Acetic Acid → HCID 58465715, compound

Participants

Reaction Conditions

Reaction Steps

To a vial containing crude ethyl 2-(1-methyl-1H-pyrrole-2-carbonyl)-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine-8-carboxylate from Step 1 above was added potassium hydroxide (0.112 g, 2 mmol), hydroxylamine hydrochloride (0.0417 g, 0.6 mmol), and methanol (2 mL). The mixture was shaken at 80° C. for 2 h then cooled to room temperature. Acetic acid (0.114 mL, 2 mmol) was added to quench the excess base. The solvent was then completely evaporated and to the residue was added DMSO (1.2 mL). After filtration, the solution was purified via Gilson prep-HPLC to give N-hydroxy-2-(1-methyl-1H-pyrrole-2-carbonyl)-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine-8-carboxamide (0.004 g, 6.5%). LC-MS (FA): ES+303; 1H NMR (CD3CN, 400 MHz) δ6.81 (s, 1 H), 6.40 (s, 1 H), 5.95 (m, 1 H), 5.81 (m, 1 H), 5.70 (m, 1 H), 4.27 (s, 2 H), 3.83 (m, 2 H), 3.51 (m, 2 H), 3.21 (s, 3 H), 1.85 (m, 2 H).

Provenance & Evidence