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

HRID 1515678Notes

Reaction equation

HRID 1515678 reaction equation
[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

Participants

4

Reactant 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

Product 1

HCID 53251084(2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-ethyl)-dimethyl-amineYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8b1975d0f3b64e1eb32b0389f1a82f86
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

Loading…