Potassium Carbonate → 1-methyl-5-phenyl-3-(pyrrolidin-1-yl)-1H-pyrazolo[3,4-c]pyridazin-4-ol

HRID 588643ノート

反応式

HRID 588643 の反応式
I[C:2]1[C:10]2[C:9]([OH:11])=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:7]=[N:6][C:5]=2[N:4]([CH3:18])[N:3]=1.[NH:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cu](I)I>[CH3:18][N:4]1[C:5]2[N:6]=[N:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:9]([OH:11])[C:10]=2[C:2]([N:19]2[CH2:26][CH2:25][CH2:24][CH2:20]2)=[N:3]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 178481918HCID 178481918、化合物

生成物 1

HCID 1784819221-methyl-5-phenyl-3-(pyrrolidin-1-yl)-1H-pyrazolo[3,4-c]pyridazin-4-ol

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

A mixture of 3-iodo-1-methyl-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-4-ol (100 mg, 0.28 mmol), copper iodide (11 mg, 0.056 mmol), L-proline (13 mg, 0.11 mmol), K2CO3 (193 mmol, 1.4 mmol) in anhydrous DMF (5.6 mL) was degassed by bubbling nitrogen through for 10 minutes, then heated to 110° C. for 20 h. The mixture was left to cool to room temperature, then partitioned between ethyl acetate and water, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried (MgSO4), filtered and evaporated. The residue (117 mg) was used as such in the next step.

後処理

  1. customwas degassed
  2. customby bubbling nitrogen through for 10 minutes
  3. waitThe mixture was left
  4. temperatureto cool to room temperature
  5. custompartitioned between ethyl acetate and water
  6. extractionthe aqueous phase was extracted with ethyl acetate
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-6b63d937842841c3b900850f8cbf256d
出典データセット
uspto-grants-2016_01
特許番号
US09227976B2

反応ノート

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