Pyridine → HCID 178485023, compound

HRID 1419240Notes

Reaction equation

HRID 1419240 reaction equation
N1C=CC=CC=1.[ClH:7].[CH3:8][N:9]([N:11]=[CH:12][NH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)[CH3:10].Cl.[C:24]([C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:33]([CH2:37][C:38](=[O:40])[NH2:39])=[C:32](O)[CH:31]=[CH:30]2)(=[NH:26])[NH2:25].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(C(C)=O)C.O.C(O)=O>[ClH:7].[ClH:7].[CH3:10][N:9]([N:11]=[CH:12][NH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([O:20][C:32]2[CH:31]=[CH:30][C:29]3[C:34](=[CH:35][CH:36]=[C:27]([C:24](=[NH:25])[NH2:26])[CH:28]=3)[C:33]=2[CH2:37][C:38](=[O:40])[NH2:39])=[O:19])=[CH:16][CH:15]=1)[CH3:8]

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochlorideHCID 178485024HCID 178485024, compound

Product 1

HCID 178485023HCID 178485023, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 131721206HCID 131721206, compoundSolvent

Procedure

40 Milliliters of 20% hydrous pyridine was added to 1.44 g of 4-dimethylaminoiminomethylaminobenzoic 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 72 hours at room temperature. Then, the precipitate was filtered and the filtrate was concentrated under reduced pressure. To the residue was added 25 ml of DMF, and the resulting solution was added dropwise to a mixed liquid of 200 ml of ether and 100 ml of acetone, followed by stirring for 2 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-formic 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 2.8 ml of concentrated hydrochloric acid, and the resultant solution was added dropwise to 150 ml of acetone, followed by stirring for 2 hours under cooling with ice. Then, the precipitate was collected by filtration, and to the collected precipitate were added 10 ml of methanol and 5 ml of ethanol, followed by stirring for 2 hours under cooling with ice. The precipitate was collected by filtration and washed with a small amount of acetone to obtain 966 mg of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. custom72 hours
  3. customat room temperature
  4. filtrationThen, the precipitate was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residue was added 25 ml of DMF
  7. additionthe resulting solution was added dropwise to a mixed liquid of 200 ml of ether and 100 ml of acetone
  8. stirringby stirring for 2 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 15 ml of methanol and 2.8 ml of concentrated hydrochloric acid
  15. additionthe resultant solution was added dropwise to 150 ml of acetone
  16. stirringby stirring for 2 hours
  17. temperatureunder cooling with ice
  18. filtrationThen, the precipitate was collected by filtration
  19. additionto the collected precipitate were added 10 ml of methanol and 5 ml of ethanol
  20. stirringby stirring for 2 hours
  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-d575ba25453142b187e523652f32feb5
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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