Triethyloxonium tetrafluoroborate → HCID 66599055、化合物

HRID 1889091ノート

反応式

HRID 1889091 の反応式
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([F: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.[S:31]1[C:35]([C:36]([NH:38][NH2:39])=O)=[N:34][CH:33]=[N:32]1.ClCCl.CO>ClCCl>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:36]([C:35]3[S:31][N:32]=[CH:33][N:34]=3)=[N:38][N:39]=[C:14]2[CH2:13]1)=[O:11]

参加物

6

反応物 4

HCID 2723982Triethyloxonium tetrafluoroborateHCID 21226129Dichloromethane methanolHCID 665993354-[(2,3-Dichloro-4-fluorophenyl)carbonyl]-2-piperazinoneHCID 67970623HCID 67970623、化合物

生成物 1

HCID 66599055HCID 66599055、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
120 °C

実験手順

4-[(2,3-Dichloro-4-fluorophenyl)carbonyl]-2-piperazinone (I34) (0.25 g, 0.859 mmol) was dissolved in dichloromethane (DCM) (2.147 ml) and stirred under an argon atmosphere. Triethyloxonium tetrafluoroborate (0.196 g, 1.031 mmol) was added and the solution was left to stir for 40 minutes. A clear solution formed. 1,2,4-Thiadiazole-5-carbohydrazide (I80) (0.149 g, 1.031 mmol) was added and the solution was left to stir under argon for 60 minutes and then the solvent was removed under reduced pressure. 1-Butanol (2.147 ml) was added and the solution was left to reflux at 120° C. under an argon atmosphere for 5 hours. The solvent was removed under reduced pressure to afford a crude light orange solid of 0.56 g. TLC (DCM/MeOH 90:10): showed amide remained but some product had been formed. The crude material was purified by flash chromatography (Biotage SP4, 50 g cartridge) with a gradient of MeOH 0-10% in DCM. The solvent was removed under reduced pressure to afford desired product but still containing some impurities. The isolated material was then purified by MDAP and the solvent was removed under reduced pressure and transferred to a vial. The material was triturated with ether to afford desired product in 5.7 mg.

後処理

  1. waitthe solution was left
  2. stirringto stir for 40 minutes
  3. customA clear solution formed
  4. waitthe solution was left
  5. stirringto stir under argon for 60 minutes
  6. customthe solvent was removed under reduced pressure
  7. addition1-Butanol (2.147 ml) was added
  8. waitthe solution was left
  9. customThe solvent was removed under reduced pressure
  10. customto afford a crude light orange solid of 0.56 g
  11. customsome product had been formed
  12. customThe crude material was purified by flash chromatography (Biotage SP4, 50 g cartridge) with a gradient of MeOH 0-10% in DCM
  13. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-ee38fe73aafb40a086ab44296573fc58
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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