Pyridine → HCID 73889501, compound

HRID 1419241Notes

Reaction equation

HRID 1419241 reaction equation
N1C=CC=CC=1.[ClH:7].[NH2:8][N:9]=[CH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.Cl.[C:21]([C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30]([CH2:34][C:35](=[O:37])[NH2:36])=[C:29](O)[CH:28]=[CH:27]2)(=[NH:23])[NH2:22].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(C(C)=O)C.O.C(O)=O.CN(C=O)C>[ClH:7].[ClH:7].[NH2:8][N:9]=[CH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([O:17][C:29]2[CH:28]=[CH:27][C:26]3[C:31](=[CH:32][CH:33]=[C:24]([C:21](=[NH:22])[NH2:23])[CH:25]=3)[C:30]=2[CH2:34][C:35](=[O:37])[NH2:36])=[O:16])=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 70133158HCID 70133158, compoundHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochloride

Product 1

HCID 73889501HCID 73889501, compoundYield 7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 131721206HCID 131721206, compoundSolvent

Procedure

20 Milliliters of 20% hydrous pyridine and 6 ml of DMF were added to 1.0 g of 4-aminoiminomethylbenzoic acid.hydrochloride, 1.39 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 1.23 g of DCC and 60.8 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 24 hours 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 resulting 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 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 10 ml of methanol and 0.9 ml of concentrated hydrochloric acid, and the resulting solution was added dropwise to 200 ml of acetone, followed by stirring for 2 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 80.2 mg of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. custom24 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 20 ml of DMF
  7. additionthe resulting solution was added dropwise to 400 ml of acetone
  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 10 ml of methanol and 0.9 ml of concentrated hydrochloric acid
  15. additionthe resulting solution was added dropwise to 200 ml of acetone
  16. stirringby stirring for 2 hours
  17. temperatureunder cooling with ice
  18. filtrationThen, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-68072f25d8254bf9bdf332e37aeb6752
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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