Hydrochloric Acid → HCID 86622759, compound

Participants

Reaction Steps

Sodium triacetoxyborohydride (86 mg, 0.4 mmol, 2.0 eq) was added to a dichloromethane (2 mL) solution of 1-(3,4-Dichloro-benzyl)-3-(4-methylaminomethyl-thiazol-2-yl)-urea (Example 132, 70 mg, 0.2 mmol) and 3,5-dimethylisoxazole-4-carbaldehyde (33 mg, 0.25 mmol, 1.25 eq). After 16 hours of stirring, methanol (1 mL) and aqueous HCl (0.5 mL, 1N) were added. The mixture was neutralized with dilute NaHCO3 solution. An aqueous work-up with dichloromethane and a chromatography (silica 0-3% MeOH in CH2Cl2) afforded the title compound. 1H NMR (400 MHz, CDCl3): 7.36 (m, 2H), 7.10 (dd, 1H), 6.64 (s, 1H), 4.32 (d, 2H), 3.46 (s, 3H), 3.21 (s, 3H), 2.28 (s, 3H), 2.16 (s, 3H), 2.07 (s, 3H). MS (ES+): M/Z 454 (M+1).

Provenance & Evidence