Dimethylformamide → HCID 178433542, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 1,2-dimethyl-1H-imidazole-4-thiol (450 mg, 1.8 mmol, prepared as described in J. Heterocyclic Chem. 1998, 35, 141) in anhydrous DMF (3 mL). Add sodium hydride (55 mg, 1.4 mmol, 60% dispersion in mineral oil) portionwise over 2 min at room temperature under a nitrogen atmosphere. Stir the yellow solution for 5 min, then add a solution of 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (300 mg, 0.9 mmol) in anhydrous DMF (3 mL) at room temperature over 2 min. Heat the mixture at 45° C. for 16 h under a nitrogen atmosphere. Cool the mixture to room temperature and quench with 10% aqueous sodium chloride (10 mL). Extract the mixture with EtOAc (2×30 mL). Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel eluting with hexane/EtOAc (7:3 to 1:1 gradient) to obtain 3-tert-butoxycarbonyl-7-chloro-6-(1,2-dimethyl-1H-imidazol-4-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (160 mg, 42%). MS (ES+) m/z: 422.0 (M+H)+.

Provenance & Evidence