HCID 58055052, compound → HCID 58055076, compound

Participants

Reaction Steps

A solution of 2-(3-(3-fluorobenzyl)ureido)-4-(N-methoxy-N-methyl-aminomethyl)-5-fluorothiazole (2.05 g, 6 mmol) in glacial acetic acid (30 mL) was treated with micronized zinc dust (12 g) and stirred at 60 C for 1-2 hours. The mixture was diluted with water (30 mL) and filtered on Celite. The filter cake was washed with 1:1 HOAc:water (3×20 mL) and the combined filtrate were brought to pH 10 with ammonium hydroxide (−82 mL). The resulting mixture was stirred in ice and the crude product was collected by filtration and washed with water (4 mL). The crude product was further purified by silica gel chromatography (5:94:1 MeOH:DCM:NH4OH) to afford Intermediate 40 as a white solid (1.25 g, 67% yield).

Provenance & Evidence