Ethanol → HCID 59336155, compound

HRID 2359465Notes

Reaction equation

HRID 2359465 reaction equation
C(O)C.Cl[C:5]1[C:10]([Cl:11])=[N:9][CH:8]=[CH:7][N:6]=1.Cl.[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH2:18])[CH3:14]>C(N(CC)CC)C>[Cl:11][C:10]1[C:5]([NH:18][CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:19])=[N:6][CH:7]=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 785752,3-DichloropyrazineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 59336155HCID 59336155, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To an ethanol solution (10 mL) of 2,3-dichloropyrazine (1.0 g), glycine ethyl ester hydrochloride (940 mg) and triethylamine (1.9 mL) were added and the mixture was irradiated with microwave (150° C., 10 min). The reaction mixture was concentrated under reduced pressure. To the resulting residue, a saturated aqueous sodium bicarbonate solution was added and the product was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by amino-coated silica gel (Fuji Sylysia Chemical Ltd.; NH-DM1020) column chromatography (hexane: ethyl acetate=10:1) to give 212 mg (15% yield) of the desired product.

Workup

  1. customthe mixture was irradiated with microwave (150° C., 10 min)
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the resulting residue, a saturated aqueous sodium bicarbonate solution was added
  4. extractionthe product was extracted with chloroform
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by amino-coated silica gel (Fuji Sylysia Chemical Ltd.; NH-DM1020) column chromatography (hexane: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-247fd4a26655493082ab3c03401a6a1a
Source dataset
uspto-grants-2014_04
Patent number
US08685989B2

Reaction notes

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