Ethyl chloroformate → 3,5-bis(benzyloxy)-N-[5-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-2-yl]benzamide

HRID 552608Notes

Reaction equation

HRID 552608 reaction equation
Cl[C:2](OCC)=[O:3].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:31]=[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([NH:29][OH:30])=[NH:28])=[CH:23][N:22]=1)=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>N1C=CC=CC=1>[CH2:35]([O:34][C:32]1[CH:31]=[C:17]([CH:16]=[C:15]([O:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:33]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[NH:28][C:2](=[O:3])[O:30][N:29]=2)=[CH:23][N:22]=1)=[O:19])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 178513344N-[5-[(E)-N'-hydroxycarbamimidoyl]-2-pyridinyl]-3,5-bis(phenylmethoxy)benzamide

Product 1

HCID 1356089023,5-bis(benzyloxy)-N-[5-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-2-yl]benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl chloroformate (32 μL, 0.33 mmol) was added to a solution of 3,5-bis(benzyloxy)-N-{5-[(hydroxyamino)(imino)methyl]pyridin-2-yl}benzamide (140 mg, 0.30 mmol) in pyridine (5 mL). This solution was heated at reflux overnight. The mixture was cooled and concentrated under reduced pressure. DCM and methanol were used to dissolve the remaining material and the solution was washed with water. The organic solution was concentrated under reduced pressure and the residue was purified on silica by MPLC (eluting firstly with 5% methanol/DCM then 10% methanol/DCM). The title compound was obtained as a colourless solid (103 mg, 70%). 1H NMR δ (d6-DMSO): 5.19 (4H, s); 6.87 (1H, s); 7.28-7.46 (12H, m); 8.21 (1H, dd); 8.38 (1H, d); 8.79 (1H, s); 11.14 (1H, br s); m/z (LCMS; ESI+) 495 (MH+).

Workup

  1. temperatureThis solution was heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionto dissolve the remaining material
  6. washthe solution was washed with water
  7. concentrationThe organic solution was concentrated under reduced pressure
  8. customthe residue was purified on silica by MPLC (
  9. washeluting firstly with 5% methanol/DCM

Sources & evidence

ORD record
ord-e395d8cd06c44bf5a213549607587538
Source dataset
uspto-grants-2011_05
Patent number
US07951830B2

Reaction notes

Loading…