Dimethylformamide dimethyl acetal → HCID 123283634, compound

HRID 1506217Notes

Reaction equation

HRID 1506217 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([NH:15][C:16]2[C:21]([C:22](=[O:24])[CH3:23])=[CH:20][N:19]=[C:18]3[N:25]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:26]=[CH:27][C:17]=23)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36]OC(OC)N(C)C>>[CH2:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([N:15]2[C:16]3[C:21](=[CH:20][N:19]=[C:18]4[N:25]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:33])([CH3:35])[CH3:34])[CH:26]=[CH:27][C:17]4=3)[C:22](=[O:24])[CH:23]=[CH:36]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 71258441HCID 71258441, compound

Product 1

HCID 123283634HCID 123283634, compoundYield 30%

Procedure

rac-1-(4-{[(3R,4R)-1-Benzyl-4-methylpiperidin-3-yl]amino}-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)ethanone (20 mg, 0.041 mmol) in N,N-dimethylformamide dimethyl acetal (1 mL) was stirred at 170° C. for 6 hours under microwave irradiation. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure, and the resulting residue was dissolved in tetrahydrofuran (1 mL) and stirred with 1 M hydrochloric acid (1 mL) at 80° C. for 1 hour. The reaction mixture was allowed to cool to room temperature and, after addition of saturated aqueous sodium hydrogen carbonate, extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol=1/1/0→0/5/1 (v/v/v)) to give the title compound as a yellow oil (6.1 mg, yield 30%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in tetrahydrofuran (1 mL)
  3. temperatureto cool to room temperature
  4. additionafter addition of saturated aqueous sodium hydrogen carbonate
  5. extractionextracted with chloroform
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol=1/1/0→0/5/1 (v/v/v))

Sources & evidence

ORD record
ord-74bad7c1d98d4786aa07d4c11899e7bd
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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