Dimethylformamide dimethyl acetal → HCID 178496581, compound

HRID 1506251Notes

Reaction equation

HRID 1506251 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]2[C:15]([C:16](=[O:18])[CH3:17])=[CH:14][N:13]=[C:12]3[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:21][C:11]=23)[CH2:5][CH2:4]1.[CH3:30]OC(OC)N(C)C>>[CH3:1][O:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([N:9]2[C:10]3[C:15](=[CH:14][N:13]=[C:12]4[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:29])[CH3:28])[CH:20]=[CH:21][C:11]4=3)[C:16](=[O:18])[CH:17]=[CH:30]2)[CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496604HCID 178496604, compound

Product 1

HCID 178496581HCID 178496581, compoundYield 77%

Procedure

1-(4-[(trans-4-Methoxycyclohexyl)amino]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)ethanone (179 mg, 0.428 mmol) in N,N-dimethylformamide dimethyl acetal (3 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 (3 mL) and stirred with 1 M hydrochloric acid (3 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 (chloroform/methanol=9/1 (v/v)) to give the title compound (141 mg, yield 77%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in tetrahydrofuran (3 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 (chloroform/methanol=9/1 (v/v))

Sources & evidence

ORD record
ord-e12fde5483da4c4b85b6d15cbd8bb295
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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