N,N-Dimethylethylenediamine → HCID 66820134, compound

HRID 241056Notes

Reaction equation

HRID 241056 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:16](S(C)(=O)=O)[S:17]([CH3:20])(=[O:19])=[O:18])[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.CN(C)CCN>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 131731197HCID 131731197, compound

Product 1

HCID 66820134HCID 66820134, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 5-bromo-3-(N-(methylsulfonyl)methylsulfonamido)pyridin-2-ylcarbamate (68 mg, 0.15 mmol) and N,N-dimethylethylenediamine (169 uL, 1.5 mmol) in dioxane (1 mL) was stirred at rt for 70 min. After diluting with ethyl acetate, the mixture was washed with aqueous citric acid (10%) followed by water. The organic phase was then dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was then diluted with dichloromethane which was then washed with 1 N HCl. After partitioning, the organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo to provide tert-butyl 5-bromo-3-(methylsulfonamido)pyridin-2-ylcarbamate (57 mg, 0.15 mmol, quantitative yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.24 (d, 1H), 8.07 (d, 1H), 2.98 (s, 3H), 1.54 (s, 9H); MS (EI) for C10H16BrN3O4S: 310, 312 (Br isotopes, MH+-t-butyl).

Workup

  1. washthe mixture was washed with aqueous citric acid (10%)
  2. dry with materialThe organic phase was then dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionThe residue was then diluted with dichloromethane which
  6. washwas then washed with 1 N HCl
  7. customAfter partitioning
  8. dry with materialthe organic phase was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11ff3ce83bf8469296ef4cd61c871ebe
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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