Dimethylformamide dimethyl acetal → 1-Cyclohexyl-7-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-di hydropyrrolo[3',2': 5,6]pyrido[3,4-b][1,4]thiazine-4,4(7H)-dione

HRID 1506213Notes

Reaction equation

HRID 1506213 reaction equation
[CH:1]1([NH:7][C:8]2[C:9]3[CH:20]=[CH:19][N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:10]=3[N:11]=[CH:12][C:13]=2[S:14]([CH3:17])(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:29]OC(OC)N(C)C>>[CH:1]1([N:7]2[CH:29]=[CH:17][S:14](=[O:15])(=[O:16])[C:13]3[CH:12]=[N:11][C:10]4[N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][C:9]=4[C:8]2=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 86726635N-Cyclohexyl-5-(methylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-amine

Product 1

HCID 712582501-Cyclohexyl-7-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-di hydropyrrolo[3',2': 5,6]pyrido[3,4-b][1,4]thiazine-4,4(7H)-dione

Procedure

N-Cyclohexyl-5-(methylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-amine (6.1 mg, 0.014 mmol) in N,N-dimethylformamide dimethyl acetal (2.5 mL) was stirred at 170° C. for 3 hours under microwave irradiation. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. 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 water, extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting pale yellow oil (8.5 mg) containing the title compound was used for the next step without further purification.

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 water
  5. extractionextracted with ethyl acetate
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionThe resulting pale yellow oil (8.5 mg) containing the title compound
  9. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-8277f012ae534affa0ec21224e7deca1
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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