Pyridine → HCID 178449882, compound

HRID 1419239Notes

Reaction equation

HRID 1419239 reaction equation
N1C=CC=CC=1.[ClH:7].[CH2:8]([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)[CH2:9][CH2:10][CH3:11].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].[CH2:8]([NH:12][N:13]=[CH:14][NH:15][C:16]1[CH:17]=[CH:18][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:23][CH:24]=1)[CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochlorideHCID 178449883HCID 178449883, compound

Product 1

HCID 178449882HCID 178449882, compoundYield 107%

Reagents, catalysts & solvents 2

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

Procedure

30 Milliliters of 20% hydrous pyridine was added to 1.6 g of 4-n-butylaminoiminomethylaminobenzoic acid.hydrochloride, 1.5 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 1.33 g of DCC and 65.5 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 4 days at room temperature. Then, the precipitate was filtered and the filtrate was concentrated under reduced pressure. To the residue was added 20 ml of DMF, and the solution was added dropwise to a mixed liquid of 300 ml of acetone and 200 ml of ether, followed by stirring for 24 hours 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 30 ml of methanol and 2.1 ml of concentrated hydrochloric acid, and the solution was added dropwise to 250 ml of acetone, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration, and to the collected precipitate were added 9 ml of methanol, 7 ml of ethanol and 6 ml of 2-propanol, followed by stirring for 1 hour under cooling with ice. The precipitate was collected by filtration and washed with a small amount of acetone to obtain 1.68 g of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. custom4 days
  3. customat room temperature
  4. filtrationThen, the precipitate was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residue was added 20 ml of DMF
  7. additionthe solution was added dropwise to a mixed liquid of 300 ml of acetone and 200 ml of ether
  8. stirringby stirring for 24 hours
  9. temperatureunder cooling with ice
  10. filtrationThen, the precipitate was collected by filtration
  11. customto obtain a crude product
  12. customthe desired fractions were collected
  13. distillationthe solvent was distilled off under reduced pressure
  14. additionTo the residue were added 30 ml of methanol and 2.1 ml of concentrated hydrochloric acid
  15. additionthe solution was added dropwise to 250 ml of acetone
  16. stirringby stirring for 24 hours
  17. temperatureunder cooling with ice
  18. filtrationThen, the precipitate was collected by filtration
  19. additionto the collected precipitate were added 9 ml of methanol, 7 ml of ethanol and 6 ml of 2-propanol
  20. stirringby stirring for 1 hour
  21. temperatureunder cooling with ice
  22. filtrationThe precipitate was collected by filtration
  23. washwashed with a small amount of acetone

Sources & evidence

ORD record
ord-1e0affd8b9d94a61a09fb00620a2d231
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

Loading…