Hydrochloric Acid → 5-(4-tert-butylphenylsulfonyl)-2-hydrazinyl-5H-pyrrolo[2,3-b]pyrazine

HRID 2204456ノート

反応式

HRID 2204456 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:18]3=[N:19][CH:20]=[C:21]([NH:23][NH:24]C(OC(C)(C)C)=O)[N:22]=[C:17]3[CH:16]=[CH:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(S(N2C3=NC=C(N(C(OC(C)(C)C)=O)N)N=C3C=C2)(=O)=O)=CC=1)(C)(C)C.Cl>O1CCOCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[C:18]3=[N:19][CH:20]=[C:21]([NH:23][NH2:24])[N:22]=[C:17]3[CH:16]=[CH:15]2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 58009893tert-butyl 2-(5-(4-tert-butylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylateHCID 58010160tert-butyl 1-(5-(4-tert-butylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate

生成物 1

HCID 580098775-(4-tert-butylphenylsulfonyl)-2-hydrazinyl-5H-pyrrolo[2,3-b]pyrazine収率 87%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

To a mixture of tert-butyl 2-(5-(4-tert-butylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate and tert-butyl 1-(5-(4-tert-butylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate (11.24 g, 25.2 mmol, Preparation #2) in 1,4-dioxane (125 mL) was added HCl (4 M in 1,4-dioxane, 125 mL, 500 mmol). The reaction mixture was heated at about 60° C. for about 1 h and then the reaction mixture was cooled to ambient temperature. The mixture was filtered, while washing with Et2O (150 mL), and the solid was partitioned between EtOAc (500 mL) and saturated aqueous NaHCO3 (500 mL). The layers were separated and the organic layer was washed with saturated aqueous NaHCO3 and brine (200 mL each), dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure, and dried in a vacuum oven at about 70° C. to give 5-(4-tert-butylphenylsulfonyl)-2-hydrazinyl-5H-pyrrolo[2,3-b]pyrazine as a tan solid (7.54 g, 87%): LC/MS (Table 2, Method a) Rt=2.20 min; MS m/z: 346 (M+H)+.

後処理

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. filtrationThe mixture was filtered
  3. washwhile washing with Et2O (150 mL)
  4. customthe solid was partitioned between EtOAc (500 mL) and saturated aqueous NaHCO3 (500 mL)
  5. customThe layers were separated
  6. washthe organic layer was washed with saturated aqueous NaHCO3 and brine (200 mL each)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customdried in a vacuum oven at about 70° C.

出典と根拠

ORDレコード
ord-fd9d0ad14c9744f68dcdbe8e351da065
出典データセット
uspto-grants-2016_06
特許番号
US09365579B2

反応ノート

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