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Acetic Acid → 4-{[(6-Butoxypyridin-2-yl)methyl]amino}-1H-imidazole-5-carboxamide

HRID 912701
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HRID 912701 반응식
[NH2:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8].[CH2:10]([O:14][C:15]1[N:20]=[C:19]([CH:21]=O)[CH:18]=[CH:17][CH:16]=1)[CH2:11][CH2:12][CH3:13].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH2:10]([O:14][C:15]1[N:20]=[C:19]([CH2:21][NH:1][C:2]2[N:6]=[CH:5][NH:4][C:3]=2[C:7]([NH2:9])=[O:8])[CH:18]=[CH:17][CH:16]=1)[CH2:11][CH2:12][CH3:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 96795-Aminoimidazole-4-carboxamideHCID 5003444Sodium cyanoborohydrideHCID 108450736-Butoxypyridine-2-carbaldehyde

생성물 1

HCID 674158084-{[(6-Butoxypyridin-2-yl)methyl]amino}-1H-imidazole-5-carboxamide

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

5-Aminoimidazole-4-carboxamide (0.30 g, 2.4 mmol) was added to the solution of 6-butoxypyridine-2-carbaldehyde (0.43 mg, 2.4 mmol, obtained from Example 17(d)) in anhydrous ethanol (30 mL) and the reaction mixture was refluxed. After 2 h, the reaction mixture was concentrated in vacuo. The light pink solid was suspended in anhydrous ethanol (25 mL), and acetic acid (0.27 mL, 4.8 mmol) was added. After 1.5 h, sodium cyanoborohydride (0.30 g, 4.8 mmol) was added to the mixture. After stirring o.n. at ambient temperature, the reaction mixture was concentrated in vacuo. The resulting 1.2 g of crude title compound was used in the next step without further purification. MS (ESI) m/z 290 (M+1)

후처리

  1. temperaturethe reaction mixture was refluxed
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. waitAfter 1.5 h
  4. concentrationat ambient temperature, the reaction mixture was concentrated in vacuo
  5. customThe resulting 1.2 g of crude title compound was used in the next step without further purification

출처 및 근거

ORD 기록
ord-b716e8f4075b4558bffcebba3f65d85d
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08026244B2

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