HCID 44817206, compound → HCID 44814619, compound

HRID 2167483Notes

Reaction equation

HRID 2167483 reaction equation
CO[C:3]([C:5]1[CH:10]=[N:9][C:8]([C:11]2[N:12]=[C:13]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[O:14][C:15]=2[S:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19]N=2)=[CH:7][N:6]=1)=O.[CH3:31][Mg]Br>C1COCC1.[NH4+].[Cl-]>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([S:16][C:15]2[O:14][C:13]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[N:12][C:11]=2[C:8]2[CH:7]=[N:6][C:5]([CH3:3])=[CH:10][N:9]=2)=[CH:31][CH:19]=1

Participants

5

Reactant 2

HCID 44817206HCID 44817206, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 44814619HCID 44814619, compoundYield 31.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of methyl-5-[5-[(4-chlorophenyl)thio]-2-(4-fluorophenyl)-1,3-oxazol-4-yl]pyrazine-2-carboxylate (Example 1) (24 mg, 0.05 mmol) in THF (5 mL) was treated with methylmagnesium bromide (0.2 mL, 0.5 mmol, 3.0 M in THF) at rt. Upon completion of the reaction as judged by TLC analysis, the solution was diluted with saturated aq NH4Cl solution and extracted with EtOAc. The organic layer was removed, dried over MgSO4, filtered and concentrated giving rise to an oil. The oil was purified on silica gel to afford the title compound (6.3 mg). LC/MS: m/e 397.0 (M+H)+. 1H NMR (500 MHz, Acetone-d6): δ 2.55 (s, 3H), 7.46 (m, 5H), 8.06 (m, 2H), 8.50 (s, 1H), 8.55 (s, 1H), 9.10 (d, J=1.1 Hz, 1H).

Workup

  1. customUpon completion of the reaction
  2. extractionextracted with EtOAc
  3. customThe organic layer was removed
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customgiving rise to an oil
  8. customThe oil was purified on silica gel

Sources & evidence

ORD record
ord-61ba5c23525046d19d38878ef28debad
Source dataset
uspto-grants-2015_06
Patent number
US09045467B2

Reaction notes

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