1,1'-Carbonyldiimidazole → HCID 178484390, compound

HRID 710497Notes

Reaction equation

HRID 710497 reaction equation
[C:1]([N:8]1C=CN=C1)([N:3]1[CH:7]=CN=[CH:4]1)=O.ON[C:15]([C:17]1[CH:25]=[CH:24][C:20]2[N:21]=[CH:22][NH:23][C:19]=2[CH:18]=1)=[NH:16].C([O-])(O)=[O:27].[Na+]>CN(C=O)C.O>[CH3:4][N:3]([CH:1]=[N:8][NH:16][C:15]([C:17]1[CH:25]=[CH:24][C:20]2[NH:21][CH:22]=[N:23][C:19]=2[CH:18]=1)=[O:27])[CH3:7]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 178513234HCID 178513234, compound

Product 1

HCID 178484390HCID 178484390, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The respective carboxylic acid (1 eq.) was dissolved in DMF (5 ml), treated with carbonyldiimidazole (1 eq.) and stirred at room temperature for 1 h. N-Hydroxy-benzimidazol-5-carboxamidine (1 eq.) was added and the mixture was heated to 110° C. over night. After cooling to room temperature, the mixture was diluted with water until a precipitate was formed, basified by means of sat. NaHCO3-solution and extracted with EtOAc (3×25 ml). The combined organic layers were dried over Na2SO4, evaporated and the residue was purified by flash chromatography on silica using a CHCl3/MeOH gradient.

Workup

  1. temperaturethe mixture was heated to 110° C. over night
  2. temperatureAfter cooling to room temperature
  3. customwas formed
  4. extractionextracted with EtOAc (3×25 ml)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customevaporated
  7. customthe residue was purified by flash chromatography on silica using a CHCl3/MeOH gradient

Sources & evidence

ORD record
ord-015c359f24674ca8b002bd2cc1896715
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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