Water → HCID 54262013, compound

HRID 353424Notes

Reaction equation

Cl.[CH3:2][N:3]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]([CH3:28])[CH:13]=[C:14]([NH:16][C:17]([C:19]3[N:23]([CH3:24])[N:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)=[O:18])[CH:15]=2)=[O:10])[CH:5]=[C:4]1[C:29]([NH:31][CH2:32][CH2:33][C:34]([NH2:36])=N)=[O:30].[OH2:37]>C(#N)C.[OH-].[Na+]>[CH3:2][N:3]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]([CH3:28])[CH:13]=[C:14]([NH:16][C:17]([C:19]3[N:23]([CH3:24])[N:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)=[O:18])[CH:15]=2)=[O:10])[CH:5]=[C:4]1[C:29]([NH:31][CH2:32][CH2:33][C:34]([NH2:36])=[O:37])=[O:30]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 200 mg of 3-(1-methyl-4 (1-methyl-4-(1-methyl-3-nitropyrazole-5-carboxamido)pyrrole-2-carboxamido)pyrrole-2-carboxamido)propionamidine hydrochloride (prepared as described in WO 96/05196) in 10 ml of acetonitrile and 10 ml of water, 2 ml of NaOH 1N were added. The solution was heated at 60° C. for 4 hours then the solvent was evaporated in vacuo and the crude residue was purified by flash chromatography (methylene chloride/methanol: 10/1) affording 175 mg of 3-(1-methyl-4(1-methyl-4-(1-methyl-3-nitropyrazole-5-carboxamido)pyrrole-2-carboxamido)pyrrole-2-carboxamido)propionamide as a light yellow solid.

Workup

customthe solvent was evaporated in vacuo
customthe crude residue was purified by flash chromatography (methylene chloride/methanol: 10/1)

Sources & evidence

ORD record: ord-5d2eec675be94a9fa5115e105418e4b3
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06753316B1

Reaction notes

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