Triethylamine → HCID 54176966, compound

HRID 382377Notes

Reaction equation

HRID 382377 reaction equation
P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.C(N(CC)CC)C.[CH:25]1([CH2:30][C:31]([OH:33])=O)[CH2:29][CH2:28][CH2:27][CH2:26]1.[NH2:34][C:35]1[N:36]=[CH:37][N:38]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:39]=1[C:40]([NH2:42])=[O:41]>CN(C)C=O>[CH2:43]([N:38]1[C:39]([C:40]([NH2:42])=[O:41])=[C:35]([NH:34][C:31](=[O:33])[CH2:30][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[N:36]=[CH:37]1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 71606Cyclopentylacetic acidHCID 75654Diphenyl chlorophosphateHCID 140006201-benzyl-4-amino-1H-imidazole-5-carboxamide

Product 1

HCID 54176966HCID 54176966, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4.14 ml (20 mmol) of diphenyl chlorophosphate and 2.8 ml (20 mmol) of triethylamine were added to a solution of 2.5 ml (20 mmol) of cyclopentylacetic acid in 20 ml of N,N-dimethylformamide while cooling with ice. The solution was stirred for one hour while cooling with ice. A solution of 2.2 g (10 mmol) of 4-amino-1-benzyl-5-imidazolecarboxamide prepared in Reference Example 2 in 200 ml of N,N-dimethylformamide was added to the reaction solution, followed by stirring overnight. After concentration under vacuum, 5% aqueous solution of sodium hydrogencarbonate was added to obtain a solid precipitate. The precipitate was collected by filtration using a funnel equipped with a glass filter, washed with 5% aqueous solution of sodium hydrogencarbonate and distilled water, and dried under vacuum to obtain a crude product. This crude product was purified by suspension in hot methanol to obtain 1.77 g of 1-benzyl-4-cyclopentylacetylamino-5-imidazolecarboxamide (yield 54%).

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice
  3. additionwas added to the reaction solution
  4. stirringby stirring overnight
  5. concentrationAfter concentration under vacuum, 5% aqueous solution of sodium hydrogencarbonate
  6. additionwas added
  7. customto obtain a solid precipitate
  8. filtrationThe precipitate was collected by filtration
  9. customequipped with a glass
  10. filtrationfilter
  11. washwashed with 5% aqueous solution of sodium hydrogencarbonate
  12. distillationdistilled water
  13. customdried under vacuum
  14. customto obtain a crude product
  15. customThis crude product was purified by suspension in hot methanol

Sources & evidence

ORD record
ord-ffed83568d2543c093b143dd473ddc99
Source dataset
uspto-grants-2001_10
Patent number
US06310070B1

Reaction notes

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