1,1'-Carbonyldiimidazole → HCID 178432062, compound

HRID 1384296Notes

Reaction equation

HRID 1384296 reaction equation
[N+:1]([O-:20])([O:3][CH2:4][CH:5]1[C:11]2=[N:12][C:13]([CH3:19])=[C:14](C(O)=O)[CH:15]=[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:2].C1N=CN([C:26]([N:28]2[CH:32]=[N:31]C=C2)=[O:27])C=1.[NH2:33]C(N)=N.C1COCC1>C1COCC1>[N+:1]([O-:20])([O:3][CH2:4][CH:5]1[C:11]2=[N:12][C:13]([CH3:19])=[C:14]([NH:33][C:32]([N:28]=[C:26]=[O:27])=[NH:31])[CH:15]=[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 21186707HCID 21186707, compoundHCID 86757137HCID 86757137, compound

Product 1

HCID 178432062HCID 178432062, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In an atmosphere of argon, 28% sodium methoxide methanol solution (1.58 ml, 8.19 mmol) was dissolved in anhydrous methanol (8.0 ml) at room temperature, and the solution was mixed with guanidine hydrochloride (782.4 mg, 8.19 mmol) at 0° C. and stirred at the same temperature for 1 hour. The thus precipitated sodium chloride was removed by filtration using a glass filter and the resulting filtrate was evaporated under reduced pressure to obtain free guanidine. In an atmosphere of argon, (3-carboxy-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl)methyl nitrate (310.0 mg, 1.17 mmol) were suspended in anhydrous THF (8.0 ml), mixed with CDI (291.2 mg, 1.76 mmol) at room temperature and then stirred at 50° C. for 1 hour. The reaction solution was added dropwise to the previously obtained guanidine THF suspension (5.0 ml), and the mixture was stirred at room temperature for 2.5 hours. The solvent was evaporated under reduced pressure, and the resulting residue was mixed with water and extracted with ethyl acetate. The thus obtained organic layer was washed with saturated sodium bicarbonate aqueous solution, water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=20:1) and then the thus obtained crystals were washed with ether to obtain the title compound (192.1 mg, 51.1%) as white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 2.5 hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe resulting residue was mixed with water
  4. extractionextracted with ethyl acetate
  5. washThe thus obtained organic layer was washed with saturated sodium bicarbonate aqueous solution, water and saturated brine in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=20:1)
  9. washthe thus obtained crystals were washed with ether

Sources & evidence

ORD record
ord-1c392e07cd004319ba2201a9642ab20f
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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