HCID 57654653, compound → HCID 57654650, compound

Participants

Reaction Conditions

Reaction Steps

8-Chloro-4,5-dihydro-2H-1,2,7-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester (320 mg; 1.15 mmol) in DMF (4 ml) is treated at 5° C. with LiOtBu (1N in THF; 1.16 ml; 1.16 m mol) for 5 minutes. 3-tert-butoxycarbonylamino-3-methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester (0.32 mg; 1.15 mmol) is added and the mixture heated to 90° C. for 30 minutes. The reaction mixture is poured on brine and extracted with TBME three times. The combined organic phases are dried over Na2SO4, evaporated to dryness and yield the title compound as colorless crystals. 1H-NMR (400 MHz; DMSO-d6: 8.38 (s, 1H); 7.65 (s, 1H); 7.42 (bs, 1H); 5.00 (bs, 2H); 4.34 (q, 2H); 4.03 (bd, 2H); 3.79 (m, 2H); 3.00 (m, 2H); 2.95 (m, 2H); 1.40 (s, 18H); 1.36 (t, 3H). MS (m/z) ES+: 562 (MH+).

Provenance & Evidence