1-Methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-N-[2-(4-morpholinyl)ethyl]-1H-pyrrole-2-carboxamide → 1-Methyl-N-[1-methyl-5-({[1-methyl-5-({[2-(4-morpholinyl)ethyl]amino}-carbonyl)-1H-pyrrol-3-yl]amino}carbonyl)-1H-pyrrol-3-yl]-4-nitro-1H-pyrrole-2-carboxamide

HRID 907391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907391
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[N:11]([CH3:18])[CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=2)=[O:9])[CH:4]=[C:3]1[C:19]([NH:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:20].[CH3:30][N:31]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[C:32]1[C:39](Cl)=[O:40]>CO.C(Cl)Cl.[Pd]>[CH3:30][N:31]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[C:32]1[C:39]([NH:15][C:13]1[CH:14]=[C:10]([C:8]([NH:7][C:5]2[CH:4]=[C:3]([C:19]([NH:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[O:20])[N:2]([CH3:1])[CH:6]=2)=[O:9])[N:11]([CH3:18])[CH:12]=1)=[O:40]

Komponenten

6

Edukt 2

HCID 108623481-Methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-N-[2-(4-morpholinyl)ethyl]-1H-pyrrole-2-carboxamideHCID 110631851-Methyl-4-nitro-1H-pyrrole-2-carbonyl chloride

Produkt 1

HCID 673927171-Methyl-N-[1-methyl-5-({[1-methyl-5-({[2-(4-morpholinyl)ethyl]amino}-carbonyl)-1H-pyrrol-3-yl]amino}carbonyl)-1H-pyrrol-3-yl]-4-nitro-1H-pyrrole-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-N-[2-(4-morpholinyl)ethyl]-1H-pyrrole-2-carboxamide (0.343 g, 0.85 mmol; see Preparation 1(iv) above) was dissolved in methanol (10 mL) and cooled to 0° C., Pd/C (200 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 (160 g, 0.85 mmol) 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.

Aufarbeitung

  1. filtrationThe solution was then filtered
  2. customthe solvent removed under reduced pressure
  3. stirringto stir for 1 h at RT
  4. customthe solvent was removed under reduced pressure
  5. customthe crude product obtained
  6. customwas separated on basified silica using a 1:1 solution of methanol ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a1645550b9084937953eb5a40a06c921
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012967B2

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