1-Methyl-4-nitro-1H-pyrrole-2-carbonyl chloride → 1-Methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-N-[3-(dimethylamino)propyl]-1H-pyrrole-2-carboxamide
Reaktionsgleichung
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[N:10]([CH3:17])[CH:11]=[C:12]([N+:14]([O-])=O)[CH:13]=1)=[O:8].[CH3:19][N:20]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[C:21]1[C:28](Cl)=[O:29]>CO.C(Cl)Cl.[Pd]>[CH3:17][N:10]1[CH:11]=[C:12]([NH:14][C:28]([C:21]2[N:20]([CH3:19])[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=2)=[O:29])[CH:13]=[C:9]1[C:7]([NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:18])=[O:8]Komponenten
6
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
N-[3-(Dimethylamino)propyl]-1-methyl-4-nitro-1H-pyrrole-2-carboxamide (0.241 g, 0.95 mmol; see step (i) above) was dissolved in methanol (10 mL) and cooled to 0° C., Pd/C (55 mg) was then added in small portions and the solution stirred under H2 for 3 h. The solution was then filtered and the solvent removed under reduced pressure. A solution of 1-methyl-4-nitro-1H-pyrrole-2-carbonyl chloride (0.179 g 0.95 mmol; see Preparation 1(ii) above) in DCM (10 mL) was then added and allowed to stir for 1 h at RT, the solvent was removed under reduced pressure, the crude product obtained was separated on basified silica using a 1:1 solution of methanol ethyl acetate to yield the sub-title compound (0.239 g, 67%).
Aufarbeitung
- filtrationThe solution was then filtered
- customthe solvent removed under reduced pressure
- stirringto stir for 1 h at RT
- customthe solvent was removed under reduced pressure
- customthe crude product obtained
- customwas separated on basified silica using a 1:1 solution of methanol ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-843c25deab984983a2d6ce0a340077e8
- Quelldatensatz
- uspto-grants-2011_09
- Patentnummer
- US08012967B2
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