Ammonia → HCID 18327562, compound

HRID 1250401Notes

Reaction equation

[Br-].[CH2:2]([N+:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16]([C:18]2[N:19]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]#[N:36])[CH:30]=3)[C:20]3[C:25]([CH:26]=2)=[CH:24][C:23]([F:27])=[CH:22][CH:21]=3)=[O:17])=[CH:10][CH:9]=1)([CH3:7])[CH3:6])[CH:3]=[CH2:4].[ClH:37].[NH3:38].C([OH:41])C>>[C:16]([OH:41])(=[O:17])[CH3:18].[Cl-:37].[CH2:2]([N+:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16]([C:18]2[N:19]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35](=[NH:38])[NH2:36])[CH:30]=3)[C:20]3[C:25]([CH:26]=2)=[CH:24][C:23]([F:27])=[CH:22][CH:21]=3)=[O:17])=[CH:10][CH:9]=1)([CH3:7])[CH3:6])[CH:3]=[CH2:4]

Participants

Reactant 4

HCID 222Ammonia

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 18327659HCID 18327659, compound

Product 1

HCID 18327562HCID 18327562, compoundYield 56%

Procedure

This compound was prepared from allyl-[4-({[1-(3-cyano-benzyl)-5-fluoro-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-dimethyl-ammonium bromide (222 mg, 0.406 mmol), ethanol (12 ml), hydrogen chloride, and liquid ammonia analogously to example 19/3. The crude product was purified by chromatography on silica gel with dichloromethane/methanol/acetic acid 3:2:0.05 to 1:4:0.05. Lyophilization gave 131 mg of the desired product (56%). M.p. 133° C. (dec.). MS: 484.3 (M+).

Workup

customThe crude product was purified by chromatography on silica gel with dichloromethane/methanol/acetic acid 3:2:0.05 to 1:4:0.05

Sources & evidence

ORD record: ord-edd47ca881d740ec83a11529143b0ea1
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337344B1

Reaction notes

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