1,1'-Carbonyldiimidazole → HCID 178446208, compound

HRID 1672358Notes

Reaction equation

HRID 1672358 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[N:8]=[C:7]([NH:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:6]([N+:15]([O-])=O)=[CH:5][CH:4]=1.C1N=CN([C:24](N2C=NC=C2)=[O:25])C=1>CO.[Pd]>[CH3:1][N:2]([CH3:18])[C:3]1[N:8]=[C:7]2[N:9]([CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:24]([OH:25])=[N:15][C:6]2=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57900559HCID 57900559, compound

Product 1

HCID 178446208HCID 178446208, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N6,N6-dimethyl-3-nitro-N2-(pentan-3-yl)pyridine-2,6-diamine (100 mg, 0.40 mmol) in MeOH (4 mL) was added a catalytic amount of Pd/C. The mixture was purged with hydrogen from a balloon fitted with a needle for 1 h. The resulting mixture was filtered through a pad of celite and concentrated in vacuo. The solid was then dissolved in THF (2 mL) and CDI (100 mg, 1.17 mmol) was added as a solid. After heating for 3 h, the reaction was cooled to room temperature. The excess CDI was quenched by the careful addition of water. The mixture was diluted with EtOAc and washed three times with water and once with brine. The solution was then dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (5%-25% EtOAc/hexanes) provided the title compound as a white solid (57 mg, 57%). m/z=249.2 (M+H)+

Workup

  1. customThe mixture was purged with hydrogen from a balloon
  2. customfitted with a needle for 1 h
  3. filtrationThe resulting mixture was filtered through a pad of celite
  4. concentrationconcentrated in vacuo
  5. dissolutionThe solid was then dissolved in THF (2 mL)
  6. temperatureAfter heating for 3 h
  7. customThe excess CDI was quenched by the careful addition of water
  8. additionThe mixture was diluted with EtOAc
  9. washwashed three times with water
  10. dry with materialThe solution was then dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e56913d25564b25b952fa16172e646a
Source dataset
uspto-grants-2011_08
Patent number
US07998976B2

Reaction notes

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