1,1'-Carbonyldiimidazole → HCID 20085575, compound

HRID 1608819Notes

Reaction equation

HRID 1608819 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:13][C:14]1[C:15]([C:20]([OH:22])=O)=[N:16][CH:17]=[CH:18][N:19]=1.[NH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1>CN(C)C=O.C(OCC)C>[NH2:13][C:14]1[C:15]([C:20]([NH:23][CH2:24][CH2:25][CH2:26][N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)=[O:22])=[N:16][CH:17]=[CH:18][N:19]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 726563-Amino-2-pyrazinecarboxylic acidHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 20085575HCID 20085575, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of 19.09 g (0.0776 mol) of 1,1'-carbonyldiimidazole in approximately 200 ml of dimethylformamide was added slowly to a cold (0° C.) solution of 15.78 g (0.1135 mol) of 3-aminopyrazine-2-carboxylic acid in 150 ml of dimethylformamide. The resulting solution was gradually warmed to 25° C. and stirred for about two hours. A solution of 14.75 g (0.118 mol) of N-(3-aminopropyl)imidazole in approximately 40 ml of dimethylformamide was added and the resulting solution was allowed to react for four hours. After four hours, the reaction solution was reduced to dryness under reduced pressure. The resultant semi-solid was suspended in diethyl ether and the portion which did not dissolve was recovered by filtration. The recovered solid was then suspended in diethyl ether containing a small amount of ethyl acetate and the resulting mixture was stirred for about 48 hours. After stirring for 48 hours, the undissolved solid was isolated by filtration. This solid was purified by filtration through silica gel using 4% methanol in dichloromethane. The resultant purified material was recrystallized from a 1:4 dichloromethane/diethyl ether solution to provide 24.4 g of the desired subtitled intermediate (m.p. 118°-120° C.).

Workup

  1. customto react for four hours
  2. waitAfter four hours
  3. dissolutionthe portion which did not dissolve
  4. filtrationwas recovered by filtration
  5. stirringthe resulting mixture was stirred for about 48 hours
  6. stirringAfter stirring for 48 hours
  7. customthe undissolved solid was isolated by filtration
  8. filtrationThis solid was purified by filtration through silica gel using 4% methanol in dichloromethane
  9. customThe resultant purified material
  10. customwas recrystallized from a 1:4 dichloromethane/diethyl ether solution

Sources & evidence

ORD record
ord-11b363759dd647d5891abd1b0abcdb53
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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