Trifluoroacetic acid → 2-(6-Dimethylaminomethyl-2-methyl-indolizin-3-yl)-acetamide

HRID 216664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216664
C([O:5][C:6](=O)[CH2:7][C:8]1[N:16]2[C:11]([CH:12]=[CH:13][C:14]([CH2:17][N:18]([CH3:20])[CH3:19])=[CH:15]2)=[CH:10][C:9]=1[CH3:21])(C)(C)C.FC(F)(F)C(O)=O.C(C1NC=CN=1)(C1[NH:33]C=CN=1)=O>C(Cl)Cl>[CH3:19][N:18]([CH2:17][C:14]1[CH:13]=[CH:12][C:11]2[N:16]([C:8]([CH2:7][C:6]([NH2:33])=[O:5])=[C:9]([CH3:21])[CH:10]=2)[CH:15]=1)[CH3:20]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 68712027(6-Dimethylaminomethyl-2-methyl-indolizin-3-yl)-acetic acid tert-butyl ester

Produkt 1

HCID 591920212-(6-Dimethylaminomethyl-2-methyl-indolizin-3-yl)-acetamideAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(6-Dimethylaminomethyl-2-methyl-indolizin-3-yl)-acetic acid tert-butyl ester (122 mg, 0.40 mmol) is dissolved in CH2Cl2 (10 ml) containing 5% of trifluoroacetic acid. The mixture is stirred for 14 hours at room temperature and then concentrated in vacuo. The residue is azeotroped twice with toluene, dissolved in N,N-dimethylformamide (2.0 ml) and treated with carbonyl diimidazole (76 mg, 0.44 mmol, 1.1 equiv). After 1 hour at room temperature, the volatiles are removed in vacuo, and the activated acid is taken up in concentrated aqueous ammonia (10 ml). The mixture is stirred for 30 minutes at room temperature and then concentrated in vacuo. The residue is purified via flash chromatography (CH2Cl2/MeOH 7:1) to afford the title compound (90 mg, 91%). 1H NMR (400 MHz, d6-DMSO): δ=7.31 (s, 1H), 7.27 (s, 1H), 6.75 (s, 1H), 6.61 (dd, J=9.3/1.5 Hz, 1H), 4.06 (s, 2H), 3.38 (s, 2H), 2.66 (s, 6H), 2.13 (s, 3H). MS (ES+): 246 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue is azeotroped twice with toluene
  3. dissolutiondissolved in N,N-dimethylformamide (2.0 ml)
  4. waitAfter 1 hour at room temperature
  5. customthe volatiles are removed in vacuo
  6. stirringThe mixture is stirred for 30 minutes at room temperature
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified via flash chromatography (CH2Cl2/MeOH 7:1)

Quellen und Nachweise

ORD-Eintrag
ord-346e8dc69f9a4e8ebdd5c172f047a2c8
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193236B2

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