N-bromobutanimide → Ethyl 5-bromo-8-morpholinoimidazo[1,2-a]pyrazine-2-carboxylate

HRID 1772632Notes

Reaction equation

HRID 1772632 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=3)[CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.C1C(=O)N([Br:28])C(=O)C1>C(Cl)Cl>[Br:28][C:10]1[N:9]2[CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=[C:8]2[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[N:12][CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 14207617Ethyl 8-morpholinoimidazo[1,2-a]pyrazine-2-carboxylate

Product 1

HCID 117727933Ethyl 5-bromo-8-morpholinoimidazo[1,2-a]pyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 1c (3.2 g, 9.0 mmol) in DCM (100 mL) at 0° C. was added NBS (1.6 g, 9.0 mmol) portionwise. The reaction mixture was allowed to stir at rt for 10 min, and subsequently was washed with a saturated aqueous sodium bicarbonate (2×100 mL). The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to give compound 21a as an off-white solid. Mass Spectrum (LCMS, ESI pos.) Calcd. For C13H15BrN4O3: 356.2 (M+H). Found 356.1.

Workup

  1. washsubsequently was washed with a saturated aqueous sodium bicarbonate (2×100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cde9cdc915ac4fc3828daca598e78800
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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