Water → HCID 57917366, 화합물

HRID 69301노트

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HRID 69301 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[CH:19][C:20]5[N:21]([C:23]([CH:26]=[CH2:27])=[CH:24][N:25]=5)[CH:22]=4)=[CH:14][N:15]=3)[N:12]=2)[CH:4]=[N:3]1.[OH2:28].[O-][Mn](=O)(=O)=O.[K+].[OH-:35].[Na+]>O1CCOCC1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[CH:19][C:20]5[N:21]([C:23]([CH:26]([OH:35])[CH2:27][OH:28])=[CH:24][N:25]=5)[CH:22]=4)=[CH:14][N:15]=3)[N:12]=2)[CH:4]=[N:3]1

참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 57917377HCID 57917377, 화합물

생성물 1

HCID 57917366HCID 57917366, 화합물

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

6-(1-Methyl-1H-pyrazol-4-yl)-3-(3-vinyl-imidazo[1,2-a]pyridin-6-ylmethyl)-imidazo[1,2-b]pyridazine (Example 299, 49 mg, 0.138 mmol) was dissolved in dioxane (0.69 mL) and water (0.69 mL) then KMnO4 (21.8 mg, 0.138 mmol) and 2.5 M NaOH solution (0.165 mL, 0.414 mmol) were added. The RM was stirred at rt for 3 h. It was then filtered through Celite and the solvent was removed. The residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA). The fractions were joined and were lyophilized. The residue was dissolved in MeOH and it was passed through an SPE cartridge of HCO3− to remove the TFA salt. The filtrate was evaporated and the residue was triturated with pentane. The precipitate was filtered off and dried to afford the title compound as a white solid (tR 0.3 min (conditions 2), MH+=390).

후처리

  1. filtrationIt was then filtered through Celite
  2. customthe solvent was removed
  3. customThe residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA)
  4. dissolutionThe residue was dissolved in MeOH
  5. customto remove the TFA salt
  6. customThe filtrate was evaporated
  7. customthe residue was triturated with pentane
  8. filtrationThe precipitate was filtered off
  9. customdried

출처 및 근거

ORD 기록
ord-07c36265571f4936981bf13ddc80f4a7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822468B2

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