Dicyclohexylcarbodiimide → HCID 178474873, compound

HRID 1419217Notes

Reaction equation

HRID 1419217 reaction equation
Br.[C:2]([NH:5][CH2:6][CH2:7][N:8]=[CH:9][NH:10][CH2:11][NH:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)(=[O:4])[CH3:3].[ClH:22].[C:23]([C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[C:32]([CH2:36][C:37](=[O:39])[NH2:38])=[C:31](O)[CH:30]=[CH:29]2)(=[NH:25])[NH2:24].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[ClH:22].[ClH:22].[C:2]([NH:5][CH2:6][CH2:7][N:8]=[CH:9][NH:10][CH2:11][NH:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][C:31]2[CH:30]=[CH:29][C:28]3[C:33](=[CH:34][CH:35]=[C:26]([C:23](=[NH:24])[NH2:25])[CH:27]=3)[C:32]=2[CH2:36][C:37](=[O:39])[NH2:38])=[O:18])=[CH:20][CH:21]=1)(=[O:4])[CH3:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochlorideHCID 178419572HCID 178419572, compound

Product 1

HCID 178474873HCID 178474873, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

20 Milliliters of 20% hydrous pyridine was added to 1.4 g of 4-[(2-acetylaminoethyl)iminomethylaminomethylamino]benzoic acid.hydrobromide, 1.0 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 884 mg of DCC and 43.6 mg of DMAP, followed by stirring for 2 hours under cooling with ice and 4 days at room temperature. The precipitate was filtered and the filtrate was added dropwise to 250 ml of a mixed liquid of ether and acetone (1:10) and this was stirred for 24 hours under cooling with ice. Then, the precipitate was collected by filtration. To this collected precipitate was added 7 ml of DMF to dissolve the precipitate with heating, and 1.46 ml of concentrated hydrochloric acid was added under cooling with ice and stirring. This solution was added dropwise to 400 ml of ether.acetone (1:20), followed by stirring for 1 hour under cooling with ice and then 24 hours under cooling with water. After the supernatant was decanted, 20 ml of DMF was again added to the residue to dissolve the residue with heating, and further 1.5 ml of concentrated hydrochloric acid was added under cooling with water and stirring. This solution was added dropwise to 400 ml of acetone, followed by stirring for 1 hour under cooling with ice and then 24 hours under cooling with water. Thereafter, the precipitate was collected by filtration to obtain a crude product.

Workup

  1. filtrationThe precipitate was filtered
  2. additionthe filtrate was added dropwise to 250 ml of a mixed liquid of ether and acetone (1:10)
  3. stirringthis was stirred for 24 hours
  4. temperatureunder cooling with ice
  5. filtrationThen, the precipitate was collected by filtration
  6. additionTo this collected precipitate was added 7 ml of DMF
  7. dissolutionto dissolve the precipitate
  8. temperaturewith heating
  9. addition1.46 ml of concentrated hydrochloric acid was added
  10. temperatureunder cooling with ice
  11. stirringstirring
  12. additionThis solution was added dropwise to 400 ml of ether
  13. stirringby stirring for 1 hour
  14. temperatureunder cooling with ice
  15. temperature24 hours under cooling with water
  16. customAfter the supernatant was decanted
  17. addition20 ml of DMF was again added to the residue
  18. dissolutionto dissolve the residue
  19. temperaturewith heating
  20. additionfurther 1.5 ml of concentrated hydrochloric acid was added
  21. temperatureunder cooling with water
  22. stirringstirring
  23. additionThis solution was added dropwise to 400 ml of acetone
  24. stirringby stirring for 1 hour
  25. temperatureunder cooling with ice
  26. temperature24 hours under cooling with water
  27. filtrationThereafter, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-efaf607bc1c54f889b96a3107f2b9548
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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