Succinic anhydride → HCID 86758533, compound

HRID 989634Notes

Reaction equation

Cl.[CH3:2][N:3]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]([CH3:44])[CH:13]=[C:14]([NH:16][C:17]([C:19]3[N:20]([CH3:43])[CH:21]=[C:22]([NH:24][C:25]([C:27]4[N:28]([CH3:42])[C:29]5[C:34]([CH:35]=4)=[CH:33][C:32]([NH:36][C:37](=[O:41])[C:38]([Br:40])=[CH2:39])=[CH:31][CH:30]=5)=[O:26])[CH:23]=3)=[O:18])[CH:15]=2)=[O:10])[CH:5]=[C:4]1[C:45]([NH:47][CH2:48][CH2:49][C:50](N)=[NH:51])=[O:46].C(=O)([O-])[O-].[K+].[K+].C1(=O)OC(=O)CC1>CN(C=O)C>[CH3:2][N:3]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]([CH3:44])[CH:13]=[C:14]([NH:16][C:17]([C:19]3[N:20]([CH3:43])[CH:21]=[C:22]([NH:24][C:25]([C:27]4[N:28]([CH3:42])[C:29]5[C:34]([CH:35]=4)=[CH:33][C:32]([NH:36][C:37](=[O:41])[C:38]([Br:40])=[CH2:39])=[CH:31][CH:30]=5)=[O:26])[CH:23]=3)=[O:18])[CH:15]=2)=[O:10])[CH:5]=[C:4]1[C:45]([NH:47][CH2:48][CH2:49][C:50]#[N:51])=[O:46]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 150 mg of 3-[1-methyl-4[1-methyl-4[1-methyl-4[1-methyl-5(α-bromoacrylamido) indole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine hydrochloride, prepared as described in step I as above, in 10 ml DMF were added 25 mg of potassium carbonate and 20 mg of succinic anhydride. The mixture was heated at 60° C. for 4 hours. The solvent evaporated under vacuum and the crude residue purified by flash chromatography (methylene chloride/methanol:8/2) to yield 100 mg of the title compound as a yellow powder.

Workup

customThe solvent evaporated under vacuum
customthe crude residue purified by flash chromatography (methylene chloride/methanol:8/2)

Sources & evidence

ORD record: ord-0df4b66eb8dc4fd2b27d1f3a8cad1a44
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06458768B1

Reaction notes

Loading…