4-(2-Aminoethyl)-1-(3,4,5-trimethoxycinnamoyl)piperazine → (2S,4S)-N-{2-[4-(3,4,5-Trimethoxycinnamoyl)piperazin-1-yl]ethyl}-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide

HRID 373508Notes

Reaction equation

HRID 373508 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:25])[CH:11]=[CH:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[CH2:6][CH2:5]1.[F:26][C:27]1[CH:28]=[C:29]2[C@:36]3([C:40](=[O:41])[NH:39][C:38](=[O:42])[NH:37]3)[CH2:35][C@@H:34]([C:43](Cl)=[O:44])[O:33][C:30]2=[CH:31][CH:32]=1>>[CH3:24][O:23][C:15]1[CH:14]=[C:13]([CH:18]=[C:17]([O:19][CH3:20])[C:16]=1[O:21][CH3:22])[CH:12]=[CH:11][C:10]([N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][C:43]([C@@H:34]2[CH2:35][C@@:36]3([C:40](=[O:41])[NH:39][C:38](=[O:42])[NH:37]3)[C:29]3[C:30](=[CH:31][CH:32]=[C:27]([F:26])[CH:28]=3)[O:33]2)=[O:44])[CH2:5][CH2:6]1)=[O:25]

Participants

3

Reactant 2

HCID 544463484-(2-Aminoethyl)-1-(3,4,5-trimethoxycinnamoyl)piperazineHCID 57210646(2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride

Product 1

HCID 67916664(2S,4S)-N-{2-[4-(3,4,5-Trimethoxycinnamoyl)piperazin-1-yl]ethyl}-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamideYield 72%

Procedure

The procedure similar to that described in Example 8 was carried out with the use of the compound of 4-(2-aminoethyl)-1-(3,4,5-trimethoxycinnamoyl)piperazine and (2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride (Reference Example 1) to give the desired compound with yield of 72.0%.

Sources & evidence

ORD record
ord-701d41924cfc4bd2932e44dc7912fdc5
Source dataset
uspto-grants-1992_11
Patent number
US05164391

Reaction notes

Loading…