Water → HCID 18779798, compound

HRID 1585873Notes

Reaction equation

HRID 1585873 reaction equation
[CH3:1][C:2]1[C:3](=[O:29])[N:4]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12]N3C(CC4C=CC(C#N)=CC=4)=CN=C3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][N:7]=1.C1C(=O)N([Br:37])C(=O)C1.S(C)C.O>C(Cl)Cl.CCOC(C)=O>[Br:37][CH2:12][C:11]1[CH:27]=[CH:28][C:8]([N:4]2[CH:5]=[CH:6][N:7]=[C:2]([CH3:1])[C:3]2=[O:29])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 67184N-bromobutanimideHCID 86754421HCID 86754421, compound

Product 1

HCID 18779798HCID 18779798, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The pyrazinone intermediate from Step 3 (430 mg, 1.99 mmol) was dissolved in CH2Cl2 and added to a yellow suspension of NBS (531 mg, 2.98 mmol) and Me2S (0.248 mL, 3.38 mmol) at -20°. The sulfoxium salt was formed at 0° then cooled to -20° before the addition of alcohol. After addition of the alcohol, the reaction mixture was stirred at 0° for several hours and then the cooling bath was allowed to expire overnight. The light brown solution was poured into H2O and extracted with CHCl3 (3×). The organic layers were combined, dried (MgSO4), filtered and concentrated to yield a dark brown oil. Dissolved in EtOAc and filtered off resulting brown solid. The filtrate solidified to give the title compound as a yellow solid which will be used in the next step without further purification.

Workup

  1. customThe sulfoxium salt was formed at 0°
  2. extractionextracted with CHCl3 (3×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a dark brown oil
  7. filtrationfiltered off
  8. customresulting brown solid

Sources & evidence

ORD record
ord-5a9b1b695e2246e8be60eb4c8052bbe1
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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