Dimethyl Sulfoxide → HCID 19975225, compound

HRID 1450146Notes

Reaction equation

HRID 1450146 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[C:9]([S:11](Cl)(=[O:13])=[O:12])[N:10]=[C:6]2[C:5]([Br:15])=[N:4][CH:3]=1.C[Si](C)(C)[NH:18][C:19]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=[CH:21][C:20]=1[F:29].CS(C)=O>C(#N)C>[F:29][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([C:25]([O:27][CH3:28])=[O:26])[C:19]=1[NH:18][S:11]([C:9]1[N:10]=[C:6]2[C:5]([Br:15])=[N:4][CH:3]=[C:2]([Br:1])[N:7]2[N:8]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 19975230HCID 19975230, compoundHCID 19975237HCID 19975237, compound

Product 1

HCID 19975225HCID 19975225, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 0.75 g (20 mmol) of 5,8-dibromo-2-chlorosulfonyl[1,2,4]triazolo[1,5-a]pyrazine in 8 mL of dry acetonitrile was placed in a flask equipped with a drying tube and was treated sequentially with 6.0 mL (6.0 mmol) of a 1M solution of N-trimethylsilyl-2-fluoro-6-methoxycarbonylaniline in acetonitrile and 25 μL (0.35 mmol) of dimethyl sulfoxide at room temperature with stirring. The reaction became progressively darker and after 1 hour, the volatiles were removed by evaporation under reduced pressure and the residue was dissolved in dichloromethane. The resulting solution was washed with water, dried over sodium sulfate, and concentrated by evaporation under reduced pressure. The residue was purified by flash column chromatography on silica gel using a 0.5 to 4 percent ethanol/dichloromethane gradient as eluent to obtain 715 mg (70 percent of theory) of the desired product as an orange glassy solid melting at 190°-195° C.; Mass Spectrum, m/e 510 (M+1).

Workup

  1. customequipped with a drying tube
  2. customthe volatiles were removed by evaporation under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThe resulting solution was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel using a 0.5 to 4 percent ethanol/dichloromethane gradient as eluent

Sources & evidence

ORD record
ord-7361439bf57f4628977d7417e5c1c624
Source dataset
uspto-grants-1997_02
Patent number
US05602075

Reaction notes

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