Ammonia → HCID 18327587, compound

HRID 1250402Notes

Reaction equation

[Br-].[C:2]([C:4]1[CH:5]=[C:6]([CH:34]=[CH:35][CH:36]=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]([CH3:33])([CH3:32])[CH2:29][C:30]#[CH:31])=[CH:24][CH:23]=1)=[O:19])#[N:3].Cl.[NH3:38].[CH2:39]([OH:41])[CH3:40]>>[C:18]([OH:19])(=[O:41])[CH3:9].[C:39]([O-:19])(=[O:41])[CH3:40].[C:2]([C:4]1[CH:5]=[C:6]([CH:34]=[CH:35][CH:36]=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]([CH3:32])([CH3:33])[CH2:29][C:30]#[CH:31])=[CH:26][CH:27]=1)=[O:19])(=[NH:38])[NH2:3]

Participants

Reactant 4

HCID 222Ammonia

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 18327549HCID 18327549, compound

Product 1

HCID 18327587HCID 18327587, compoundYield 56%

Procedure

This compound was prepared from [4-({[1-(3-cyano-benzyl)-5-fluoro-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-dimethyl-2-propynyl-ammonium bromide (220 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. 109° C. (dec.). MS: 482.3 (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-06b28cb70a174d07a73c915776fe765d
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337344B1

Reaction notes

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