Pyridine → HCID 178496048, compound

HRID 1419231Notes

Reaction equation

HRID 1419231 reaction equation
N1C=CC=CC=1.[ClH:7].[CH3:8][O:9][CH2:10][CH2:11][NH:12][N:13]=[CH:14][NH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1.Cl.[C:26]([C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[C:35]([CH2:39][C:40](=[O:42])[NH2:41])=[C:34](O)[CH:33]=[CH:32]2)(=[NH:28])[NH2:27].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(C(C)=O)C.O.C(O)(=O)C>[ClH:7].[ClH:7].[CH3:8][O:9][CH2:10][CH2:11][NH:12][N:13]=[CH:14][NH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([O:22][C:34]2[CH:33]=[CH:32][C:31]3[C:36](=[CH:37][CH:38]=[C:29]([C:26](=[NH:27])[NH2:28])[CH:30]=3)[C:35]=2[CH2:39][C:40](=[O:42])[NH2:41])=[O:21])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochlorideHCID 178496049HCID 178496049, compound

Product 1

HCID 178496048HCID 178496048, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 131721204Methyl ethyl ketone acetic acid waterSolvent

Procedure

50 Milliliters of 10% hydrous pyridine was added to 1.5 g of 4-[(2-methoxyethyl)aminoiminomethylamino]benzoic acid.hydrochloride, 1.22 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 1.7 g of DCC and 67 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 24 hours at room temperature. The precipitate was filtered and the filtrate was concentrated under reduced pressure. To the residue was added 15 ml of ethanol and 15 ml of isopropanol, and the precipitate was collected by filtration. To the collected precipitate were added 15 ml of DMF and 1.34 ml of concentrated hydrochloric acid to dissolve the precipitate. Furthermore, 1 g of active carbon was added, followed by stirring for 2 hours at room temperature. The insoluble matter was filtered off and the filtrate was added dropwise to 400 ml of acetone, followed by stirring for 24 hour under cooling with ice. Then, the precipitate was collected by filtration to obtain a crude product. Then, the product was subjected to silica gel column chromatography using methyl ethyl ketone-water-acetic acid (80:15:5) as an eluent, and the desired fractions were collected and the solvent was distilled off under reduced pressure. To the residue were added 15 ml of methanol and 1.34 ml of concentrated hydrochloric acid, and the solution was added dropwise to 400 ml of acetone, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 1.25 g of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. custom24 hours
  3. customat room temperature
  4. filtrationThe precipitate was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residue was added 15 ml of ethanol and 15 ml of isopropanol
  7. filtrationthe precipitate was collected by filtration
  8. additionTo the collected precipitate were added 15 ml of DMF and 1.34 ml of concentrated hydrochloric acid
  9. dissolutionto dissolve the precipitate
  10. additionFurthermore, 1 g of active carbon was added
  11. stirringby stirring for 2 hours at room temperature
  12. filtrationThe insoluble matter was filtered off
  13. additionthe filtrate was added dropwise to 400 ml of acetone
  14. stirringby stirring for 24 hour
  15. temperatureunder cooling with ice
  16. filtrationThen, the precipitate was collected by filtration
  17. customto obtain a crude product
  18. customthe desired fractions were collected
  19. distillationthe solvent was distilled off under reduced pressure
  20. additionTo the residue were added 15 ml of methanol and 1.34 ml of concentrated hydrochloric acid
  21. additionthe solution was added dropwise to 400 ml of acetone
  22. stirringby stirring for 24 hours
  23. temperatureunder cooling with ice
  24. filtrationThen, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-3898e9d3d0354fc18dcce7145daf8b03
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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