SK&F 105809 → 5h-Pyrrolo[1,2-a]imidazole,6,7-dihydro-2-[4-(methylsulfonyl)phenyl]-3-(4-pyridinyl)-

HRID 1885580노트

반응식

HRID 1885580 반응식
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH2:23][CH2:22][CH2:21][N:13]3[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)=[O:3].[Mn]([O-])(=O)(=O)=[O:25].[K+]>O>[CH3:1][S:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]3[CH2:23][CH2:22][CH2:21][N:13]3[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)(=[O:25])=[O:3]

참가 물질

4

반응물 2

HCID 129725SK&F 105809HCID 516875Potassium Permanganate

생성물 1

HCID 198792325h-Pyrrolo[1,2-a]imidazole,6,7-dihydro-2-[4-(methylsulfonyl)phenyl]-3-(4-pyridinyl)-

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A stirred solution of 0.64 g (1.98 mmoles) of 2-(4-methylsulfinylphenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]pyrrolo[1,2-a]imidazole of Example 4 in water was treated dropwise over 45 minutes with an aqueous solution of 0.209 g (1.32 mmoles) of potassium permanganate. After stirring overnight, the suspension was extracted with methylene chloride. The organic phase was dried over anhydrous potassium carbonate and stripped in vacuo. The residue flash chromatographed in silica eluting with 2 to 4% methanol in chloroform. The solvent was removed in vacuo and the residue recrystallized from ethyl acetate to afford the desired titled compound, mp 222.5°-224° C. 1H NMR (250 MHz, CDCl3) δ 8.62 (2H,d), 7.85 (2H,d), 7.72 (2H,d), 7.26 (2H,d), 4.05 (2H,t), 3.05(s) superimposed upon 3.03(t) (5H total), 2.70 (2H,q).

후처리

  1. extractionthe suspension was extracted with methylene chloride
  2. dry with materialThe organic phase was dried over anhydrous potassium carbonate
  3. customThe residue flash chromatographed in silica eluting with 2 to 4% methanol in chloroform
  4. customThe solvent was removed in vacuo
  5. customthe residue recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-26bd276e5cf6432a9997313a77ec3fcc
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05145858

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