Dimethyl Sulfoxide → HCID 19975246, compound

HRID 1450151

Reaction equation

HRID 1450151 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([O:15][CH3:16])[C:5]2[N:6]([N:8]=[C:9]([S:11](Cl)(=[O:13])=[O:12])[N:10]=2)[CH:7]=1.[NH2:17][C:18]1[C:19]([F:25])=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24].N1C=CC=CC=1.CS(C)=O>C(#N)C>[F:25][C:19]1[C:18]([NH:17][S:11]([C:9]2[N:10]=[C:5]3[C:4]([O:15][CH3:16])=[N:3][C:2]([Br:1])=[CH:7][N:6]3[N:8]=2)(=[O:13])=[O:12])=[C:23]([CH3:24])[CH:22]=[CH:21][N:20]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 27631612-Fluoro-4-methylpyridin-3-amineHCID 19975236HCID 19975236, compound

Product 1

HCID 19975246HCID 19975246, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.36 g (4.14 mmol) of 6-bromo-2-chlorosulfonyl-8-methoxy[1,2,4]triazolo[1,5-a]pyrazine in 15 mL of dry acetonitrile was placed in a flask equipped with a drying tube and was treated sequentially with 1.56 g (12.4 mmol) of 3-amino-2-fluoro-4-methylpyridine, 0.34 mL (4.21 mmol) of pyridine and 60 μL (0.85 mmol) of dimethyl sulfoxide at room temperature. The reaction became progressively darker and after 15 hours the volatiles were removed by evaporation under reduced pressure and the residue was dissolved in dichloromethane. The resulting solution was washed with four portions of 1M hydrochloric acid and one portion of water and was dried over sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the residue obtained was purified by flash column chromatography on silica gel using a 0.5 to 4 percent ethanol/dichloromethane gradient as eluent. The solid obtained was further purified by extraction with diethyl ether to obtain 373 mg (22 percent of theory) of the desired product as an off-white powder melting at 210°-211° C. (dec); Mass Spectrum, m/e 417 (M+1).

Workup

  1. customequipped with a drying tube
  2. customafter 15 hours the volatiles were removed by evaporation under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThe resulting solution was washed with four portions of 1M hydrochloric acid and one portion of water
  5. dry with materialwas dried over sodium sulfate
  6. customThe solvent was then removed by evaporation under reduced pressure
  7. customthe residue obtained
  8. customwas purified by flash column chromatography on silica gel using a 0.5 to 4 percent ethanol/dichloromethane gradient as eluent
  9. customThe solid obtained
  10. customwas further purified by extraction with diethyl ether

Sources & evidence

ORD record
ord-c34e634c2e454d3a9d50c5dd0ec0e4f1
Source dataset
uspto-grants-1997_02
Patent number
US05602075

Linked notes

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