Succinic anhydride → HCID 11479496, compound

HRID 1018714Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 350 mg of 3-[1-methyl-4[1-methyl-4[1-methyl-4-[1-methyl-4-(α-bromoacrylamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine hydrochloride (prepared as reported in WO 90/11277) in 20 ml of DMF, were added 120 mg of succinic anhydride and 165 mg of K2CO3. The solution was heated at 60° C. for 3 hours then the solvent evaporated under reduced pressure and the crude residue was purified by flash chromatography (methylene chloride/methanol: 95/5) to yield 150 mg of the title compound as a pale yellow solid.

Workup

customthe solvent evaporated under reduced pressure
customthe crude residue was purified by flash chromatography (methylene chloride/methanol: 95/5)

Sources & evidence

ORD record: ord-8d7fe273960c4028809fadcfc7ac9a06
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06482920B1

Reaction notes

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