Water → 8-(2,6-Dichlorobenzoylamino)-4-(2,5-dioxopyrrolidin-1-ylamino)quinoline

HRID 613568Notes

Reaction equation

HRID 613568 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][NH:18][C:19](=[O:25])[CH2:20][CH2:21][C:22](O)=[O:23])=[O:5].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.O>CN(C)C=O>[Cl:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:2]([Cl:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][N:18]1[C:22](=[O:23])[CH2:21][CH2:20][C:19]1=[O:25])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19592904HCID 19592904, compound

Product 1

HCID 195928128-(2,6-Dichlorobenzoylamino)-4-(2,5-dioxopyrrolidin-1-ylamino)quinolineYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-(2,6-dichlorobenzoylamino)-4-[2-(3-carboxypropanoyl)hydrazino]quinoline (138 mg) in dimethylformamide (3 ml) were added 1-hydroxybenzotriazole (45.9 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (65.1 mg) at ambient temperature, and the mixture was stirred at the same temperature overnight. To the mixture was added water, and the resulting precipitates were collected by filtration to give 8-(2,6-dichlorobenzoylamino)-4-(2,5-dioxopyrrolidin-1-ylamino)quinoline (72 mg).

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-c5f2a3e94c0f49d0b3b3cd5edaddeb81
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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