Diisopropylethylamine → 1-ethyl-3-[7-[(E)-methoxyiminomethyl]-5-phenylmethoxy-1,3-benzothiazol-2-yl]urea

Participants

Reaction Conditions

Reaction Steps

1-(5-(Benzyloxy)-7-formylbenzo[d]thiazol-2-yl)-3-ethylurea (425 mg, 1.20 mmol), methoxylamine hydrochloride (105.2 mg, 1.26 mmol) and N,N′-diisopropylethylamine (0.77 g, 1.05 ml) were stirred in DMF degassed with N2. The reaction was purged with N2, sealed and heated to 105° C. for 18 h. LCMS after indicated complete consumption of starting material. The solvents were removed under reduced pressure and the resulting residue absorbed onto silica and purified by flash column chromatography eluting with 0 to 100% EtOAc in petroleum-ether to afford the product as a white solid 325 mg (70%) which was used directly in the next step.

Provenance & Evidence