Potassium Carbonate → 1-[1-(6-Chloro-pyridazin-3-yl)-piperidin-4-yl]-4-(4-methanesulfonyl-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1931735Notes

Reaction equation

HRID 1931735 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.[CH3:16][S:17]([C:20]1[CH:41]=[CH:40][C:23]([O:24][C:25]2[N:30]=[CH:29][N:28]=[C:27]3[N:31]([CH:34]4[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]4)[N:32]=[CH:33][C:26]=23)=[CH:22][CH:21]=1)(=[O:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:37]2[CH2:38][CH2:39][CH:34]([N:31]3[C:27]4=[N:28][CH:29]=[N:30][C:25]([O:24][C:23]5[CH:22]=[CH:21][C:20]([S:17]([CH3:16])(=[O:18])=[O:19])=[CH:41][CH:40]=5)=[C:26]4[CH:33]=[N:32]3)[CH2:35][CH2:36]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 673313,6-DichloropyridazineHCID 669153264-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2×

Product 1

HCID 579650581-[1-(6-Chloro-pyridazin-3-yl)-piperidin-4-yl]-4-(4-methanesulfonyl-phenoxy)-1H-pyrazolo[3,4-d]pyrimidineYield 0.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3,6-Dichloropyridazine (0.2 mmol) was added to a mixture of 4-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt (Intermediate 27; 75 mg, 0.15 mmol) and potassium carbonate (69 mg, 0.5 mmol) in dimethylformamide (1 mL). The mixture was heated to 60° C. overnight and then poured into saturated aqueous ammonium chloride solution. This mixture was extracted three times with ethyl acetate. The combined organic phases were washed twice with water and once with brine, dried (magnesium sulfate), filtered, evaporated, and purified on a silica gel column, eluting with ethyl acetate, to give 1-[1-(6-Chloro-pyridazin-3-yl)-piperidin-4-yl]-4-(4-methanesulfonyl-phenoxy)-1H-pyrazolo[3,4-d]pyrimidine (0.5 mg, 0.7%) as a white powder.

Workup

  1. extractionThis mixture was extracted three times with ethyl acetate
  2. washThe combined organic phases were washed twice with water and once with brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified on a silica gel column
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-cb9647f5187543889a23e77e25aface9
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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