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2,3-Diaminopyridine → 8-Amino-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine

HRID 2073793
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HRID 2073793 반응식
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.S(O[CH:14]([CH2:18][C:19]#[CH:20])[C:15](=O)[CH3:16])(C)(=O)=O>CO>[NH2:8][C:7]1[C:2]2[N:3]([C:14]([CH2:18][C:19]#[CH:20])=[C:15]([CH3:16])[N:1]=2)[CH:4]=[CH:5][CH:6]=1
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참가 물질

4

반응물 2

HCID 99562,3-DiaminopyridineHCID 143683463-Mesyloxy-5-hexyn-2-one

생성물 1

HCID 144998058-Amino-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine수율 17.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 2,3-diaminopyridine (62.8 g) and 3-mesyloxy-5-hexyn-2-one (109.5 g) in methanol (126 ml) was refluxed for 20 hours. After methanol was evaporated in vacuo, sodium bicarbonate aqueous solution was added to the residue and then the mixture was extracted with ethyl acetate, washed with water and sodium chloride aqueous solution, and evaporated in vacuo. The resultant residue was subjected to column chromatography on silica gel (310 g) and eluted with a mixture of methylene chloride and acetonitrile. The eluates containing the object compound were combined and evaporated in vacuo. The residue was suspended in diethyl ether and the resultant precipitates were collected by filtration to give 8-amino-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (18.42 g).

후처리

  1. temperaturewas refluxed for 20 hours
  2. customAfter methanol was evaporated in vacuo, sodium bicarbonate aqueous solution
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water and sodium chloride aqueous solution
  6. customevaporated in vacuo
  7. washeluted with a mixture of methylene chloride and acetonitrile
  8. additionThe eluates containing the object compound
  9. customevaporated in vacuo
  10. customthe resultant precipitates
  11. filtrationwere collected by filtration

출처 및 근거

ORD 기록
ord-1da87bd06eb541a8b8577f5e8c67e128
출처 데이터셋
uspto-grants-1990_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04920129

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