Isobutyraldehyde → 6-Chloro-3-isopropyl-[1,2,4]triazolo[4,3-a]pyrazine

HRID 1930074ノート

反応式

HRID 1930074 の反応式
[Cl:1][C:2]1[CH:7]=[N:6][C:5]([NH:8][NH2:9])=[CH:4][N:3]=1.[CH:10](=O)[CH:11]([CH3:13])[CH3:12].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([C:10]([CH:11]([CH3:13])[CH3:12])=[N:9][N:8]=2)[CH:7]=1

参加物

5

反応物 3

HCID 6561IsobutyraldehydeHCID 12217721Iodo benzene diacetateHCID 158645972-Chloro-5-hydrazinylpyrazine

生成物 1

HCID 579299536-Chloro-3-isopropyl-[1,2,4]triazolo[4,3-a]pyrazine収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

The 2-chloro-5-hydrazinylpyrazine (0.325 g, 2.248 mmol) was suspended in DCM (4 mL) then the isobutyraldehyde (0.195 g, 2.70 mmol) was added. The mixture was stirred for about 30 min, the solvent was concentrated under reduced pressure and the solid was dissolved in DCM (4 mL). Iodobenzene diacetate (0.724 g, 2.24 mmol) was added and the solution was stirred at ambient temperature for about 2 h. The mixture was diluted with DCM (20 mL), extracted with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified by flash chromatography on silica gel using DCM/EtOAc (1:1) as an eluent to give the title compound (0.278 g, 63%): LC/MS (Table 1, Method g) Rt=1.74 min; MS m/z: 197.1 (M+H)+.

後処理

  1. concentrationthe solvent was concentrated under reduced pressure
  2. dissolutionthe solid was dissolved in DCM (4 mL)
  3. stirringthe solution was stirred at ambient temperature for about 2 h
  4. extractionextracted with saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe material was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-0ea8c00f8abc44d5a693c652c258ff6d
出典データセット
uspto-grants-2012_05
特許番号
US08188083B2

反応ノート

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