1,2-Dichloroethane → 4-methyl-5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde

HRID 1072173

Reaktionsgleichung

Reaktionsgleichung von HRID 1072173
[CH:1]([C:3]1[NH:7][C:6]([C:8]([OH:10])=O)=[C:5]([CH3:11])[CH:4]=1)=[O:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>CN(C=O)C.C(OCC)(=O)C>[CH3:11][C:5]1[CH:4]=[C:3]([CH:1]=[O:2])[NH:7][C:6]=1[C:8]([N:30]1[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]1)=[O:10]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 156940785-Formyl-3-methyl-1H-pyrrole-2-carboxylic acid

Produkt 1

HCID 223909764-methyl-5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehydeAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-formyl-3-methyl-1H-pyrrole-2-carboxylic acid (306.3 mg, 2 mmol) in DMF 5 mL was added HOBt (324.3 mg, 2.4 mmol), EDC (460.1 mg, 2.4 mmol) and then 1-methylpiperazine (0.27 mL, 2.4 mmol). The mixture was stirred at room temperature under nitrogen for overnight. The reaction was diluted with ethyl acetate and washed with sodium bicarbonate. The aqueous layer was extracted several times with ethyl acetate. The combined organic layer was washed with brine, dried, concentrated and column chromatographed (MeOH/DCM) to give 310 mg (66%) of 4-methyl-5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde as a light yellow foam solid. 1H NMR (360 MHz, DMSO-d6) 12.20 (br s, 1H, NH), 9.47 (s, 1H, CHO), 6.80 (s, 1H), 3.58 (m, 4H, 2×CH2), 3.44 (m, 4H, 2×CH2), 2.03 (s, 3H, CH3).

Aufarbeitung

  1. washwashed with sodium bicarbonate
  2. extractionThe aqueous layer was extracted several times with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customcolumn chromatographed (MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-0dab9c84ef764eb0a966883ff2583c1c
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908930B2

Verknüpfte Notizen

Wird geladen…