Aluminium lithium hydride → (2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-ethyl)-dimethyl-amine

HRID 1515678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515678
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:32][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][C:27]([N:29]([CH3:31])[CH3:30])=O)[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:32][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][CH2:27][N:29]([CH3:30])[CH3:31])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 532510832-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-N,N-dimethyl-acetamide

Produkt 1

HCID 53251084(2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-ethyl)-dimethyl-amineAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-N,N-dimethyl-acetamide (as prepared in Example 39, 30 mg, 0.066 mmol) and lithium aluminum hydride (5 mg, 0.13 mmol) in dry tetrahydrofuran (3 mL) was refluxed for 4 h. The mixture was then cooled to room temperature, quenched with a 15% aqueous sodium hydroxide solution, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded (2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-ethyl)-dimethyl-amine (15 mg, 50%) as a colorless oil: LC/MS m/e calcd for C25H33N3O2S [M+H]+ 440.62, observed 440.2; 1H NMR (400 MHz, CDCl3) δ ppm 1.20 (m, 2H), 1.49 (m, 2H), 1.64 (m, 2H), 1.67-1.86 (m, 3H), 2.09 (m, 1H), 2.26 (m, 1H), 2.56 (br. s., 6H), 2.81 (s, 2H), 3.03 (s, 2H), 3.05 (s, 3H), 4.27 (t, J=7.8 Hz, 1H), 6.33 (s, 1H), 7.49 (d, J=8.3 Hz, 2H), 7.74 (d, J=1.8 Hz, 1H), 7.84 (br. s., 1H), 7.90 (d, J=8.3 Hz, 2H), 10.38 (br. s., 1H).

Aufarbeitung

  1. temperaturewas refluxed for 4 h
  2. customquenched with a 15% aqueous sodium hydroxide solution
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-8b1975d0f3b64e1eb32b0389f1a82f86
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222416B2

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