Methanol → Ammonia

Participants

Reaction Steps

1-(3,4-Dichloro-benzyl)-3-(4-methylaminomethyl-thiazol-2-yl)-urea (Example 132) was taken up in DCM with 1.5 equivalents of 2,4-Dimethoxy-benzaldehyde and several drops of acetic acid. Reaction was stirred for several hours at ambient temperature. Sodium cyanoborohydride (1.5 equivalents) was added at once and the reaction was stirred overnight at ambient temperature. An aqueous work-up with dichloromethane and chromatography (silica, DCM, 0-10% MeOH saturated with NH3) afforded the title compound. 1H NMR (400 MHz, DMSO-d6): 10.65 (br s, 1H), 7.60 (d, 1H), 7.54 (d, 1H), 7.29 (dd, 1H), 7.27 (br d, 1H), 7.12 (br s, 1H), 6.58 (br s, 1H), 6.56-6.46 (m, 2H), 4.33 (d, 2H), 3.75 (s, 6H), 3.46 (br s, 4H), 2.12 (br s, 3H). MS (ES+): M/Z 495 and 497 (M+1).

Provenance & Evidence