1,1'-Carbonyldiimidazole → N,N-Dimethyl-4-[2-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzoyl-oxyacetamide

HRID 1417079Notes

Reaction equation

HRID 1417079 reaction equation
[CH3:1][N:2]([CH3:33])[C:3](=[O:32])[CH2:4][O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[C:16](C3C=CC(F)=CC=3)[N:17]=2)=[CH:9][CH:8]=1.[F:34][C:35]1[CH:40]=[CH:39][C:38](C2N=C(C3C=CC(C(O)=O)=CC=3)NC=2C2C=CN=CC=2)=[CH:37][CH:36]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.CN(C)C(=O)CO>CN(C=O)C.O>[CH3:1][N:2]([CH3:33])[C:3](=[O:32])[CH2:4][O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:38]3[CH:39]=[CH:40][C:35]([F:34])=[CH:36][CH:37]=3)[NH:17][CH:16]=[C:15]([C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)[NH:14]2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 110574684-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzoic acidHCID 128746822-Hydroxy-N,N-dimethylacetamideHCID 70237481N,N-Dimethyl-4-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]-benzoyl-oxyacetamide

Product 1

HCID 69303855N,N-Dimethyl-4-[2-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzoyl-oxyacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N,N-Dimethyl-4-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]-benzoyl-oxyacetamide--To a solution of 4-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzoic acid (0.15 g, 0.42 mmol) [See Ex. 9 above] in DMF(10 ml) was added carbonyldiimidazole (0.34 g, 2.1 mmol). After stirring for 18 h at rt, N,N-dimethylglycolamide (0.43 g, 4.2 mmol) was added and stirring was continued for an additional 3 h at rt. The reaction mixture was poured into H2O, extracted with EtOAc and evaporated. The residue was purified by flash chromatography eluting with a solvent gradient of 2% MeOH/CHCl3 to afford the title compound: CIMS (NH3, m/z): 445 (M+ +H).

Workup

  1. stirringstirring
  2. waitwas continued for an additional 3 h at rt
  3. extractionextracted with EtOAc
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. washeluting with a solvent gradient of 2% MeOH/CHCl3

Sources & evidence

ORD record
ord-c8593becb19e459a9d3431d0bcba83a1
Source dataset
uspto-grants-1999_06
Patent number
US05916891

Reaction notes

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