Ethyl 4-bromobutyrate → Ethyl 4-[9-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]butanoate

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Reaction Steps

A solution of 9-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride (Example 31) (179 mg, 0.424 mmol), ethyl 4-bromobutanoate (0.061 ml, 0.424 mmol) and DIPEA (0.074 ml, 0.424 mmol) in Acetonitrile (5 ml) was heated at 70° C. overnight. Additional ethyl 4-bromobutanoate (0.061 ml, 0.424 mmol) and DIPEA (0.074 ml, 0.424 mmol) were added and the reaction heated for a further 5 hrs. The cooled reaction was diluted with EtOAc/water, separated, the organics dried over magnesium sulphate and evaporated. Purified by flash chromatography eluting with EtOAc/iso-hexane 1:2 to give the title compound (135 mg) as a colourless oil. MS (ES): C26H3035ClN3O5 requires 499; found 500 [M+H]+.

Provenance & Evidence