Malonic Acid → 6-Amidino-2-naphthyl 5-carboxyacetylaminomethylfuran-2-carboxylate hydrochloride

HRID 1734102Notes

Reaction equation

HRID 1734102 reaction equation
CN(C=O)C.[ClH:6].Cl.[NH2:8][CH2:9][C:10]1[O:14][C:13]([C:15]([O:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:28](=[NH:30])[NH2:29])[CH:24]=3)[CH:19]=2)=[O:16])=[CH:12][CH:11]=1.[C:31](O)(=[O:36])[CH2:32][C:33]([OH:35])=[O:34].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[ClH:6].[C:33]([CH2:32][C:31]([NH:8][CH2:9][C:10]1[O:14][C:13]([C:15]([O:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:28](=[NH:29])[NH2:30])[CH:24]=3)[CH:19]=2)=[O:16])=[CH:12][CH:11]=1)=[O:36])([OH:35])=[O:34]

Participants

7

Reactant 4

HCID 867Malonic AcidHCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 223988156-Amidino-2-naphthyl 5-aminomethylfuran-2-carboxylate dihydrochloride

Product 1

HCID 700460566-Amidino-2-naphthyl 5-carboxyacetylaminomethylfuran-2-carboxylate hydrochlorideYield 57.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a mixture of 210 ml of DMF and 90 ml of pyridine were added 10 g of 6-amidino-2-naphthyl 5-aminomethylfuran-2-carboxylate dihydrochloride, 13.6 g of malonic acid and 320 mg of DMAP, then 10.8 g of DCC was added to the mixture with stirring and ice-cooling, and the mixture was stirred for 24 hours. The precipitate was removed by filtration and the filtrate was added dropwise to 3 l of acetone. The precipitate was collected by filtration to obtain 6.5 g of the intended product as a white solid.

Workup

  1. temperatureice-cooling
  2. stirringthe mixture was stirred for 24 hours
  3. customThe precipitate was removed by filtration
  4. additionthe filtrate was added dropwise to 3 l of acetone
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-34fa5b17c47a4ce9b59ea870bd7ada9a
Source dataset
uspto-grants-1996_07
Patent number
US05532267

Reaction notes

Loading…