Methyl N-(triethylammoniosulfonyl)carbamate → HCID 58329498, compound

Participants

Reaction Conditions

Reaction Steps

N′-acetyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carbohydrazide was dissolved in 0.8 mL of mixture of N,N-dimethylformamide/tetrahydrofuran (9:1). To the solution was added Burgess Reagent (120 mg, 500 μmol). The reaction was heated at 120° C. for 24 hours. The solvent was removed under reduced pressure. residues were purified The crude product was purified using reverse phase chromatography (HPLC, C-18) using trifluoroacetic acid as a modifier to give 2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-5-methyl-1,3,4-oxadiazole (56) as a yellow solid. Mp=70-72° C.; 400 MHz 1HNMR (DMSO-d6) δ 8.01 (s, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.15 (t, J=7.6 Hz, 1H), 7.02 (d, J=7.2 Hz, 1H), 4.27 (t, J=5.6 Hz, 2H), 2.97 (t, J=6.0 Hz, 2H), 2.56 (s, 3H), 2.18-2.14 (m, 2H); LCMS [M+H]: 240.

Provenance & Evidence