Acetyl chloride → 1-{4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-ethanone

HRID 1297071Notes

Reaction equation

HRID 1297071 reaction equation
[CH3:1][N:2]([CH:12]1[CH:17]([CH3:18])[CH2:16][CH2:15][NH:14][CH2:13]1)[C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl.N1C=CC=CC=1>[CH3:18][CH:17]1[CH2:16][CH2:15][N:14]([C:19](=[O:21])[CH3:20])[CH2:13][CH:12]1[N:2]([CH3:1])[C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 12084830N-Methyl-N-[(3S,4S)-4-methyl-3-piperidyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 120848311-{4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-ethanoneYield 15%

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

To a stirred solution of the product from Method C (0.03 grams, 0.114 mmol) dissolved in 5 mL of 10:1 dichloromethane/pyridine was added (0.018 grams, 0.228 mmol) of acetylchloride and the resulting mixture stirred at room temperature for 18 hours. The reaction mixture was then partitioned between dichloromethane and saturated sodium bicarbonate (NaHCO3). The organic layer was washed again with saturated NaHCO3, dried over sodium sulfate and concentrated to dryness in vacuo. The residue was purified by preparative thin layer chromatography (PTLC) (silica; 4% methanol in dichloromethane) affording 0.005 mg (15%) of the title compound as a colorless oil. LRMS: 288.1 (M+1).

Workup

  1. customThe reaction mixture was then partitioned between dichloromethane and saturated sodium bicarbonate (NaHCO3)
  2. washThe organic layer was washed again with saturated NaHCO3
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (PTLC) (silica; 4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-762766bbcd754479a51d4f9f10da27e8
Source dataset
uspto-grants-2007_07
Patent number
US07250420B2

Reaction notes

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