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

HRID 1854307Notes

Reaction equation

HRID 1854307 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

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)+.

Workup

  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.

Sources & evidence

ORD record
ord-bc5e10ce4ea1413d83469a9672053f5c
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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