Aziridine → HCID 11290689, compound
Reaction equation
Cl[C:2]1[C:3]([N+:20]([O-:22])=[O:21])=[CH:4][C:5]([N+:17]([O-:19])=[O:18])=[C:6]([CH:16]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:8].[NH:23]1[CH2:25][CH2:24]1>C(Cl)Cl>[N:23]1([C:2]2[C:3]([N+:20]([O-:22])=[O:21])=[CH:4][C:5]([N+:17]([O-:19])=[O:18])=[C:6]([CH:16]=2)[C:7]([NH:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:8])[CH2:25][CH2:24]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of the above amide (315 mg, 0.95 mmol) in CH2Cl2 (35 mL) was treated with aziridine (197 μL, 3.81 mmol) at room temperature for 8 h. The mixture was partitioned between more CH2Cl2 and water, and the organic layer was dried and concentrated under reduced pressure. The residue was dissolved in EtOAc and filtered through a short column of silica gel to give 8 (269 mg, 84%): mp (CH2Cl2/iPr2O) 137° C.; 1H NMR [(CD3)2SO] δ8.86 (t, J=5.6 Hz, 1 H, NH), 8.66 (s, 1H, H-3), 7.40 (s, 1H, H-6), 3.63 (s, 3H, Me), 3.51-3.43 (m, 2H, NHCH2), 2.61 (t, J=6 8 Hz, 2H, CH2CO), 2 48 (s, 4H, aziridine-H). Anal. Calcd for C13H14N4O7: C, 46.15;H, 4 17; N, 16 57. Found: C, 45.89,H, 3.89; N, 16.45%.