Bis-(1H-imidazol-2-YL)-methanone → HCID 178446214, compound

HRID 2262690Notes

Reaction equation

HRID 2262690 reaction equation
[Cl:1][C:2]1[C:3]([CH3:15])=[C:4]([NH:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:5]([NH2:8])=[N:6][CH:7]=1.[C:16](C1NC=CN=1)(C1NC=CN=1)=[O:17]>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:15])=[C:4]2[N:9]([CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:16]([OH:17])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 59594569HCID 59594569, compound

Product 1

HCID 178446214HCID 178446214, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room-temperature solution of 5-chloro-4-methyl-N3-(pentan-3-yl)pyridine-2,3-diamine (49 mg, 0.22 mmol, 1.0 equiv) in THF (10 mL) was added carbonyl diimidazole (211 mg, 1.3 mmol, 6.0 equiv) as a solid in one portion. The resulting mixture was heated to reflux overnight. After the reaction was cooled to room temperature, the excess carbonyl diimidazole was quenched by the careful addition of water. The mixture was then diluted with EtOAc, washed with saturated aq. NaHCO3, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel preparative thin layer chromatography (0.5% Et3N, 5% MeOH, 94.5% CH2Cl2) provided the title compound as a solid (10 mg, 22%). m/z=252.3 [M−H]−

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight
  3. customthe excess carbonyl diimidazole was quenched by the careful addition of water
  4. additionThe mixture was then diluted with EtOAc
  5. washwashed with saturated aq. NaHCO3
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel preparative thin layer chromatography (0.5% Et3N, 5% MeOH, 94.5% CH2Cl2)

Sources & evidence

ORD record
ord-2b1eb307fda54a22920f2d0944b40b4b
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

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