1-Methyl-2-pyrrolecarboxylic acid → HCID 86757056, Verbindung

HRID 1069110

Reaktionsgleichung

Reaktionsgleichung von HRID 1069110
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)/[CH:5]=[CH:6]/[C:7]([O:9][CH3:10])=[O:8].[CH3:14][N:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20](O)=[O:21].CCN=C=NCCCN(C)C.Cl>N1C=CC=CC=1.O.C(Cl)Cl>[CH3:14][N:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20]([NH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)/[CH:5]=[CH:6]/[C:7]([O:9][CH3:10])=[O:8])=[O:21]

Komponenten

7

Edukt 3

HCID 814531-Methyl-2-pyrrolecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12394366methyl (E)-3-(3-aminophenyl)acrylate

Produkt 1

HCID 86757056HCID 86757056, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of methyl (E)-3-aminocinnamate (9) (1.20 g, 6.77 mmol), 1-methylpyrrole-2-carboxylic acid (0.89 g, 7.11 mmol) and EDCI.HCl (1.56 g, 8.14 mmol) in pyridine (8 mL) was stirred at 50° C. for 2.5 h and then cooled and diluted with water. The precipitated semi-solid was dissolved in CH2Cl2, the solution was washed with 0.5 N HCl (2×) and water (2×) and then dried and concentrated under reduced pressure below 30° C. The residue was chromatographed on silica gel, eluting with CH2Cl2/EtOAc (10:1), to yield a solid which was triturated with i-Pr2O/petroleum ether to give thermally unstable methyl (E) -3- (l-methylpyrrole-2-carboxamido)cinnamate (10) (1.42 g, 74%), mp 89-90° C. 1H NMR [(CD3)2SO] δ9.83 (s, 1 H, NH), 8.01 (d, J=1.4 Hz, 1 H, H-2), 7.76 (dt, J=7.8, 1.4 Hz, 1 H, H-4), 7.63 (d, J=16.0 Hz, 1 H, PhCH═CH), 7.45-7.35 (m, 2 H, H-5,6), 7.05 (dd, J=4.0, 1.7 Hz, 1 H, H-pyrrole), 7.03 (t, J=2.0 Hz, 1 H, H-pyrrole), 6.54 (d, J=16.0 Hz, 1 H, Ph CH═CH), 6.11 (dd, J=3.8, 2.6 Hz, 1 H, H-pyrrole), 3.89 (s, 3 H, NCH3), 3.74 (s, 3 H, CO2CH3).

Aufarbeitung

  1. temperaturecooled
  2. washthe solution was washed with 0.5 N HCl (2×) and water (2×)
  3. customdried
  4. concentrationconcentrated under reduced pressure below 30° C
  5. customThe residue was chromatographed on silica gel
  6. washeluting with CH2Cl2/EtOAc (10:1)
  7. customto yield a solid which
  8. customwas triturated with i-Pr2O/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-b1fa6f32e10d483cae481bed6920f927
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251933B1

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