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

HRID 588643노트

반응식

HRID 588643 반응식
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

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 178481918HCID 178481918, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매

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온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6b63d937842841c3b900850f8cbf256d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227976B2

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