,2-dimethyl-1,3-propanediamine (2.00 g, 19.5 mmol) was stirred for 16 h at 75° C. in a sealed propanediamine (2.00 g, 19.5 mmol) was stirred for 16 h at 75° C. in a sealed NaHCO3 and ethyl acetate. The organic layer was dried (MgSO4) and concentrated onto silica, then chromatographed eluting with 5% then 10% methanol/CH2Cl2+0.5% 880 aqueous ammonia to give the title compound as a white solid (0.19 g, 23%). δH (CDCl3) 0.99 (6H, s, C(CH3)2), 2.57 (2H, s, 2′-H), 3.41 (2H, s, 4′-H), 3.96 (3H, s, OCH3), 5.98 (1H, s, 3-H), 7.12-7.93 (4H, m, ArH). MS (ES+) 260 (MH+).

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