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

HRID 1931735ノート

反応式

HRID 1931735 の反応式
[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

参加物

6

反応物 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 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cb9647f5187543889a23e77e25aface9
出典データセット
uspto-grants-2012_05
特許番号
US08188098B2

反応ノート

読み込み中…