Aziridine → HCID 11290689, compound

HRID 1058506Notes

Reaction equation

HRID 1058506 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]1

Participants

4

Reactant 2

HCID 9033AziridineHCID 11404780HCID 11404780, compound

Product 1

HCID 11290689HCID 11290689, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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%.

Workup

  1. customThe mixture was partitioned between more CH2Cl2 and water
  2. customthe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. filtrationfiltered through a short column of silica gel

Sources & evidence

ORD record
ord-6a6ff077b85a4b75840ba69f52bb6406
Source dataset
uspto-grants-2003_02
Patent number
US06517836B1

Reaction notes

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