Triethylamine → HCID 9865119, compound

HRID 248878Notes

Reaction equation

HRID 248878 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[C:13]([N:16]([OH:37])[CH:17]([C:19]1[C:20]([Cl:36])=[C:21]([NH:25][C:26]2[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=2[C:28]([NH:30][NH2:31])=[O:29])[CH:22]=[CH:23][CH:24]=1)[CH3:18])(=[O:15])[CH3:14].C(N(CC)CC)C>C1COCC1.CCOC(C)=O>[O:7]=[C:6]1[O:29][C:28]([C:27]2[CH:32]=[CH:33][CH:34]=[CH:35][C:26]=2[NH:25][C:21]2[C:20]([Cl:36])=[C:19]([CH:17]([N:16]([OH:37])[C:13](=[O:15])[CH3:14])[CH3:18])[CH:24]=[CH:23][CH:22]=2)=[N:30][NH:31]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 86746849HCID 86746849, compound

Product 1

HCID 9865119HCID 9865119, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

CDI (0.63 g, 3.9 mmoles) is added to a solution of 2-[[3-[1-(acetylhydroxyamino)ethyl]-2-chlorophenyl]amino]benzoic acid hydrazide (1.4 g, 3.9 mmoles) and triethylamine (0.81 g, 8.1 mmoles,) in 25 mL of THF at 0° C. under an argon atmosphere. The reaction mixture is stirred at 0° C. for 30 minutes under Ar, and then at room temperature overnight. The reaction mixture is partitioned between 50 mL of 1.0 N HCl and 50 mL of EtOAc. The organic layer is washed with 100 mL of 1.0 N HCl, 100 mL of water, and 100 mL of brine. Drying over MgSO4 and evaporation of the solvent gives an off white solid. Flash chromatography over silica gel in EtOAc gives 0.27 g (18%) of N-[1-[3-[[2-(4,5-dihydro-5-oxo-1,3,4-oxadiazol-2-yl) phenyl]amino]-2-chlorophenyl]ethyl] -N-hydroxyacetamide; m.p. 186°-189° C. dec.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe reaction mixture is partitioned between 50 mL of 1.0 N HCl and 50 mL of EtOAc
  4. washThe organic layer is washed with 100 mL of 1.0 N HCl, 100 mL of water, and 100 mL of brine
  5. dry with materialDrying over MgSO4 and evaporation of the solvent
  6. customgives an off white solid

Sources & evidence

ORD record
ord-444c42a9ba6840eeadbec0d653138ba3
Source dataset
uspto-grants-1993_05
Patent number
US05212189

Reaction notes

Loading…