Acetyl chloride → 1H-Indolamine

HRID 966484

Reaktionsgleichung

Reaktionsgleichung von HRID 966484
C(OC([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17](NCCN3CCCC3)[CH:18]=2)[NH:13][C:12]=1C)=O)C1C=CC=CC=1.C([N:31](CC)CC)C.C(Cl)(=O)C>C(#N)C>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[C:12]1[NH2:31]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 101996102-methyl-5-(2-pyrrolidine-1-yl-ethylamino)-1H-indole-3-carboxylic Acid Benzyl Ester

Produkt 1

HCID 1220741H-IndolamineAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a stirred solution of the 2-methyl-5-(2-pyrrolidine-1-yl-ethylamino)-1H-indole-3-carboxylic acid benzyl ester (147 mg, 0.39 mmol, 1.0 eq) and triethylamine (47.6 mg, 0.47 mmol, 1.2 eq) in acetonitrile in an ice-water bath was added dropwise a solution of acetyl chloride in acetonitrile. After the ice-water bath was removed, the reaction mixture was heated to reflux for overnight. After the mixture was concentrated, the residue was purified by preparative HPLC (reverse-phase, 10-100 CH3CN:H2O, 0.1% TFA) to yield the desire indole amine in 33.0% yield. Elemental Analysis: C25H29N3O3.2HCl.0.3H2O Calcd: C: 60.31; H: 6.40; N: 8.44. Found: C: 60.63; H: 6.40; N: 8.04. ESI-MS: m/z 420.78 (M+H)+.

Aufarbeitung

  1. customAfter the ice-water bath was removed
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for overnight
  4. concentrationAfter the mixture was concentrated
  5. customthe residue was purified by preparative HPLC (reverse-phase, 10-100 CH3CN:H2O, 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-9030612110934d018806ad9dc72b55bc
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951848B2

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