Water ethanol trifluoroacetic acid → [4-({[1-(3-Amidino-benzyl)-5-fluoro-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-trimethyl-ammonium trifluoroacetate trifluoroacetic acid salt

HRID 1250394Notes

Reaction equation

HRID 1250394 reaction equation
C(O)(=O)C.C([O-])(=O)C.[C:9]([C:12]1[CH:13]=[C:14]([CH:40]=[CH:41][CH:42]=1)[CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=2)[CH:18]=[C:17]1[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([CH3:39])([CH3:38])[CH3:37])=[CH:32][CH:31]=1)=[O:27])(=[NH:11])[NH2:10].O.C(O)C.[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50]>>[F:47][C:48]([F:53])([F:52])[C:49]([OH:51])=[O:50].[F:47][C:48]([F:53])([F:52])[C:49]([O-:51])=[O:50].[C:9]([C:12]1[CH:13]=[C:14]([CH:40]=[CH:41][CH:42]=1)[CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=2)[CH:18]=[C:17]1[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([CH3:37])([CH3:38])[CH3:39])=[CH:32][CH:31]=1)=[O:27])(=[NH:10])[NH2:11]

Participants

3

Reactant 2

HCID 18377865Water ethanol trifluoroacetic acidHCID 69779712[4-({[1-(3-Amidino-benzyl)-5-fluoro-1h-indole-2-carbonyl]-amino}-methyl)-phenyl]-trimethyl-ammonium acetate acetic acid salt

Product 1

HCID 86757719[4-({[1-(3-Amidino-benzyl)-5-fluoro-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-trimethyl-ammonium trifluoroacetate trifluoroacetic acid saltYield 100%

Procedure

[4-({[1-(3-Amidino-benzyl)-5-fluoro-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-trimethyl-ammonium acetate acetic acid salt (32/2) was dissolved in water/ethanol/trifluoroacetic acid 1:1:0.1. The product was separated by flash chromatography on RP18 material with water/ethanol/trifluoroacetic acid 1:1:0.1 to give the trifluoroacetic acid salt in 100% yield. M.p.120-124° C. MS: 458.2 (M+).

Workup

  1. customThe product was separated by flash chromatography on RP18 material with water/ethanol/trifluoroacetic acid 1:1:0.1

Sources & evidence

ORD record
ord-a28cd31aafa94a24b75f7ce4e5251f9a
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

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