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

HRID 2257384
Notes
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Reaction equation

HRID 2257384 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 69303855
N,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 3h 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. extractionextracted with EtOAc
  3. customevaporated
  4. customThe residue was purified by flash chromatography
  5. washeluting with a solvent gradient of 2% MeOH/CHCl3

Sources & evidence

ORD record
ord-d059349f84544cc296df2df439988458
Source dataset
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05656644

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes