Potassium Carbonate → HCID 66732646, compound

HRID 1966833Notes

Reaction equation

HRID 1966833 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3]I.C(=O)([O-])[O-].[K+].[K+].[CH2:13]1[C:16]2([CH2:20][C:19]([C:21]3[CH:26]=[N:25][C:24]4[NH:27][N:28]=[CH:29][C:23]=4[C:22]=3[NH:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[N:18][O:17]2)[CH2:15][CH2:14]1>CN(C)C=O.O>[CH2:15]1[C:16]2([CH2:20][C:19]([C:21]3[CH:26]=[N:25][C:24]4[N:27]([CH2:3][C:2]([F:6])([F:5])[F:1])[N:28]=[CH:29][C:23]=4[C:22]=3[NH:30][CH:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[N:18][O:17]2)[CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 66732718HCID 66732718, compound

Product 1

HCID 66732646HCID 66732646, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1,1,1-Trifluoro-2-iodoethane (0.07 gm, 0.33 mmol) and potassium carbonate (0.125 gm, 0.9 mmol) were added to the solution of 5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (0.1 gm, 0.3 mmol) (example 29) in dimethylformamide and the reaction mixture was heated at 80° C. for about 3 hours. It was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c3b16a8a840d4f4f9f566bb785723cf6
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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