Aziridine → HCID 11279428, compound

HRID 1058504Notes

Reaction equation

HRID 1058504 reaction equation
Cl[C:2]1[C:3]([N+:21]([O-:23])=[O:22])=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[C:7]([NH:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)=[O:8].[NH:24]1[CH2:26][CH2:25]1>C1COCC1>[N:24]1([C:2]2[C:3]([N+:21]([O-:23])=[O:22])=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=2)[C:7]([NH:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[O:8])[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 9033Aziridine2×HCID 11279228HCID 11279228, compound

Product 1

HCID 11279428HCID 11279428, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of the above benzamide (150 mg, 0.44 mmol) in THF (40 mL) was treated with aziridine (91 μL, 1.76 mmol) at room temperature for 4 h, then additional aziridine (91 μL) was added. After a further 4 h, the mixture was concentrated under reduced pressure below 25° C., and the residue was partitioned between EtOAc and saturated NaCl. Evaporation of the organic layer gave a product that was triturated with EtOAc then recrystallized from MeCN/EtOAc/petroleum ether to give 7 (56 mg, 37%): mp >250° C.; 1H NMR [(CD3)2SO] δ8.91 (t, J=5.6 Hz, 1H, NH), 8.66 (s, 1H, H-3), 7.67 (s, 1H, imidazole-H), 7.29 (s, 1H, H-6), 7.24 & 6.93 (2xs, 2H, imidazole-H), 4 16 (t, J=5.9 Hz, 2H, NHCH2CH2), 3 62-3.51 (m, 2H, NHCH2), 2.49 (s, 4H, aziridine-H). Anal. Calcd. for C14H14N6O5: C, 48.55;H, 4.07; N, 24.27. Found: C, 48.69;H, 4.00; N, 24.10%.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure below 25° C.
  2. customthe residue was partitioned between EtOAc and saturated NaCl
  3. customEvaporation of the organic layer
  4. customgave a product that
  5. customwas triturated with EtOAc
  6. customthen recrystallized from MeCN/EtOAc/petroleum ether

Sources & evidence

ORD record
ord-248c82330f7a44299127d69de4d1f460
Source dataset
uspto-grants-2003_02
Patent number
US06517836B1

Reaction notes

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