Dicyclohexylcarbodiimide → HCID 178484649, compound

HRID 1419260Notes

Reaction equation

HRID 1419260 reaction equation
[NH2:1][N:2]=[CH:3][NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.CS([O-])(=O)=O.Cl.[C:20]([C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29]([C:33]([O:35][CH2:36][C:37](=[O:41])[N:38]([CH3:40])[CH3:39])=[O:34])=[C:28](O)[CH:27]=[CH:26]2)(=[NH:22])[NH2:21].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[NH2:1][N:2]=[CH:3][NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][C:28]2[CH:27]=[CH:26][C:25]3[C:30](=[CH:31][CH:32]=[C:23]([C:20](=[NH:21])[NH2:22])[CH:24]=3)[C:29]=2[C:33]([O:35][CH2:36][C:37](=[O:41])[N:38]([CH3:39])[CH3:40])=[O:34])=[O:10])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 85257MethanesulfonateHCID 1364775066-Amidino-1-dimethylcarbamoylmethoxycarbonyl-2-naphthol.hydrochlorideHCID 178514393HCID 178514393, compound

Product 1

HCID 178484649HCID 178484649, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

3 Milliliters of anhydrous pyridine was added to 418 mg of 4-aminoiminomethylaminobenzoic acid.methanesulfonate, 500 mg of 6-amidino-1-dimethylcarbamoylmethoxycarbonyl-2-naphthol.hydrochloride, 400 mg of DCC and 18 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 24 hours at room temperature. Then, the precipitate was collected by filtration and dissolved with addition of 20 ml of warm DMF, followed by stirring for 1 hour under cooling with ice. The precipitate was filtered and the filtrate was added dropwise to 400 ml of ether, followed by stirring for 24 hours under cooling with ice. The precipitate was collected by filtration and dissolved with addition of 20 ml of water, and the solution was added dropwise to 100 ml of aqueous sodium bicarbonate solution, followed by stirring for 2 hours under cooling with ice. Then, the precipitate was collected by filtration and washed with small amounts of water and acetone. This was added to a solution comprising 20 ml of DMF and 0.36 ml of methanesulfonic acid. The resulting solution was added dropwise to 450 ml of acetone, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 312.5 mg of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. custom24 hours
  3. customat room temperature
  4. filtrationThen, the precipitate was collected by filtration
  5. dissolutiondissolved with addition of 20 ml of warm DMF
  6. stirringby stirring for 1 hour
  7. temperatureunder cooling with ice
  8. filtrationThe precipitate was filtered
  9. additionthe filtrate was added dropwise to 400 ml of ether
  10. stirringby stirring for 24 hours
  11. temperatureunder cooling with ice
  12. filtrationThe precipitate was collected by filtration
  13. dissolutiondissolved with addition of 20 ml of water
  14. additionthe solution was added dropwise to 100 ml of aqueous sodium bicarbonate solution
  15. stirringby stirring for 2 hours
  16. temperatureunder cooling with ice
  17. filtrationThen, the precipitate was collected by filtration
  18. washwashed with small amounts of water and acetone
  19. additionThis was added to a solution
  20. additionThe resulting solution was added dropwise to 450 ml of acetone
  21. stirringby stirring for 24 hours
  22. temperatureunder cooling with ice
  23. filtrationThen, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-338d8d9eecc0467ba0a5855eaab7f53c
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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