Acetic Acid → 1-(3-Methyl[1,2,4]triazolo[4,3-a]pyridin-6-yl)cyclopropanecarboxylic acid

HRID 2245950노트

반응식

HRID 2245950 반응식
[NH:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2([C:12]([O:14]C)=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)[NH2:2].[CH:16](=O)[CH3:17].C(O)(=O)C.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C>[CH3:16][C:17]1[N:8]2[CH:7]=[C:6]([C:9]3([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]3)[CH:5]=[CH:4][C:3]2=[N:1][N:2]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 12217721Iodo benzene diacetateHCID 59216299Methyl 1-(6-hydrazinopyridin-3-yl)cyclopropanecarboxylate

생성물 1

HCID 592162871-(3-Methyl[1,2,4]triazolo[4,3-a]pyridin-6-yl)cyclopropanecarboxylic acid수율 30.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of methyl 1-(6-hydrazinopyridin-3-yl)cyclopropanecarboxylate (150 mg, 0.72 mol) in ethanol (3 mL) was added acetaldehyde (33.5 mg, 0.760 mmol) and acetic acid (41 μL, 0.72 mmol). The mixture was stirred at RT for 2 h, and then concentrated to dryness. The residue was dissolved in methylene chloride (3 mL), and iodobenzene diacetate (256 mg, 0.796 mmol) was added dropwise. The reaction mixture was stirred at RT overnight. The reaction solution was concentrated to dryness. The residue was purified through silica gel chromatograph using 10% MeOH in CH2Cl2 to afford the desired compound (50 mg, 30%). Analytical LCMS: (M+H)+=218.0.

후처리

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in methylene chloride (3 mL)
  3. stirringThe reaction mixture was stirred at RT overnight
  4. concentrationThe reaction solution was concentrated to dryness
  5. customThe residue was purified through silica gel chromatograph

출처 및 근거

ORD 기록
ord-349c30f243564a2ea62098f2a86ba7e6
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683060B2

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