Sodium hydride → HCID 69021140, compound

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Reaction Steps

Sodium hydride (0.0016 mol, 60% in oil) was added portionwise at 10° C. to a mixture of 5-(3-chlorophenyl)-7-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-1,5-dihydro-4,1-benzothiazepin-2(3H)-one (0.0013 mol), obtained in Example B2, in DMF (7 ml). The mixture was stirred for 30 minutes. (Bromomethyl)-cyclopropane (0.0016 mol) was added. The mixture was brought to room temperature, then stirred for 3 hours, poured out into ice water and stirred again for 30 minutes. The precipitate was filtered and taken up in DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (0.6 g) was purified by column chromatography over kromasil (eluent: CH2Cl2/CH3OH/NEt3 97/3/0.1; 10 μm). The pure fractions were collected and the solvent was evaporated. The residue (0.16 g) was crystallized from acetonitrile. The precipitate was filtered off and dried, yielding 0.13 g (17%) of 5-(3-chlorophenyl)-7-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-1-(cyclopropylmethyl)-1,5-dihydro-4,1-benzothiazepin-2(3H)-one, mp. 245° C.

Provenance & Evidence