Dimethylformamide → HCID 178505339, compound

HRID 1284600Notes

Reaction equation

HRID 1284600 reaction equation
CN(C)C=O.[CH3:6][S:7]([OH:10])(=[O:9])=[O:8].[NH:11]([CH2:15][C:16]1[O:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=1)[C:12]([NH2:14])=[NH:13].[CH3:24][S:25]([O:28][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:39](=[NH:41])[NH2:40])[CH:35]=2)[CH:30]=1)(=[O:27])=[O:26].C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:6][S:7]([OH:10])(=[O:9])=[O:8].[CH3:24][S:25]([OH:28])(=[O:27])=[O:26].[NH:11]([CH2:15][C:16]1[O:20][C:19]([C:21]([O:23][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([C:39](=[NH:40])[NH2:41])[CH:35]=3)[CH:30]=2)=[O:22])=[CH:18][CH:17]=1)[C:12]([NH2:14])=[NH:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonateHCID 178505354HCID 178505354, compound

Product 1

HCID 178505339HCID 178505339, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

##STR50## In a solvent mixture of 8 ml of dry N,N-dimethylformamide (DMF) and dry pyridine, were dissolved 2.0 g of 5-guanidinomethyl-furan-2-carboxylic acid methanesulfonate and 1.8 g of 6-amidino-2-naphthol methanesulfonate. To the resulting solution, while being cooled in ice, were added 1.8 g of DCC and a catalytic amount of 4-dimethylaminopyridine. The mixture was stirred for 30 minutes with cooling in ice and then overnight at 30° C. The insolubles were removed by filtration and ethyl ether was added to the filtrate. The supernatant was removed by decantation. The residue was dissolved in a small amount of methanol and the methanol solution was added dropwise to ethyl ether. After precipitation the supernatant was removed by decantation. These procedures were repeated twice. Finally, the precipitate was collected by filtration and dried to obtain 1.2 g of a pale yellow substance of 6-amidino-2-naphthyl 5-guanidinomethyl-furan-2-carboxylate dimethanesulfonate.

Workup

  1. temperatureTo the resulting solution, while being cooled in ice
  2. temperaturewith cooling in ice
  3. customovernight
  4. customat 30° C
  5. customThe insolubles were removed by filtration and ethyl ether
  6. additionwas added to the filtrate
  7. customThe supernatant was removed by decantation
  8. dissolutionThe residue was dissolved in a small amount of methanol
  9. additionthe methanol solution was added dropwise to ethyl ether
  10. customAfter precipitation the supernatant
  11. customwas removed by decantation
  12. filtrationFinally, the precipitate was collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-6726dafa016f417eaaf13bce33836631
Source dataset
uspto-grants-1986_01
Patent number
US04563527

Reaction notes

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