Triethyloxonium tetrafluoroborate → HCID 66599276、化合物

HRID 1889097ノート

反応式

HRID 1889097 の反応式
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH2:17][CH2:16][NH:15][C:14](=O)[CH2:13]1)=[O:11].F[B-](F)(F)F.C([O+](CC)CC)C.[CH3:31][O:32][C:33]1[N:38]=[C:37]([C:39]([NH:41][NH2:42])=O)[CH:36]=[CH:35][CH:34]=1>ClCCl>[Cl:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:39]([C:37]3[CH:36]=[CH:35][CH:34]=[C:33]([O:32][CH3:31])[N:38]=3)=[N:41][N:42]=[C:14]2[CH2:13]1)=[O:11]

参加物

5

反応物 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 242291726-Methoxypyridine-2-carbohydrazideHCID 665993614-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-2-piperazinone

生成物 1

HCID 66599276HCID 66599276、化合物収率 78.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-2-piperazinone (I37)(0.25 g, 0.859 mmol) was dissolved in Dichloromethane (DCM) (2.147 ml) and triethyloxonium tetrafluoroborate (0.196 g, 1.031 mmol) was added. The solution was left to stir under an argon atmosphere for 18 hours. 6-(Methyloxy)-2-pyridinecarbohydrazide (I95) (0.172 g, 1.031 mmol) was added and the solution was left to stir under argon for a further 60 minutes. The Dichloromethane was removed under reduced pressure and 1-butanol (2.147 ml) was added and the reaction mixture was left at reflux for 3 hours. LCMS showed the product had formed so the solvent was removed under reduced pressure and the crude material was purified by flash chromatography (Biotage Isolera 4, 25 g cartridge) with a gradient of methanol 0-10% in Dichloromethane. The solvent was removed under reduced pressure to afford 0.285 g of material that was further purified using MDAP. The solvent was removed to afford the purified desired product in 0.108 g.

後処理

  1. waitThe solution was left
  2. waitthe solution was left
  3. stirringto stir under argon for a further 60 minutes
  4. customThe Dichloromethane was removed under reduced pressure and 1-butanol (2.147 ml)
  5. additionwas added
  6. waitthe reaction mixture was left
  7. temperatureat reflux for 3 hours
  8. customhad formed so the solvent
  9. customwas removed under reduced pressure
  10. customthe crude material was purified by flash chromatography (Biotage Isolera 4, 25 g cartridge) with a gradient of methanol 0-10% in Dichloromethane
  11. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-4478eff674054fd2aa805d590b504fa5
出典データセット
uspto-grants-2013_08
特許番号
US08501946B2

反応ノート

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