Dimethyl Sulfoxide → HCID 86696616, compound

HRID 717146Notes

Reaction equation

HRID 717146 reaction equation
Br[C:2]1[C:3]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[CH:16]([NH2:19])([CH3:18])[CH3:17].C(N(CC)C(C)C)(C)C.CS(C)=O>O>[Br:8][C:6]1[N:7]=[C:2]([NH:19][CH:16]([CH3:18])[CH3:17])[C:3]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:4][CH:5]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 57550751Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate

Product 1

HCID 86696616HCID 86696616, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate (See Example 6.B) (1.5 g, 4.43 mmol), isopropylamine (0.17 g, 4.87 mmol), N,N-diisopropylethylamine (1.14 g, 8.84 mmol) and dimethylsulfoxide (10 mL) in a reaction vial was heated in an oil bath at 150° C. for 16 h. After being cooled to room temperature, the resulting mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, evaporated under reduced pressure and purified on silica gel column chromatography (10-20% ethyl acetate in petroleum ether) to give the title compound (780 mg, 55.7% yield). MS (ESI) m/z 316.9 [M+1]+.

Workup

  1. customin a reaction
  2. temperatureAfter being cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. custompurified on silica gel column chromatography (10-20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-4625f886d38b4569a7668305155d3df8
Source dataset
uspto-grants-2015_11
Patent number
US09193692B2

Reaction notes

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