1-(3-Aminopropyl)-2-pyrrolidinone → 5-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(3-(2-oxopyrrolidin-1-yl)propyl)thiophene-2-carboxamide

HRID 1192125Notes

Reaction equation

HRID 1192125 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14](Cl)=[O:15])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].[NH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][C:26]1=[O:30]>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:21][CH2:22][CH2:23][CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][C:26]2=[O:30])=[O:15])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 602073375-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carbonyl chloride

Product 1

HCID 602073415-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(3-(2-oxopyrrolidin-1-yl)propyl)thiophene-2-carboxamide

Procedure

Prepared according to the procedure described for example 50 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carbonyl chloride (150 mg, 0.41 mmol) and 1-(3-amino-propyl)-2-pyrrolidinone (69 mg, 0.49 mmol). The title compound was obtained as a yellow solid (130 mg, 66% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.98 (2H, s), 8.32(1H, m), 8.40 (1H, s), 3.33 (1H, m), 3.20 (4H, m), 2.21 (2H, m), 1.90 (2H, m), 1.66 (2H, m). MS m/z: 475.03, 477.05 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-54acc8211f4a4fdda23fd832b793f3cf
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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