Trifluoroacetic acid → HCID 86757724, compound

HRID 1250400Notes

Reaction equation

HRID 1250400 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([O-:12])=[O:11].C([O:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39](=[NH:41])[NH2:40])[CH:34]=1)[C:27]([C:42]([NH:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([N+:52]([CH3:55])([CH3:54])[CH3:53])=[CH:48][CH:47]=1)=[O:43])=[CH:26]2)C1C=CC=CC=1.FC(F)(F)C(O)=O>C(O)C.[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([O-:12])=[O:11].[C:39]([C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=1)[CH2:32][N:28]1[C:29]2[C:25](=[CH:24][C:23]([OH:22])=[CH:31][CH:30]=2)[CH:26]=[C:27]1[C:42]([NH:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([N+:52]([CH3:53])([CH3:54])[CH3:55])=[CH:48][CH:47]=1)=[O:43])(=[NH:40])[NH2:41]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86757725HCID 86757725, compound

Product 1

HCID 86757724HCID 86757724, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The starting material, [4-({[5-benzyloxy-1-(3-amidino-benzyl)-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-trimethyl-ammonium trifluoroacetate trifluoroacetic acid salt (example 56), was dissolved in ethanol, 2 equivalents of trifluoroacetic acid and Pd/C (10%) were added and the mixture was hydrogenated. The reaction mixture was concentrated and purified by flash-chromatography on silica gel with dichloromethane/methanol/trifluoroacetic acid 9:1:0.1. The product was concentrated and lyophilized to give 53% of the desired product. M.p. 78° C. (dec.). MS: 456.4 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash-chromatography on silica gel with dichloromethane/methanol/trifluoroacetic acid 9:1:0.1
  3. concentrationThe product was concentrated

Sources & evidence

ORD record
ord-50c53e7843e94c94bf4a21ad2df1f597
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

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