Ammonia → HCID 18327546, compound

HRID 1250405Notes

Reaction equation

[I-].[Br:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([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])[N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=1.Cl.[NH3:36].[CH2:37]([OH:39])[CH3:38]>>[C:21]([OH:22])(=[O:39])[CH3:6].[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:7]1[C:8]2[C:4](=[C:3]([Br:2])[CH:11]=[CH:10][CH:9]=2)[CH:5]=[C:6]1[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])(=[NH:36])[NH2:20]

Participants

Reactant 4

HCID 222Ammonia

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 18327563HCID 18327563, compound

Product 1

HCID 18327546HCID 18327546, compound

Procedure

This compound was prepared from [4-({[4-bromo-1-(3-cyano-benzyl)-1H-indole-2-carbonyl]-amino}-methyl)-phenyl]-trimethyl-ammonium iodide (200 mg, 0.32 mmol), ethanol (13 ml), 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 249 mg of the desired product as trifluoroacetic acid salt. This compound was converted into the acetic acid salt by ion exchanger chromatography analogously to example 64. Yield: 150 mg (74%). M.p. 145° C. (dec.). MS: 518.2 (M+; 79Br).

Workup

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

Sources & evidence

ORD record: ord-c858b46a195140f595186165a8423fb4
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337344B1

Reaction notes

Loading…