N,N-Dimethylglycine → HCID 66825545, compound

HRID 1046506Notes

Reaction equation

HRID 1046506 reaction equation
I[C:2]1[C:6]2[C:7]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:3]=1.[C:27]1([OH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O>O1CCOCC1>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:4]2[C:5]3[CH:10]=[CH:9][N:8]=[C:7]([NH:11][CH:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)[C:6]=3[C:2]([O:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:3]2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 673N,N-DimethylglycineHCID 996PhenolHCID 10796Cesium carbonateHCID 68069663HCID 68069663, compound

Product 1

HCID 66825545HCID 66825545, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a pressure tube was added 3-iodo-1-(4-methoxybenzyl)-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[4,3-c]pyridin-4-amine (0.60 g, 1.3 mmol), phenol (0.36 g, 3.9 mmol), Cu(I) iodide (25 mg, 0.13 mmol), caesium carbonate (1.3 g, 0.39 mol), N,N-dimethylglycine (33 mg, 0.32 mmol) and 1,4-dioxane (3.0 mL). The tube was flushed with nitrogen, sealed, and stirred at 120° C. for 24 hours. The reaction mixture was cooled, filtered and concentrated under reduced pressure. The residue was re-dissolved in ethyl acetate, filtered through a pad of silica gel, and concentrated to give crude 1-(4-methoxybenzyl)-3-phenoxy-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[4,3-c]pyridin-4-amine which was used directly in the following step.

Workup

  1. customThe tube was flushed with nitrogen
  2. customsealed
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was re-dissolved in ethyl acetate
  7. filtrationfiltered through a pad of silica gel
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e9db4515d34b49e8a1b7c21fcf3f1740
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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