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

HRID 1931735노트

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HRID 1931735 반응식
[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

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 673313,6-DichloropyridazineHCID 669153264-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt2회

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cb9647f5187543889a23e77e25aface9
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188098B2

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