Ammonia → HCID 18327672, compound

HRID 1250406Notes

Reaction equation

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

Participants

Reactant 4

HCID 222Ammonia

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 18327593HCID 18327593, compound

Product 1

HCID 18327672HCID 18327672, compound

Procedure

This compound was prepared from [4-({[5-bromo-1-(3-cyano-benzyl)-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-trimethyl-ammonium iodide (200 mg, 0.32 mmol), ethanol, hydrogen chloride, and liquid ammonia analogously to example 19/3. Purification by reversed phase chromatography on RP18 material with water/ethanol/trifluoroacetic acid 1:1:0.1 gave 199 mg of the desired product as trifluoroacetic acid salt. This compound was converted into the acetic acid salt by ion exchange chromatography analogously to example 64. Yield: 130 mg (64 %). M.p. 86° C. (dec.). MS: 520.2 (M+; 81Br).

Workup

customPurification by reversed phase chromatography on RP18 material with water/ethanol/trifluoroacetic acid 1:1:0.1

Sources & evidence

ORD record: ord-6d5e4aa5730d415996c5308f2cc42683
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337344B1

Reaction notes

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