Pyridine → HCID 178492415, compound

HRID 1981416Notes

Reaction equation

HRID 1981416 reaction equation
N1C=CC=CC=1.[ClH:7].[NH:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:9]([NH2:11])=[NH:10].C1CCC(N=C=NC2CCCCC2)CC1.[CH3:35][S:36]([O:39][C:40]1[CH:45]=[CH:44][C:43]([C:46](=[NH:48])[NH2:47])=[CH:42][C:41]=1[O:49][CH3:50])(=[O:38])=[O:37]>CN(C=O)C.O.CC(C)=O.C(OCC)C>[ClH:7].[CH3:35][S:36]([OH:39])(=[O:38])=[O:37].[NH:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][C:40]1[CH:45]=[CH:44][C:43]([C:46](=[NH:47])[NH2:48])=[CH:42][C:41]=1[O:49][CH3:50])=[O:18])[C:9]([NH2:11])=[NH:10]

Participants

9

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 54016649HCID 54016649, compoundHCID 178479438HCID 178479438, compound

Product 1

HCID 178492415HCID 178492415, compoundYield 77%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To 40 ml of anhydrous pyridine, was added 2.1 g of 6-guanidinocaproic acid hydrochloride. To the mixture, while being cooled in ice, was added 2.5 g of DCC. The mixture was stirred for one hour, admixed with 2.6 g of 4-amidino-2-methoxyphenol methanesulfonate, and further stirred overnight at room temperature. After addition of ethyl ether to the reaction mixture, the supernatant was removed to obtain an oily substance as the residue. The oily substance was dissolved in DMF, then freed from insolubles by filtration, and mixed with ethyl ether to obtain 4.0 g of a colorless oily substance. This substance was dissolved in water by heating, then treated with activated carbon, and mixed with acetone to isolate 3.5 g of 4-amidino-2-methoxyphenyl 6-guanidinocaproate methanesulfonate hydrochloride in the form of colorless oil.

Workup

  1. temperatureTo the mixture, while being cooled in ice
  2. customthe supernatant was removed
  3. customto obtain an oily substance as the residue
  4. filtrationfreed from insolubles by filtration
  5. additionmixed with ethyl ether
  6. customto obtain 4.0 g of a colorless oily substance
  7. temperatureby heating
  8. additiontreated with activated carbon

Sources & evidence

ORD record
ord-5d68d18b716c41ef84a33a728da8aaa5
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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