Hydrochloric Acid → HCID 58557841, compound

HRID 1969538Notes

Reaction equation

HRID 1969538 reaction equation
[CH3:1][C:2]1[N:19]([S:20]([C:23]2[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=[C:8]([NH:10][NH:11]C(OC(C)(C)C)=O)[N:9]=[C:4]2[CH:3]=1.Cl>O1CCOCC1>[NH:10]([C:8]1[N:9]=[C:4]2[CH:3]=[C:2]([CH3:1])[N:19]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:21])=[O:22])[C:5]2=[N:6][CH:7]=1)[NH2:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58557307HCID 58557307, compound

Product 1

HCID 58557841HCID 58557841, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 2-(6-methyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazine carboxylate (0.16 g, 0.38 mmol) was stirred in 1,4-dioxane (1.9 mL) in a sealed vial to give a brown solution. HCl (4 M in 1,4-dioxane, 0.958 mL, 3.83 mmol) was added and the reaction stirred at ambient temperature for about 20 h. The solvents were removed under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 (10 mL) and EtOAc (10 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×10 mL). The combined organic extracts were washed with brine (20 mL), dried over anhydrous Na2SO4, filtered, and concd in vacuo to provide 2-hydrazinyl-6-methyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (0.089 g, 73%): LC/MS (Table 1, Method a) Rt=1.92 min; MS m/z: 318 (M+H)+.

Workup

  1. customto give a brown solution
  2. customThe solvents were removed under reduced pressure
  3. customThe residue was partitioned between saturated aqueous NaHCO3 (10 mL) and EtOAc (10 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×10 mL)
  6. washThe combined organic extracts were washed with brine (20 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-4e75b37cfb1742b28f36a990f1af013f
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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