Water → 5-(4-Chlorophenyl)-4-cyclopropyl-2-(1H-1,2,4-triazol-5-ylsulfonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714651ノート

反応式

HRID 714651 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:14]3[CH2:16][CH2:15]3)[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[NH:23]1[C:27]([S:28](Cl)(=[O:30])=[O:29])=[N:26][CH:25]=[N:24]1.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH:14]3[CH2:16][CH2:15]3)[C:10](=[O:13])[N:11]([S:28]([C:27]3[NH:23][N:24]=[CH:25][N:26]=3)(=[O:30])=[O:29])[N:12]=2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 143044504H-1,2,4-Triazole-3-sulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 580121993-(4-Chlorophenyl)-4-cyclopropyl-1H-1,2,4-triazol-5(4H)-one

生成物 1

HCID 699405625-(4-Chlorophenyl)-4-cyclopropyl-2-(1H-1,2,4-triazol-5-ylsulfonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

300 mg (1.27 mmol) of 5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one [preparation according to WO 2007/134862 Example 36A] were dissolved in 10 ml of THF, and 143 mg (1.27 mmol) of potassium tert-butoxide were added at −78° C. Over a period of 30 min, the reaction mixture was warmed to RT, and the mixture was stirred at this temperature for a further 20 min. The mixture was then once more cooled to −78° C., and 213 mg (1.27 mmol) of 1H-1,2,4-triazole-5-sulfonyl chloride, dissolved in 5 ml of THF, were added. Over a period of 30 min, the reaction mixture was warmed to RT, and the mixture was stirred at this temperature for a further 20 h. For work-up, 10 ml of water were added. The mixture was extracted twice with in each case 15 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 136 mg (29% of theory) of the target compound.

後処理

  1. temperatureThe mixture was then once more cooled to −78° C.
  2. additionwere added
  3. waitOver a period of 30 min
  4. temperaturethe reaction mixture was warmed to RT
  5. stirringthe mixture was stirred at this temperature for a further 20 h
  6. extractionThe mixture was extracted twice with in each case 15 ml of ethyl acetate
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified chromatographically [Method 19]

出典と根拠

ORDレコード
ord-1ce72ef443a84f00be37825f8d449e79
出典データセット
uspto-grants-2015_11
特許番号
US09187466B2

反応ノート

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