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

HRID 479760Notes

Reaction equation

HRID 479760 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:40][N:41]([CH3:46])[C:42](=[O:45])[CH2:43]O.O>CN(C=O)C>[CH3:40][N:41]([CH3:46])[C:42](=[O:45])[CH2:43][O:24][C:23](=[O:25])[C:22]1[CH:26]=[CH:27][C:19]([C:10]2[NH:11][C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:9]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 110574684-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzoic acidHCID 128746822-Hydroxy-N,N-dimethylacetamide

Product 1

HCID 70237481N,N-Dimethyl-4-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]-benzoyl-oxyacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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-bf35fa2740e6406f988f7eccd752034b
Source dataset
uspto-grants-2003_11
Patent number
US06645989B2

Reaction notes

Loading…