Ammonia → [4-({[1-(3-Amidino-benzyl)-5-fluoro-1h-indole-2-carbonyl]-amino}-methyl)-phenyl]-trimethyl-ammonium acetate acetic acid salt

HRID 1250393Notes

Reaction equation

HRID 1250393 reaction equation
[I-].[C:2]([C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=1)=[O:19])#[N:3].Cl.[NH3:36].[C:37]([OH:40])(=[O:39])[CH3:38].F[C:42](F)(F)[C:43]([OH:45])=[O:44]>>[C:37]([OH:40])(=[O:39])[CH3:38].[C:43]([O-:45])(=[O:44])[CH3:42].[C:2]([C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:18]([NH:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([N+:28]([CH3:30])([CH3:31])[CH3:29])=[CH:26][CH:27]=1)=[O:19])(=[NH:36])[NH2:3]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 18327608[4-({[1-(3-cyano-benzyl)-5-fluoro-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-trimethyl-ammonium iodideHCID 23437676Trifluoroacetic acid acetate

Product 1

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

Procedure

This compound was prepared from [4-({[1-(3-cyano-benzyl)-5-fluoro-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-trimethyl-ammonium iodide, hydrogen chloride, and liquid ammonia analogously to example 19/3. Instead of trifluoroacetic acid acetic acid was used for chromatography. Yield: 74%. M.p. 172° C. (dec.). MS: 458.2 (M+).

Sources & evidence

ORD record
ord-f27051570b5c493a85a6260e159f7822
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

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