Pyridine → HCID 86742467, compound

HRID 867914Notes

Reaction equation

HRID 867914 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1([NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)[CH2:10][CH2:9][N:8]=[CH:7]1.[CH3:21][S:22]([O:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:36](=[NH:38])[NH2:37])[CH:32]=2)[CH:27]=1)(=[O:24])=[O:23].C1CCC(N=C=NC2CCCCC2)CC1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.CC(C)=O>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:21][S:22]([OH:25])(=[O:24])=[O:23].[N:6]1([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[C:31]([C:36](=[NH:37])[NH2:38])[CH:32]=4)[CH:27]=3)=[O:17])=[CH:19][CH:20]=2)[CH2:10][CH2:9][N:8]=[CH:7]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonateHCID 86742469HCID 86742469, compound

Product 1

HCID 86742467HCID 86742467, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolvent

Procedure

To 1.03 g of 4-(2-imidazolinyl)amino-benzoic acid methanesulfonate, 0.96 g of 6-amidino-2-naphthol methanesulfonate, 42 mg of DMAP and 1.06 g of DCC was added 5 ml of anhydrous pyridine. The resulting mixture was stirred overnight at room temperature. To the mixture was added 50 ml of acetone and the precipitate which was formed was collected by filtration. To the precipitate was added 40 ml of DMF. After stirring the precipitate which was formed was collected by filtration and 20 ml of water was added to the precipitate. The insolubles were removed by filtration. The filtrate was distilled under reduced pressure. To the residue was added 200 ml of acetone. The precipitate which was formed was collected by filtration to obtain 0.8 g of 6-amidino-2-naphthyl 4-(2-imidazolinyl)amino-benzoate dimethanesulfonate.

Workup

  1. customthe precipitate which was formed
  2. filtrationwas collected by filtration
  3. additionTo the precipitate was added 40 ml of DMF
  4. stirringAfter stirring the precipitate which
  5. customwas formed
  6. filtrationwas collected by filtration and 20 ml of water
  7. additionwas added to the precipitate
  8. customThe insolubles were removed by filtration
  9. distillationThe filtrate was distilled under reduced pressure
  10. additionTo the residue was added 200 ml of acetone
  11. customThe precipitate which was formed
  12. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-1d68487e3b5c485697314b1e944ed6ec
Source dataset
uspto-grants-1988_10
Patent number
US04777182

Reaction notes

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