N,N'-Dimethylethylenediamine → HCID 59618741, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-[(4-tert-butylphenyl)sulfonyl]-8-iodo-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (intermediate 52, 109 mg, 0.19 mmol) in DMF (4 mL) was added 1,2,3-triazole (39 mg, 0.56 mmol), CuI (71 mg, 0.37 mmol), N,N′-dimethylethylenediamine (0.08 mL, 0.74 mmol), and KOtBu (1.0M/THF, 1.5 mL, 1.5 mmol). The resulting solution was heated to 180° C. in a microwave reactor for 1 h. The solution was diluted with EtOAc and washed with sat aqueous NaHCO3. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated, and the oily residue was purified by silica gel chromatography to give the title compound. 1H NMR (500 MHz, (CD3)2CO): δ 8.60 (s, 1H), 8.20 (s, 1H), 8.00 (m, 2H), 7.78 (d, 1H), 7.50 (d, 1H), 7.22 (d, 2H), 7.18 (d, 1H), 7.05 (d, 2H), 4.90 (br s, 2H), 1.20 (s, 9H). LCMS: m/e 529.0 (M+H)+.

Provenance & Evidence