Methanesulfonic Acid → HCID 13176912, compound

HRID 1263000Notes

Reaction equation

HRID 1263000 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][C:7]1[CH:8]=[C:9]([CH:26]=[CH:27][C:28]=1[N+:29]([O-])=O)[C:10]([O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:23](=[NH:25])[NH2:24])[CH:19]=2)[CH:14]=1)=[O:11].[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[H][H]>[Pd].CN(C=O)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[NH2:29][C:28]1[CH:27]=[CH:26][C:9]([C:10]([O:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:23](=[NH:24])[NH2:25])[CH:19]=3)[CH:14]=2)=[O:11])=[CH:8][C:7]=1[CH3:6]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 13176910HCID 13176910, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13176912HCID 13176912, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To 25 ml of DMF (anhydrous), were added 2.2 g of 6-amidino-2-naphthyl 3-methyl-4-nitrobenzoate methanesulfonate, 0.63 g of methanesulfonic acid, and 0.23 g of 10% Pd-C. Into the mixture, while being vigorously stirred, was introduced hydrogen. After removal of Pd-C by filtration, the reaction mixture was mixed with ethyl ether to separate an oily substance which was washed with ether and recrystallized from an ethanol-ethyl ether mixture to obtain 2.8 g of a white to pale brown powder of 6-amidino-2-naphthyl 4-amino-3-methylbenzoate dimethanesulfonate.

Workup

  1. customAfter removal of Pd-C
  2. filtrationby filtration
  3. additionthe reaction mixture was mixed with ethyl ether
  4. customto separate an oily substance which
  5. washwas washed with ether
  6. customrecrystallized from an ethanol-ethyl ether mixture

Sources & evidence

ORD record
ord-12489be73c0c4e8c8c25ea533aaef721
Source dataset
uspto-grants-1984_06
Patent number
US04454338

Reaction notes

Loading…