1,1'-Carbonyldiimidazole → HCID 136400729, compound

HRID 639680Notes

Reaction equation

HRID 639680 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:13]([N:20]1[C:28]2[CH:27]=[C:26]([C:29]([OH:31])=O)[N:25]=[C:24]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:23]=2[NH:22][C:21]1=[O:40])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH:41][NH:42][C:43](=[NH:45])[CH3:44].[Al]>CN(C=O)C>[OH:41][N:42]=[C:43]([NH:45][C:29]([C:26]1[N:25]=[C:24]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:23]2[NH:22][C:21](=[O:40])[N:20]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:28]=2[CH:27]=1)=[O:31])[CH3:44]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 5359268AluminumHCID 67453942HCID 67453942, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 136400729HCID 136400729, compoundYield 132.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

CDI (52 mg, 0.32 mmol) was added to a solution of 1-benzyl-4-benzylamino-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid (80 mg, 0.21 mmol) and Hunnigs base (83 μl, 0.64 mmol) in dry DMF in a ReactiVial. The vial was sealed and the mixture was stirred at room temperature for 15 minutes. N-Hydroxyacetamidine (24 mg, 0.32 mmol) was added and mixture heated to 60° C. in an aluminium block. The mixture was left to stir at this temperature for 3 hrs then allowed to cool and concentrated in vacuo. The residue was partitioned between EtOAc (15 ml) and water (5 ml). The layers were separated and the organic phase was washed with brine (5 ml). At this point, some solid precipitated and was left inside the separating funnel. This was washed into the organic phase with MeOH then the organics were dried (MgSO4) and evaporated to yield the final product as a white solid (120 mg, 130%). Material probably contains inorganic material, but taken on with a view to purification after next step.

Workup

  1. customThe vial was sealed
  2. waitThe mixture was left
  3. stirringto stir at this temperature for 3 hrs
  4. temperatureto cool
  5. concentrationconcentrated in vacuo
  6. customThe residue was partitioned between EtOAc (15 ml) and water (5 ml)
  7. customThe layers were separated
  8. washthe organic phase was washed with brine (5 ml)
  9. customAt this point, some solid precipitated
  10. waitwas left inside the separating funnel
  11. washThis was washed into the organic phase with MeOH
  12. dry with materialthe organics were dried (MgSO4)
  13. customevaporated

Sources & evidence

ORD record
ord-37539855743f4dd4a606a6475c870c63
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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