Acetohydrazide → HCID 68699551, compound

Participants

Reaction Steps

To a solution of 1-(3-chloro-4-cyano-2-methylphenyl)proline (0.600 g, 2.268 mmol), N,N-diisopropylethylamine (0.876 g, 6.816 mmol) and TBTU (1.092 g, 3.402 mmol) in DMF add a solution of acetic hydrazide (0.252 g, 3.402 mmols) in DMF. Leave to stand for 30 mins then partition between ethyl acetate and 2N aqueous hydrochloric acid. Extract the organic with 10% (w/w) aqueous sodium carbonate solution, then brine. Dry over magnesium sulphate, filter and concentrate under reduced pressure gives the title compound. (0.598 g, 82%) mass spectrum (m/e): 321 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.77 (s, 1H) 7.60 (bs, 1H) 7.40 (d, 1H), 6.88 (d, 1H), 4.35 (t, 1H), 3.86 (m, 1H), 3.04 (m, 1H), 2.51 (m, 1H), 2.44 (s, 3H), 2.00 (s, 3H), 2.22-1.85 (m. 3H).

Provenance & Evidence