Nitrogen → HCID 20086705, compound

HRID 1078045Notes

Reaction equation

HRID 1078045 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([CH2:48][CH2:49][CH3:50])[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28]([C:29]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:7]=1[C:8]([OH:10])=[O:9])[CH3:2].Br[CH:52]([CH3:62])[C:53]([NH:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)=[O:54].C([O-])([O-])=O.[K+].[K+].N#N>CN(C=O)C>[CH2:1]([C:3]1[N:4]=[C:5]([CH2:48][CH2:49][CH3:50])[N:6]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28]([C:29]([C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:27]=[N:26][N:25]=3)=[CH:16][CH:17]=2)[C:7]=1[C:8]([O:10][CH2:62][CH2:52][C:53]([NH:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)=[O:54])=[O:9])[CH3:2]

Participants

6

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 991132-Bromo-N-phenylpropanamideHCID 15228887HCID 15228887, compound

Product 1

HCID 20086705HCID 20086705, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution/suspension of 0.66 g 4-ethyl-2-propyl-1-[[2'-(N-triphenylmethyl(tetrazol-5-yl))biphenyl-4-yl]methyl]imidazole-5-carboxylic acid, 0.23 g 2-bromo-N-phenylpropionamide, and 0.15 g K2CO3 in 7 mL of DMF was added 0.17 g of KI. The reaction was stirred 10 minutes at room temperature, then heated in a N2 atmosphere at 70° C. overnight. The reaction was partitioned between H2O and EtOAc, and the organic extract washed with brine and dried with MgSO4. Filtration, concentration, and flash chromatography with a 10-60% EtOAc/hexanes gradient provided 0.35 g of pure product.

Workup

  1. additionwas added 0.17 g of KI
  2. customThe reaction was partitioned between H2O and EtOAc
  3. extractionthe organic extract
  4. washwashed with brine
  5. dry with materialdried with MgSO4
  6. filtrationFiltration, concentration, and flash chromatography with a 10-60% EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-9ec3fffdd39243338490a7be1392f518
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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